Vacation Rentals in Siesta Key, Florida
Nightly rates from: $57* – Average nightly rate per bedroom: $73* – Deals available: 73
- bedrooms 2
- baths 2
- ($75)
- 10% off = $1,305 per week
about Siesta Key
Deals on Siesta Key, Florida Rentals
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.
- What more help planning your vacation? Read our full Siesta Key Travel Guide!
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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rental results
DEAL!! Sundance 1 to 6 BRs - Key West Style - Pool
-
20% off = $1,080 per week
-
Free WIFI, Beach wagon/chairs
($199)
- bedrooms 3
- community Siesta Key Village
- rental type Apartment
- sleeps 10
- baths 3
- rates (USD)
$1,350
- $1,845
/wk
DEAL!! Direct Gulf-Front Retreat - 2 Bedroom - Upscale - Siesta Key
-
20% off = $916 per week
-
Free WIFI, beach chairs
($99)
- bedrooms 2
- community Fisherman's Cove
- rental type Condo
- sleeps 6
- baths 2
- rates (USD)
$1,145
- $1,645
/wk
DEAL!! Siesta Key - Gulf-Front Retreat - 2 Bedroom - Upscale
-
20% off = $916 per week
-
Free WIFI
($99)
- bedrooms 2
- community Fisherman's Cove
- rental type Condo
owner badge
- sleeps 6
- baths 2
- rates (USD)
$1,145
- $1,645
/wk
DEAL!! Remodeled, Faces Gulf/Sunset, with Private Dock
-
10% off = $580 per week
-
WiFi, DVR, Bikes, umbrella and chairs
($300)
- bedrooms 2
- community Mariner's Inlet
- rental type Condo
- sleeps 4
- baths 2
- rates (USD)
$92
- $200
/nt
$645 - $1,195 /wk
$1,700 - $3,500 /mth
DEAL!! Deluxe Townhouse & Garden Apartment (4BR's) - Pool
-
20% off = $1,696 per week
-
Free: WIFI, beach chairs/wagons
($199)
- bedrooms 4
- community Seista Key Village
- rental type Townhome
- owner badge
- sleeps 12
- baths 3½
- rates (USD)
$2,120
- $2,945
/wk
DEAL!! Awesome Siesta Key 1st Floor Condo-Siesta Dunes on #1 Beach
-
10% off = $1,057 per week
- bedrooms 2
- community Siesta Dunes
- rental type Condo
- owner badge
- sleeps 6
- baths 2
- rates (USD)
$1,175
- $1,625
/wk
DEAL!! Siesta Key-Siesta Dunes Beach Gulf Front Condo #1 Beach USA
-
10% off = $1,305 per week
-
Bottle of wine & Free WiFi & HDTV
($75)
- bedrooms 2
- community Siesta Dunes
- rental type Condo
- owner badge
- sleeps 6
- baths 2
- rates (USD)
$1,450
- $1,890
/wk
DEAL!! Siesta Key, Siesta Beach, Twin Palms, Condo, Villa
-
free night valued at USD $99
-
WiFi,HBO/SHOWTIME,BCH CHAIRS+UMBRELLA
($109)
- bedrooms 0
- community Twin Palms
- rental type Studio
- owner badge
- sleeps 2
- baths 1
- rates (USD)
$99
- $139
/nt
$594 - $834 /wk
$1,960 - $2,752 /mth
DEAL!! SeaSide Villas - Luxurious - Upscale - Elegant Townhouse
-
20% off = $500 per week
-
Free WIFI, Beach Wagons/Chairs
($99)
- bedrooms 3
- community
- rental type Villa
- owner badge
- sleeps 8
- baths 3
- rates (USD)
$600
- $2,050
/wk
DEAL!! Beautiful 2br/2ba Garden Unit on Crescent Beach, Free WIFI
-
Free week
($895)
- bedrooms 2
- community Siesta Key
- rental type Condo
- sleeps 6
- baths 2
- rates (USD)
$895
- $1,595
/wk
$3,222 - $5,605 /mth
DEAL!! Midnight Cove II
-
Free Boat Docking
($75)
- bedrooms 2
- community Midnight Cove 2
- rental type Condo
- sleeps 6
- baths 1½
- rates (USD)
$101
- $152
/nt
$710 - $1,070 /wk
$2,840 - $4,280 /mth
DEAL!! Midnight Cove: Living on the Water! Across from "Best Beach"
-
35% off = $438 per week
- bedrooms 2
- community Midnight Cove
- rental type Apartment
- owner badge
- sleeps 5
- baths 1½
- rates (USD)
$84
- $158
/nt
$675 - $1,125 /wk
$2,140 - $4,150 /mth
DEAL!! Siesta Key 2/2 Condo, Gulf Side. Beach. Pool
-
$325 off = $825 per week
- bedrooms 2
- community
- rental type Condo
- owner badge
- sleeps 4
- baths 2
- rates (USD)
$850
- $1,200
/wk
$3,300 - $4,600 /mth
DEAL!! Crescent Beach - 2-Bedroom - Beachfront Condo Complex
-
20% off = $980 per week
-
Free WIFI
($99)
- bedrooms 2
- community Sea Shell Condos
- rental type Condo
- sleeps 6
- baths 2
- rates (USD)
$1,225
- $1,625
/wk
DEAL!! Sundance Rental - 1-6 BRs - Key West Style - Private Pool
-
20% off = $708 per week
-
Free WIFI, Beach Wagons/Chairs
($99)
- bedrooms 2
- community Siesta Village
- rental type Apartment
- owner badge
- sleeps 6
- baths 2
- rates (USD)
$885
- $1,210
/wk
DEAL!! Seaside Villas - One Bedroom - Deluxe Garden Apartment -Pool
-
20% off = $500 per week
-
Free; WIFI, beach chairs/wagons
($99)
- bedrooms 1
- community Siesta Key Village
- rental type Villa
- owner badge
- sleeps 4
- baths 1
- rates (USD)
$625
- $900
/wk
DEAL!! 3BR Luxury Townhouse - Siesta Key Beach - Gulf View - Pool
-
20% off = $1,196 per week
-
Free beach chairs/wagons
($199)
- bedrooms 3
- community Siesa Key Beach
- rental type Townhome
- sleeps 8
- baths 2½
- rates (USD)
$1,495
- $2,045
/wk
DEAL!! Luxury Townhouse (3BR) Private Pool - Crescent Beach - Villa
-
20% off = $1,196 per week
-
Free WIFI, Beach Wagons/Chairs
($99)
- bedrooms 3
- community
- rental type Townhome
- owner badge
- sleeps 8
- baths 2½
- rates (USD)
$1,495
- $2,045
/wk
DEAL!! Gorgeous Siesta Key Home w/Pool - Tons of EXTRAS!
-
FREE WiFi, Cable, Beach Chairs, Bikes,...
($199)
- bedrooms 3
- community
- rental type House
- owner badge
- sleeps 8
- baths 2
- rates (USD)
$1,150
- $1,700
/wk
$4,200 - $6,500 /mth
DEAL!! Lovely Condo with Great Views & Amenities at Harbor Towers!
-
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
DEAL!! Beautiful Condo Across from the #1 Beach in the USA
-
Free WiFi, Cable, Beach Chairs
($99)
- bedrooms 2
- community
- rental type Condo
- sleeps 6
- baths 2
- rates (USD)
$134
- $186
/nt
$938 - $1,302 /wk
$3,752 - $5,208 /mth
DEAL!! Stay On Siesta Key Beach - No Shoes Required!
-
Free WiFi, Free Cable
($99)
- bedrooms 2
- community Sea Shell Condos
- rental type Condo
- sleeps 6
- baths 2
- rates (USD)
$171
- $271
/nt
$1,195 - $1,895 /wk
DEAL!! Sensational Condo & Fantastic Amenities at Palm Bay Club!
-
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 - $5,800 /mth
DEAL!! Siesta Key Condos - Vacation Condo Rentals
-
$64 off = $750 per week
-
Free WiFi and long distance
($75)
- bedrooms 2
- community Anchorage
- rental type Condo
- sleeps 4
- baths 2
- rates (USD)
$814
- $1,187
/wk
DEAL!! Siesta Key - Beachfront - 2-Bedroom - Ground Floor
-
20% off = $916 per week
-
Free Wifi, Kayak, Beach chairs
($199)
- bedrooms 2
- community Fisherman's Cove
- rental type Condo
- sleeps 6
- baths 2
- rates (USD)
$1,145
- $1,645
/wk
DEAL!! Sundance Rentals - 1-6 BRs - Key West Style - Private Pool
-
20% off = $480 per week
-
FREE: WIFI, beach chairs/wagons
($199)
- bedrooms 1
- community Siesta Key Village
- rental type Apartment
- owner badge
- sleeps 4
- baths 1
- rates (USD)
$600
- $825
/wk
DEAL!! Beachfront Condo - Three Bedroom - Luxury
-
20% off = $1,236 per week
-
Free WIFI
($99)
- bedrooms 3
- community Fisherman's Cove
- rental type Condo
- owner badge
- sleeps 8
- baths 2
- rates (USD)
$1,545
- $2,095
/wk
DEAL!! Beachfront Luxury Condo 3-Bedroom - Turtle Beach/Siesta Key
-
20% off = $1,236 per week
-
Free WIFI, beach chairs
($99)
- bedrooms 3
- community Fisherman's Cove
- rental type Condo
- sleeps 8
- baths 2
- rates (USD)
$1,545
- $2,095
/wk
DEAL!! Tropical Oasis 2-5 miles from SIESTA BEACH !!
-
60% off = $800 per week
-
HBO & WI-FI
($150)
- bedrooms 3
- community Siesta Key Beach
- rental type Condo
- owner badge
- sleeps 8
- baths 2
- rates (USD)
$99
- $199
/nt
$499 - $2,500 /wk
$1,500 - $4,800 /mth
DEAL!! Direct Gulf Front Beach w/ Boat Dock On Siesta Key
-
$200 off = $945 per week
-
FREE WI - FI, Beach Chairs, Linens &...
($125)
- bedrooms 2
- community Fisherman's Cove
- rental type Condo
- owner badge
- sleeps 6
- baths 2
- rates (USD)
$1,020
- $1,745
/wk
DEAL!! Gorgeous Gulf & Bay Bayside Resort - Steps to Crescent Beach
-
$150 off = $835 per week
-
FREE Beach Gear with Cart & FREE Wi-Fi
($50)
- bedrooms 2
- community Gulf and Bay Bayside
- rental type Townhome
- sleeps 6
- baths 2
- rates (USD)
$985
- $1,355
/wk
DEAL!! Paradise on Earth: SUMMER sale-Save $$$
-
$200 off = $1,600 per month
- bedrooms 1
- community White Sands Village
- rental type Condo
- sleeps 2
- baths 1
- rates (USD)
$499
- $899
/wk
$1,500 - $3,400 /mth
DEAL!! Beach Place - Discounting June Rentals
-
$100 off = $600 per week
- bedrooms 1
- community Siesta Key Beach
- rental type Cottage
- sleeps 6
- baths 1
- rates (USD)
$600
- $1,800
/wk
DEAL!! *Sun, Sand & SAVE 25% to 55%* per Week at Midnight Cove #532
-
40% off = $605 per week
- bedrooms 2
- community Midnight Cove
- rental type Condo
- owner badge
- sleeps 4
- baths 1½
- rates (USD)
$587
- $1,579
/wk
$1,988 - $4,174 /mth
DEAL!! *Sun, Sand & SAVE 25% to 55%* per Week at Midnight Cove #714
-
35% off = $655 per week
- bedrooms 2
- community Midnight Cove
- rental type Condo
- owner badge
- sleeps 4
- baths 1½
- rates (USD)
$587
- $1,579
/wk
$1,988 - $4,174 /mth
DEAL!! Siesta Key Delight !
-
$100 off = $550 per week
- bedrooms 2
- community Bay Oaks
- rental type Condo
- owner badge
- sleeps 6
- baths 2
- rates (USD)
$600
- $1,000
/wk
DEAL!! Our Tropical Island Home
-
Restaurant gift card
($50)
- bedrooms 2
- community
- rental type House
- sleeps 6
- baths 2
- rates (USD)
$750
- $990
/wk
DEAL!! Sun, Sand & SAVE 25% to 55% per Week at Siesta Breakers #603
-
40% off = $880 per week
- bedrooms 2
- community Siesta Breakers
- rental type Condo
- owner badge
- sleeps 6
- baths 2
- rates (USD)
$853
- $2,180
/wk
$2,986 - $5,885 /mth
DEAL!! Siesta Palms
-
$100 off = $790 per week
- bedrooms 2
- community S K North Village
- rental type Townhome
- sleeps 4
- baths 2
- rates (USD)
$890
- $1,300
/wk
DEAL!! On The Beach Choice 5 Star Top Floor Unit
-
10% off = $1,215 per week
-
free cleaning
($100)
- bedrooms 2
- community El Presidente
- rental type Condo
- sleeps 6
- baths 2
- rates (USD)
$1,250
- $1,943
/wk
DEAL!! "Sittin' on the Dock of the Bay Specials "
-
$51 off = $500 per week
- bedrooms 1
- community
- rental type Condo
- sleeps 4
- baths 1
- rates (USD)
$500
- $870
/wk
DEAL!! Beautiful Sunsets on Siesta Key
-
Free Wifi
($40)
- bedrooms 1
- community Harbor Towers
- rental type Condo
- owner badge
- sleeps 4
- baths 1
- rates (USD)
$535
- $835
/wk
$2,140 - $3,340 /mth
DEAL!! Beautiful Gulf Front Condo With Ocean View **RATES REDUCED**
-
$200 off = $930 per week
-
Free secured WiFi and Free beach chairs...
($199)
- bedrooms 2
- community Sea Shell
- rental type Condo
- owner badge
- sleeps 6
- baths 2
- rates (USD)
$930
- $1,696
/wk
DEAL!! Walk to the beautiful white sand of Siesta Beach
-
10% off = $495 per week
-
Free Wi-Fi
($15)
- bedrooms 2
- community White Sands Village
- rental type Condo
- sleeps 6
- baths 2
- rates (USD)
$550
- $1,025
/wk
$1,800 - $3,800 /mth
DEAL!! Stunning Views of Sarasota Bay & access to private beach
-
Exit cleaning charge
($125)
- bedrooms 2
- community Bay Tree Club
- rental type Condo
- owner badge
- sleeps 4
- baths 2
- rates (USD)
$850
- $850
/wk
$3,400 - $3,900 /mth
DEAL!! Nice Condo, in a great location across from the beach
-
Beach Chairs, Beach Umbrella, Beach...
($99)
- bedrooms 2
- community White Sands Village
- rental type Condo
- sleeps 6
- baths 2
- rates (USD)
$78
- $146
/nt
$550 - $1,025 /wk
$1,800 - $3,800 /mth
DEAL!! Casa Van Lopik (j) Our Siesta Key Village 3BR
-
35% off = $156 per night
- bedrooms 3
- community Siesta Key Village
- rental type House
- sleeps 10
- baths 2
- rates (USD)
$240
- $540
/nt
$1,300 - $3,600 /wk
$3,700 - $8,200 /mth
DEAL!! Casa Van Lopik (c) Our Siesta Key Village 3BR
-
35% off = $156 per night
- bedrooms 3
- community
- rental type House
- sleeps 10
- baths 2
- rates (USD)
$240
- $540
/nt
$1,300 - $3,300 /wk
$3,700 - $9,000 /mth
DEAL!! Venice Florida Rialto Mansion, 6 Bedrooms, Sleeps 16, HDTV
-
10% off = $315 per night
- bedrooms 6
- community
- rental type House
- sleeps 16
- baths 4
- rates (USD)
$350
- $750
/nt
$1,395 - $2,995 /wk
$6,036 - $10,809 /mth
DEAL!! La Siesta Condos Fully Equipped units on Siesta Key Beach
-
$60 off = $730 per week
- bedrooms 2
- community La Siesta Condos
- rental type Condo
- sleeps 5
- baths 1
- rates (USD)
$740
- $1,310
/wk
DEAL!! Siesta Dunes Beach 201, 2nd Floor, Spa, Heated Pool, Wifi
-
10% off = $112 per night
- bedrooms 2
- community
- rental type Condo
- owner badge
- sleeps 6
- baths 2
- rates (USD)
$125
- $350
/nt
$575 - $1,595 /wk
$2,417 - $5,251 /mth
DEAL!! Siesta Key Palm and Bay Club G88 tower rental, Siesta Key FL
-
10% off = $112 per night
- bedrooms 1
- community
- rental type Condo
- owner badge
- sleeps 4
- baths 1
- rates (USD)
$125
- $400
/nt
$695 - $1,995 /wk
$2,902 - $6,308 /mth
DEAL!! Siesta Key Our House at the Beach 1171
-
10% off = $102 per night
- bedrooms 2
- community Siesta Dunes
- rental type Townhome
- owner badge
- sleeps 4
- baths 2
- rates (USD)
$114
- $166
/nt
$556 - $1,249 /wk
$2,495 - $5,185 /mth
DEAL!! Palm and Bay Club G46 tower rental, from $695 a week
-
10% off = $112 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
DEAL!! Siesta Dunes Beach 38A, Gulf Side 2 bedrooms, Heated Pool
-
10% off = $134 per night
- bedrooms 2
- community House of sun
- rental type Condo
- sleeps 6
- baths 2
- rates (USD)
$149
- $350
/nt
$600 - $1,595 /wk
$2,417 - $5,495 /mth
DEAL!! Jamaica Royale 91 Siesta Key Rental, heated pool
-
10% off = $134 per night
- bedrooms 2
- community Jamaica Royale
- rental type Condo
- sleeps 6
- baths 2
- rates (USD)
$149
- $350
/nt
$575 - $1,595 /wk
$2,417 - $5,495 /mth
DEAL!! House of Sun 307 Siesta Key, Large Heated Pool, Gulf View
-
10% off = $135 per night
- bedrooms 2
- community
- rental type Condo
- owner badge
- sleeps 6
- baths 2
- rates (USD)
$150
- $450
/nt
$750 - $2,095 /wk
$2,902 - $6,308 /mth
DEAL!! Siesta Dunes Beach 104, Siesta Key Gulf, Spa, Heated Pool
-
10% off = $107 per night
- bedrooms 2
- community
- rental type Condo
- owner badge
- sleeps 6
- baths 2
- rates (USD)
$119
- $350
/nt
$575 - $1,595 /wk
$2,417 - $5,251 /mth
DEAL!! Castaway Cove 3B, on lagoon near beach, pet friendly
-
10% off = $85 per night
- bedrooms 2
- community
- rental type Condo
- owner badge
- sleeps 5
- baths 2
- rates (USD)
$95
- $250
/nt
$454 - $1,395 /wk
$1,933 - $4,621 /mth
DEAL!! Our House at the Beach 504, 5th Floor, Gulf Views, Pool
-
10% off = $102 per night
- bedrooms 2
- community
- rental type Condo
- sleeps 6
- baths 2
- rates (USD)
$114
- $166
/nt
$529 - $1,249 /wk
$1,930 - $5,185 /mth
DEAL!! Jamaica Royale 91 Siesta Key Rental, heated pool, wifi
-
10% off = $202 per night
- bedrooms 2
- community
- rental type Condo
- sleeps 6
- baths 2
- rates (USD)
$119
- $350
/nt
$575 - $1,595 /wk
$2,417 - $5,251 /mth
SR #114, at Siesta Beach with gorgeous sunsets
- bedrooms 2
- community Sunset Royale
- rental type Condo
- owner badge
- sleeps 4
- baths 2
- rates (USD)
$599
- $1,165
/wk
Cortez Cottage at the beach
- bedrooms 3
- community
- rental type Cottage
- owner badge
- sleeps 6
- baths 2
- rates (USD)
$875
- $1,250
/wk
$3,500 - $3,750 /mth
Sunny Siesta Key Beach House
- bedrooms 2
- community
- rental type House
- owner badge
- sleeps 4
- baths 2
- rates (USD)
$800
- $1,300
/wk
$3,000 - $4,300 /mth
Beachfront Luxury 2BR condo
- bedrooms 2
- community Siesta Breakers
- rental type Condo
- owner badge
- sleeps 6
- baths 2
- rates (USD)
$1,288
- $1,911
/wk
GORGEOUS Condo across from #1 Beach SIESTA KEY
- bedrooms 2
- community La Siesta
- rental type Condo
- owner badge
- sleeps 6
- baths 1
- rates (USD)
$800
- $1,135
/wk
Island Style Luxury Beach House
- bedrooms 3
- community Sarasota Beach
- rental type House
- owner badge
- sleeps 9
- baths 2½
- rates (USD)
$285
- $285
/nt
$2,000 - $2,000 /wk
$6,800 - $6,800 /mth
Sunset Royale #104, at the beach with beautiful sunsets
- bedrooms 1
- community Sunset Royale
- rental type Condo
- owner badge
- sleeps 2
- baths 1
- rates (USD)
$499
- $999
/wk
Gulf Front-Cresent Beach-Completely Renovated-Immaculate
- bedrooms 2
- community House of Sun Condos
- rental type Condo
- owner badge
- sleeps 6
- baths 2
- rates (USD)
$150
- $250
/nt
$1,050 - $1,650 /wk
Palm Bay Club bayside condo on Siesta Key - fairly priced
- bedrooms 2
- community Palm Bay Club
- rental type Condo
- owner badge
- sleeps 6
- baths 2
- rates (USD)
$850
- $1,600
/wk
Siesta Village Oasis II - Private Pool & Jacuzzi
- bedrooms 2
- community
- rental type House
- owner badge
- sleeps 4
- baths 1
- rates (USD)
$185
- $185
/nt
$1,050 - $1,050 /wk
Siesta Village Oasis- Private Pool & Jacuzzi
- bedrooms 3
- community
- rental type House
- owner badge
- sleeps 8
- baths 2
- rates (USD)
$225
- $225
/nt
$1,250 - $1,600 /wk
Beachfront Dreamcondo in Paradise:NewUpgrades/Many Amenities
- bedrooms 2
- community Fisherman's Cove
- rental type Condo
- owner badge
- sleeps 6
- baths 2
- rates (USD)
$1,120
- $1,745
/wk
GREAT Value, Siesta Key Beach,Voted #1 Best Beach in U.S/Fl
- bedrooms 2
- community Casa Blanca
- rental type Villa
- owner badge
- sleeps 4
- baths 2
- rates (USD)
$125
- $204
/nt
$880 - $1,394 /wk
$2,640 - $4,200 /mth
Palm Bay Club condo -bayfront large - reasonable -Siesta Key
- bedrooms 2
- community Palm Bay Club
- rental type Condo
- sleeps 6
- baths 2
- rates (USD)
$1,075
- $1,950
/wk
Full Gulf View across from Siesta Public Beach
- bedrooms 2
- community Our House @the Beach
- rental type Condo
- sleeps 6
- baths 2
- rates (USD)
$1,025
- $1,435
/wk
20% off July-Oct. Across from Siesta #1 Beach
- bedrooms 2
- community Midnight Cove II
- rental type Condo
- sleeps 6
- baths 1½
- rates (USD)
$568
- $1,070
/wk
Crescent Beach - 2-Bedroom - Beachfront Condo - Luxury
- bedrooms 2
- community Crescent Arms
- rental type Condo
- sleeps 6
- baths 2
- rates (USD)
$1,425
- $1,825
/wk
Unwind in an Affordable Healing Island Retreat
- bedrooms 4
- community
- rental type Hotel
- sleeps 14
- baths 4
- rates (USD)
$105
- $150
/nt
$544 - $1,118 /wk
$2,067 - $4,248 /mth
Banyan Tree Beach Resort
- bedrooms 20
- community
- rental type Hotel
- sleeps 35
- baths 20
- rates (USD)
$95
- $210
/nt
$404 - $1,521 /wk
$1,596 - $6,086 /mth
The Sandpiper
- bedrooms 1
- community Jamaica Royale
- rental type Condo
- sleeps 4
- baths 1
- rates (USD)
$110
- $135
/nt
$713 - $972 /wk
$2,790 - $3,693 /mth
Hummingbird Beach House
- bedrooms 6
- community
- rental type Condo
- sleeps 20
- baths 6
- rates (USD)
$110
- $180
/nt
$544 - $1,118 /wk
$2,067 - $4,248 /mth
5 Star "True" Direct Beach-Front ! (The Best of the Best !)
- bedrooms 2
- community Siesta Key Beach
- rental type Condo
- owner badge
- sleeps 5
- baths 1½
- rates (USD) $4,995 - $6,995 /mth
Siesta Sands Beach Resort - 1BR
- bedrooms 1
- community
- rental type Condo
- sleeps 6
- baths 1
- rates (USD)
$1,075
- $1,075
/wk
Romantic Beachfront Condo #304 Siesta Key Beautiful Views
- bedrooms 1
- community Sunset Royale
- rental type Condo
- owner badge
- sleeps 4
- baths 1
- rates (USD)
$90
- $147
/nt
$629 - $1,029 /wk
Upscale - Beachfront One Bedroom Condo at Fisherman's Cove
- bedrooms 1
- community Fisherman's Cove
- rental type Condo
- sleeps 4
- baths 1
- rates (USD)
$890
- $1,390
/wk
Great Deals on Siesta Key
- bedrooms 0
- community
- rental type Studio
- sleeps 4
- baths 1
- rates (USD)
$80
- $135
/nt
$620 - $1,000 /wk
Siesta Key Beach Private Pool Home
- bedrooms 3
- community
- rental type House
- sleeps 6
- baths 3
- rates (USD)
$250
- $420
/nt
$1,600 - $2,900 /wk
$4,500 - $7,500 /mth
Gorgeous Bay Views - Beautifully Updated!
- bedrooms 3
- community Gulf & Bay Bayside
- rental type Townhome
- owner badge
- sleeps 6
- baths 2
- rates (USD)
$183
- $238
/nt
$1,275 - $1,660 /wk
Polynesian Gardens
- bedrooms 2
- community Polynesian Gardens
- rental type Villa
- sleeps 5
- baths 1½
- rates (USD)
$85
- $150
/nt
$500 - $1,200 /wk
$2,400 - $3,800 /mth
4 bedroom beachfront- world's top-rated beach
- bedrooms 4
- community Aloha Kai
- rental type Villa
- owner badge
- sleeps 8
- baths 2
- rates (USD)
$2,095
- $3,795
/wk
DIRECT Beach front 3/2 Step Directly on to the sand
- bedrooms 3
- community
- rental type Villa
- sleeps 8
- baths 2
- rates (USD)
$1,600
- $2,950
/wk
$6,400 - $11,900 /mth
Beach & Surf at your Doorstep! 1 week just isn't enough!
- bedrooms 2
- community Fisherman's Cove
- rental type Condo
- owner badge
- sleeps 6
- baths 2
- rates (USD)
$1,120
- $1,745
/wk
518 Canal - Close walk to beach and village
- bedrooms 2
- community
- rental type House
- sleeps 6
- baths 1
- rates (USD)
$125
- $160
/nt
$800 - $1,000 /wk
$2,400 - $3,000 /mth
Siesta Beach Hideaway
- bedrooms 4
- community Siesta Key
- rental type House
- sleeps 11
- baths 3
- rates (USD)
$1,800
- $2,200
/wk
$5,700 - $7,000 /mth
3-Bdr.Townhouse w/ Private Access to Siesta Beach-# 1 Beach!
- bedrooms 3
- community Gulf & Bay Club Bays
- rental type Townhome
- sleeps 6
- baths 2
- rates (USD)
$1,200
- $1,975
/wk
$3,300 - $5,100 /mth
Sensational Gulf Views from Beach Front Condo
- bedrooms 2
- community Siesta Sands
- rental type Condo
- sleeps 6
- baths 2
- rates (USD)
$1,350
- $2,295
/wk
Tropical Paradise with full Gulf-front View
- bedrooms 2
- community Siesta Sands
- rental type House
- sleeps 6
- baths 2
- rates (USD)
$1,350
- $2,295
/wk
Beach Front View at Siesta Key Unit #212
- bedrooms 2
- community Siesta Sands
- rental type Condo
- sleeps 6
- baths 2
- rates (USD)
$1,350
- $2,295
/wk
What a view of the best beach!!
- bedrooms 2
- community Midnight Cove
- rental type Condo
- sleeps 4
- baths 2
- rates (USD)
$1,200
- $1,600
/wk
Adorable Villa on Siesta Key, Villa A
- bedrooms 2
- community
- rental type Villa
- sleeps 4
- baths 1
- rates (USD)
$103
- $142
/nt
$725 - $995 /wk
$2,600 - $3,200 /mth
Steps to Beach!
- bedrooms 2
- community Vista Hermosa
- rental type Condo
- sleeps 5
- baths 2
- rates (USD)
$650
- $1,000
/wk
2 BDRs 2 Bath Villa - Crescent Beach-Siesta Key
- bedrooms 2
- community Casa Blanca
- rental type Villa
- sleeps 6
- baths 2
- rates (USD)
$880
- $1,250
/wk
Generous Early Booking Discount Siesta Key Beach Front Condo
- bedrooms 2
- community
- rental type Condo
- owner badge
- sleeps 4
- baths 2
- rates (USD)
$1,095
- $1,895
/wk
Sunset Royale Beachfront Full Gulf View
- bedrooms 2
- community Sunset Royale # 314
- rental type Condo
- owner badge
- sleeps 5
- baths 2
- rates (USD)
$749
- $1,325
/wk
Waterfront Canal~Walk to Beach& Siesta Village/Pool/Jacuzzi
- bedrooms 3
- community
- rental type House
- owner badge
- sleeps 6
- baths 2
- rates (USD)
$1,500
- $2,100
/wk
$4,800 - $6,700 /mth
Adorable Villa on Siesta Key, Villa B
- bedrooms 2
- community
- rental type Villa
- sleeps 4
- baths 1
- rates (USD)
$103
- $142
/nt
$725 - $995 /wk
$2,600 - $3,200 /mth
Steps to Siesta Key Beach
- bedrooms 2
- community Gulf Haven
- rental type Villa
- owner badge
- sleeps 4
- baths 2
- rates (USD) $3,300 - $4,800 /mth
Closest Condo to World-Famous Siesta Beach
- bedrooms 1
- community La Siesta
- rental type Condo
- owner badge
- sleeps 4
- baths 1
- rates (USD)
$675
- $1,040
/wk
$2,700 - $3,975 /mth
The Shells Villa - Stay next to Beach and Village
- bedrooms 3
- community
- rental type Villa
- owner badge
- sleeps 10
- baths 2½
- rates (USD)
$1,275
- $1,985
/wk
$4,000 - $6,850 /mth
Siesta Key Beachfront 2B/2B Condo
- bedrooms 2
- community Crescent Arms
- rental type Condo
- owner badge
- sleeps 6
- baths 2
- rates (USD)
$995
- $1,950
/nt
$995 - $1,950 /wk
The Ringling Beach House
- bedrooms 2
- community
- rental type Hotel
- sleeps 6
- baths 1
- rates (USD)
$140
- $220
/nt
$670 - $1,100 /wk
$2,412 - $3,960 /mth
Sunset Siesta
- bedrooms 2
- community
- rental type Condo
- sleeps 4
- baths 1
- rates (USD)
$850
- $1,250
/wk
$3,100 - $4,200 /mth
Full Gulf View, Beach, Tennis, Island Reef Condo
- bedrooms 2
- community Siesta Key
- rental type Condo
- sleeps 6
- baths 2
- rates (USD) $2,500 - $4,000 /mth
SPRING Special $100 OFF/week, Book Now!
- bedrooms 2
- community Sea Shell Condos
- rental type Condo
- sleeps 6
- baths 2
- rates (USD)
$142
- $256
/nt
$895 - $1,795 /wk
$3,980 - $6,780 /mth
Siesta Key Escape
- bedrooms 3
- community Twin Oak Park
- rental type House
- owner badge
- sleeps 6
- baths 3
- rates (USD)
$1,600
- $2,000
/wk
$4,500 - $5,000 /mth
Sunset Royale #206,JUST REMODELED! 2 bd 2 bath, ocean view
- bedrooms 2
- community 0
- rental type Condo
- owner badge
- sleeps 6
- baths 2
- rates (USD)
$749
- $1,249
/wk
Landau Vacation Beach Rentals
- bedrooms 2
- community Siesta Key
- rental type Condo
- sleeps 8
- baths 2
- rates (USD)
$800
- $1,400
/wk
Siesta Key-Crescent Beach -Midnight Cove I - 2 BDRs 2 Bath
- bedrooms 2
- community Midnight Cove I
- rental type Condo
- owner badge
- sleeps 6
- baths 2
- rates (USD)
$735
- $1,267
/wk
** Siesta Key #1 Beach in USA** WiFi & Pool
- bedrooms 2
- community The Casa Blanca
- rental type Villa
- sleeps 6
- baths 1
- rates (USD)
$120
- $172
/nt
$820 - $1,232 /wk
Palm Bay Club Private Beach 3 doors from pool,jacuzzi,fishin
- bedrooms 2
- community Palm Bay Club #310
- rental type Condo
- owner badge
- sleeps 6
- baths 2
- rates (USD)
$165
- $250
/nt
$850 - $1,600 /wk
$3,400 - $5,200 /mth
Great beach view Preferred Location
- bedrooms 2
- community La Siesta
- rental type Condo
- sleeps 6
- baths 2
- rates (USD)
$850
- $1,310
/wk
Siesta Key Beach House
- bedrooms 3
- community
- rental type House
- sleeps 7
- baths 2½
- rates (USD)
$1,000
- $1,450
/wk
Directly On The Beach & Walk To Village
- bedrooms 2
- community
- rental type Condo
- owner badge
- sleeps 5
- baths 2
- rates (USD)
$805
- $1,995
/wk
$2,635 - $5,000 /mth
Beachfront Condo - Full Gulf View - Updated Yearly
- bedrooms 1
- community Siesta Key
- rental type Condo
- sleeps 4
- baths 1
- rates (USD)
$629
- $1,029
/wk
luxury single story home private pool with all day sun
- bedrooms 3
- community
- rental type House
- owner badge
- sleeps 6
- baths 2
- rates (USD)
$220
- $300
/nt
$1,450 - $2,200 /wk
$4,800 - $6,750 /mth
Luxurious Gulf Condo - Short Walk to Siesta Beach
- bedrooms 2
- community White Sands Village
- rental type Condo
- sleeps 6
- baths 2
- rates (USD)
$450
- $1,050
/wk
$1,600 - $3,800 /mth
Best Prices at Siesta Key Comfort
- bedrooms 1
- community Sea Winds
- rental type Condo
- sleeps 4
- baths 1
- rates (USD)
$400
- $775
/wk
Siesta Key Home with Pool Near SK Village
- bedrooms 3
- community
- rental type House
- sleeps 8
- baths 2
- rates (USD)
$1,300
- $2,300
/wk
$3,900 - $6,100 /mth
Luxury Beachfront Siesta Key Condo #212 Beautiful Views
- bedrooms 2
- community Sunset Royale
- rental type Condo
- owner badge
- sleeps 6
- baths 2
- rates (USD)
$107
- $178
/nt
$749 - $1,249 /wk
Beautiful Siesta Key House
- bedrooms 5
- community
- rental type House
- sleeps 11
- baths 4
- rates (USD)
$500
- $600
/nt
$1,000 - $1,200 /wk
$3,500 - $5,000 /mth
Awesome Siesta Key Village Condo/Villa
- bedrooms 2
- community Navarra on the Key
- rental type Villa
- sleeps 5
- baths 2
- rates (USD)
$122
- $225
/nt
$850 - $1,150 /wk
$3,300 - $4,000 /mth
No Better Location for the Price
- bedrooms 1
- community
- rental type Condo
- sleeps 4
- baths 1
- rates (USD)
$655
- $959
/wk
Harbor Towers - Gulf and Bay Access
- bedrooms 2
- community
- rental type Condo
- owner badge
- sleeps 6
- baths 2
- rates (USD)
$650
- $1,000
/wk
Crescent Beach Condo
- bedrooms 1
- community Sea Crest on Siesta
- rental type Condo
- sleeps 4
- baths 1
- rates (USD)
$125
- $180
/nt
$675 - $990 /wk
Midnight Cove II Bayside #734
- bedrooms 2
- community Midnight Cove II Bay
- rental type Condo
- sleeps 5
- baths 1½
- rates (USD)
$150
- $250
/nt
$750 - $1,550 /wk
Next to the Best - Village 1 Bedroom Apartment
- bedrooms 1
- community
- rental type Apartment
- sleeps 2
- baths 1
- rates (USD)
$125
- $200
/nt
$550 - $900 /wk
$1,800 - $3,200 /mth
Next to the Best- Village 2 Bedroom Apartments
- bedrooms 2
- community
- rental type Apartment
- sleeps 4
- baths 2
- rates (USD)
$175
- $225
/nt
$750 - $1,400 /wk
Bay Oaks Hideway on Siesta Key
- bedrooms 2
- community Bay Oaks Condominium
- rental type Condo
- owner badge
- sleeps 6
- baths 2½
- rates (USD)
$750
- $850
/wk
$2,100 - $3,500 /mth
Bella Vista: Elegant Beachfront Condo - Full Gulf View
- bedrooms 2
- community Whispering Sands
- rental type Condo
- sleeps 4
- baths 2
- rates (USD) $3,600 - $5,800 /mth
2 Bedroom Penthouse On Crescent Beach
- bedrooms 2
- community Excelsior
- rental type Condo
- sleeps 6
- baths 2
- rates (USD)
$900
- $1,400
/wk
Our top location! Gertrude's Village House.
- bedrooms 3
- community Siesta Gardens
- rental type House
- sleeps 10
- baths 2
- rates (USD)
$240
- $600
/nt
$1,300 - $3,600 /wk
$3,700 - $9,200 /mth
Overlooking Private Beach Private Pool Home
- bedrooms 4
- community
- rental type House
- sleeps 11
- baths 2
- rates (USD)
$395
- $495
/nt
Breathtaking Views of Gulf!
- bedrooms 3
- community
- rental type House
- sleeps 8
- baths 2
- rates (USD)
$395
- $495
/nt
Cozy Cove
- bedrooms 2
- community Cozy Cove
- rental type Condo
- owner badge
- sleeps 4
- baths 2½
- rates (USD)
$96
- $164
/nt
$675 - $1,150 /wk
"A Beautiful Vacation at a Great Location" - MVProperties
- bedrooms 2
- community Sarasota- By-The-Sea
- rental type Villa
- owner badge
- sleeps 5
- baths 1
- rates (USD)
$650
- $1,100
/wk
$2,300 - $4,400 /mth
Lovely Beachside Villa with Pool, HDTV, WI-FI
- bedrooms 2
- community Gulf Haven
- rental type Villa
- sleeps 5
- baths 2
- rates (USD) $3,000 - $4,500 /mth
Private Tropical Key West Style
- bedrooms 3
- community
- rental type House
- sleeps 7
- baths 3½
- rates (USD)
$500
- $650
/nt
$1,500 - $2,000 /wk
$8,000 - $10,000 /mth
The Siesta Key Village Studio
- bedrooms 0
- community Siesta Key Village
- rental type Studio
- sleeps 2
- baths 1
- rates (USD)
$90
- $170
/nt
$440 - $650 /wk
$1,200 - $2,200 /mth
A true showplace-The Palm Island House
- bedrooms 4
- community
- rental type House
- sleeps 14
- baths 4
- rates (USD)
$310
- $490
/nt
$1,350 - $4,000 /wk
$5,400 - $13,000 /mth
47 Beach Road
- bedrooms 2
- community
- rental type Townhome
- sleeps 4
- baths 2
- rates (USD)
$190
- $250
/nt
$1,095 - $2,100 /wk
$4,400 - $6,900 /mth
643 Calle de Peru
- bedrooms 4
- community
- rental type House
- sleeps 8
- baths 3
- rates (USD)
$215
- $292
/nt
$1,300 - $1,750 /wk
Crescent Arms 204
- bedrooms 2
- community Crescent Arms
- rental type Condo
- sleeps 4
- baths 4
- rates (USD)
$147
- $242
/nt
$882 - $1,450 /wk
4638 Gleason Ave
- bedrooms 3
- community
- rental type House
- sleeps 8
- baths 2
- rates (USD)
$192
- $399
/nt
$1,150 - $2,394 /wk
$3,500 - $5,700 /mth
345 Avenida Leona
- bedrooms 3
- community
- rental type House
- sleeps 7
- baths 2
- rates (USD)
$135
- $250
/nt
$810 - $1,500 /wk
$2,900 - $4,700 /mth
Wow! Siesta Key -Best Beach! Gulfside 2 -Bdr - 2 Bath Condo
- bedrooms 2
- community Peppertree Bay
- rental type Condo
- sleeps 6
- baths 2
- rates (USD) $2,800 - $4,600 /mth
Midnight Cove II/Top Floor/Avail Summer Months
- bedrooms 2
- community Midnight Cove II
- rental type Condo
- owner badge
- sleeps 4
- baths 1½
- rates (USD)
$750
- $1,050
/wk
Siesta Key overlooking Private Beach
- bedrooms 1
- community
- rental type Apartment
- sleeps 4
- baths 1
- rates (USD)
$125
- $225
/nt
Peppertree Bay 6th Fl. Penthouse with Expansive Bay View!
- bedrooms 2
- community Peppertree Bay
- rental type Condo
- sleeps 4
- baths 2
- rates (USD) $2,795 - $4,195 /mth
Siesta Key Sunset, Beach/Gulf Front Rentals
- bedrooms 2
- community Fisherman's Cove
- rental type Condo
- sleeps 6
- baths 2
- rates (USD)
$175
- $279
/nt
$895 - $1,600 /wk
$3,580 - $6,400 /mth
Pet Friendly Siesta Key
- bedrooms 3
- community
- rental type House
- sleeps 8
- baths 3
- rates (USD)
$125
- $392
/nt
$750 - $2,350 /wk
$1,950 - $4,250 /mth
Harbor Towers 520
- bedrooms 2
- community Harbor Towers
- rental type Condo
- sleeps 6
- baths 2
- rates (USD)
$111
- $198
/nt
$656 - $1,188 /wk
Open the door to the #1 Beach- Siesta Key~
- bedrooms 2
- community Beach Way
- rental type Condo
- sleeps 4
- baths 2
- rates (USD) $5,000 - $5,000 /mth
Whispering Sands Unit #205
- bedrooms 2
- community Whispering Sands
- rental type Condo
- sleeps 5
- baths 2
- rates (USD) $2,100 - $5,200 /mth
Twin Palms Condos
- bedrooms 0
- community Twin Palms
- rental type Studio
- sleeps 2
- baths 1
- rates (USD)
$595
- $800
/wk
$1,100 - $2,550 /mth
Casa Mar
- bedrooms 0
- community Casa Mar
- rental type Studio
- sleeps 5
- baths 1
- rates (USD)
$675
- $800
/wk
$1,200 - $2,800 /mth
2 Bedroom Beautiful Bay View Fully Updated
- bedrooms 2
- community Midnight Cove 2
- rental type Condo
- owner badge
- sleeps 4
- baths 1½
- rates (USD)
$700
- $1,200
/wk
$1,000 - $4,450 /mth
6005 Midnight Pass Rd
- bedrooms 2
- community Provencial Gardens
- rental type Condo
- sleeps 4
- baths 2
- rates (USD)
$900
- $1,000
/wk
$3,200 - $3,200 /mth
Penthouse Gulf and Bay Views
- bedrooms 2
- community Anchorage
- rental type Condo
- sleeps 6
- baths 2
- rates (USD)
$975
- $1,395
/wk
Just Steps To Beautiful Crescent Beach
- bedrooms 2
- community Casa Mar
- rental type Condo
- sleeps 4
- baths 1
- rates (USD)
$1,150
- $1,300
/wk
8911 midnight pass rd
- bedrooms 2
- community sunrise cove yacht
- rental type Condo
- sleeps 4
- baths 2
- rates (USD) $2,240 - $4,200 /mth
Horizons West Gulf Front Full View 1 BR condo
- bedrooms 1
- community Horizons West
- rental type Condo
- sleeps 4
- baths 1
- rates (USD)
$1,430
- $1,430
/wk
Condo at Siesta Key Beach
- bedrooms 2
- community La Siesta Condos
- rental type House
- sleeps 4
- baths 1
- rates (USD)
$755
- $1,110
/wk
Siesta Key Condo in Beautiful Sarasota, Florida
- bedrooms 2
- community Anchorage
- rental type Condo
- sleeps 5
- baths 2
- rates (USD)
$852
- $1,226
/wk
Closest condo to Siesta Key Public Beach
- bedrooms 2
- community LaSiesta
- rental type Condo
- sleeps 4
- baths 1
- rates (USD) $3,000 - $4,500 /mth
1136 Peppertree Dr. #113
- bedrooms 2
- community Pepper Tree Bay
- rental type Condo
- sleeps 4
- baths 1½
- rates (USD) $2,500 - $4,800 /mth
Deals on Beautiful Siesta Key!
- bedrooms 2
- community Crescent Royale
- rental type Condo
- sleeps 5
- baths 2
- rates (USD)
$900
- $1,335
/wk
$2,400 - $3,600 /mth
Pepper Tree Bay
- bedrooms 2
- community Pepper Tree Bay
- rental type Condo
- owner badge
- sleeps 6
- baths 2
- rates (USD)
$750
- $1,100
/wk
$3,000 - $4,400 /mth
Luxury Vacation Rental in Siesta Key
- bedrooms 3
- community
- rental type House
- sleeps 8
- baths 2
- rates (USD) $6,000 - $7,500 /mth
2 Bdrm Condo on Beautiful Crescent Beach - Siesta Key, FL
- bedrooms 2
- community PepperTree Bay
- rental type Condo
- sleeps 4
- baths 2
- rates (USD)
$1,200
- $1,400
/wk
$3,750 - $5,000 /mth
Villa De Palmas
- bedrooms 2
- community Vista Hermosa
- rental type Villa
- owner badge
- sleeps 4
- baths 2
- rates (USD)
$575
- $900
/wk
Banana Bay Club- "Beachside & Waterside" Resorts
- bedrooms 0
- community
- rental type Studio
- sleeps 4
- baths 1
- rates (USD)
$70
- $588
/nt
$450 - $3,568 /wk
$1,600 - $14,272 /mth
Banana Bay Club "Beachside of the Road" Villas
- bedrooms 0
- community Siesta Key
- rental type Studio
- sleeps 4
- baths 1
- rates (USD)
$79
- $588
/nt
$499 - $3,568 /wk
$1,799 - $14,272 /mth
Banana Bay Club "Waterside" Resort on Heron Lagoon
- bedrooms 10
- community
- rental type Cottage
- sleeps 35
- baths 9
- rates (USD)
$70
- $329
/nt
$450 - $2,019 /wk
$1,600 - $8,075 /mth
Enjoy Your Siesta!
- bedrooms 2
- community
- rental type House
- sleeps 4
- baths 1
- rates (USD)
$130
- $170
/nt
$650 - $900 /wk
$1,900 - $2,300 /mth
Walk out onto beach -safe,family complex - 3 pools
- bedrooms 1
- community Jamaica Royale
- rental type House
- sleeps 1
- baths 1
- rates (USD)
$100
- $143
/nt
$700 - $1,000 /wk
$2,800 - $4,000 /mth
Siesta Key Bay Tree 106, 2 bedrooms, 2 heated pools, spa
- bedrooms 2
- community
- rental type Condo
- owner badge
- sleeps 6
- baths 2
- rates (USD)
$450
- $1,249
/wk
$1,930 - $5,185 /mth
Gulf and Bay Club 305C GulfView 3 pools, fitness room, spa,
- bedrooms 2
- community
- rental type Condo
- owner badge
- sleeps 6
- baths 2
- rates (USD)
$564
- $1,750
/wk
$2,417 - $7,252 /mth
Excelsior 107, 1st Floor, 2 heated pool, spa, wifi, beach ac
- bedrooms 2
- community
- rental type Condo
- owner badge
- sleeps 6
- baths 2
- rates (USD)
$563
- $1,499
/wk
$2,414 - $6,252 /mth
Crystal Sand 406, 4th floor, Gulf View, 2 heated Pools
- bedrooms 1
- community Crystal Sands
- rental type Condo
- sleeps 4
- baths 1
- rates (USD)
$450
- $1,249
/wk
$1,930 - $5,078 /mth
Clean & Contemporary Home on Grand Canal in Siesta Isles
- bedrooms 3
- community Siesta Isles
- rental type House
- sleeps 6
- baths 2
- rates (USD) $3,000 - $4,500 /mth
Beach Front Property Siesta Key Area
- bedrooms 2
- community FIshermans Cove
- rental type Condo
- sleeps 6
- baths 2
- rates (USD)
$1,120
- $1,745
/wk
Siesta:Ground floor-Big TV-King sized bed-screened lanai
- bedrooms 2
- community Midnight Cove II
- rental type Condo
- sleeps 4
- baths 1½
- rates (USD)
$700
- $1,100
/wk
Siesta Key 2BR 2Bath AFFORDABLE vista hermosa 1st floor
- bedrooms 2
- community Vista Hermosa
- rental type Condo
- sleeps 6
- baths 2
- rates (USD)
$650
- $950
/wk
Sunset Royale Luxury Condo - #310
- bedrooms 1
- community Sunset Royale
- rental type Condo
- sleeps 4
- baths 1
- rates (USD)
$799
- $1,099
/wk
Sunset Royale Luxury Condo #208
- bedrooms 1
- community Sunset Royale Assoc.
- rental type Condo
- sleeps 4
- baths 1
- rates (USD)
$799
- $1,099
/wk
Affordable relax in paradise= * * * BEACHAVEN * * *
- bedrooms 1
- community Beachaven Assoc.
- rental type Condo
- sleeps 4
- baths 1
- rates (USD)
$65
- $140
/nt
$455 - $980 /wk
$1,950 - $4,190 /mth
Fully Updated 2 Bedroom Condo at Tivoli by the Sea
- bedrooms 2
- community Tivoli By The Sea
- rental type Condo
- sleeps 4
- baths 2
- rates (USD)
$1,225
- $2,150
/wk
Heaven on earth (this is a new listing)
- bedrooms 2
- community Gulf Haven
- rental type Villa
- sleeps 6
- baths 2
- rates (USD)
$1,000
- $1,400
/wk
$3,000 - $4,600 /mth
Siesta Key Beach Villa
- bedrooms 1
- community Gulf and Bay Bayside
- rental type Condo
- sleeps 4
- baths 1½
- rates (USD)
$749
- $1,059
/wk
Beach Front Condo
- bedrooms 2
- community
- rental type Condo
- sleeps 6
- baths 2
- rates (USD) $3,500 - $6,000 /mth
Beautiful 2 bedroom Condo on Siesta Key
- bedrooms 2
- community Siesta Key
- rental type Condo
- sleeps 6
- baths 2
- rates (USD) $2,000 - $4,500 /mth
Luxury at it's Finest ! The Crescent on Siesta Key
- bedrooms 3
- community Crescent Siesta Key
- rental type Condo
- sleeps 6
- baths 2
- rates (USD)
$1,950
- $2,150
/wk
$9,000 - $9,750 /mth
Beach Front Condo
- bedrooms 2
- community Crescent Arms
- rental type Condo
- owner badge
- sleeps 5
- baths 2
- rates (USD)
$1,250
- $1,700
/wk
Direct Gulf Front Condo
- bedrooms 2
- community Sea Shell Condos
- rental type Condo
- sleeps 6
- baths 2
- rates (USD)
$995
- $1,695
/wk
Siesta Key Getaways
- bedrooms 2
- community Sarasota By The Sea
- rental type Villa
- sleeps 4
- baths 1
- rates (USD)
$700
- $1,200
/wk
Siesta Sands Beach Resort
- bedrooms 2
- community Siesta Sands
- rental type House
- sleeps 6
- baths 2
- rates (USD)
$85
- $400
/nt
$950 - $2,200 /wk
Gulf Haven
- bedrooms 2
- community Gulf Haven
- rental type Villa
- sleeps 6
- baths 2
- rates (USD) $2,770 - $4,515 /mth
Sun and Sea Island Hideaways-Tropical Bungalows
- bedrooms 2
- community Sarasota by the Sea
- rental type Condo
- owner badge
- sleeps 5
- baths 1
- rates (USD)
$650
- $1,495
/wk
Old Man & the Sea Inn 1BR- 1 marlin from the sand
- bedrooms 1
- community
- rental type House
- sleeps 4
- baths 1
- rates (USD)
$140
- $325
/nt
$900 - $1,700 /wk
$2,900 - $5,100 /mth
Island Living at its Best!
- bedrooms 2
- community Siesta Beach House
- rental type Condo
- sleeps 5
- baths 1
- rates (USD)
$250
- $390
/nt
$750 - $1,620 /wk
Old Man & the Sea Inn 2BR- 1 marlin from the sand
- bedrooms 2
- community
- rental type House
- sleeps 8
- baths 1
- rates (USD)
$190
- $470
/nt
$1,100 - $2,900 /wk
$3,300 - $6,600 /mth
Calini Beach Club
- bedrooms 2
- community Calini Beach Club
- rental type Condo
- sleeps 6
- baths 2
- rates (USD)
$120
- $260
/nt
$800 - $1,700 /wk
Gulf and Bay Club 409B Beach Front
- bedrooms 2
- community
- rental type Condo
- owner badge
- sleeps 6
- baths 2
- rates (USD)
$451
- $1,750
/wk
$1,933 - $7,285 /mth
Gulf View Condo, Sunset Royale on Siesta Key
- bedrooms 2
- community Sunset Royale
- rental type Condo
- sleeps 6
- baths 2
- rates (USD)
$1,016
- $1,690
/wk
3 Bedroom- Full Gulf Front- Ultimate Luxury!
- bedrooms 3
- community Hyatt Siesta Key
- rental type Condo
- sleeps 6
- baths 3
- rates (USD)
$630
- $770
/nt
$3,225 - $4,130 /wk
Beautiful Beachfront Unit at the Crescent
- bedrooms 3
- community Crescent
- rental type Condo
- sleeps 6
- baths 3
- rates (USD)
$640
- $800
/nt
$3,200 - $4,000 /wk
$11,000 - $13,000 /mth
Island House Penthouse on Siesta Key 5000 SqFt
- bedrooms 5
- community Island House
- rental type Condo
- sleeps 12
- baths 4
- rates (USD)
$2,600
- $4,000
/wk
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