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Vacation Rentals in Siesta Key, Florida

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about Siesta Key

Siesta Key, Florida Vacation Rentals and Tourism

Tropical bliss awaits you in beach rentals on Siesta Key, an island situated just off Florida’s central gulf coast. You can't help but relax when you dip your toes in the soft white sand and warm water near Siesta Key vacation rentals. The best starting place for your Siesta Key vacation is to choose from our selection of Siesta Key beach condos, Siesta Key vacation rental homes and oceanfront Siesta Key vacation rentals for a vacation with all the comforts of home; comfort Siesta Key hotels just can’t offer.

Siesta Key vacation rental homes are near three beaches where you can find shells, swim, play beach volleyball, and soak in the sunshine. Siesta Key weather is inviting year round, perfect for your next golf vacation destination. Siesta Key rentals are near many golf courses, plus Siesta Key condo rentals are near restaurants and boat rentals, bicycle rentals, fishing outfitters and boat charters. You won't run out of vacation fun or helpful services since Siesta Key is a vibrant beach town. Be sure to check out the events calendar for beach concerts, volleyball tournaments and October's annual art festival.

Siesta Key vacation rentals are about eight miles from Sarasota, FL, and about 53 miles from St. Petersburg, FL. You'll be at your Siesta Key vacation condo in no time by flying into Sarasota Bradenton International Airport, about 15 minutes from the Siesta Key rentals. Book your Siesta Key vacation rental home soon for winter and spring beach vacations and find some great values in the fall. Most Siesta Key apartments, homes, and ocndos are available year round for your next beach vacation.

Find the right Siesta Key accommodation for your Siesta Key vacation right here! With all the Siesta Key beach rentals on display here, there's no reason you shouldn't find your dream vacation home with speed and ease. We even have a guide to Siesta Key resorts for you to use!

With our Siesta Key Travel Guide, you can learn all about this lovely beach town. Find out about Siesta Key Village, beach activities, top restaurants, and more.

Deals on Siesta Key, Florida Rentals

If you want to spend some time in Siesta Key, don't let your budget get in the way of staying in a nice, roomy place—find a great deal on cheap Siesta Key lodging. Choose from a wide variety of money-saving Siesta Key beach houses, spacious and luxurious villas, and sizable – but reasonably priced – town homes. Because we accommodate the size of any budget as well as the size of any group, we're positive that you'll find a low-cost Siesta Key vacation rental perfect for your next vacation. Among all of the snorkeling, bird watching, surfing, boating, and sun bathing, don't forget to take a siesta of your own in the comfort of a cheap but luxurious Siesta Key rental home.

Remember, if you're looking for great deals on vacation rentals, Siesta Key and Vacation Rentals.com has them in spades!

 

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DEAL!! Beautiful Gulf Front Condo With Ocean View **RATES REDUCED**
Siesta Key Condo Rental Picture
  • Condo Rental Deals and Discounts $200 off = $1,015 per week
  • Condo Rental Deals and Specials Free secured WiFi and Free beach chairs... ($199)
  • bedrooms 2
  • community Sea Shell Condos
  • rental type Condo
  • owner badgeowner badge
  • sleeps 6
  • baths 2
  • rates (USD) $1,015 - $1,696 /wk
 
 
 
 
 

3 reviews write a review

DEAL!! Siesta Village Oasis- Private Pool & Jacuzzi
Siesta Key House Rental Picture
  • House Rental Deals and Discounts 25% off = $975 per week
  • House Rental Deals and Specials WIFI, HBO, CINAMAX, SHOWTIME, STARZ,... ($200)
  • bedrooms 3
  • community
  • rental type House
  • owner badgeowner badge
  • sleeps 8
  • baths 2
  • rates (USD) $225 /nt
    $1,300 - $1,600 /wk
 
 
 
 
 

20 reviews write a review

DEAL!! Seaside Villas - One Bedroom - Deluxe Garden Apartment -Pool
Siesta Key Villa Rental Picture
  • Villa Rental Deals and Discounts 20% off = $520 per week
  • Villa Rental Deals and Specials Free; WIFI, beach chairs/wagons ($99)
  • bedrooms 1
  • community Siesta Key Village
  • rental type Villa
  • owner badgeowner badge
  • sleeps 4
  • baths 1
  • rates (USD) $650 - $925 /wk
 
 
 
 
 

6 reviews write a review

DEAL!! Crescent Beach - 2-Bedroom - Beachfront Condo - Luxury
Siesta Key Condo Rental Picture
  • Condo Rental Deals and Discounts 20% off = $1,140 per week
  • Condo Rental Deals and Specials HighSpeed WIFI ($99)
  • bedrooms 2
  • community Crescent Arms
  • rental type Condo
  • owner badgeowner badge
  • sleeps 6
  • baths 2
  • rates (USD) $1,425 - $1,825 /wk
 
 
 
 
 

5 reviews write a review

DEAL!! 2-Bedroom - Crescent Beach - Beachfront Complex
Siesta Key Condo Rental Picture
  • Condo Rental Deals and Discounts 20% off = $900 per week
  • bedrooms 2
  • community Crescent Arms
  • rental type Condo
  • owner badgeowner badge
  • sleeps 6
  • baths 2
  • rates (USD) $1,125 - $1,525 /wk
 
 
 
 
 

6 reviews write a review

DEAL!! Excelsior Luxury Condos Family Friendly
Siesta Key Condo Rental Picture
  • Condo Rental Deals and Specials Free end of stay cleaning ($125)
  • bedrooms 2
  • community Excelsior Beach
  • rental type Condo
  • owner badgeowner badge
  • sleeps 6
  • baths 2
  • rates (USD) $900 - $1,380 /wk
    $3,600 - $5,480 /mth
 
 
 
 
 

3 reviews write a review

DEAL!! Luxury Townhouse (3BR) Private Pool - Crescent Beach - Villa
Siesta Key Townhome Rental Picture
  • Townhome Rental Deals and Discounts 20% off = $1,196 per week
  • Townhome Rental Deals and Specials Free WIFI, Beach Wagons/Chairs ($99)
  • bedrooms 3
  • community Siesta Key Beach
  • rental type Townhome
  • owner badgeowner badge
  • sleeps 8
  • baths
  • rates (USD) $1,495 - $2,045 /wk
 
 
 
 
 

9 reviews write a review

DEAL!! Crescent Beach - 2-Bedroom - Beachfront Condo Complex
Siesta Key Condo Rental Picture
  • Condo Rental Deals and Discounts 20% off = $980 per week
  • Condo Rental Deals and Specials Free WIFI ($99)
  • bedrooms 2
  • community Sea Shell Condos
  • rental type Condo
  • sleeps 6
  • baths 2
  • rates (USD) $1,225 - $1,625 /wk
 
 
 
 
 

5 reviews write a review

DEAL!! 3BR Luxury Townhouse - Siesta Key Beach - Gulf View - Pool
Siesta Key Townhome Rental Picture
  • Townhome Rental Deals and Discounts 20% off = $1,196 per week
  • Townhome Rental Deals and Specials Free beach chairs/wagons ($199)
  • bedrooms 3
  • community Siesta Key Beach
  • rental type Townhome
  • sleeps 8
  • baths
  • rates (USD) $1,495 - $2,045 /wk
 
 
 
 
 

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DEAL!! Paradise on Earth: Remodeled condo: SUMMER/FALL Sale
Siesta Key Condo Rental Picture
  • Condo Rental Deals and Discounts $200 off = $1,600 per month
  • Condo Rental Deals and Specials WIFI,Beach Chairs and ice chest ($100)
  • bedrooms 1
  • community White Sands Village
  • rental type Condo
  • sleeps 2
  • baths 1
  • rates (USD) $500 - $800 /wk
    $1,600 - $3,400 /mth
 
 
 
 
 

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DEAL!! Siesta Key Delight !
Siesta Key Condo Rental Picture
  • Condo Rental Deals and Discounts $100 off = $900 per week
  • bedrooms 2
  • community Bay Oaks Condos
  • rental type Condo
  • owner badgeowner badge
  • sleeps 6
  • baths 2
  • rates (USD) $600 - $1,000 /wk
 
 
 
 
 

2 reviews write a review

DEAL!! Beechwood
Siesta Key House Rental Picture
  • House Rental Deals and Discounts free night valued at USD $142
  • bedrooms 4
  • community Stickney Point
  • rental type House
  • sleeps 7
  • baths
  • rates (USD) $1,000 - $1,750 /wk
    $3,800 - $6,200 /mth
 
 
 
 
 

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DEAL!! Enjoy the World Class Sands of Siesta Beach!
Siesta Key Condo Rental Picture
  • Condo Rental Deals and Discounts 40% off = $1,080 per week
  • Condo Rental Deals and Specials HBO & WI-FI ($100)
  • bedrooms 3
  • community Siesta Key Beach
  • rental type Condo
  • owner badgeowner badge
  • sleeps 8
  • baths 2
  • rates (USD) $299 - $399 /nt
    $999 - $2,500 /wk
    $3,000 - $7,000 /mth
 
 
 
 
 

22 reviews write a review

DEAL!! Deluxe Townhouse & Garden Apartment (4BR's) - Pool
Siesta Key Townhome Rental Picture
  • Townhome Rental Deals and Discounts 20% off = $1,756 per week
  • Townhome Rental Deals and Specials Free: WIFI, beach chairs/wagons ($199)
  • bedrooms 4
  • community Siesta Key Village
  • rental type Townhome
  • owner badgeowner badge
  • sleeps 12
  • baths
  • rates (USD) $2,195 - $3,020 /wk
 
 
 
 
 

7 reviews write a review

DEAL!! Beachfront Luxury Condo 3-Bedroom - Turtle Beach/Siesta Key
Siesta Key Condo Rental Picture
  • Condo Rental Deals and Discounts 20% off = $1,236 per week
  • Condo Rental Deals and Specials Free WIFI, beach chairs ($99)
  • bedrooms 3
  • community Fisherman's Cove
  • rental type Condo
  • owner badgeowner badge
  • sleeps 8
  • baths 2
  • rates (USD) $1,545 - $2,095 /wk
 
 
 
 
 

5 reviews write a review

DEAL!! Beachfront One BR Condo at Fisherman's Cove - GROUND FLOOR
Siesta Key Condo Rental Picture
  • Condo Rental Deals and Discounts 10% off = $801 per week
  • Condo Rental Deals and Specials FREE: WIFI, beach chairs/wagons ($199)
  • bedrooms 1
  • community Fisherman's Cove
  • rental type Condo
  • owner badgeowner badge
  • sleeps 4
  • baths 1
  • rates (USD) $890 - $1,390 /wk
 
 
 
 
 

10 reviews write a review

DEAL!! Upscale - Beachfront One Bedroom Condo at Fisherman's Cove
Siesta Key Condo Rental Picture
  • Condo Rental Deals and Discounts 10% off = $801 per week
  • Condo Rental Deals and Specials Free WIFI ($99)
  • bedrooms 1
  • community Fisherman's Cove
  • rental type Condo
  • owner badgeowner badge
  • sleeps 4
  • baths 1
  • rates (USD) $890 - $1,390 /wk
 
 
 
 
 

4 reviews write a review

DEAL!! SeaSide Villas - Luxurious - Upscale - Elegant Townhouse
Siesta Key Villa Rental Picture
  • Villa Rental Deals and Discounts 20% off = $1,236 per week
  • Villa Rental Deals and Specials Free WIFI, Beach Wagons/Chairs ($99)
  • bedrooms 3
  • community Siesta Key Village
  • rental type Villa
  • owner badgeowner badge
  • sleeps 8
  • baths 3
  • rates (USD) $1,545 - $2,095 /wk
 
 
 
 
 

16 reviews write a review

DEAL!! Beachfront Condo - Three Bedroom - Luxury
Siesta Key Condo Rental Picture
  • Condo Rental Deals and Discounts 20% off = $1,236 per week
  • Condo Rental Deals and Specials Free WIFI ($99)
  • bedrooms 3
  • community Fisherman's Cove
  • rental type Condo
  • owner badgeowner badge
  • sleeps 8
  • baths 2
  • rates (USD) $1,545 - $2,095 /wk
 
 
 
 
 

18 reviews write a review

DEAL!! Beachfront Condo - Three Bedroom - Upscale in Siesta Key
Siesta Key Condo Rental Picture
  • Condo Rental Deals and Discounts 20% off = $1,236 per week
  • Condo Rental Deals and Specials Free WIFI, Beach wagon/chairs ($199)
  • bedrooms 3
  • community Fisherman's Cove
  • rental type Condo
  • owner badgeowner badge
  • sleeps 8
  • baths 2
  • rates (USD) $1,545 - $2,095 /wk
 
 
 
 
 

23 reviews write a review

DEAL!! Gorgeous Siesta Key Home w/Pool - Tons of EXTRAS!
Siesta Key House Rental Picture
  • House Rental Deals and Specials FREE WiFi, Cable, Beach Chairs, Bikes,... ($199)
  • bedrooms 3
  • community
  • rental type House
  • owner badgeowner badge
  • sleeps 8
  • baths 2
  • rates (USD) $1,200 - $1,700 /wk
    $4,500 - $6,500 /mth
 
 
 
 
 

9 reviews write a review

DEAL!! Lovely Condo with Great Views & Amenities at Harbor Towers!
Siesta Key Condo Rental Picture
  • Condo Rental Deals and Specials Free WiFi, Cable, Beach chairs ($99)
  • bedrooms 2
  • community Harbor Towers
  • rental type Condo
  • sleeps 4
  • baths 2
  • rates (USD) $606 - $922 /wk
    $2,424 - $3,688 /mth
 
 
 
 
 

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DEAL!! Beautiful Condo Across from the #1 Beach in the USA
Siesta Key Condo Rental Picture
  • Condo Rental Deals and Specials Free WiFi, Cable, Beach Chairs ($99)
  • bedrooms 2
  • community Our House at the Beach
  • rental type Condo
  • sleeps 6
  • baths 2
  • rates (USD) $134 - $186 /nt
    $938 - $1,239 /wk
    $3,752 - $4,956 /mth
 
 
 
 
 

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DEAL!! Stay On Siesta Key Beach - No Shoes Required!
Siesta Key Condo Rental Picture
  • Condo Rental Deals and Specials Free WiFi, Free Cable ($99)
  • bedrooms 2
  • community Sea Shell Condos
  • rental type Condo
  • owner badgeowner badge
  • sleeps 6
  • baths 2
  • rates (USD) $171 - $271 /nt
    $1,195 - $1,895 /wk
 
 
 
 
 

2 reviews write a review

DEAL!! Sensational Condo & Fantastic Amenities at Palm Bay Club!
Siesta Key Condo Rental Picture
  • Condo Rental Deals and Specials Free WiFi - Free Cable w/HBO ($99)
  • bedrooms 2
  • community Palm Bay Club
  • rental type Condo
  • sleeps 6
  • baths 2
  • rates (USD) $145 - $225 /nt
    $1,015 - $1,575 /wk
    $3,900 - $6,100 /mth
 
 
 
 
 

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DEAL!! Terrific Tropical Townhouse at Bay Oaks, unit G-12
Siesta Key Townhome Rental Picture
  • Townhome Rental Deals and Specials Free WiFi, Cable, Beach Chairs, Fishing... ($99)
  • bedrooms 2
  • community Bay Oaks
  • rental type Townhome
  • sleeps 6
  • baths
  • rates (USD) $100 - $172 /nt
    $700 - $1,200 /wk
    $2,100 - $3,900 /mth
 
 
 
 
 

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DEAL!! Tropical Beauty at an Affordable Price at Bay Oaks, unit E33
Siesta Key Condo Rental Picture
  • Condo Rental Deals and Specials Free WiFi, Cable, Beach Chairs, Bicycles... ($99)
  • bedrooms 2
  • community Bay Oaks
  • rental type Condo
  • sleeps 6
  • baths 2
  • rates (USD) $97 - $140 /nt
    $675 - $975 /wk
    $2,295 - $3,510 /mth
 
 
 
 
 

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DEAL!! Affordable Tropical Townhouse at Bay Oaks, unit B-62
Siesta Key Townhome Rental Picture
  • Townhome Rental Deals and Specials Free WiFi, Cable, Nintendo, Playstation,... ($99)
  • bedrooms 2
  • community Bay Oaks
  • rental type Townhome
  • sleeps 6
  • baths
  • rates (USD) $93 - $143 /nt
    $650 - $1,000 /wk
    $2,200 - $3,750 /mth
 
 
 
 
 

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DEAL!! Relax in Style at Bay Oaks in Siesta Key - unit E-81
Siesta Key Condo Rental Picture
  • Condo Rental Deals and Specials Fantastic Freebies ($99)
  • bedrooms 2
  • community Bay Oaks
  • rental type Condo
  • sleeps 6
  • baths 2
  • rates (USD) $675 - $975 /wk
    $2,295 - $3,315 /mth
 
 
 
 
 

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DEAL!! Siesta Key - Beachfront Condo - 2BR - Upscale - Free Boat Do
Siesta Key Condo Rental Picture
  • Condo Rental Deals and Discounts 20% off = $916 per week
  • bedrooms 2
  • community Fisherman's Cove
  • rental type Condo
  • sleeps 6
  • baths 2
  • rates (USD) $965 - $1,665 /wk
 
 
 
 
 

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DEAL!! Crescent Beach Condo
Siesta Key Condo Rental Picture
  • Condo Rental Deals and Discounts $50 off = $625 per week
  • bedrooms 1
  • community Sea Crest on Siesta
  • rental type Condo
  • sleeps 4
  • baths 1
  • rates (USD) $125 - $180 /nt
    $675 - $990 /wk
 
 
 
 
 

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DEAL!! "Sittin' on the Dock of the Bay Specials "
Siesta Key Condo Rental Picture
  • Condo Rental Deals and Discounts $58 off = $522 per week
  • bedrooms 1
  • community
  • rental type Condo
  • sleeps 4
  • baths 1
  • rates (USD) $83 - $123 /nt
    $580 - $980 /wk
 
 
 
 
 

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DEAL!! Remodeled, Faces Gulf/Sunset, with Private Dock
Siesta Key Condo Rental Picture
  • Condo Rental Deals and Specials WiFi, DVR, Bikes, umbrella and chairs ($300)
  • bedrooms 2
  • community Mariner's Inlet
  • rental type Condo
  • owner badgeowner badge
  • sleeps 4
  • baths 2
  • rates (USD) $92 - $200 /nt
    $645 - $1,195 /wk
    $1,700 - $3,200 /mth
 
 
 
 
 

15 reviews write a review

DEAL!! Siesta Key Condos - Vacation Condo Rentals
Siesta Key Condo Rental Picture
  • Condo Rental Deals and Discounts $64 off = $750 per week
  • Condo Rental Deals and Specials Free WiFi & free beach chairs ($100)
  • bedrooms 2
  • community Anchorage
  • rental type Condo
  • sleeps 4
  • baths 2
  • rates (USD) $814 - $1,187 /wk
 
 
 
 
 

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DEAL!! Couples Paradise - Gulf & Bay Club Bayside Condo
Siesta Key Condo Rental Picture
  • Condo Rental Deals and Discounts $40 off = $700 per week
  • Condo Rental Deals and Specials Free Wifi, washer/dryer, and beach... ($100)
  • bedrooms 1
  • community Gulf and Bay Club
  • rental type Condo
  • sleeps 2
  • baths 1
  • rates (USD) $740 - $1,080 /wk
 
 
 
 
 

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DEAL!! Beautiful Condo with Sensational Gulf Views - 6th floor unit
Siesta Key Condo Rental Picture
  • Condo Rental Deals and Specials Free WiFi, Free Cable, Beach Chairs &... ($99)
  • bedrooms 2
  • community Our House at the Beach
  • rental type Condo
  • sleeps 6
  • baths 2
  • rates (USD) $144 - $196 /nt
    $1,008 - $1,372 /wk
 
 
 
 
 

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DEAL!! Best Summer Rates on Siesta Key
Siesta Key Condo Rental Picture
  • Condo Rental Deals and Discounts 10% off = $486 per week
  • bedrooms 1
  • community Harbor Towers
  • rental type Condo
  • owner badgeowner badge
  • sleeps 4
  • baths 1
  • rates (USD) $540 - $870 /wk
    $2,160 - $3,480 /mth
 
 
 
 
 

2 reviews write a review

DEAL!! LaSiesta Condo
Siesta Key Condo Rental Picture
  • Condo Rental Deals and Discounts $245 off = $650 per week
  • bedrooms 2
  • community
  • rental type Condo
  • sleeps 6
  • baths 1
  • rates (USD) $895 /wk
 
 
 
 
 

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DEAL!! Paradise On Siesta Key-Harbor Towers
Siesta Key Condo Rental Picture
  • Condo Rental Deals and Specials WIFI ($75)
  • bedrooms 2
  • community Harbor Towers
  • rental type Condo
  • sleeps 6
  • baths 2
  • rates (USD) $850 - $1,300 /wk
    $2,700 - $4,000 /mth
 
 
 
 
 

1 reviews write a review

DEAL!! Sun, Sand & *SAVE 20% to 50%* per Week at Midnight Cove #532
Siesta Key Condo Rental Picture
  • Condo Rental Deals and Discounts 30% off = $706 per week
  • bedrooms 2
  • community Midnight Cove
  • rental type Condo
  • owner badgeowner badge
  • sleeps 4
  • baths
  • rates (USD) $636 - $1,579 /wk
    $2,244 - $4,483 /mth
 
 
 
 
 

3 reviews write a review

DEAL!! Sun, Sand & *SAVE 20%to50%* per Week at Siesta Breakers #603
Siesta Key Condo Rental Picture
  • Condo Rental Deals and Discounts 35% off = $973 per week
  • bedrooms 2
  • community Siesta Breakers
  • rental type Condo
  • owner badgeowner badge
  • sleeps 6
  • baths 2
  • rates (USD) $944 - $2,227 /wk
    $3,444 - $6,263 /mth
 
 
 
 
 

4 reviews write a review

DEAL!! Sun, Sand & *SAVE 20% to 50%* per Week at Midnight Cove #714
Siesta Key Condo Rental Picture
  • Condo Rental Deals and Discounts 30% off = $706 per week
  • bedrooms 2
  • community Midnight Cove
  • rental type Condo
  • owner badgeowner badge
  • sleeps 4
  • baths
  • rates (USD) $636 - $1,579 /wk
    $2,244 - $4,483 /mth
 
 
 
 
 

2 reviews write a review

DEAL!! Siesta Palms
Siesta Key Townhome Rental Picture
  • Townhome Rental Deals and Discounts $100 off = $790 per week
  • bedrooms 2
  • community North Village
  • rental type Townhome
  • sleeps 4
  • baths 2
  • rates (USD) $890 - $1,300 /wk
 
 
 
 
 

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DEAL!! Stunning Views of Sarasota Bay & access to private beach
Siesta Key Condo Rental Picture
  • Condo Rental Deals and Specials Free exit clean ($150)
  • bedrooms 2
  • community Bay Tree Club
  • rental type Condo
  • owner badgeowner badge
  • sleeps 4
  • baths 2
  • rates (USD) $925 - $1,000 /wk
    $3,700 - $4,000 /mth
 
 
 
 
 

11 reviews write a review

DEAL!! Our House at the Beach 504, 5th Floor, Gulf Views, Pool
Siesta Key Condo Rental Picture
  • Condo Rental Deals and Discounts 10% off = $126 per night
  • bedrooms 2
  • community Our House at Beach
  • rental type Condo
  • sleeps 6
  • baths 2
  • rates (USD) $114 - $166 /nt
    $529 - $1,249 /wk
    $1,930 - $5,185 /mth
 
 
 
 
 

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DEAL!! Jamaica Royale 91 Siesta Key Rental, heated pool, wifi
Siesta Key Condo Rental Picture
  • Condo Rental Deals and Discounts 10% off = $210 per night
  • bedrooms 2
  • community Jamaica Royale
  • rental type Condo
  • sleeps 6
  • baths 2
  • rates (USD) $119 - $350 /nt
    $575 - $1,595 /wk
    $2,417 - $5,251 /mth
 
 
 
 
 

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DEAL!! Our House at the beach 222
Siesta Key Townhome Rental Picture
  • Townhome Rental Deals and Discounts 10% off = $126 per night
  • bedrooms 2
  • community Our House at Beach
  • rental type Townhome
  • sleeps 4
  • baths 2
  • rates (USD) $114 - $166 /nt
    $529 - $1,930 /wk
    $1,933 - $5,188 /mth
 
 
 
 
 

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DEAL!! Siesta Dunes Beach 201, 2nd Floor, Spa, Heated Pool, Wifi
Siesta Key Condo Rental Picture
  • Condo Rental Deals and Discounts 10% off = $213 per night
  • bedrooms 2
  • community Siesta Dunes
  • rental type Condo
  • owner badgeowner badge
  • sleeps 6
  • baths 2
  • rates (USD) $125 - $350 /nt
    $575 - $1,595 /wk
    $2,417 - $5,251 /mth
 
 
 
 
 

37 reviews write a review

DEAL!! Siesta Key Palm and Bay Club G88 tower rental, Siesta Key FL
Siesta Key Condo Rental Picture
  • Condo Rental Deals and Discounts 10% off = $235 per night
  • bedrooms 1
  • community Palm Bay Club
  • rental type Condo
  • owner badgeowner badge
  • sleeps 4
  • baths 1
  • rates (USD) $125 - $400 /nt
    $695 - $1,995 /wk
    $2,902 - $6,308 /mth
 
 
 
 
 

20 reviews write a review

DEAL!! Gulf & Bay Club: Bayside, 2 Bedrooms, Ground Floor, 2 pools,
Siesta Key Condo Rental Picture
  • Condo Rental Deals and Discounts 10% off = $213 per night
  • bedrooms 2
  • community Gulf & Bay Club BS
  • rental type Condo
  • owner badgeowner badge
  • sleeps 6
  • baths 2
  • rates (USD) $125 - $350 /nt
    $650 - $1,795 /wk
    $2,414 - $5,962 /mth
 
 
 
 
 

3 reviews write a review

DEAL!! Palm and Bay Club G46 tower rental, from $695 a week
Siesta Key Condo Rental Picture
  • Condo Rental Deals and Discounts 10% off = $235 per night
  • bedrooms 1
  • community Palm Bay Club
  • rental type Condo
  • sleeps 4
  • baths 1
  • rates (USD) $125 - $400 /nt
    $636 - $1,795 /wk
    $2,000 - $6,361 /mth
 
 
 
 
 

1 reviews write a review

DEAL!! Siesta Dunes Beach 38A, Gulf Side 2 bedrooms, Heated Pool
Siesta Key Condo Rental Picture
  • Condo Rental Deals and Discounts 10% off = $224 per night
  • bedrooms 2
  • community Siesta Dunes
  • rental type Condo
  • sleeps 6
  • baths 2
  • rates (USD) $149 - $350 /nt
    $600 - $1,595 /wk
    $2,417 - $5,495 /mth
 
 
 
 
 

3 reviews write a review

DEAL!! Palm Bay Club Bayside #328, tennis courts, beach, pool
Siesta Key Condo Rental Picture
  • Condo Rental Deals and Discounts 10% off = $280 per night
  • bedrooms 2
  • community Palm Bay Club
  • rental type Condo
  • sleeps 4
  • baths 2
  • rates (USD) $225 - $400 /nt
    $1,095 - $1,995 /wk
    $3,995 - $6,476 /mth
 
 
 
 
 

3 reviews write a review

DEAL!! House of Sun 307 Siesta Key, Large Heated Pool, Gulf View
Siesta Key Condo Rental Picture
  • Condo Rental Deals and Discounts 10% off = $270 per night
  • bedrooms 2
  • community House of the Sun
  • rental type Condo
  • owner badgeowner badge
  • sleeps 6
  • baths 2
  • rates (USD) $150 - $450 /nt
    $750 - $2,095 /wk
    $2,902 - $6,308 /mth
 
 
 
 
 

47 reviews write a review

DEAL!! Siesta Dunes Beach 104, Siesta Key Gulf, Spa, Heated Pool
Siesta Key Condo Rental Picture
  • Condo Rental Deals and Discounts 10% off = $210 per night
  • bedrooms 2
  • community Siesta Dunes
  • rental type Condo
  • owner badgeowner badge
  • sleeps 6
  • baths 2
  • rates (USD) $119 - $350 /nt
    $575 - $1,595 /wk
    $2,417 - $5,251 /mth
 
 
 
 
 

29 reviews write a review

DEAL!! Castaway Cove 3B, on lagoon near beach, pet friendly, Siesta
Siesta Key House Rental Picture
  • House Rental Deals and Discounts 10% off = $164 per night
  • bedrooms 2
  • community Private Beach House
  • rental type House
  • sleeps 5
  • baths 2
  • rates (USD) $100 - $266 /nt
    $595 - $1,595 /wk
    $1,946 - $5,005 /mth
 
 
 
 
 

13 reviews write a review

Adorable Villa on Siesta Key, Villa B
Siesta Key Villa Rental Picture
  • bedrooms 2
  • community
  • rental type Villa
  • sleeps 4
  • baths 1
  • rates (USD) $125 - $146 /nt
    $750 - $1,020 /wk
    $2,700 - $3,500 /mth
 
 
 
 
 

1 reviews write a review

4 bedroom beachfront- world's top-rated beach
Siesta Key Villa Rental Picture
  • bedrooms 4
  • community Aloha Kai
  • rental type Villa
  • owner badgeowner badge
  • sleeps 8
  • baths 2
  • rates (USD) $2,595 - $3,845 /wk
 
 
 
 
 

2 reviews write a review

Siesta Key - Gulf-Front Retreat - 2 Bedroom - Upscale
Siesta Key Condo Rental Picture
  • bedrooms 2
  • community Fisherman's Cove
  • rental type Condo
  • owner badgeowner badge
  • sleeps 6
  • baths 2
  • rates (USD) $1,165 - $1,665 /wk
 
 
 
 
 

4 reviews write a review

Palm Bay Club bayside condo on Siesta Key - fairly priced
Siesta Key Condo Rental Picture
  • bedrooms 2
  • community Palm Bay Club
  • rental type Condo
  • owner badgeowner badge
  • sleeps 6
  • baths 2
  • rates (USD) $850 - $1,600 /wk
 
 
 
 
 

20 reviews write a review

Siesta Village Oasis II - Private Pool & Jacuzzi
Siesta Key House Rental Picture
  • bedrooms 2
  • community
  • rental type House
  • owner badgeowner badge
  • sleeps 4
  • baths 1
  • rates (USD) $185 /nt
    $1,150 /wk
 
 
 
 
 

5 reviews write a review

Siesta Key Beach House
Siesta Key House Rental Picture
  • bedrooms 3
  • community
  • rental type House
  • owner badgeowner badge
  • sleeps 7
  • baths
  • rates (USD) $1,000 - $1,450 /wk
 
 
 
 
 

2 reviews write a review

Next to the Best - Village 1 Bedroom Apartment
Siesta Key Apartment Rental Picture
  • bedrooms 1
  • community
  • rental type Apartment
  • sleeps 2
  • baths 1
  • rates (USD) $125 - $200 /nt
    $750 - $900 /wk
    $2,500 - $3,200 /mth
 
 
 
 
 

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Next to the Best- Village 2 Bedroom Apartments
Siesta Key Apartment Rental Picture
  • bedrooms 2
  • community
  • rental type Apartment
  • sleeps 4
  • baths 2
  • rates (USD) $175 - $225 /nt
    $900 - $1,750 /wk
    $3,100 - $6,500 /mth
 
 
 
 
 

1 reviews write a review

Siesta Key Beach Private Pool Home
Siesta Key House Rental Picture
  • bedrooms 3
  • community
  • rental type House
  • sleeps 6
  • baths 3
  • rates (USD) $300 - $500 /nt
    $6,400 - $10,000 /mth
 
 
 
 
 

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Midnight Cove II Bayside #734
Siesta Key Condo Rental Picture
  • bedrooms 2
  • community Midnight Cove II
  • rental type Condo
  • sleeps 5
  • baths
  • rates (USD) $175 - $250 /nt
    $900 - $1,650 /wk
    $3,100 - $6,200 /mth
 
 
 
 
 

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Island Style Luxury Beach House
Siesta Key House Rental Picture
  • bedrooms 3
  • community Sarasota Beach
  • rental type House
  • owner badgeowner badge
  • sleeps 9
  • baths
  • rates (USD) $285 /nt
    $2,000 /wk
    $6,800 /mth
 
 
 
 
 

11 reviews write a review

Adorable Villa on Siesta Key, Villa A
Siesta Key Villa Rental Picture
  • bedrooms 2
  • community
  • rental type Villa
  • sleeps 4
  • baths 1
  • rates (USD) $125 - $146 /nt
    $750 - $1,020 /wk
    $2,700 - $3,500 /mth
 
 
 
 
 

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Harbor Towers 520
Siesta Key Condo Rental Picture
  • bedrooms 2
  • community Harbor Towers
  • rental type Condo
  • sleeps 6
  • baths 2
  • rates (USD) $750 - $1,400 /wk
 
 
 
 
 

1 reviews write a review

4638 Gleason Ave
Siesta Key House Rental Picture
  • bedrooms 3
  • community
  • rental type House
  • sleeps 8
  • baths 2
  • rates (USD) $1,200 - $1,850 /wk
 
 
 
 
 

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Siesta Key Home with Pool Near SK Village
Siesta Key House Rental Picture
  • bedrooms 3
  • community
  • rental type House
  • sleeps 6
  • baths 2
  • rates (USD) $1,500 - $1,750 /wk
    $6,000 - $9,000 /mth
 
 
 
 
 

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Siesta Towers #2A-MUST be monthly or more rentals!
Siesta Key Condo Rental Picture
  • bedrooms 2
  • community Siesta Towers
  • rental type Condo
  • sleeps 6
  • baths 2
  • rates (USD) $1,500 - $2,500 /wk
    $5,500 - $6,500 /mth
 
 
 
 
 

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516 Beach Road #E / On The Beach!!
Siesta Key Cottage Rental Picture
  • bedrooms 2
  • community
  • rental type Cottage
  • sleeps 6
  • baths 2
  • rates (USD) $1,000 - $1,850 /wk
    $4,800 - $6,500 /mth
 
 
 
 
 

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Shells 306
Siesta Key Townhome Rental Picture
  • bedrooms 3
  • community Near Siesta Village
  • rental type Townhome
  • sleeps 8
  • baths
  • rates (USD) $1,325 - $2,035 /wk
 
 
 
 
 

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House of the Sun Gulf Front Condo on Beach
Siesta Key House Rental Picture
  • bedrooms 2
  • community House of the Sun
  • rental type House
  • sleeps 6
  • baths 2
  • rates (USD) $1,539 - $2,182 /wk
 
 
 
 
 

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Sensational Gulf Views from Beach Front Condo
Siesta Key Condo Rental Picture
  • bedrooms 2
  • community Siesta Sands
  • rental type Condo
  • sleeps 6
  • baths 2
  • rates (USD) $1,350 - $2,295 /wk
 
 
 
 
 

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Palm Bay Club Private Beach 3 doors from pool,jacuzzi,fishin
Siesta Key Condo Rental Picture
  • bedrooms 2
  • community Palm Bay Club
  • rental type Condo
  • owner badgeowner badge
  • sleeps 6
  • baths 2
  • rates (USD) $165 - $250 /nt
    $850 - $1,600 /wk
    $3,400 - $5,200 /mth
 
 
 
 
 

14 reviews write a review

Palm Bay Club condo -bayfront large - reasonable -Siesta Key
Siesta Key Condo Rental Picture
  • bedrooms 2
  • community Palm Bay Club
  • rental type Condo
  • owner badgeowner badge
  • sleeps 6
  • baths 2
  • rates (USD) $1,075 - $1,950 /wk
 
 
 
 
 

5 reviews write a review

19 Whispering Sands Unit #506 Corner Unit On the Beach
Siesta Key Condo Rental Picture
  • bedrooms 2
  • community Whispering Sands
  • rental type Condo
  • sleeps 6
  • baths 2
  • rates (USD) $3,250 - $5,500 /mth
 
 
 
 
 

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Direct Gulf-Front Retreat - 2 Bedroom - Upscale - Siesta Key
Siesta Key Condo Rental Picture
  • bedrooms 2
  • community Fisherman's Cove
  • rental type Condo
  • owner badgeowner badge
  • sleeps 6
  • baths 2
  • rates (USD) $1,165 - $1,665 /wk
 
 
 
 
 

14 reviews write a review

Steps to Siesta Key Beach-Fully Renovated in 2013
Siesta Key Villa Rental Picture
  • bedrooms 2
  • community Gulf Haven
  • rental type Villa
  • owner badgeowner badge
  • sleeps 4
  • baths 2
  • rates (USD) $3,300 - $4,800 /mth
 
 
 
 
 

7 reviews write a review

Bella Vista: Elegant Beachfront Condo - Full Gulf View
Siesta Key Condo Rental Picture
  • bedrooms 2
  • community Whispering Sands
  • rental type Condo
  • sleeps 4
  • baths 2
  • rates (USD) $4,000 - $5,900 /mth
 
 
 
 
 

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Sunny Siesta Key Beach House
Siesta Key House Rental Picture
  • bedrooms 2
  • community Palm Island
  • rental type House
  • owner badgeowner badge
  • sleeps 4
  • baths 2
  • rates (USD) $900 - $1,300 /wk
    $3,200 - $4,300 /mth
 
 
 
 
 

7 reviews write a review

On The Beach Choice 5 Star Top Floor Unit
Siesta Key Condo Rental Picture
  • bedrooms 2
  • community El Presidente
  • rental type Condo
  • sleeps 6
  • baths 2
  • rates (USD) $1,250 - $2,043 /wk
 
 
 
 
 

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Siesta Key - Gulf-Front Condo- 2 Bedroom - Upscale
Siesta Key Condo Rental Picture
  • bedrooms 2
  • community Fisherman's Cove
  • rental type Condo
  • owner badgeowner badge
  • sleeps 6
  • baths 2
  • rates (USD) $1,165 - $1,665 /wk
 
 
 
 
 

3 reviews write a review

Siesta Key - Beachfront - 2-Bedroom - Ground Floor
Siesta Key Condo Rental Picture
  • bedrooms 2
  • community Fisherman's Cove
  • rental type Condo
  • sleeps 6
  • baths 2
  • rates (USD) $1,165 - $1,665 /wk
 
 
 
 
 

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Tropical Paradise with full Gulf-front View
Siesta Key House Rental Picture
  • bedrooms 2
  • community Siesta Sands
  • rental type House
  • sleeps 6
  • baths 2
  • rates (USD) $1,350 - $2,295 /wk
 
 
 
 
 

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Beach Front View at Siesta Key Unit #212
Siesta Key Condo Rental Picture
  • bedrooms 2
  • community Siesta Sands
  • rental type Condo
  • sleeps 6
  • baths 2
  • rates (USD) $1,350 - $2,295 /wk
 
 
 
 
 

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Crescent Beach 1st Level Beach Front Condo
Siesta Key Condo Rental Picture
  • bedrooms 2
  • community Siesta Sands
  • rental type Condo
  • owner badgeowner badge
  • sleeps 6
  • baths 2
  • rates (USD) $1,350 - $2,295 /wk
 
 
 
 
 

18 reviews write a review

Beachfront Condo - Full Gulf View - Updated Yearly
Siesta Key Condo Rental Picture
  • bedrooms 1
  • community
  • rental type Condo
  • sleeps 4
  • baths 1
  • rates (USD) $629 - $1,029 /wk
 
 
 
 
 

3 reviews write a review

Sunset Royale Beachfront Full Gulf View
Siesta Key Condo Rental Picture
  • bedrooms 2
  • community Sunset Royale
  • rental type Condo
  • owner badgeowner badge
  • sleeps 5
  • baths 2
  • rates (USD) $749 - $1,325 /wk
 
 
 
 
 

7 reviews write a review

2 Minute Walk to Siesta Beach (really) - Great Value !!
Siesta Key Villa Rental Picture
  • bedrooms 2
  • community Sarasota by the Sea
  • rental type Villa
  • owner badgeowner badge
  • sleeps 5
  • baths 1
  • rates (USD) $750 - $1,200 /wk
    $2,300 - $4,700 /mth
 
 
 
 
 

9 reviews write a review

Whispering Sands North Tower Unit 606, Siesta Key
Siesta Key Condo Rental Picture
  • bedrooms 2
  • community Whispering Sands
  • rental type Condo
  • sleeps 6
  • baths 2
  • rates (USD) $3,250 - $5,500 /mth
 
 
 
 
 

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Beautiful 2br/2ba Garden Unit on Crescent Beach, Free WIFI
Siesta Key Condo Rental Picture
  • bedrooms 2
  • community Crescent Beach
  • rental type Condo
  • sleeps 6
  • baths 2
  • rates (USD) $925 - $1,595 /wk
    $3,330 - $5,605 /mth
 
 
 
 
 

1 reviews write a review

Beautiful 2 bedroom Condo on Siesta Key
Siesta Key Condo Rental Picture
  • bedrooms 2
  • community
  • rental type Condo
  • sleeps 6
  • baths 2
  • rates (USD) $2,000 - $4,500 /mth
 
 
 
 
 

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Beautiful unit, beautiful view, steps from Siesta Beach!
Siesta Key Condo Rental Picture
  • bedrooms 2
  • community Midnight Cove II
  • rental type Condo
  • sleeps 4
  • baths
  • rates (USD) $600 - $1,130 /wk
 
 
 
 
 

1 reviews write a review

Sunset Royale #104, at the beach with beautiful sunsets
Siesta Key Condo Rental Picture
  • bedrooms 1
  • community Sunset Royale
  • rental type Condo
  • owner badgeowner badge
  • sleeps 2
  • baths 1
  • rates (USD) $649 - $1,100 /wk
 
 
 
 
 

5 reviews write a review

Midnight Cove II
Siesta Key Condo Rental Picture
  • bedrooms 2
  • community Midnight Cove II
  • rental type Condo
  • sleeps 6
  • baths
  • rates (USD) $107 - $161 /nt
    $750 - $1,130 /wk
    $2,996 - $4,508 /mth
 
 
 
 
 

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GREAT Value, Siesta Key Beach,Voted #1 Best Beach in U.S/Fl
Siesta Key Villa Rental Picture
  • bedrooms 2
  • community Casa Blanca
  • rental type Villa
  • owner badgeowner badge
  • sleeps 4
  • baths 2
  • rates (USD) $143 - $204 /nt
    $1,001 - $1,394 /wk
    $3,604 - $5,018 /mth
 
 
 
 
 

9 reviews write a review

Direct Gulf Front Beach w/FREE Boat Dock GROUND FLOOR UNIT
Siesta Key Condo Rental Picture
  • bedrooms 2
  • community Fisherman's Cove
  • rental type Condo
  • owner badgeowner badge
  • sleeps 6
  • baths 2
  • rates (USD) $1,020 - $1,745 /wk
 
 
 
 
 

28 reviews write a review

Siesta Key-Siesta Dunes Beach Gulf Front Condo #1 Beach USA
Siesta Key Condo Rental Picture
  • bedrooms 2
  • community Siesta Dunes
  • rental type Condo
  • owner badgeowner badge
  • sleeps 4
  • baths 2
  • rates (USD) $1,450 - $1,890 /wk
 
 
 
 
 

37 reviews write a review

Our Tropical Island Home
Siesta Key House Rental Picture
  • bedrooms 2
  • community Waterside East
  • rental type House
  • sleeps 6
  • baths 2
  • rates (USD) $750 - $990 /wk
 
 
 
 
 

10 reviews write a review

Landau Vacation Beach Rentals
Siesta Key Condo Rental Picture
  • bedrooms 2
  • community
  • rental type Condo
  • sleeps 6
  • baths 2
  • rates (USD) $850 - $1,500 /wk
 
 
 
 
 

1 reviews write a review

Great beach view Preferred Location
Siesta Key Condo Rental Picture
  • bedrooms 2
  • community La Siesta Condos 412
  • rental type Condo
  • sleeps 5
  • baths 2
  • rates (USD) $133 - $201 /nt
    $930 - $1,410 /wk
    $885 - $1,340 /mth
 
 
 
 
 

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Siesta Key Beachfront & Walk To Village
Siesta Key Condo Rental Picture
  • bedrooms 2
  • community Siesta Key Beach
  • rental type Condo
  • owner badgeowner badge
  • sleeps 5
  • baths 2
  • rates (USD) $1,000 - $1,995 /wk
    $3,000 - $5,250 /mth
 
 
 
 
 

27 reviews write a review

Unwind in an Affordable Healing Island Retreat
Siesta Key Hotel Rental Picture
  • bedrooms 4
  • community Siesta Key Village
  • rental type Hotel
  • sleeps 14
  • baths 4
  • rates (USD) $120 - $155 /nt
    $577 - $1,112 /wk
    $2,192 - $4,225 /mth
 
 
 
 
 

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Banyan Tree Beach Resort
Siesta Key Hotel Rental Picture
  • bedrooms 20
  • community Siesta Key Village
  • rental type Hotel
  • sleeps 35
  • baths 20
  • rates (USD) $125 - $210 /nt
    $598 - $1,508 /wk
    $2,272 - $5,730 /mth
 
 
 
 
 

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The Sandpiper
Siesta Key Condo Rental Picture
  • bedrooms 1
  • community Jamaica Royale
  • rental type Condo
  • sleeps 4
  • baths 1
  • rates (USD) $135 - $160 /nt
    $760 - $1,028 /wk
    $2,888 - $3,906 /mth
 
 
 
 
 

1 reviews write a review

Hummingbird Beach House
Siesta Key Apartment Rental Picture
  • bedrooms 6
  • community Siesta Key Village
  • rental type Apartment
  • sleeps 20
  • baths 6
  • rates (USD) $120 - $175 /nt
    $600 - $1,363 /wk
    $2,256 - $5,125 /mth
 
 
 
 
 

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luxury single story home private pool with all day sun
Siesta Key House Rental Picture
  • bedrooms 3
  • community PRIVATE CUL DE SAC
  • rental type House
  • owner badgeowner badge
  • sleeps 6
  • baths 2
  • rates (USD) $220 - $360 /nt
    $1,680 - $2,200 /wk
    $6,200 - $7,300 /mth
 
 
 
 
 

4 reviews write a review

Closest Condo to World-Famous Siesta Beach
Siesta Key Condo Rental Picture
  • bedrooms 1
  • community La Siesta Condos
  • rental type Condo
  • owner badgeowner badge
  • sleeps 4
  • baths 1
  • rates (USD) $795 - $1,170 /wk
 
 
 
 
 

4 reviews write a review

Peppertree Bay 6th Fl. Penthouse with Expansive Bay View!
Siesta Key Condo Rental Picture
  • bedrooms 2
  • community Peppertree Bay
  • rental type Condo
  • sleeps 4
  • baths 2
  • rates (USD) $2,895 - $4,295 /mth
 
 
 
 
 

1 reviews write a review

Beach & Surf at your Doorstep! 1 week just isn't enough!
Siesta Key Condo Rental Picture
  • bedrooms 2
  • community Fisherman's Cove
  • rental type Condo
  • owner badgeowner badge
  • sleeps 6
  • baths 2
  • rates (USD) $1,045 - $1,745 /wk
 
 
 
 
 

23 reviews write a review

Beach Place - Discounting Sept. & Oct. Rentals
Siesta Key Cottage Rental Picture
  • bedrooms 1
  • community Siesta Key Beach
  • rental type Cottage
  • sleeps 6
  • baths 1
  • rates (USD) $120 - $225 /nt
    $600 - $1,800 /wk
 
 
 
 
 

1 reviews write a review

Gulf Front-Cresent Beach-Completely Renovated-Immaculate
Siesta Key Condo Rental Picture
  • bedrooms 2
  • community House of the Sun
  • rental type Condo
  • owner badgeowner badge
  • sleeps 6
  • baths 2
  • rates (USD) $150 - $250 /nt
    $1,095 - $1,850 /wk
 
 
 
 
 

16 reviews write a review

Modern ocean front condo/full views of Siesta key Beach!
Siesta Key Condo Rental Picture
  • bedrooms 2
  • community
  • rental type Condo
  • owner badgeowner badge
  • sleeps 6
  • baths 2
  • rates (USD) $749 - $1,249 /wk
 
 
 
 
 

3 reviews write a review

2 Bedroom Beautiful Bay View Fully Updated
Siesta Key Condo Rental Picture
  • bedrooms 2
  • community Midnight Cove II
  • rental type Condo
  • owner badgeowner badge
  • sleeps 4
  • baths
  • rates (USD) $700 - $1,200 /wk
    $1,100 - $4,450 /mth
 
 
 
 
 

4 reviews write a review

Beautiful Siesta Key Beach!
Siesta Key Condo Rental Picture
  • bedrooms 2
  • community Crescent Royale
  • rental type Condo
  • sleeps 6
  • baths 2
  • rates (USD) $850 - $1,255 /wk
 
 
 
 
 

1 reviews write a review

Best Prices at Siesta Key Comfort
Siesta Key Condo Rental Picture
  • bedrooms 1
  • community Sea Winds
  • rental type Condo
  • sleeps 4
  • baths 1
  • rates (USD) $450 - $775 /wk
 
 
 
 
 

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Steps to Beach!
Siesta Key Condo Rental Picture
  • bedrooms 2
  • community Vista Hermosa
  • rental type Condo
  • owner badgeowner badge
  • sleeps 5
  • baths 2
  • rates (USD) $750 - $1,000 /wk
 
 
 
 
 

7 reviews write a review

Rachel B. Baker Revocable Trust
Siesta Key Condo Rental Picture
  • bedrooms 2
  • community Island Reef
  • rental type Condo
  • sleeps 6
  • baths 2
  • rates (USD) $1,900 - $3,500 /mth
 
 
 
 
 

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Cozy Cove
Siesta Key Condo Rental Picture
  • bedrooms 2
  • community Cozy Cove
  • rental type Condo
  • owner badgeowner badge
  • sleeps 4
  • baths
  • rates (USD) $96 - $164 /nt
    $675 - $1,150 /wk
 
 
 
 
 

12 reviews write a review

Siesta Key Beachfront 2B/2B Condo
Siesta Key Condo Rental Picture
  • bedrooms 2
  • community Crescent Arms
  • rental type Condo
  • owner badgeowner badge
  • sleeps 6
  • baths 2
  • rates (USD) $995 - $2,000 /nt
    $995 - $2,000 /wk
 
 
 
 
 

4 reviews write a review

Nice Condo, in a great location across from the beach
Siesta Key Condo Rental Picture
  • bedrooms 2
  • community White Sands Village
  • rental type Condo
  • sleeps 6
  • baths 2
  • rates (USD) $550 - $1,050 /wk
    $1,800 - $3,900 /mth
 
 
 
 
 

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Walk to the beautiful white sand of Siesta Beach
Siesta Key Condo Rental Picture
  • bedrooms 2
  • community White Sands Village
  • rental type Condo
  • owner badgeowner badge
  • sleeps 6
  • baths 2
  • rates (USD) $550 - $1,025 /wk
    $1,800 - $3,800 /mth
 
 
 
 
 

3 reviews write a review

Old Man & the Sea Inn 2BR- 1 marlin from the sand
Siesta Key House Rental Picture
  • bedrooms 2
  • community Crescent Beach
  • rental type House
  • sleeps 8
  • baths 1
  • rates (USD) $190 - $440 /nt
    $950 - $2,200 /wk
    $2,850 - $6,600 /mth
 
 
 
 
 

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Old Man & the Sea Inn 1BR- 1 marlin from the sand
Siesta Key House Rental Picture
  • bedrooms 1
  • community
  • rental type House
  • sleeps 4
  • baths 1
  • rates (USD) $170 - $360 /nt
    $850 - $1,800 /wk
    $2,550 - $5,400 /mth
 
 
 
 
 

1 reviews write a review

Whispering Sands Unit #205
Siesta Key Condo Rental Picture
  • bedrooms 2
  • community Whispering Sands
  • rental type Condo
  • sleeps 5
  • baths 2
  • rates (USD) $2,100 - $5,500 /mth
 
 
 
 
 

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Siesta Key-Crescent Beach -Midnight Cove I - 2 BDRs 2 Bath
Siesta Key Condo Rental Picture
  • bedrooms 2
  • community Midnight Cove I
  • rental type Condo
  • owner badgeowner badge
  • sleeps 6
  • baths 2
  • rates (USD) $735 - $1,267 /wk
 
 
 
 
 

11 reviews write a review

Our top location! Gertrude's Village House.
Siesta Key House Rental Picture
  • bedrooms 3
  • community Siesta Gardens
  • rental type House
  • sleeps 10
  • baths 2
  • rates (USD) $380 - $580 /nt
    $1,900 - $3,100 /wk
    $5,700 - $9,900 /mth
 
 
 
 
 

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Palm Island House - featured in NYC Fall Homes magazine!
Siesta Key House Rental Picture
  • bedrooms 4
  • community Siesta Key Village
  • rental type House
  • sleeps 14
  • baths 4
  • rates (USD) $310 - $610 /nt
    $2,400 - $4,300 /wk
    $7,200 - $10,800 /mth
 
 
 
 
 

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The Siesta Key Village Studio
Siesta Key Studio Rental Picture
  • bedrooms 0
  • community Siesta Key Village
  • rental type Studio
  • sleeps 2
  • baths 1
  • rates (USD) $110 - $170 /nt
    $750 - $1,200 /wk
    $1,875 - $3,600 /mth
 
 
 
 
 

1 reviews write a review

Gertrude's Twin Banyan NEW!- POOL BEACH OASIS
Siesta Key Condo Rental Picture
  • bedrooms 2
  • community Siesta Key Village
  • rental type Condo
  • sleeps 7
  • baths 1
  • rates (USD) $150 - $315 /nt
    $1,100 - $2,200 /wk
    $3,300 - $6,600 /mth
 
 
 
 
 

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Casa Van Lopik (j)- Your lush island getaway!
Siesta Key House Rental Picture
  • bedrooms 3
  • community Siesta Key Village
  • rental type House
  • sleeps 10
  • baths 2
  • rates (USD) $380 - $660 /nt
    $1,900 - $3,300 /wk
    $5,700 - $9,900 /mth
 
 
 
 
 

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Casa Van Lopik (c)- Your lush island getaway!
Siesta Key House Rental Picture
  • bedrooms 3
  • community Siesta Key Village
  • rental type House
  • sleeps 10
  • baths 2
  • rates (USD) $380 - $660 /nt
    $1,900 - $3,300 /wk
    $3,900 - $8,700 /mth
 
 
 
 
 

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8th Floor Penthouse View of Siesta Key
Siesta Key Condo Rental Picture
  • bedrooms 2
  • community Jamaica Royale
  • rental type Condo
  • sleeps 6
  • baths 2
  • rates (USD) $1,505 - $1,960 /wk
 
 
 
 
 

1 reviews write a review

Wow! Siesta Key -Best Beach! Gulfside 2 -Bdr - 2 Bath Condo
Siesta Key Condo Rental Picture
  • bedrooms 2
  • community Peppertree Bay
  • rental type Condo
  • sleeps 6
  • baths 2
  • rates (USD) $2,800 - $4,800 /mth
 
 
 
 
 

1 reviews write a review

Single Family Home / Close to Siesta Beach and Village
Siesta Key House Rental Picture
  • bedrooms 4
  • community Siest Key
  • rental type House
  • sleeps 8
  • baths
  • rates (USD) $2,000 - $2,500 /wk
    $5,000 - $8,000 /mth
 
 
 
 
 

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3-Bdr.Townhouse w/ Private Access to Siesta Beach-# 1 Beach!
Siesta Key Townhome Rental Picture
  • bedrooms 3
  • community Gulf and Bay Club
  • rental type Townhome
  • owner badgeowner badge
  • sleeps 6
  • baths 2
  • rates (USD) $1,200 - $1,975 /wk
    $3,300 - $5,100 /mth
 
 
 
 
 

2 reviews write a review

Bay Oaks Hideway on Siesta Key
Siesta Key Condo Rental Picture
  • bedrooms 2
  • community Bay Oaks
  • rental type Condo
  • owner badgeowner badge
  • sleeps 6
  • baths
  • rates (USD) $750 - $850 /wk
    $2,100 - $3,500 /mth
 
 
 
 
 

2 reviews write a review

2 Bedroom Penthouse On Crescent Beach
Siesta Key Condo Rental Picture
  • bedrooms 2
  • community Excelsior Beach
  • rental type Condo
  • sleeps 6
  • baths 2
  • rates (USD) $900 - $1,400 /wk
 
 
 
 
 

1 reviews write a review

Beautiful Siesta Key Home with Pool
Siesta Key House Rental Picture
  • bedrooms 4
  • community
  • rental type House
  • sleeps 8
  • baths 3
  • rates (USD) $400 - $500 /nt
    $2,200 - $2,500 /wk
    $7,500 - $8,500 /mth
 
 
 
 
 

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Siesta:Ground floor-Big TV-King sized bed-glassed--in lanai
Siesta Key Condo Rental Picture
  • bedrooms 2
  • community Midnight Cove II
  • rental type Condo
  • sleeps 4
  • baths
  • rates (USD) $770 - $1,100 /wk
 
 
 
 
 

1 reviews write a review

Sea Crest Unit 24
Siesta Key Condo Rental Picture
  • bedrooms 1
  • community Siesta Key Beach
  • rental type Condo
  • sleeps 4
  • baths 1
  • rates (USD) $125 - $180 /nt
    $675 - $990 /wk
 
 
 
 
 

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Full Gulf View across from Siesta Public Beach
Siesta Key Condo Rental Picture
  • bedrooms 2
  • community Our House at the Beach
  • rental type Condo
  • sleeps 6
  • baths 2
  • rates (USD) $1,065 - $1,435 /wk
 
 
 
 
 

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SR #114, at Siesta Beach with gorgeous sunsets
Siesta Key Condo Rental Picture
  • bedrooms 2
  • community Sunset Royale
  • rental type Condo
  • owner badgeowner badge
  • sleeps 4
  • baths 2
  • rates (USD) $599 - $1,165 /wk
 
 
 
 
 

2 reviews write a review

Luxurious Gulf Condo - Short Walk to Siesta Beach
Siesta Key Condo Rental Picture
  • bedrooms 2
  • community White Sands Village
  • rental type Condo
  • sleeps 6
  • baths 2
  • rates (USD) $550 - $1,075 /wk
    $1,800 - $3,900 /mth
 
 
 
 
 

1 reviews write a review

Aloha Kai #46
Siesta Key Cottage Rental Picture
  • bedrooms 1
  • community Aloha Kai
  • rental type Cottage
  • sleeps 2
  • baths 1
  • rates (USD) $950 /wk
 
 
 
 
 

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1100 Point of Rocks Apt B
Siesta Key Apartment Rental Picture
  • bedrooms 1
  • community
  • rental type Apartment
  • sleeps 4
  • baths 1
  • rates (USD) $100 - $165 /nt
    $500 - $900 /wk
    $2,000 - $3,550 /mth
 
 
 
 
 

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Full Gulf View, Beach, Tennis, Island Reef Condo
Siesta Key Condo Rental Picture
  • bedrooms 2
  • community
  • rental type Condo
  • sleeps 6
  • baths 2
  • rates (USD) $2,500 - $4,000 /mth
 
 
 
 
 

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Polynesian Gardens
Siesta Key Villa Rental Picture
  • bedrooms 2
  • community Polynesian Gardens
  • rental type Villa
  • sleeps 5
  • baths
  • rates (USD) $85 - $150 /nt
    $500 - $1,200 /wk
    $2,400 - $3,800 /mth
 
 
 
 
 

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Island Living at its Best!
Siesta Key Condo Rental Picture
  • bedrooms 2
  • community
  • rental type Condo
  • sleeps 5
  • baths 1
  • rates (USD) $250 - $390 /nt
    $750 - $1,620 /wk
 
 
 
 
 

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Gulf View Condo, Sunset Royale on Siesta Key
Siesta Key Condo Rental Picture
  • bedrooms 2
  • community Sunset Royale
  • rental type Condo
  • sleeps 6
  • baths 2
  • rates (USD) $1,016 - $1,690 /wk
 
 
 
 
 

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Island House Penthouse on Siesta Key 5000 SqFt
Siesta Key Condo Rental Picture
  • bedrooms 5
  • community Island House
  • rental type Condo
  • sleeps 12
  • baths 4
  • rates (USD) $2,600 - $4,000 /wk
 
 
 
 
 

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Gulf and Bay Club 102B Beach Front, Luxury Ground Floor unit
Siesta Key Condo Rental Picture
  • bedrooms 2
  • community Gulf and Bay Club
  • rental type Condo
  • sleeps 4
  • baths 2
  • rates (USD) $563 - $1,750 /wk
    $2,414 - $7,000 /mth
 
 
 
 
 

20 reviews write a review

Calini Beach Club
Siesta Key Condo Rental Picture
  • bedrooms 2
  • community Calini Beach Club
  • rental type Condo
  • sleeps 6
  • baths 2
  • rates (USD) $120 - $260 /nt
    $800 - $1,700 /wk
 
 
 
 
 

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Gulf and Bay Club 409B Beach Front
Siesta Key Condo Rental Picture
  • bedrooms 2
  • community Gulf and Bay Club
  • rental type Condo
  • owner badgeowner badge
  • sleeps 6
  • baths 2
  • rates (USD) $451 - $1,750 /wk
    $1,933 - $7,285 /mth
 
 
 
 
 

59 reviews write a review

3 Bedroom- Full Gulf Front- Ultimate Luxury!
Siesta Key Condo Rental Picture
  • bedrooms 3
  • community Hyatt
  • rental type Condo
  • sleeps 6
  • baths 3
  • rates (USD) $630 - $770 /nt
    $3,225 - $4,130 /wk
 
 
 
 
 

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Siesta Key Getaway!
Siesta Key House Rental Picture
  • bedrooms 3
  • community Siest Key
  • rental type House
  • sleeps 8
  • baths 3
  • rates (USD) $950 - $1,600 /wk
 
 
 
 
 

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Siesta Key #1 Beach USA* * WiFi & Pool* Gulfside
Siesta Key Villa Rental Picture
  • bedrooms 2
  • community The Casa Blanca
  • rental type Villa
  • sleeps 6
  • baths 1
  • rates (USD) $120 - $172 /nt
    $820 - $1,232 /wk
 
 
 
 
 

12 reviews write a review

Lovely Beachside Villa with Pool, HDTV, WI-FI
Siesta Key Villa Rental Picture
  • bedrooms 2
  • community Gulf Haven
  • rental type Villa
  • sleeps 5
  • baths 2
  • rates (USD) $3,000 - $4,500 /mth
 
 
 
 
 

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Affordable relax in paradise= * * * BEACHAVEN * * *
Siesta Key Condo Rental Picture
  • bedrooms 2
  • community Beachaven Assoc
  • rental type Condo
  • sleeps 6
  • baths 2
  • rates (USD) $59 - $152 /nt
    $409 - $1,060 /wk
    $1,750 - $4,540 /mth
 
 
 
 
 

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Villa De Palmas
Siesta Key Villa Rental Picture
  • bedrooms 2
  • community Vista Hermosa
  • rental type Villa
  • owner badgeowner badge
  • sleeps 4
  • baths 2
  • rates (USD) $575 - $900 /wk
 
 
 
 
 

6 reviews write a review

Bay Tree
Siesta Key Condo Rental Picture
  • bedrooms 2
  • community Turtle Beach
  • rental type Condo
  • sleeps 4
  • baths 2
  • rates (USD) $4,000 /mth
 
 
 
 
 

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Heaven on earth (this is a new listing)
Siesta Key Villa Rental Picture
  • bedrooms 2
  • community Gulf Haven
  • rental type Villa
  • sleeps 6
  • baths 2
  • rates (USD) $1,000 - $1,400 /wk
    $3,000 - $4,600 /mth
 
 
 
 
 

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Beachfront Dreamcondo in Paradise:NewUpgrades/Many Amenities
Siesta Key Condo Rental Picture
  • bedrooms 2
  • community Fisherman's Cove
  • rental type Condo
  • owner badgeowner badge
  • sleeps 6
  • baths 2
  • rates (USD) $1,120 - $1,745 /wk
 
 
 
 
 

2 reviews write a review

Condo at Siesta Key Beach
Siesta Key House Rental Picture
  • bedrooms 2
  • community La Siesta Condos
  • rental type House
  • sleeps 4
  • baths 1
  • rates (USD) $755 - $1,110 /wk
 
 
 
 
 

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Great Deals on Siesta Key
Siesta Key Studio Rental Picture
  • bedrooms 0
  • community Crescent Beach
  • rental type Studio
  • owner badgeowner badge
  • sleeps 4
  • baths 1
  • rates (USD) $80 - $135 /nt
    $620 - $1,000 /wk
 
 
 
 
 

12 reviews write a review

Harbor Towers - Gulf and Bay Access
Siesta Key Condo Rental Picture
  • bedrooms 2
  • community
  • rental type Condo
  • owner badgeowner badge
  • sleeps 6
  • baths 2
  • rates (USD) $650 - $1,000 /wk
 
 
 
 
 

2 reviews write a review

Exquisitely Renovated - Harbor Towers Yacht & Racquet Club
Siesta Key Condo Rental Picture
  • bedrooms 2
  • community Harbor Towers
  • rental type Condo
  • sleeps 6
  • baths 2
  • rates (USD) $950 - $1,200 /wk
    $2,500 - $4,800 /mth
 
 
 
 
 

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Casarina
Siesta Key Condo Rental Picture
  • bedrooms 2
  • community
  • rental type Condo
  • sleeps 4
  • baths 2
  • rates (USD) $4,800 - $6,500 /mth
 
 
 
 
 

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2 Bdrm Condo on Beautiful Crescent Beach - Siesta Key, FL
Siesta Key Condo Rental Picture
  • bedrooms 2
  • community Peppertree Bay
  • rental type Condo
  • sleeps 4
  • baths 2
  • rates (USD) $4,200 - $4,500 /mth
 
 
 
 
 

1 reviews write a review

Siesta Key Beach Villa
Siesta Key Condo Rental Picture
  • bedrooms 1
  • community Gulf and Bay Club
  • rental type Condo
  • sleeps 4
  • baths
  • rates (USD) $749 - $1,059 /wk
 
 
 
 
 

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Siesta Key Beach - Gulf Side
Siesta Key Condo Rental Picture
  • bedrooms 2
  • community Crescent Beach
  • rental type Condo
  • owner badgeowner badge
  • sleeps 6
  • baths 2
  • rates (USD) $750 - $1,100 /wk
    $3,000 - $4,400 /mth
 
 
 
 
 

3 reviews write a review

Enjoy Your Siesta!
Siesta Key House Rental Picture
  • bedrooms 2
  • community
  • rental type House
  • sleeps 4
  • baths 1
  • rates (USD) $130 - $170 /nt
    $650 - $900 /wk
    $1,900 - $2,300 /mth
 
 
 
 
 

3 reviews write a review

Siesta Key Escape
Siesta Key House Rental Picture
  • bedrooms 3
  • community Twin Oak Park
  • rental type House
  • owner badgeowner badge
  • sleeps 6
  • baths 3
  • rates (USD) $1,600 - $2,000 /wk
    $4,500 - $5,000 /mth
 
 
 
 
 

11 reviews write a review

Beach Front Condo
Siesta Key Condo Rental Picture
  • bedrooms 2
  • community
  • rental type Condo
  • sleeps 6
  • baths 2
  • rates (USD) $3,500 - $6,000 /mth
 
 
 
 
 

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No Better Location for the Price
Siesta Key Condo Rental Picture
  • bedrooms 1
  • community
  • rental type Condo
  • sleeps 4
  • baths 1
  • rates (USD) $655 - $959 /wk
 
 
 
 
 

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Siesta Key Sunset, Beach/Gulf Front Rentals
Siesta Key Condo Rental Picture
  • bedrooms 2
  • community Fisherman's Cove
  • rental type Condo
  • sleeps 6
  • baths 2
  • rates (USD) $175 - $295 /nt
    $895 - $1,650 /wk
    $3,580 - $6,600 /mth
 
 
 
 
 

1 reviews write a review

Horizons West Gulf Front Full View 1 BR condo
Siesta Key Condo Rental Picture
  • bedrooms 1
  • community Horizons West
  • rental type Condo
  • sleeps 4
  • baths 1
  • rates (USD) $1,430 /wk
 
 
 
 
 

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La Siesta Condos Steps to Siesta Key Beach
Siesta Key Condo Rental Picture
  • bedrooms 2
  • community La Siesta Condos
  • rental type Condo
  • sleeps 5
  • baths 1
  • rates (USD) $740 - $1,310 /wk
 
 
 
 
 

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Gulf and Bay Club 502D Beach Front, 3 Heated Pools, Gym, Spa
Siesta Key Condo Rental Picture
  • bedrooms 2
  • community Gulf & Bay
  • rental type Condo
  • sleeps 6
  • baths 2
  • rates (USD) $563 - $1,750 /wk
    $2,414 - $7,000 /mth
 
 
 
 
 

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Siesta Key Bay Tree 106, 2 bedrooms, 2 heated pools, spa
Siesta Key Condo Rental Picture
  • bedrooms 2
  • community Bay Tree Club
  • rental type Condo
  • owner badgeowner badge
  • sleeps 6
  • baths 2
  • rates (USD) $450 - $1,249 /wk
    $1,930 - $5,185 /mth
 
 
 
 
 

19 reviews write a review

Siesta Key Gulf and Bay 204G Beach Front, 3 pools.
Siesta Key Condo Rental Picture
  • bedrooms 2
  • community Gulf and Bay Club
  • rental type Condo
  • owner badgeowner badge
  • sleeps 6
  • baths 2
  • rates (USD) $564 - $1,750 /wk
    $2,417 - $7,000 /mth
 
 
 
 
 

5 reviews write a review

Excelsior 107, 1st Floor, 2 heated pool, spa, wifi, beach ac
Siesta Key Condo Rental Picture
  • bedrooms 2
  • community Excelsior Beach
  • rental type Condo
  • owner badgeowner badge
  • sleeps 6
  • baths 2
  • rates (USD) $563 - $1,499 /wk
    $2,414 - $6,252 /mth
 
 
 
 
 

8 reviews write a review

Crystal Sand 406, 4th floor, Gulf View, 2 heated Pools
Siesta Key Condo Rental Picture
  • bedrooms 1
  • community Crystal Sands
  • rental type Condo
  • sleeps 4
  • baths 1
  • rates (USD) $450 - $1,249 /wk
    $1,930 - $5,078 /mth
 
 
 
 
 

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Sunset Royale Luxury Condo #208
Siesta Key Condo Rental Picture
  • bedrooms 1
  • community Sunset Royale
  • rental type Condo
  • sleeps 4
  • baths 1
  • rates (USD) $799 - $1,099 /wk
 
 
 
 
 

1 reviews write a review

Fully Updated 2 Bedroom Condo at Tivoli by the Sea
Siesta Key Condo Rental Picture
  • bedrooms 2
  • community Tivoli By The Sea
  • rental type Condo
  • sleeps 4
  • baths 2
  • rates (USD) $1,225 - $2,150 /wk
 
 
 
 
 

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Siesta Beach Luxury Gated Condo
Siesta Key Condo Rental Picture
  • bedrooms 2
  • community Siesta Breakers
  • rental type Condo
  • sleeps 5
  • baths 2
  • rates (USD) $1,288 - $1,911 /wk
 
 
 
 
 

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Luxury at it's Finest ! The Crescent on Siesta Key
Siesta Key Condo Rental Picture
  • bedrooms 3
  • community Crescent
  • rental type Condo
  • sleeps 6
  • baths 2
  • rates (USD) $1,950 - $2,150 /wk
    $9,000 - $9,750 /mth
 
 
 
 
 

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Direct Gulf Front Condo
Siesta Key Condo Rental Picture
  • bedrooms 2
  • community Sea Shell Condos
  • rental type Condo
  • sleeps 6
  • baths 2
  • rates (USD) $995 - $1,695 /wk
 
 
 
 
 

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Siesta Key Getaways
Siesta Key Villa Rental Picture
  • bedrooms 2
  • community Sarasota by the Sea
  • rental type Villa
  • sleeps 4
  • baths 1
  • rates (USD) $700 - $1,200 /wk
 
 
 
 
 

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Siesta Sands Beach Resort
Siesta Key House Rental Picture
  • bedrooms 2
  • community Siesta Sands
  • rental type House
  • sleeps 6
  • baths 2
  • rates (USD) $85 - $400 /nt
    $950 - $2,200 /wk
 
 
 
 
 

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Sheila's Shang-Ra-La
Siesta Key Condo Rental Picture
  • bedrooms 2
  • community Midnight Cove II
  • rental type Condo
  • sleeps 4
  • baths
  • rates (USD) $700 - $1,050 /wk
 
 
 
 
 

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Your Private Tropical Getaway - Walk to the beach!
Siesta Key House Rental Picture
  • bedrooms 3
  • community
  • rental type House
  • owner badgeowner badge
  • sleeps 8
  • baths 2
  • rates (USD) $1,200 - $1,750 /wk
    $3,750 - $5,600 /mth
 
 
 
 
 

2 reviews write a review

Our House at the Beach
Siesta Key Condo Rental Picture
  • bedrooms 2
  • community Our House at Beach
  • rental type Condo
  • sleeps 6
  • baths 2
  • rates (USD) $875 - $1,386 /wk
 
 
 
 
 

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4 BR/3BA Poolhouse is 10 Min Drive to Famous Siesta Key Beach
Siesta Key House Rental Picture
  • bedrooms 4
  • rental type House
  • owner badgeowner badge
  • sleeps 8
  • baths 0
  • rates (USD) $135 - $175 /nt
    $890 /wk
 
 
 
 
 

17 reviews write a review

SIESTA GEM! Ebb Tide Villa 1 POOL/BEACH ACCESS/PATIO
Siesta Key Villa Rental Picture
  • bedrooms 1
  • rental type Villa
  • owner badgeowner badge
  • sleeps 4
  • baths 1
  • rates (USD) $100 - $169 /nt
    $700 - $1,150 /wk
    $2,500 - $4,300 /mth
 
 
 
 
 

20 reviews write a review

Ebb Tide Villa #2 w Patio; Heated Pool; Beach 3 min walk!
Siesta Key Villa Rental Picture
  • bedrooms 1
  • rental type Villa
  • owner badgeowner badge
  • sleeps 4
  • baths 1
  • rates (USD) $100 - $169 /nt
    $700 - $1,150 /wk
    $2,500 - $4,300 /mth
 
 
 
 
 

25 reviews write a review

FALL 2014 DISCOUNT!! Prestigious BEACHFRONT Complex. Updated Condo, 1,640 sq ft
Siesta Key Condo Rental Picture
  • bedrooms 2
  • rental type Condo
  • owner badgeowner badge
  • sleeps 4
  • baths 2
  • rates (USD) $100 - $220 /nt
    $2,800 - $6,380 /mth
 
 
 
 
 

9 reviews write a review

Beautiful Gulf Front Condo-Ocean View-**Rates Reduced**
Siesta Key Condo Rental Picture
  • bedrooms 2
  • rental type Condo
  • owner badgeowner badge
  • sleeps 6
  • baths 2
  • rates (USD) $149 - $364 /nt
    $1,045 - $2,550 /wk
    $6,820 /mth
 
 
 
 
 

22 reviews write a review

Charming Key West style condo with Free US Calls
Siesta Key Condo Rental Picture
  • bedrooms 2
  • rental type Condo
  • owner badgeowner badge
  • sleeps 6
  • baths 2
  • rates (USD) $985 /wk
 
 
 
 
 

8 reviews write a review

BEACHFRONT CONDO COMPLEX - TWO BR - HEATED POOL - LUXURY - Siesta Key
Siesta Key Condo Rental Picture
  • bedrooms 2
  • rental type Condo
  • sleeps 6
  • baths 2
  • rates (USD) $1,115 - $1,795 /wk
 
 
 
 
 

1 reviews write a review

Luxury Beach Condo with Best views and Sunsets on Siesta Key
Siesta Key Condo Rental Picture
  • bedrooms 2
  • rental type Condo
  • owner badgeowner badge
  • sleeps 6
  • baths 3
  • rates (USD) $8,000 - $9,000 /mth
 
 
 
 
 

18 reviews write a review

EBB TIDE VILLA 3 w Patio, Heated Pool, Beach Access 3 min. walk
Siesta Key Villa Rental Picture
  • bedrooms 1
  • rental type Villa
  • owner badgeowner badge
  • sleeps 4
  • baths 1
  • rates (USD) $100 - $169 /nt
    $700 - $1,150 /wk
    $2,500 - $4,300 /mth
 
 
 
 
 

10 reviews write a review

Morgan - Crystal Sands #702 - Completely Renovated 2 Bedroom / 2 Bath
Siesta Key Condo Rental Picture
  • bedrooms 2
  • rental type Condo
  • owner badgeowner badge
  • sleeps 6
  • baths 2
  • rates (USD) $1,750 - $2,600 /wk
    $7,500 - $11,143 /mth
 
 
 
 
 

28 reviews write a review

Gulf & Bay Bayside 3 BR w/ Bay Views
Siesta Key Townhome Rental Picture
  • bedrooms 3
  • rental type Townhome
  • owner badgeowner badge
  • sleeps 6
  • baths 2
  • rates (USD) $1,285 - $1,685 /wk
 
 
 
 
 

23 reviews write a review

Luxury 3 Bedroom Siesta key Pool
Siesta Key Villa Rental Picture
  • bedrooms 3
  • rental type Villa
  • owner badgeowner badge
  • sleeps 7
  • baths 2
  • rates (GBP) £80 - £95 /nt
    £570 - £665 /wk
    £2,250 - £2,660 /mth
 
 
 
 
 

3 reviews write a review

Siesta Beach Beautiful 2 Bed, 2 Bath.
Siesta Key Apartment Rental Picture
  • bedrooms 2
  • rental type Apartment
  • sleeps 4
  • baths 2
  • rates (USD) $85 - $136 /nt
    $595 /wk
    $2,200 - $3,600 /mth
 
 
 
 
 

5 reviews write a review

Crescent Beach - 2 Bedroom - Beachfront Condo Complex - Heated Pool
Siesta Key Condo Rental Picture
  • bedrooms 2
  • rental type Condo
  • sleeps 6
  • baths 2
  • rates (USD) $895 - $1,525 /wk
 
 
 
 
 

6 reviews write a review

Penthouse Condo on a Top Ten Beach
Siesta Key Condo Rental Picture
  • bedrooms 3
  • rental type Condo
  • owner badgeowner badge
  • sleeps 6
  • baths 3
  • rates (USD) $3,600 - $4,350 /wk
 
 
 
 
 

10 reviews write a review

Completely Renovated - 1Br/1Ba - Amazing Beach and Gulf Views from an open Lanai
Siesta Key Condo Rental Picture
  • bedrooms 1
  • rental type Condo
  • sleeps 4
  • baths 1
  • rates (USD) $163 - $305 /nt
    $1,141 - $1,995 /wk
 
 
 
 
 

16 reviews write a review

BEACHWALK - SIESTA KEY BEACH - 3BR TOWNHOUSE - HEATED POOL - Private Elevator
Siesta Key Townhome Rental Picture
  • bedrooms 3
  • rental type Townhome
  • sleeps 8
  • baths
  • rates (USD) $1,195 - $2,045 /wk
 
 
 
 
 

2 reviews write a review

Cute Beach Bungalow, Sept Specials, Patio,WiFi
Siesta Key Villa Rental Picture
  • bedrooms 1
  • rental type Villa
  • owner badgeowner badge
  • sleeps 4
  • baths 1
  • rates (USD) $82 - $136 /nt
    $675 - $950 /wk
    $2,300 - $3,600 /mth
 
 
 
 
 

9 reviews write a review

At the Beach - Where Tomorrow is Just Another Day in Paradise
Siesta Key Apartment Rental Picture
  • bedrooms 2
  • rental type Apartment
  • owner badgeowner badge
  • sleeps 5
  • baths 1
  • rates (USD) $200 - $275 /nt
    $995 - $1,395 /wk
    $3,781 - $5,301 /mth
 
 
 
 
 

11 reviews write a review

At the Beach - Where Tomorrow is Just Another Day in Paradise
Siesta Key Apartment Rental Picture
  • bedrooms 2
  • rental type Apartment
  • owner badgeowner badge
  • sleeps 6
  • baths 2
  • rates (USD) $275 - $350 /nt
    $1,195 - $1,595 /wk
    $4,541 - $6,494 /mth
 
 
 
 
 

18 reviews write a review

Siesta Key Vacation Rental with Dock and Beach Access
Siesta Key Townhome Rental Picture
  • bedrooms 4
  • rental type Townhome
  • sleeps 10
  • baths
  • rates (USD) $1,200 - $2,000 /wk
    $4,000 - $8,320 /mth
 
 
 
 
 

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Beachfront with Panoramic View
Siesta Key Condo Rental Picture
  • bedrooms 2
  • rental type Condo
  • sleeps 6
  • baths 2
  • rates (USD) $260 - $470 /nt
    $1,638 - $2,961 /wk
    $5,850 - $10,590 /mth
 
 
 
 
 

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Siesta Key: Tranquil Bay-Side Beach Condo
Siesta Key Apartment Rental Picture
  • bedrooms 2
  • rental type Apartment
  • sleeps 6
  • baths
  • rates (USD) $89 - $200 /nt
    $499 - $699 /wk
    $1,799 - $3,900 /mth
 
 
 
 
 

1 reviews write a review

Beachwalk - Siesta Key Beach - 3BR Upscale Townhouse - Heated Pool
Siesta Key Townhome Rental Picture
  • bedrooms 3
  • rental type Townhome
  • owner badgeowner badge
  • sleeps 8
  • baths
  • rates (USD) $1,195 - $2,045 /wk
 
 
 
 
 

9 reviews write a review

Crescent Beach - 2-Bedroom - Beachfront Condo Complex
Siesta Key Condo Rental Picture
  • bedrooms 2
  • rental type Condo
  • sleeps 6
  • baths 2
  • rates (USD) $980 - $1,625 /wk
 
 
 
 
 

5 reviews write a review

REMODELED,100 STEPS YOU'RE ON CRESCENT BEACH,RENTING SINCE 1998, SLEEP 6 IN BEDS
Siesta Key Condo Rental Picture
  • bedrooms 2
  • rental type Condo
  • owner badgeowner badge
  • sleeps 6
  • baths 2
  • rates (USD) $150 - $285 /nt
    $1,250 - $1,995 /wk
    $3,800 - $4,400 /mth
 
 
 
 
 

2 reviews write a review

Palm Bay Club #334, Premier Beach to Bay Resort
Siesta Key Condo Rental Picture
  • bedrooms 2
  • rental type Condo
  • owner badgeowner badge
  • sleeps 6
  • baths 2
  • rates (USD) $175 - $325 /nt
    $1,134 - $2,051 /wk
    $4,050 - $7,320 /mth
 
 
 
 
 

14 reviews write a review

BEACHFRONT ONE BEDROOM CONDO AT FISHERMAN'S COVE - Ground Floor
Siesta Key Condo Rental Picture
  • bedrooms 1
  • rental type Condo
  • owner badgeowner badge
  • sleeps 4
  • baths 1
  • rates (USD) $795 - $1,390 /wk
 
 
 
 
 

10 reviews write a review

Beachfront - One Bedroom Condo at Fisherman's Cove - Free Boat Docks
Siesta Key Condo Rental Picture
  • bedrooms 1
  • rental type Condo
  • owner badgeowner badge
  • sleeps 4
  • baths 1
  • rates (USD) $795 - $1,390 /wk
 
 
 
 
 

4 reviews write a review

Luxury Siesta Beach Oceanfront Condo #212 with Beautiful Views
Siesta Key Condo Rental Picture
  • bedrooms 2
  • rental type Condo
  • owner badgeowner badge
  • sleeps 6
  • baths 2
  • rates (USD) $749 - $1,249 /wk
 
 
 
 
 

31 reviews write a review

Deluxe Town home, Heated Pool, In Siesta Village, 2 Min to Crescent Beach
Siesta Key Townhome Rental Picture
  • bedrooms 4
  • rental type Townhome
  • owner badgeowner badge
  • sleeps 12
  • baths
  • rates (USD) $1,755 - $3,020 /wk
 
 
 
 
 

7 reviews write a review

Deluxe 3-Bedroom Town home, Private Pool, Siesta Village-close to Crescent Beach
Siesta Key Townhome Rental Picture
  • bedrooms 3
  • rental type Townhome
  • owner badgeowner badge
  • sleeps 8
  • baths
  • rates (USD) $1,235 - $2,095 /wk
 
 
 
 
 

16 reviews write a review

Deluxe Town home - Garden Apartment, Heated Pool, Right in Siesta Village
Siesta Key Condo Rental Picture
  • bedrooms 1
  • rental type Condo
  • owner badgeowner badge
  • sleeps 4
  • baths 1
  • rates (USD) $520 - $925 /wk
 
 
 
 
 

6 reviews write a review

SIESTA KEY - DIRECT GULF-FRONT CONDO - 2 BEDROOM - HEATED POOL - UPSCALE
Siesta Key Condo Rental Picture
  • bedrooms 2
  • rental type Condo
  • owner badgeowner badge
  • sleeps 6
  • baths 2
  • rates (USD) $955 - $1,665 /wk
 
 
 
 
 

3 reviews write a review

Siesta Key - Beachfront - 2 Bedroom - Upscale- Ground Floor - Free Boat Docks
Siesta Key Condo Rental Picture
  • bedrooms 2
  • rental type Condo
  • sleeps 6
  • baths 2
  • rates (USD) $955 - $1,665 /wk
 
 
 
 
 

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Your Own Beach And Boat Dock!
Siesta Key Condo Rental Picture
  • bedrooms 2
  • rental type Condo
  • owner badgeowner badge
  • sleeps 6
  • baths 2
  • rates (USD) $955 - $1,665 /wk
 
 
 
 
 

4 reviews write a review

Siesta Key - Gulf-Front Retreat - 2 Bedroom - Upscale
Siesta Key Condo Rental Picture
  • bedrooms 2
  • rental type Condo
  • owner badgeowner badge
  • sleeps 6
  • baths 2
  • rates (USD) $955 - $1,665 /wk
 
 
 
 
 

14 reviews write a review

2-Bedroom - Beachfront Condo - Luxury - Directly on Crescent Beach
Siesta Key Condo Rental Picture
  • bedrooms 2
  • rental type Condo
  • owner badgeowner badge
  • sleeps 6
  • baths 2
  • rates (USD) $1,275 - $1,825 /wk
 
 
 
 
 

5 reviews write a review

Beachfront - 3 Bedroom Condo - Upscale - Free Boat Docks - Stunning Views
Siesta Key Condo Rental Picture
  • bedrooms 3
  • rental type Condo
  • owner badgeowner badge
  • sleeps 8
  • baths 2
  • rates (USD) $1,235 - $2,095 /wk
 
 
 
 
 

5 reviews write a review

10% DISCOUNT FOR AUGUST & SEPTEMBER! Classy, Clean & Close to the Beach & a Dock
Siesta Key Condo Rental Picture
  • bedrooms 2
  • rental type Condo
  • owner badgeowner badge
  • sleeps 4
  • baths
  • rates (USD) $795 - $1,200 /wk
 
 
 
 
 

42 reviews write a review

Panoramic Gulf View from Every Room, 2BR/2BA, Wifi, Steps from Beach, 6th Fl
Siesta Key Condo Rental Picture
  • bedrooms 2
  • rental type Condo
  • sleeps 6
  • baths 2
  • rates (USD) $157 - $264 /nt
    $1,100 - $1,850 /wk
    $3,960 - $5,940 /mth
 
 
 
 
 

2 reviews write a review

BEACHFRONT CONDO - THREE BEDROOM - HEATED POOL - FREE BOAT DOCKS - UPSCALE
Siesta Key Condo Rental Picture
  • bedrooms 3
  • rental type Condo
  • owner badgeowner badge
  • sleeps 8
  • baths 2
  • rates (USD) $1,235 - $2,095 /wk
 
 
 
 
 

23 reviews write a review

Beachfront Condo - Three Bedroom - Luxury
Siesta Key Condo Rental Picture
  • bedrooms 3
  • rental type Condo
  • owner badgeowner badge
  • sleeps 8
  • baths 2
  • rates (USD) $1,235 - $2,095 /wk
 
 
 
 
 

18 reviews write a review

Beautiful Beachfront Unit at the Crescent
Siesta Key Condo Rental Picture
  • bedrooms 3
  • rental type Condo
  • owner badgeowner badge
  • sleeps 6
  • baths 3
  • rates (USD) $3,267 - $5,000 /wk
    $12,000 - $14,467 /mth
 
 
 
 
 

4 reviews write a review

Walk to Crescent & Siesta Beach!
Siesta Key House Rental Picture
  • bedrooms 2
  • rental type House
  • owner badgeowner badge
  • sleeps 6
  • baths 2
  • rates (USD) $179 - $289 /nt
    $1,250 - $2,025 /wk
    $3,200 - $5,400 /mth
 
 
 
 
 

35 reviews write a review

Spectacular Fall Rates!! Walk to Crescent & Siesta Beach!
Siesta Key Apartment Rental Picture
  • bedrooms 1
  • rental type Apartment
  • owner badgeowner badge
  • sleeps 4
  • baths 1
  • rates (USD) $119 - $166 /nt
    $840 - $1,165 /wk
    $2,000 - $3,500 /mth
 
 
 
 
 

26 reviews write a review

Siesta Beach Apartment
Siesta Key Apartment Rental Picture
  • bedrooms 2
  • rental type Apartment
  • sleeps 5
  • baths 1
  • rates (USD) $200 /nt
    $1,200 /wk
    $4,800 /mth
 
 
 
 
 

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Large Private Home On Water With Pool/Spa On #1Beach In Us! - Siesta Key
Siesta Key House Rental Picture
  • bedrooms 5
  • rental type House
  • sleeps 10
  • baths
  • rates (USD) $2,800 - $4,500 /wk
    $9,000 - $14,000 /mth
 
 
 
 
 

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Morgan - Palm Bay Club #151 Club Suite Gulf Side-Renovated 2 Bedroom / 2 Bath
Siesta Key Condo Rental Picture
  • bedrooms 2
  • rental type Condo
  • sleeps 6
  • baths 2
  • rates (USD) $180 - $225 /nt
    $1,260 - $1,995 /wk
    $5,400 - $8,550 /mth
 
 
 
 
 

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Overlooking Beach on Siesta Key
Siesta Key Apartment Rental Picture
  • bedrooms 1
  • rental type Apartment
  • owner badgeowner badge
  • sleeps 4
  • baths 0
  • rates (USD) $125 - $225 /nt
    $1,575 /wk
 
 
 
 
 

31 reviews write a review

Morgan - Crystal Sands #901 - Completely Renovated 2 Bed / 2 Bath
Siesta Key Condo Rental Picture
  • bedrooms 2
  • rental type Condo
  • sleeps 6
  • baths 2
  • rates (USD) $1,750 - $2,600 /wk
    $7,500 - $11,143 /mth
 
 
 
 
 

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Morgan - Crystal Sands #607 - Completely Renovated 2 Bedroom / 2 Bath
Siesta Key Condo Rental Picture
  • bedrooms 2
  • rental type Condo
  • owner badgeowner badge
  • sleeps 6
  • baths 2
  • rates (USD) $1,750 - $2,600 /wk
    $7,500 - $11,143 /mth
 
 
 
 
 

8 reviews write a review

Morgan - Crystal Sands #1107 - Completely Renovated 2 Bed / 2 Bath
Siesta Key Condo Rental Picture
  • bedrooms 2
  • rental type Condo
  • owner badgeowner badge
  • sleeps 6
  • baths 2
  • rates (USD) $1,750 - $2,600 /wk
    $7,500 - $11,143 /mth
 
 
 
 
 

8 reviews write a review

Morgan - Palm Bay Club #84 Tower - Completely Renovated 1 Bedroom / 1 Bath
Siesta Key Condo Rental Picture
  • bedrooms 1
  • rental type Condo
  • owner badgeowner badge
  • sleeps 4
  • baths 1
  • rates (USD) $200 - $257 /nt
    $1,400 - $2,100 /wk
    $6,000 - $9,000 /mth
 
 
 
 
 

20 reviews write a review

Morgan - Crystal Sands #V4 - Updated 2 Bedroom / 2 Bath with Garage
Siesta Key Villa Rental Picture
  • bedrooms 2
  • rental type Villa
  • owner badgeowner badge
  • sleeps 6
  • baths 2
  • rates (USD) $975 - $1,600 /wk
    $4,179 - $6,857 /mth
 
 
 
 
 

8 reviews write a review

Beautiful newly renovated Sarasota rental home minutes to Siesta Key beach
Siesta Key House Rental Picture
  • bedrooms 4
  • rental type House
  • sleeps 8
  • baths
  • rates (USD) $179 - $236 /nt
    $4,650 - $4,950 /mth
 
 
 
 
 

4 reviews write a review

Best Prices at Siesta Key Comfort
Siesta Key Condo Rental Picture
  • bedrooms 1
  • rental type Condo
  • sleeps 4
  • baths 1
  • rates (USD) $450 - $725 /wk
 
 
 
 
 

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Direct Beach Front 3BR 2 BA Villa Near Siesta Key Village
Siesta Key House Rental Picture
  • bedrooms 3
  • rental type House
  • owner badgeowner badge
  • sleeps 8
  • baths 2
  • rates (USD) $2,000 - $3,950 /wk
    $12,000 - $14,000 /mth
 
 
 
 
 

22 reviews write a review

Morgan - Crystal Sands #107 - Renovated 2 Bedroom / 2 Bath
Siesta Key Condo Rental Picture
  • bedrooms 2
  • rental type Condo
  • owner badgeowner badge
  • sleeps 6
  • baths 2
  • rates (USD) $1,750 - $2,600 /wk
    $7,500 - $11,143 /mth
 
 
 
 
 

47 reviews write a review

Next to the Beach & 1 Block to the Village
Siesta Key Villa Rental Picture
  • bedrooms 3
  • rental type Villa
  • owner badgeowner badge
  • sleeps 10
  • baths
  • rates (USD) $189 - $291 /nt
    $1,325 - $2,035 /wk
    $4,100 - $6,920 /mth
 
 
 
 
 

29 reviews write a review

Crystal Sands Villa #7- Crescent Beach- Summer Rates thru 2014!
Siesta Key Condo Rental Picture
  • bedrooms 2
  • rental type Condo
  • owner badgeowner badge
  • sleeps 6
  • baths 2
  • rates (USD) $130 - $180 /nt
    $910 - $1,260 /wk
    $3,900 - $5,400 /mth
 
 
 
 
 

15 reviews write a review

Waterfront Canal~Walk to Beach & Siesta Village/Pool/Jacuzzi
Siesta Key House Rental Picture
  • bedrooms 3
  • rental type House
  • owner badgeowner badge
  • sleeps 6
  • baths 2
  • rates (USD) $1,900 - $2,100 /wk
    $5,200 - $5,900 /mth
 
 
 
 
 

13 reviews write a review

Romantic Siesta Beach Oceanfront Condo 304 Beautiful Views
Siesta Key Condo Rental Picture
  • bedrooms 1
  • rental type Condo
  • owner badgeowner badge
  • sleeps 4
  • baths 1
  • rates (USD) $629 - $1,029 /wk
 
 
 
 
 

20 reviews write a review

Beachfront Penthouse - Expansive Gulf View! 2 BR/BA, WiFi, Clean, Updated
Siesta Key Condo Rental Picture
  • bedrooms 2
  • rental type Condo
  • owner badgeowner badge
  • sleeps 6
  • baths 2
  • rates (USD) $157 - $264 /nt
    $1,100 - $1,850 /wk
    $3,900 - $5,950 /mth
 
 
 
 
 

23 reviews write a review

Beach Front Condo On Siesta Key #1 Beach In The Usa, With Gulf Views
Siesta Key Condo Rental Picture
  • bedrooms 2
  • rental type Condo
  • owner badgeowner badge
  • sleeps 6
  • baths 2
  • rates (USD) $1,350 - $2,148 /wk
 
 
 
 
 

19 reviews write a review

Simply Stunning Views!!! Beautiful Custom Home, 3 Bedrooms, 3 Baths and Pool
Siesta Key House Rental Picture
  • bedrooms 3
  • rental type House
  • sleeps 6
  • baths 3
  • rates (USD) $2,500 - $3,500 /wk
    $15,000 /mth
 
 
 
 
 

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Cozy Cottage with perfect location, close to beach, two blocks to Siesta Vill
Siesta Key Cottage Rental Picture
  • bedrooms 1
  • rental type Cottage
  • sleeps 4
  • baths 1
  • rates (USD) $93 - $158 /nt
    $635 - $1,575 /wk
    $1,660 - $6,755 /mth
 
 
 
 
 

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Beautiful Ground Floor Bay View Condo!!
Siesta Key Condo Rental Picture
  • bedrooms 2
  • rental type Condo
  • sleeps 4
  • baths 1
  • rates (USD) $2,883 - $3,534 /mth
 
 
 
 
 

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Beach Road Penthouse with Gulf Views
Siesta Key Condo Rental Picture
  • bedrooms 3
  • rental type Condo
  • sleeps 8
  • baths 2
  • rates (USD) $228 - $368 /nt
    $1,585 - $3,675 /wk
    $6,780 - $15,750 /mth
 
 
 
 
 

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Gulf View Penthouse
Siesta Key Condo Rental Picture
  • bedrooms 3
  • rental type Condo
  • owner badgeowner badge
  • sleeps 6
  • baths
  • rates (USD) $2,310 - $3,310 /wk
    $8,400 - $14,185 /mth
 
 
 
 
 

3 reviews write a review

Elegant Two Story Townhouse - Three Bedroom, Close to the Beach and Siesta Vi
Siesta Key Townhome Rental Picture
  • bedrooms 3
  • rental type Townhome
  • owner badgeowner badge
  • sleeps 5
  • baths
  • rates (USD) $1,680 - $2,760 /wk
    $5,985 - $11,820 /mth
 
 
 
 
 

10 reviews write a review

Morgan - Crystal Sands #1106 - Completely Renovated 2 Bed / 2 Bath
Siesta Key Condo Rental Picture
  • bedrooms 2
  • rental type Condo
  • owner badgeowner badge
  • sleeps 6
  • baths 2
  • rates (USD) $1,750 - $2,600 /wk
    $7,500 - $11,143 /mth
 
 
 
 
 

3 reviews write a review

Spacious Siesta Key Canal Front Vacation Rental Home
Siesta Key House Rental Picture
  • bedrooms 4
  • rental type House
  • sleeps 10
  • baths 3
  • rates (USD) $1,500 - $2,250 /wk
    $3,500 - $8,000 /mth
 
 
 
 
 

2 reviews write a review

Steps from Beach with Gulf Views
Siesta Key Condo Rental Picture
  • bedrooms 1
  • rental type Condo
  • sleeps 4
  • baths 1
  • rates (USD)
 
 
 
 
 

1 reviews write a review

Click & play our HD Virtual Video of this 3 bedroom vacation rental!
Siesta Key Condo Rental Picture
  • bedrooms 3
  • rental type Condo
  • owner badgeowner badge
  • sleeps 8
  • baths
  • rates (USD) $1,190 - $1,517 /wk
 
 
 
 
 

25 reviews write a review

Cortez Beach Cottage Siesta Key Village
Siesta Key Cottage Rental Picture
  • bedrooms 3
  • rental type Cottage
  • owner badgeowner badge
  • sleeps 6
  • baths 2
  • rates (USD) $190 - $200 /nt
    $1,000 - $1,400 /wk
 
 
 
 
 

8 reviews write a review

Beach View, Renovated Ground Floor 2 BR/2 Bath Corner Unit/ Sleeps 6+
Siesta Key Condo Rental Picture
  • bedrooms 2
  • rental type Condo
  • owner badgeowner badge
  • sleeps 8
  • baths 2
  • rates (USD) $930 - $1,410 /wk
 
 
 
 
 

7 reviews write a review

Fr $ 430/wk nr. Siesta Key WIFI, gym, pool, king bed
Siesta Key Condo Rental Picture
  • bedrooms 2
  • rental type Condo
  • owner badgeowner badge
  • sleeps 6
  • baths 2
  • rates (USD) $70 - $150 /nt
    $430 - $997 /wk
    $1,622 - $3,382 /mth
 
 
 
 
 

4 reviews write a review

3 Bedroom, Luxury Penthouse Flat Located Right On Siesta Key Beach.
Siesta Key Condo Rental Picture
  • bedrooms 3
  • rental type Condo
  • sleeps 6
  • baths 2
  • rates (USD) $3,100 /wk
    $9,000 /mth
 
 
 
 
 

5 reviews write a review

Intercoastal Condo with View - Close to Big Beach
Siesta Key Condo Rental Picture
  • bedrooms 2
  • rental type Condo
  • owner badgeowner badge
  • sleeps 6
  • baths 2
  • rates (USD)
 
 
 
 
 

7 reviews write a review

Siesta Beach Hideaway
Siesta Key House Rental Picture
  • bedrooms 4
  • rental type House
  • owner badgeowner badge
  • sleeps 14
  • baths 3
  • rates (USD) $1,995 - $2,443 /wk
 
 
 
 
 

25 reviews write a review

Beach Chic 3 Bdrm Apartment - Remodeled 2014!
Siesta Key Apartment Rental Picture
  • bedrooms 3
  • rental type Apartment
  • sleeps 8
  • baths 2
  • rates (USD) $175 - $290 /nt
    $1,225 - $2,000 /wk
    $4,600 - $8,000 /mth
 
 
 
 
 

2 reviews write a review

2 Bdrm Contemporary/Modern Apartment
Siesta Key Apartment Rental Picture
  • bedrooms 2
  • rental type Apartment
  • owner badgeowner badge
  • sleeps 5
  • baths 1
  • rates (USD) $130 - $225 /nt
    $775 - $1,450 /wk
    $2,800 - $5,000 /mth
 
 
 
 
 

12 reviews write a review

El Presidente Renovated Beachfront Condo on White Sand Beach- REDUCED RATES
Siesta Key Condo Rental Picture
  • bedrooms 2
  • rental type Condo
  • owner badgeowner badge
  • sleeps 6
  • baths 2
  • rates (USD) $1,150 - $1,938 /wk
 
 
 
 
 

16 reviews write a review

Tropical Pool Home Just Off World Famous Siesta Key
Siesta Key House Rental Picture
  • bedrooms 2
  • rental type House
  • sleeps 4
  • baths 2
  • rates (USD) $215 - $295 /nt
    $1,225 - $1,550 /wk
    $2,800 - $3,800 /mth
 
 
 
 
 

3 reviews write a review

...Just steps to the beach & 3 blocks to Village!
Siesta Key Condo Rental Picture
  • bedrooms 1
  • rental type Condo
  • owner badgeowner badge
  • sleeps 6
  • baths 1
  • rates (USD) $179 - $235 /nt
    $1,075 - $1,650 /wk
 
 
 
 
 

16 reviews write a review

Siesta Key Luxurious Beachfront Condo: Openings mid-August thru Fall
Siesta Key Condo Rental Picture
  • bedrooms 2
  • rental type Condo
  • sleeps 6
  • baths 2
  • rates (USD) $1,320 - $1,898 /wk
 
 
 
 
 

1 reviews write a review

$ 49/Day $330/wk $ 1,250/Mo Nr Siesta 1BR Condo/Pool/Wifi/C.C
Siesta Key Condo Rental Picture
  • bedrooms 1
  • rental type Condo
  • owner badgeowner badge
  • sleeps 4
  • baths 1
  • rates (USD) $49 - $150 /nt
    $330 - $980 /wk
    $1,250 - $2,997 /mth
 
 
 
 
 

31 reviews write a review

El Presidente, Beautifully Remodeled, Best Beach Location, *Great Special Rates*
Siesta Key Condo Rental Picture
  • bedrooms 2
  • rental type Condo
  • owner badgeowner badge
  • sleeps 6
  • baths 2
  • rates (USD) $1,150 - $1,838 /wk
 
 
 
 
 

59 reviews write a review

Luxury Home, Beauty In The Heart Of Siesta Key!!
Siesta Key House Rental Picture
  • bedrooms 3
  • rental type House
  • owner badgeowner badge
  • sleeps 6
  • baths
  • rates (USD) $2,800 - $4,800 /wk
    $12,000 - $20,575 /mth
 
 
 
 
 

5 reviews write a review

Awesome Views - Beachfront - Tennis/Pool - New Luxury Renovation- Weekly Rental
Siesta Key Condo Rental Picture
  • bedrooms 2
  • rental type Condo
  • owner badgeowner badge
  • sleeps 6
  • baths 2
  • rates (USD) $1,288 - $1,624 /wk
 
 
 
 
 

2 reviews write a review

BEACHFRONT CONDO - THREE BR - HEATED POOL - LUXURY - Siesta Key
Siesta Key Condo Rental Picture
  • bedrooms 3
  • rental type Condo
  • sleeps 8
  • baths 2
  • rates (USD) $1,745 - $2,345 /wk
 
 
 
 
 

1 reviews write a review

Luxury Elegance, 4 BR/4.5 BA, Home, Pool, Spa, Close to Beach
Siesta Key House Rental Picture
  • bedrooms 4
  • rental type House
  • owner badgeowner badge
  • sleeps 9
  • baths
  • rates (USD) $3,150 - $4,300 /wk
    $15,000 /mth
 
 
 
 
 

6 reviews write a review

New 6 Bedroom, Luxury Home In Gated Community
Siesta Key House Rental Picture
  • bedrooms 6
  • rental type House
  • sleeps 14
  • baths
  • rates (USD) $4,200 - $5,320 /wk
    $15,000 - $18,000 /mth
 
 
 
 
 

1 reviews write a review

New, Large, Private Home, Pool/ Spa, Short Walk Beach/ Village
Siesta Key House Rental Picture
  • bedrooms 5
  • rental type House
  • owner badgeowner badge
  • sleeps 12
  • baths
  • rates (USD) $3,150 - $4,300 /wk
    $12,000 - $15,000 /mth
 
 
 
 
 

5 reviews write a review

NEW PRIVATE Luxuary 4 Br 4 1/2 Bath Pool Spa short walk beach/village
Siesta Key House Rental Picture
  • bedrooms 4
  • rental type House
  • owner badgeowner badge
  • sleeps 10
  • baths
  • rates (USD) $3,150 - $4,300 /wk
    $15,000 /mth
 
 
 
 
 

6 reviews write a review

Best Two Bedroom Condo In The Building Directly On The Beach
Siesta Key Condo Rental Picture
  • bedrooms 2
  • rental type Condo
  • sleeps 6
  • baths 2
  • rates (USD) $1,350 - $2,048 /wk
 
 
 
 
 

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Beautifully Decorated First Floor 2br Condo Directly Across Siesta Key Beach!
Siesta Key Condo Rental Picture
  • bedrooms 2
  • rental type Condo
  • sleeps 4
  • baths 2
  • rates (USD) $983 /wk
 
 
 
 
 

1 reviews write a review

PARADISE AWAITS! 2BD/2BA LATE SUMMER-FALL SPECIAL
Siesta Key Condo Rental Picture
  • bedrooms 2
  • rental type Condo
  • owner badgeowner badge
  • sleeps 6
  • baths 2
  • rates (USD) $150 - $200 /nt
    $1,400 /wk
 
 
 
 
 

19 reviews write a review

Luxury Condo Ground Floor Across the Street from the #1 Beach
Siesta Key Condo Rental Picture
  • bedrooms 2
  • rental type Condo
  • owner badgeowner badge
  • sleeps 6
  • baths 2
  • rates (USD) $135 - $205 /nt
    $790 - $1,220 /wk
    $2,600 - $4,392 /mth
 
 
 
 
 

9 reviews write a review

Morgan - Crystal Sands #608 - Completely Renovated 2 Bed / 2 Bath
Siesta Key Condo Rental Picture
  • bedrooms 2
  • rental type Condo
  • owner badgeowner badge
  • sleeps 6
  • baths 2
  • rates (USD) $1,750 - $2,600 /wk
    $7,500 - $11,143 /mth
 
 
 
 
 

7 reviews write a review

Morgan - Crystal Sands #V6 - Completely Renovated 3 Bed / 2 Bath w/ Garage
Siesta Key Villa Rental Picture
  • bedrooms 3
  • rental type Villa
  • owner badgeowner badge
  • sleeps 6
  • baths 2
  • rates (USD) $1,400 - $2,400 /wk
    $6,000 - $10,286 /mth
 
 
 
 
 

7 reviews write a review

Morgan - Crystal Sands #V22 - Completely Renovated 2 Bed / 2 Bath w/ Garage
Siesta Key Villa Rental Picture
  • bedrooms 2
  • rental type Villa
  • owner badgeowner badge
  • sleeps 6
  • baths 2
  • rates (USD) $975 - $1,600 /wk
    $4,179 - $6,857 /mth
 
 
 
 
 

6 reviews write a review

Morgan - Crystal Sands #1111- THE NEWEST renovated condo at Crystal Sands !
Siesta Key Condo Rental Picture
  • bedrooms 2
  • rental type Condo
  • sleeps 6
  • baths 2
  • rates (USD) $1,750 - $2,600 /wk
    $7,500 - $11,143 /mth
 
 
 
 
 

1 reviews write a review

Morgan - Crystal Sands #504 - Completely Renovated 2 Bedroom / 2 Bath
Siesta Key Condo Rental Picture
  • bedrooms 2
  • rental type Condo
  • owner badgeowner badge
  • sleeps 6
  • baths 2
  • rates (USD) $1,750 - $2,600 /wk
    $7,500 - $11,143 /mth
 
 
 
 
 

39 reviews write a review

Morgan - Crystal Sands #206 - Completely Renovated 2 Bedroom / 2 Bath
Siesta Key Condo Rental Picture
  • bedrooms 2
  • rental type Condo
  • owner badgeowner badge
  • sleeps 6
  • baths 2
  • rates (USD) $1,750 - $2,600 /wk
    $7,500 - $11,143 /mth
 
 
 
 
 

22 reviews write a review

!Stunning Boutique Duplex & Best Location! 200 feet to Village 2 Blocks to Beach
Siesta Key Townhome Rental Picture
  • bedrooms 2
  • rental type Townhome
  • owner badgeowner badge
  • sleeps 6
  • baths
  • rates (USD) $193 - $357 /nt
    $1,350 - $2,500 /wk
    $4,500 - $8,000 /mth
 
 
 
 
 

16 reviews write a review

Siesta Key - Beachfront Condo - 2BR - Upscale - Free Boat Docks
Siesta Key Condo Rental Picture
  • bedrooms 2
  • rental type Condo
  • sleeps 6
  • baths 2
  • rates (USD) $955 - $1,665 /wk
 
 
 
 
 

1 reviews write a review

Beautiful Condo With 2 Master Suites
Siesta Key Condo Rental Picture
  • bedrooms 2
  • rental type Condo
  • owner badgeowner badge
  • sleeps 6
  • baths 2
  • rates (USD) $560 - $840 /wk
    $2,400 - $3,600 /mth
 
 
 
 
 

8 reviews write a review

Luxury Waterfront Villa on the Door Step to the Beach
Siesta Key Villa Rental Picture
  • bedrooms 3
  • rental type Villa
  • owner badgeowner badge
  • sleeps 9
  • baths 2
  • rates (GBP) £112 /nt
    £785 /wk
    £3,000 /mth
 
 
 
 
 

2 reviews write a review

Siesta Key Beach House - Pet Friendly! STEPS TO THE BEACH!!
Siesta Key House Rental Picture
  • bedrooms 2
  • rental type House
  • owner badgeowner badge
  • sleeps 6
  • baths 2
  • rates (USD) $145 - $175 /nt
    $1,155 /wk
    $4,293 - $4,753 /mth
 
 
 
 
 

16 reviews write a review

BEAUTIFUL GULF-FRONT ! COME TO PARADISE!
Siesta Key Condo Rental Picture
  • bedrooms 2
  • rental type Condo
  • owner badgeowner badge
  • sleeps 4
  • baths 2
  • rates (USD) $186 - $257 /nt
    $5,200 - $7,200 /mth
 
 
 
 
 

91 reviews write a review

Siesta Villa 2, Perfect Beach Vacation Villa, 5 Min. Walk To Beach, Great Value
Siesta Key Villa Rental Picture
  • bedrooms 2
  • rental type Villa
  • sleeps 5
  • baths 1
  • rates (USD) $110 - $143 /nt
    $2,030 - $4,281 /mth
 
 
 
 
 

4 reviews write a review

Siesta Key Vacation Condo
Siesta Key Condo Rental Picture
  • bedrooms 2
  • rental type Condo
  • owner badgeowner badge
  • sleeps 6
  • baths 2
  • rates (USD) $1,150 /wk
 
 
 
 
 

3 reviews write a review

Mediterrean Style Pool Home Near #1 Siesta Key Beach -3 Bdrm 3 Bath
Siesta Key House Rental Picture
  • bedrooms 3
  • rental type House
  • owner badgeowner badge
  • sleeps 8
  • baths 3
  • rates (USD) $214 - $343 /nt
    $1,500 - $2,400 /wk
    $6,800 /mth
 
 
 
 
 

6 reviews write a review

Pet Friendly............ Bike To Siesta Key Beaches
Siesta Key Condo Rental Picture
  • bedrooms 1
  • rental type Condo
  • sleeps 3
  • baths 1
  • rates (USD) $57 - $100 /nt
    $1,400 - $2,800 /mth
 
 
 
 
 

2 reviews write a review

completely remodeled condo/on beach 1st floor
Siesta Key Condo Rental Picture
  • bedrooms 2
  • rental type Condo
  • sleeps 6
  • baths 2
  • rates (USD) $1,200 /wk
 
 
 
 
 

7 reviews write a review

Siesta Key Year Round 3 Bedroom Getaway
Siesta Key Condo Rental Picture
  • bedrooms 3
  • rental type Condo
  • sleeps 6
  • baths
  • rates (USD) $1,225 /wk
 
 
 
 
 

1 reviews write a review

Newly renovated condominum. Must see on beautiful Siesta Key Beach
Siesta Key Condo Rental Picture
  • bedrooms 2
  • rental type Condo
  • sleeps 6
  • baths 2
  • rates (USD) $750 - $1,300 /wk
    $3,000 - $4,900 /mth
 
 
 
 
 

6 reviews write a review

5 Bedroom Brand New Siesta Key Beach Penthouse
Siesta Key Condo Rental Picture
  • bedrooms 5
  • rental type Condo
  • owner badgeowner badge
  • sleeps 10
  • baths
  • rates (USD) $3,500 /wk
 
 
 
 
 

9 reviews write a review

Unique, Lovely Retreat with Private Pool Near Siesta Key
Siesta Key House Rental Picture
  • bedrooms 2
  • rental type House
  • owner badgeowner badge
  • sleeps 4
  • baths 2
  • rates (USD) $650 - $800 /wk
    $2,600 - $3,200 /mth
 
 
 
 
 

15 reviews write a review

Resort across from Crescent Beach! All NEW!
Siesta Key Townhome Rental Picture
  • bedrooms 2
  • rental type Townhome
  • owner badgeowner badge
  • sleeps 6
  • baths 2
  • rates (USD) $1,000 - $1,385 /wk
 
 
 
 
 

18 reviews write a review

BEACHFRONT CONDO WITH BREATHTAKING VIEWS
Siesta Key Condo Rental Picture
  • bedrooms 2
  • rental type Condo
  • sleeps 6
  • baths 2
  • rates (USD) $1,772 - $2,718 /wk
 
 
 
 
 

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EL PRESIDENTE IS ON THE BEACH, 1800 SQ.FT UPDATED CONDO ON USA # 1 BEACH
Siesta Key Condo Rental Picture
  • bedrooms 2
  • rental type Condo
  • owner badgeowner badge
  • sleeps 6
  • baths 2
  • rates (USD) $1,400 - $2,074 /wk
    $8,296 /mth
 
 
 
 
 

14 reviews write a review

Siesta Key Luxury Condo Across the Street from the Beaches
Siesta Key Condo Rental Picture
  • bedrooms 2
  • rental type Condo
  • owner badgeowner badge
  • sleeps 6
  • baths 1
  • rates (USD) $115 - $180 /nt
    $685 - $1,058 /wk
    $2,000 - $3,889 /mth
 
 
 
 
 

12 reviews write a review

Luxury Beach Front Condo in Siesta Key with Beach Cabana
Siesta Key Condo Rental Picture
  • bedrooms 2
  • rental type Condo
  • owner badgeowner badge
  • sleeps 6
  • baths 2
  • rates (USD) $136 - $279 /nt
    $1,950 /wk
    $3,500 - $6,000 /mth
 
 
 
 
 

6 reviews write a review

Beautiful Bay View! Beautiful Condo! Perfect Resort Setting W/ Beach Access!
Siesta Key Condo Rental Picture
  • bedrooms 2
  • rental type Condo
  • sleeps 6
  • baths 2
  • rates (USD) $3,200 - $6,200 /mth
 
 
 
 
 

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Pool Home Overlooking Siesta Beach
Siesta Key House Rental Picture
  • bedrooms 3
  • rental type House
  • owner badgeowner badge
  • sleeps 11
  • baths 2
  • rates (USD) $450 - $525 /nt
    $3,675 /wk
 
 
 
 
 

6 reviews write a review

3 Bedroom Pool Home On The Canal And Walking Distance Of Beach And Village
Siesta Key House Rental Picture
  • bedrooms 3
  • rental type House
  • sleeps 6
  • baths 3
  • rates (USD) $2,000 - $2,400 /wk
    $4,300 - $5,800 /mth
 
 
 
 
 

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Luxury Siesta Key Private Canal Home
Siesta Key House Rental Picture
  • bedrooms 3
  • rental type House
  • owner badgeowner badge
  • sleeps 6
  • baths 2
  • rates (USD) $910 - $1,800 /wk
    $3,900 - $5,800 /mth
 
 
 
 
 

7 reviews write a review

Beautifully Remodeled Midnight Cove II Condo w/Free Boat Dock
Siesta Key Condo Rental Picture
  • bedrooms 2
  • rental type Condo
  • owner badgeowner badge
  • sleeps 6
  • baths
  • rates (USD) $750 - $1,130 /wk
 
 
 
 
 

2 reviews write a review

Beautiful VILLA 2 - Upscale Decor - Private and Quiet
Siesta Key Villa Rental Picture
  • bedrooms 2
  • rental type Villa
  • owner badgeowner badge
  • sleeps 6
  • baths 2
  • rates (USD) $945 - $1,550 /wk
 
 
 
 
 

21 reviews write a review

Sunny Siesta Key- Vacation Destination
Siesta Key Condo Rental Picture
  • bedrooms 1
  • rental type Condo
  • sleeps 4
  • baths 2
  • rates (USD) $850 - $1,150 /wk
    $2,500 - $2,700 /mth
 
 
 
 
 

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Remodeled Condo - Resort is on #1 Beach in the USA
Siesta Key Condo Rental Picture
  • bedrooms 1
  • rental type Condo
  • owner badgeowner badge
  • sleeps 4
  • baths 1
  • rates (USD) $119 - $164 /nt
    $850 - $1,150 /wk
    $3,125 - $4,140 /mth
 
 
 
 
 

6 reviews write a review

Gorgeous Cottage Steps From Beach - OUR CALENDAR IS UP TO DATE!!!
Siesta Key Cottage Rental Picture
  • bedrooms 2
  • rental type Cottage
  • sleeps 6
  • baths 2
  • rates (USD) $200 - $300 /nt
    $1,300 - $2,000 /wk
    $3,500 - $5,500 /mth
 
 
 
 
 

6 reviews write a review

Great Spacious 3 Bedroom Unit, Bayside at the Beautiful Gulf
Siesta Key Condo Rental Picture
  • bedrooms 3
  • rental type Condo
  • sleeps 7
  • baths 2
  • rates (USD) $1,050 - $1,450 /wk
 
 
 
 
 

1 reviews write a review

Luxury 2 BR/2 BA- 1st Fl Wifi/HDTV - Hurry book your Fall Vacation!
Siesta Key Condo Rental Picture
  • bedrooms 2
  • rental type Condo
  • owner badgeowner badge
  • sleeps 5
  • baths 2
  • rates (USD) $635 - $1,097 /wk
 
 
 
 
 

26 reviews write a review

Siesta Key Gulf And Bay
Siesta Key Townhome Rental Picture
  • bedrooms 2
  • rental type Townhome
  • sleeps 4
  • baths 2
  • rates (USD) $800 - $1,300 /wk
    $4,000 /mth
 
 
 
 
 

1 reviews write a review

Fabulous Crescent Beach Condo on Siesta Key
Siesta Key Condo Rental Picture
  • bedrooms 3
  • rental type Condo
  • owner badgeowner badge
  • sleeps 6
  • baths 2
  • rates (USD) $285 - $414 /nt
    $1,995 - $2,900 /wk
    $9,900 /mth
 
 
 
 
 

24 reviews write a review

Newly Updated - 2 Bed/2 Bath - Amazing Beach And Gulf Views From 9th Floor Tower
Siesta Key Condo Rental Picture
  • bedrooms 2
  • rental type Condo
  • sleeps 6
  • baths 2
  • rates (USD) $234 - $423 /nt
    $1,638 - $2,961 /wk
 
 
 
 
 

8 reviews write a review

SIESTA KEY BEACH! Only A Hop, Skip & Jump away! SALE JULY & AUGUST $1200 TOTAL!
Siesta Key House Rental Picture
  • bedrooms 2
  • rental type House
  • sleeps 4
  • baths
  • rates (USD) $750 - $1,500 /wk
    $2,200 - $4,500 /mth
 
 
 
 
 

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Siesta Key - Siesta Dunes Resort - Gulf Front Beautiful 2 BR Condo
Siesta Key Condo Rental Picture
  • bedrooms 2
  • rental type Condo
  • owner badgeowner badge
  • sleeps 4
  • baths 2
  • rates (USD) $1,370 - $1,876 /wk
 
 
 
 
 

7 reviews write a review

Minutes To Fabulous Siesta Key Beach and Your Dream Vacation
Siesta Key Apartment Rental Picture
  • bedrooms 1
  • rental type Apartment
  • owner badgeowner badge
  • sleeps 4
  • baths 1
  • rates (USD) $71 /nt
    $1,700 /mth
 
 
 
 
 

7 reviews write a review

Upscale 4 Bed Private Heated Pool Home-Near Siesta Key Beach.
Siesta Key Villa Rental Picture
  • bedrooms 4
  • rental type Villa
  • owner badgeowner badge
  • sleeps 9
  • baths 2
  • rates (USD) $171 - $207 /nt
    $1,200 - $1,450 /wk
    $4,700 /mth
 
 
 
 
 

25 reviews write a review

On World Famous Cresent Beach
Siesta Key Condo Rental Picture
  • bedrooms 2
  • rental type Condo
  • owner badgeowner badge
  • sleeps 6
  • baths 2
  • rates (USD)
 
 
 
 
 

4 reviews write a review

Beautifully Renovated Gulf Side 1 BR Condo on Crescent Beach
Siesta Key Condo Rental Picture
  • bedrooms 1
  • rental type Condo
  • owner badgeowner badge
  • sleeps 4
  • baths 1
  • rates (USD) $800 - $1,250 /wk
    $2,200 - $3,800 /mth
 
 
 
 
 

39 reviews write a review

Modern beachfront condo/full views of Siesta key Beach!
Siesta Key Condo Rental Picture
  • bedrooms 2
  • rental type Condo
  • sleeps 6
  • baths 2
  • rates (USD) $749 - $849 /wk
 
 
 
 
 

6 reviews write a review

Gorgeous Cottages Steps From Beach - OUR CALENDAR IS UP TO DATE
Siesta Key Cottage Rental Picture
  • bedrooms 1
  • rental type Cottage
  • sleeps 4
  • baths 1
  • rates (USD) $200 /nt
 
 
 
 
 

9 reviews write a review

Large Home Sleeps 8. Walk to the Village. Perfect Family Getaway!
Siesta Key House Rental Picture
  • bedrooms 3
  • rental type House
  • owner badgeowner badge
  • sleeps 8
  • baths 2
  • rates (USD) $1,000 - $1,900 /wk
    $4,125 - $6,650 /mth
 
 
 
 
 

14 reviews write a review

Closest Condo to World-Famous Siesta Beach!
Siesta Key Condo Rental Picture
  • bedrooms 1
  • rental type Condo
  • owner badgeowner badge
  • sleeps 4
  • baths 1
  • rates (USD) $795 - $1,170 /wk
 
 
 
 
 

4 reviews write a review

Just steps to Siesta Key Beach! Aug 10th to Sept 3rd still available!
Siesta Key Condo Rental Picture
  • bedrooms 2
  • rental type Condo
  • sleeps 6
  • baths 2
  • rates (USD) $1,213 - $1,635 /wk
 
 
 
 
 

1 reviews write a review

Siesta Key Beach Oasis 1BR/1BA For 4
Siesta Key Condo Rental Picture
  • bedrooms 1
  • rental type Condo
  • owner badgeowner badge
  • sleeps 4
  • baths 1
  • rates (USD) $800 - $1,170 /wk
 
 
 
 
 

4 reviews write a review

July 20-27th 50% off !!!!!!!!
Siesta Key House Rental Picture
  • bedrooms 6
  • rental type House
  • sleeps 16
  • baths 2
  • rates (USD) $414 - $620 /nt
 
 
 
 
 

7 reviews write a review

Palm Bay Club, Beautiful Gulf Side Condo 2BR/2BA-#161
Siesta Key Condo Rental Picture
  • bedrooms 2
  • rental type Condo
  • owner badgeowner badge
  • sleeps 6
  • baths 2
  • rates (USD) $180 - $220 /nt
    $1,190 - $1,400 /wk
 
 
 
 
 

10 reviews write a review

Spectacular Gulf Front And Beach Views Of Crescent Beach, Siesta Key
Siesta Key Condo Rental Picture
  • bedrooms 2
  • rental type Condo
  • owner badgeowner badge
  • sleeps 6
  • baths 2
  • rates (USD) $1,500 - $2,100 /wk
 
 
 
 
 

8 reviews write a review

Siesta Key Gem ! -50' Lap Pool, Hot Tub and just one Block to Siesta Key Beach!
Siesta Key House Rental Picture
  • bedrooms 2
  • rental type House
  • owner badgeowner badge
  • sleeps 6
  • baths 2
  • rates (USD) $1,540 - $1,650 /wk
    $5,000 - $5,500 /mth
 
 
 
 
 

20 reviews write a review

2014 Renovated Gem Of House - 4 BR/3 BA - Pool on Canal - Walk To Beach/Village
Siesta Key House Rental Picture
  • bedrooms 4
  • rental type House
  • sleeps 8
  • baths 3
  • rates (USD) $400 - $500 /nt
    $2,500 - $3,000 /wk
    $9,000 - $11,000 /mth
 
 
 
 
 

1 reviews write a review

Townhouse with Garage - Across from Siesta Key Beach!
Siesta Key Condo Rental Picture
  • bedrooms 2
  • rental type Condo
  • owner badgeowner badge
  • sleeps 6
  • baths 2
  • rates (USD)
 
 
 
 
 

14 reviews write a review

Crystal Sands Gulf-Front Condo
Siesta Key Condo Rental Picture
  • bedrooms 2
  • rental type Condo
  • owner badgeowner badge
  • sleeps 7
  • baths 2
  • rates (USD)
 
 
 
 
 

9 reviews write a review

Siesta Key True Beachfront Cozy Villa Beach Walkout 2B/2B Private Lanai Big Pool
Siesta Key Villa Rental Picture
  • bedrooms 2
  • rental type Villa
  • owner badgeowner badge
  • sleeps 7
  • baths 2
  • rates (USD) $1,400 - $2,200 /wk
 
 
 
 
 

8 reviews write a review

Our House at the Beach 504, 5th Floor, Gulf Views, with Heated Pool
Siesta Key Condo Rental Picture
  • bedrooms 2
  • rental type Condo
  • owner badgeowner badge
  • sleeps 6
  • baths 2
  • rates (USD) $114 - $166 /nt
    $795 - $1,248 /wk
 
 
 
 
 

12 reviews write a review

Gulf and Bay Club 502D Beach Front, 3 Heated Pools, Gym, Spa, Beach
Siesta Key Condo Rental Picture
  • bedrooms 2
  • rental type Condo
  • owner badgeowner badge
  • sleeps 6
  • baths 2
  • rates (USD) $125 - $250 /nt
    $3,500 - $7,000 /mth
 
 
 
 
 

19 reviews write a review

Gulf & Bay Club 305C
Siesta Key Condo Rental Picture
  • bedrooms 2
  • rental type Condo
  • owner badgeowner badge
  • sleeps 6
  • baths 2
  • rates (USD) $3,995 - $7,500 /mth
 
 
 
 
 

13 reviews write a review

Excelsior 107, 1st Flr, 2 Heated Pool, Spa, Wifi, Beach Access
Siesta Key Condo Rental Picture
  • bedrooms 2
  • rental type Condo
  • owner badgeowner badge
  • sleeps 6
  • baths 2
  • rates (USD) $747 - $1,499 /wk
 
 
 
 
 

8 reviews write a review

Beautiful Condo On The # 1 Beach In The USA
Siesta Key Condo Rental Picture
  • bedrooms 2
  • rental type Condo
  • owner badgeowner badge
  • sleeps 4
  • baths 2
  • rates (USD) $166 - $242 /nt
    $1,164 - $1,622 /wk
 
 
 
 
 

4 reviews write a review

Siesta Dunes Beach 38A, Gulf Side, Large Heated Pool, Wifi
Siesta Key Condo Rental Picture
  • bedrooms 2
  • rental type Condo
  • owner badgeowner badge
  • sleeps 6
  • baths 2
  • rates (USD) $125 - $350 /nt
    $650 - $1,595 /wk
 
 
 
 
 

37 reviews write a review

Siesta Dunes Beach 104, Siesta Key Gulf, Spa, Heated Pool
Siesta Key Condo Rental Picture
  • bedrooms 2
  • rental type Condo
  • owner badgeowner badge
  • sleeps 6
  • baths 2
  • rates (USD) $125 - $250 /nt
    $650 - $1,395 /wk
 
 
 
 
 

29 reviews write a review

Jamaica Royale 91 Rental, Heated Pool, Beach Access,Wifi
Siesta Key Condo Rental Picture
  • bedrooms 2
  • rental type Condo
  • owner badgeowner badge
  • sleeps 6
  • baths 2
  • rates (USD) $200 - $350 /nt
    $895 - $1,595 /wk
 
 
 
 
 

16 reviews write a review

Beautiful Sarasota Bayfront Home with Spectacular View and Boat Dock
Siesta Key House Rental Picture
  • bedrooms 4
  • rental type House
  • owner badgeowner badge
  • sleeps 6
  • baths
  • rates (USD) $282 - $425 /nt
    $6,800 - $9,950 /mth
 
 
 
 
 

4 reviews write a review

Palm and Bay Club G88 tower rental, Siesta Key Florida
Siesta Key Condo Rental Picture
  • bedrooms 1
  • rental type Condo
  • sleeps 4
  • baths 1
  • rates (USD)
 
 
 
 
 

1 reviews write a review

Gulf and Bay Club 102B Beach Front, Luxury Ground Floor unit
Siesta Key Condo Rental Picture
  • bedrooms 2
  • rental type Condo
  • sleeps 4
  • baths 2
  • rates (USD) $4,083 - $5,000 /mth
 
 
 
 
 

1 reviews write a review

Jamaica Royale 91 Siesta Key Rental, Heated Pool, Beach Access
Siesta Key Condo Rental Picture
  • bedrooms 2
  • rental type Condo
  • owner badgeowner badge
  • sleeps 6
  • baths 2
  • rates (USD) $125 - $250 /nt
    $650 - $1,395 /wk
 
 
 
 
 

10 reviews write a review

House of Sun 307 Siesta Key, Large Heated Pool, Gulf View, Wifi
Siesta Key Condo Rental Picture
  • bedrooms 2
  • rental type Condo
  • owner badgeowner badge
  • sleeps 6
  • baths 2
  • rates (USD)
 
 
 
 
 

12 reviews write a review

Two Bedroom Condo 400 yards from Siesta Key Beach (Crescent Beach).
Siesta Key Condo Rental Picture
  • bedrooms 2
  • rental type Condo
  • sleeps 6
  • baths 2
  • rates (USD) $3,060 - $4,671 /mth
 
 
 
 
 

1 reviews write a review

Our Siesta Key Villa, The Perfect Place To Call Your Island Home!
Siesta Key Villa Rental Picture
  • bedrooms 2
  • rental type Villa
  • sleeps 5
  • baths
  • rates (USD) $95 - $143 /nt
    $1,000 /wk
    $2,650 - $3,675 /mth
 
 
 
 
 

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Short Walk to Crescent Beach on Siesta Key!
Siesta Key Condo Rental Picture
  • bedrooms 2
  • rental type Condo
  • owner badgeowner badge
  • sleeps 6
  • baths 2
  • rates (USD) $630 - $945 /wk
 
 
 
 
 

17 reviews write a review

Beautiful Siesta Key Beach Getaway
Siesta Key Condo Rental Picture
  • bedrooms 2
  • rental type Condo
  • owner badgeowner badge
  • sleeps 6
  • baths 2
  • rates (USD)
 
 
 
 
 

2 reviews write a review

Beachfront Luxury Condo Overlooking Gulf with Lowest Price Guarantee
Siesta Key Condo Rental Picture
  • bedrooms 2
  • rental type Condo
  • owner badgeowner badge
  • sleeps 5
  • baths 2
  • rates (USD) $850 - $1,400 /wk
 
 
 
 
 

20 reviews write a review

Newly Decorated Condo, Just Minutes From The Beach
Siesta Key Condo Rental Picture
  • bedrooms 3
  • rental type Condo
  • sleeps 6
  • baths 2
  • rates (USD) $1,500 - $1,800 /wk
    $2,800 - $4,000 /mth
 
 
 
 
 

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Siesta Key Beach, Gulf View, Totally remodeled, Sleeps 6, excellent location!!!
Siesta Key Condo Rental Picture
  • bedrooms 2
  • rental type Condo
  • sleeps 6
  • baths 2
  • rates (USD) $275 - $375 /nt
    $1,950 - $2,625 /wk
    $5,500 - $9,000 /mth
 
 
 
 
 

1 reviews write a review

So close to the best beach sand you will ever sink your toes into! Siesta Key!!!
Siesta Key Condo Rental Picture
  • bedrooms 1
  • rental type Condo
  • sleeps 4
  • baths 1
  • rates (USD) $175 - $286 /nt
    $1,200 - $2,000 /wk
    $3,000 - $6,000 /mth
 
 
 
 
 

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Spend Spring Break on the beach rated #1 by Dr. Beach
Siesta Key Condo Rental Picture
  • bedrooms 2
  • rental type Condo
  • owner badgeowner badge
  • sleeps 6
  • baths 2
  • rates (USD) $175 - $300 /nt
 
 
 
 
 

3 reviews write a review

Charming, private cottage just steps away from award winning Crescent Beach
Siesta Key Cottage Rental Picture
  • bedrooms 2
  • rental type Cottage
  • owner badgeowner badge
  • sleeps 6
  • baths 2
  • rates (USD) $767 - $1,255 /wk
 
 
 
 
 

4 reviews write a review

Paradise on the Gulfside of Siesta Key
Siesta Key Villa Rental Picture
  • bedrooms 1
  • rental type Villa
  • sleeps 4
  • baths 1
  • rates (USD) $868 - $1,155 /wk
 
 
 
 
 

1 reviews write a review

Private Home with Private Beach Access
Siesta Key House Rental Picture
  • bedrooms 3
  • rental type House
  • sleeps 8
  • baths 2
  • rates (USD) $300 /nt
    $2,100 /wk
    $8,400 /mth
 
 
 
 
 

2 reviews write a review

Bayside Condo With Private Beach Access from condo property across street
Siesta Key Condo Rental Picture
  • bedrooms 1
  • rental type Condo
  • sleeps 2
  • baths 1
  • rates (USD) $650 - $875 /wk
    $2,200 - $3,617 /mth
 
 
 
 
 

4 reviews write a review

Luxury Kid Friendly 4BR/5BA With Heated Pool 3200 Sq/Ft. Walk Or Bike To Beach
Siesta Key Chateau_/_country_house Rental Picture
  • bedrooms 4
  • rental type Chateau / country house
  • sleeps 10
  • baths
  • rates (USD) $229 - $429 /nt
    $1,610 /wk
    $4,900 - $12,000 /mth
 
 
 
 
 

4 reviews write a review

Gulf Side Condo Close To Pool & Beach! New Furniture & Decor!
Siesta Key Condo Rental Picture
  • bedrooms 2
  • rental type Condo
  • sleeps 6
  • baths 2
  • rates (USD) $240 /nt
    $1,596 /wk
    $5,400 /mth
 
 
 
 
 

4 reviews write a review

Family Friendly Cute Old Florida Bungalow
Siesta Key House Rental Picture
  • bedrooms 2
  • rental type House
  • sleeps 8
  • baths
  • rates (USD) $1,885 - $3,173 /mth
 
 
 
 
 

1 reviews write a review

Under 2 Minute Walk To America's Number 1 Beach with your feet in the Water!!
Siesta Key House Rental Picture
  • bedrooms 4
  • rental type House
  • sleeps 10
  • baths 2
  • rates (USD)
 
 
 
 
 

1 reviews write a review

'Gumbo Limbo Vaction Rentals'
Siesta Key Apartment Rental Picture
  • bedrooms 2
  • rental type Apartment
  • sleeps 4
  • baths 2
  • rates (USD) $175 - $263 /nt
    $1,250 - $1,840 /wk
 
 
 
 
 

1 reviews write a review

Siesta Key Bayside Condo
Siesta Key Condo Rental Picture
  • bedrooms 2
  • rental type Condo
  • sleeps 6
  • baths 1
  • rates (USD) $600 - $1,100 /wk
    $2,000 - $4,000 /mth
 
 
 
 
 

1 reviews write a review

Unique Waterfront 4BR/3BA w/ Heated Pool and Spa, Close to Beach
Siesta Key Cottage Rental Picture
  • bedrooms 4
  • rental type Cottage
  • owner badgeowner badge
  • sleeps 12
  • baths 3
  • rates (USD) $400 - $600 /nt
    $2,600 - $4,250 /wk
    $6,240 - $9,510 /mth
 
 
 
 
 

11 reviews write a review

5 BR Waterfront w/ Heated Pool and Spa near Village/Beach
Siesta Key Cottage Rental Picture
  • bedrooms 5
  • rental type Cottage
  • owner badgeowner badge
  • sleeps 10
  • baths 3
  • rates (USD) $425 - $650 /nt
    $2,800 - $4,200 /wk
    $6,720 - $9,600 /mth
 
 
 
 
 

2 reviews write a review

Euro Contemporary Getaway with Amazing Beach View!
Siesta Key Condo Rental Picture
  • bedrooms 1
  • rental type Condo
  • sleeps 4
  • baths 1
  • rates (USD) $871 - $1,398 /wk
 
 
 
 
 

9 reviews write a review

4 Bedroom Canal Front Home, W/ Heated Pool. ** Minimum Stay Required **
Siesta Key House Rental Picture
  • bedrooms 4
  • rental type House
  • sleeps 10
  • baths 3
  • rates (USD) $3,000 - $3,600 /wk
    $6,800 - $8,000 /mth
 
 
 
 
 

1 reviews write a review

2 BR, 2 Bath, Siesta Key Village Condo With Pool, Tiki Bar, Washer/Dryer In Unit
Siesta Key Condo Rental Picture
  • bedrooms 2
  • rental type Condo
  • sleeps 4
  • baths 2
  • rates (USD) $150 - $217 /nt
    $3,420 - $5,220 /mth
 
 
 
 
 

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2 BR, 2 Bath, Siesta Key Village Condo With Pool, Patio, Washer/Dryer
Siesta Key Condo Rental Picture
  • bedrooms 2
  • rental type Condo
  • sleeps 4
  • baths 2
  • rates (USD) $150 - $217 /nt
    $3,420 - $5,220 /mth
 
 
 
 
 

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Siesta Key Beach Retreat
Siesta Key Estate Rental Picture
  • bedrooms 3
  • rental type Estate
  • sleeps 12
  • baths 2
  • rates (USD) $6,500 /mth
 
 
 
 
 

5 reviews write a review

2B / 1.5 Br, Pool, Canal
Siesta Key House Rental Picture
  • bedrooms 2
  • rental type House
  • sleeps 6
  • baths
  • rates (USD) $1,500 /wk
 
 
 
 
 

1 reviews write a review

Townhouse Condo Directly on the Water with Sweeping Views of the Gulf
Siesta Key Townhome Rental Picture
  • bedrooms 2
  • rental type Townhome
  • sleeps 6
  • baths 2
  • rates (USD) $1,500 - $2,100 /wk
    $6,000 - $8,400 /mth
 
 
 
 
 

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Charming & Modern Siesta Key Beach Condo - You'll Love It :)
Siesta Key Condo Rental Picture
  • bedrooms 1
  • rental type Condo
  • sleeps 6
  • baths 1
  • rates (USD) $125 - $175 /nt
    $650 - $950 /wk
    $2,200 - $3,500 /mth
 
 
 
 
 

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Beachfront, Gulf Of Mexico Views, Best Location!
Siesta Key House Rental Picture
  • bedrooms 3
  • rental type House
  • sleeps 8
  • baths
  • rates (USD) $495 - $600 /nt
    $2,400 - $4,200 /wk
    $9,000 - $14,000 /mth
 
 
 
 
 

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Coastal Living and Spacious Four Bedroom Home, Steps to Siesta Key Public Beach
Siesta Key House Rental Picture
  • bedrooms 4
  • rental type House
  • sleeps 12
  • baths
  • rates (USD) $450 - $625 /nt
    $2,700 - $4,200 /wk
    $9,000 - $15,500 /mth
 
 
 
 
 

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Tropical Oasis - Laarge Pool - Spa - At Village, Walk To Beach
Siesta Key Cottage Rental Picture
  • bedrooms 4
  • rental type Cottage
  • sleeps 14
  • baths 4
  • rates (USD) $350 - $500 /nt
    $1,675 - $2,975 /wk
    $4,950 - $7,500 /mth
 
 
 
 
 

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Directly on the beach. Unobstructed views. Prime well maintained updated unit
Siesta Key Condo Rental Picture
  • bedrooms 2
  • rental type Condo
  • owner badgeowner badge
  • sleeps 6
  • baths 2
  • rates (USD) $165 - $307 /nt
 
 
 
 
 

5 reviews write a review

Newly Listed! Beautiful Siesta Key Condo
Siesta Key Townhome Rental Picture
  • bedrooms 2
  • rental type Townhome
  • sleeps 6
  • baths 2
  • rates (USD) $166 - $210 /nt
    $1,162 /wk
    $3,950 - $4,998 /mth
 
 
 
 
 

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Kid Friendly Island Home In Paradise
Siesta Key House Rental Picture
  • bedrooms 4
  • rental type House
  • sleeps 8
  • baths 2
  • rates (USD) $1,850 /wk
    $5,310 /mth
 
 
 
 
 

5 reviews write a review

Affordable 5-Star Condo Steps from Beach! Views! Amenities!
Siesta Key Condo Rental Picture
  • bedrooms 2
  • rental type Condo
  • sleeps 6
  • baths 2
  • rates (USD)
 
 
 
 
 

2 reviews write a review

Siesta Key - Voted Best Beach in America!!! Siesta Beach House for Rent
Siesta Key House Rental Picture
  • bedrooms 3
  • rental type House
  • sleeps 8
  • baths
  • rates (USD) $306 /nt
    $8,568 - $8,874 /mth
 
 
 
 
 

2 reviews write a review

A Tropical Retreat on a Florida Isle
Siesta Key Condo Rental Picture
  • bedrooms 1
  • rental type Condo
  • sleeps 4
  • baths 1
  • rates (USD) $229 - $257 /nt
    $1,299 - $1,799 /wk
    $4,999 - $5,900 /mth
 
 
 
 
 

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Cozy Retreat
Siesta Key Townhome Rental Picture
  • bedrooms 2
  • rental type Townhome
  • sleeps 8
  • baths
  • rates (USD)
 
 
 
 
 

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Beach To Bay Complex On The #1 Rated Beach For Several Years
Siesta Key Condo Rental Picture
  • bedrooms 2
  • rental type Condo
  • sleeps 7
  • baths 2
  • rates (USD) $360 /nt
 
 
 
 
 

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Beach Villa on Siesta Key-Office with Wi-Fi
Siesta Key Villa Rental Picture
  • bedrooms 2
  • rental type Villa
  • owner badgeowner badge
  • sleeps 6
  • baths 2
  • rates (USD)
 
 
 
 
 

2 reviews write a review

Siesta Key Poolside Villa
Siesta Key Villa Rental Picture
  • bedrooms 2
  • rental type Villa
  • sleeps 4
  • baths
  • rates (USD)
 
 
 
 
 

1 reviews write a review

3BR/2BA: 'Villas # 6 & 7 on Siesta Key, Near o Point of rocks. 6 June 4 Night
Siesta Key Villa Rental Picture
  • bedrooms 2
  • rental type Villa
  • owner badgeowner badge
  • sleeps 10
  • baths 2
  • rates (USD)
 
 
 
 
 

2 reviews write a review

4BR/2BA 'Beach House with Studio Villa, Near Beach. June 30th 3 nights
Siesta Key Villa Rental Picture
  • bedrooms 4
  • rental type Villa
  • sleeps 12
  • baths 2
  • rates (USD)
 
 
 
 
 

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Stunning 2 Bedrm Townhouse Across from Siesta Beach/300 Yds
Siesta Key Condo Rental Picture
  • bedrooms 2
  • rental type Condo
  • owner badgeowner badge
  • sleeps 6
  • baths 2
  • rates (USD)
 
 
 
 
 

3 reviews write a review

All Inclusive Beach Paradise On Siesta Key
Siesta Key Condo Rental Picture
  • bedrooms 0
  • rental type Condo
  • sleeps 4
  • baths 0
  • rates (USD) $143 /nt
    $1,650 /mth
 
 
 
 
 

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Beachfront View On Siesta Key Access To Private Beach
Siesta Key Condo Rental Picture
  • bedrooms 2
  • rental type Condo
  • sleeps 6
  • baths 2
  • rates (USD) $150 - $167 /nt
    $4,200 /mth
 
 
 
 
 

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Pet-Friendly, Family-Friendly, 1/2 Mile To Beach
Siesta Key House Rental Picture
  • bedrooms 3
  • rental type House
  • sleeps 6
  • baths
  • rates (USD) $1,283 - $2,200 /wk
    $5,500 - $5,995 /mth
 
 
 
 
 

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An Oasis at the edge of Siesta Village & 3 block walk to Siesta Beach!
Siesta Key Condo Rental Picture
  • bedrooms 2
  • rental type Condo
  • sleeps 6
  • baths 0
  • rates (USD) $189 /nt
    $1,141 - $1,242 /wk
    $3,450 - $4,984 /mth
 
 
 
 
 

1 reviews write a review

Vacation on Siesta Beach,USA #1 Beach
Siesta Key Condo Rental Picture
  • bedrooms 2
  • rental type Condo
  • sleeps 4
  • baths 2
  • rates (USD) $2,500 /mth
 
 
 
 
 

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FALL DISCOUNT-DIRECT GULF FRONT CLEAN/NEAT WEEKLY-FREE WI-FI
Siesta Key Condo Rental Picture
  • bedrooms 2
  • rental type Condo
  • owner badgeowner badge
  • sleeps 6
  • baths 2
  • rates (USD)
 
 
 
 
 

8 reviews write a review