Vacation Rentals in Siesta Key, Florida
Nightly rates from: $51* – Average nightly rate per bedroom: $74* – Deals available: 65
- bedrooms 6
- baths 6
-
rates (USD)
110
- 180
/nt
544 - 1,118 /wk
2,067 - 4,248 /mth
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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Check out more areas which feature homes, villas, cabins, cottages, or condos.
Siesta Key things to do
Robin Hood Rentals
Rented 2 bicycles for a month! He could not have been nicer making sure everything was the way we wanted it. He was competitive with other places however...read more
CaliFlorida Surf Shop & Rentals
CaliFlorida has the BEST local surf apparel and they will match any price for rentals on Siesta Key! A cool surf shop indeed!! ~FLIP~read more
Siesta Key Beach
This is a nice Gulf beach with gorgeous sand beaches, warm waters and a nice shopping area nearby. By far this is the best beach in the area.read more
The John & Mable Ringling Museum of Art
Amazing museum with ever evolving and rotating international exhibitions. Something for everyone ranging from the extensive Baroque collection through the...read more
Sarasota Bayfront Park
oh Island park. I don't go that often but it's a nice place to hang out if you have a dog and kids. It's always very calm and on occasion there will be a...read more
Lido Beach
This is my favorite beach in Sarasota. Really it is two separate beaches North Lido and South Lido. North Lido is great when you want to get away from all...read more
Longboat Key Club & Resort
This review is for the golf only. We did not stay at the hotel. I snuck in a round of golf on this trip even though I was with the in-law's side of the...read more
Lakewood Ranch Cinemas
The Burns Court Cinema's prettier, taller younger sister, basically. The staff is friendly. You can drink beer with your popcorn (with real butter) and...read more
AMC Sarasota 12
Very good seating. Place is clean. no sound interference from other theaters. Went to 5pm showing so didn't notice many teenage knuckle heads although I...read more
Smugglers Cove Adventure Golf
This place has a fun, creative course, but it is just too easy compared to other mini-golf courses. My three year old finished it in 20 minutes. The...read more
O'leary's Water Sports & Grill
I've been enjoying O'leary's for as long as I can remember. It's been there just as long if not longer than I've been around. I have never had a bad...read more
Sarasota Family YMCA
A solid YMCA. 25 yard pool, open weights, cardio, great group classes, the works. I've been enjoying this YMCA for a few months now every Wednesday...read more
Uppercut Boxing & Fitness
I came to Uppercut after taking my son to another boxing trainer in town. The other trainer never showed up. My son was scared to go in and felt hurt from...read more
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$1,000 off = $2,300 per month
- bedrooms 1
- community Harbor Towers
- rental type Condo
owner badge
- sleeps 4
- baths 1
- rates (USD)
$500
- $827
/wk
$2,000 - $3,308 /mth
-
FREE WiFi, Cable, Beach Chairs, Bikes
($150)
- bedrooms 3
- community
- rental type House
- sleeps 10
- baths 2
- rates (USD)
$1,100
- $1,700
/wk
$4,200 - $6,500 /mth
-
Free WiFi, Cable, Beach chairs
($99)
- bedrooms 2
- community
- rental type House
- sleeps 6
- baths 2
- rates (USD)
$900
- $1,500
/wk
$3,500 - $6,000 /mth
-
5% off = $950 per week
- 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
-
10% off = $1,033 per week
- bedrooms 2
- community Siesta Dunes
- rental type Townhome
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- sleeps 4
- baths 2
- rates (USD)
$695
- $2,295
/wk
$1,995 - $4,500 /mth
-
Beach Chairs, Beach Umbrella, Beach...
($99)
- bedrooms 2
- community White Sands Village
- rental type Condo
- sleeps 6
- baths 2
- rates (USD)
$65
- $132
/nt
$450 - $775 /wk
$1,600 - $3,600 /mth
-
10% off = $1,345 per week
- bedrooms 1
- community Palm Bay Club
- rental type Condo
- sleeps 4
- baths 1
- rates (USD)
$125
- $400
/nt
$695 - $1,795 /wk
-
10% off = $1,255 per week
- bedrooms 2
- community House of sun
- rental type Condo
- sleeps 6
- baths 2
- rates (USD)
$150
- $350
/nt
$650 - $1,595 /wk
$2,495 - $4,995 /mth
-
10% off = $1,255 per week
- bedrooms 2
- community Jamaica Royale
- rental type Condo
- sleeps 6
- baths 2
- rates (USD)
$200
- $350
/nt
$895 - $1,595 /wk
$2,495 - $4,995 /mth
-
10% off = $1,033 per week
- bedrooms 1
- community Crystal Sands
- rental type Condo
- sleeps 4
- baths 1
- rates (USD)
$100
- $175
/nt
$650 - $1,150 /wk
$2,495 - $4,500 /mth
-
FREE WIFI, Beach Chairs, Beach Cart
($99)
- bedrooms 2
- community Gulf & Bay Bayside
- rental type Townhome
owner badge
- sleeps 6
- baths 2
- rates (USD)
$141
- $194
/nt
$985 - $1,355 /wk
-
50% off = $1,250 per week
-
HBO & WI-FI
($150)
- bedrooms 3
- community Siesta Key Beach
- rental type Condo
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- sleeps 7
- baths 2
- rates (USD)
$99
- $199
/nt
$499 - $2,500 /wk
$1,500 - $4,800 /mth
-
$681 off = $1,015 per week
-
Free secured WiFi and Free beach chairs...
($199)
- bedrooms 2
- community Sea Shell
- rental type Condo
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- sleeps 6
- baths 2
- rates (USD)
$845
- $1,696
/wk
-
10% off = $540 per week
- bedrooms 1
- community Seawinds
- rental type Apartment
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- sleeps 4
- baths 1
- rates (USD)
$70
- $125
/nt
$450 - $760 /wk
$1,495 - $3,045 /mth
-
10% off = $823 per week
- bedrooms 2
- community Midnight Cove
- rental type Apartment
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- sleeps 5
- baths 1½
- rates (USD)
$84
- $158
/nt
$675 - $1,125 /wk
$2,140 - $4,000 /mth
-
10% off = $765 per week
- bedrooms 2
- community Bay Tree Club
- rental type Condo
- sleeps 4
- baths 2
- rates (USD)
$850
- $850
/wk
$3,400 - $3,900 /mth
-
Free WiFi, Free Cable
($99)
- bedrooms 2
- community Siesta Harbor
- rental type Condo
- sleeps 4
- baths 2
- rates (USD) $2,300 - $3,700 /mth
-
Free WiFi, Cable, Beach Chairs
($99)
- bedrooms 2
- community
- rental type Condo
- sleeps 6
- baths 2
- rates (USD)
$850
- $1,160
/wk
$3,400 - $4,640 /mth
-
Free WiFi, Free Cable
($89)
- bedrooms 2
- community Sea Shell Condos
- rental type Condo
- sleeps 6
- baths 2
- rates (USD)
$157
- $257
/nt
$1,095 - $1,795 /wk
-
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
-
10% off = $985 per week
-
Free WIFI, cable, bikes, beach needs
($300)
- bedrooms 3
- community
- rental type House
owner badge
- sleeps 6
- baths 2
- rates (USD)
$195
- $250
/nt
$1,095 - $1,295 /wk
$2,995 - $3,995 /mth
-
$25 off = $950 per week
-
wi fi
($20)
- bedrooms 2
- community
- rental type Cottage
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- sleeps 4
- baths 1
- rates (USD)
$125
- $175
/nt
$600 - $975 /wk
$1,800 - $3,400 /mth
-
free night valued at USD $95
-
WiFi,HBO/SHOWTIME,BCH CHAIRS+UMBRELLA
($199)
- bedrooms 0
- community Twin Palms
- rental type Studio
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- sleeps 2
- baths 1
- rates (USD)
$85
- $130
/nt
$510 - $780 /wk
$1,683 - $2,574 /mth
-
$100 off = $1,200 per week
- bedrooms 2
- community
- rental type Townhome
- sleeps 4
- baths 2
- rates (USD)
$800
- $1,300
/wk
-
Restaurant gift card
($50)
- bedrooms 2
- community
- rental type House
- sleeps 6
- baths 2
- rates (USD)
$750
- $990
/wk
-
Welcome gift
($45)
- bedrooms 2
- community
- rental type Apartment
- sleeps 4
- baths 1
- rates (USD)
$150
- $225
/nt
$900 - $1,400 /wk
$2,500 - $4,000 /mth
-
$100 off = $650 per week
- bedrooms 1
- community
- rental type Cottage
- sleeps 6
- baths 1
- rates (USD)
$600
- $1,800
/wk
-
$500 off = $1,300 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
-
$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
-
$200 off = $900 per week
- bedrooms 2
- community Peppertree Bay
- rental type Condo
owner badge
- sleeps 4
- baths 2
- rates (USD)
$1,100
- $1,300
/wk
$3,300 - $4,600 /mth
-
$100 off = $859 per week
- bedrooms 1
- community Sea Crest on Siesta
- rental type Condo
- sleeps 4
- baths 1
- rates (USD)
$122
- $175
/nt
$655 - $959 /wk
-
Housekeeping
($125)
- bedrooms 2
- community Excelsior Beach
- rental type Condo
- sleeps 6
- baths 2
- rates (USD)
$840
- $1,280
/wk
$3,960 - $5,120 /mth
-
$400 off = $1,245 per week
-
FREE WI-FI, Beach Chairs, Linens &...
($125)
- bedrooms 2
- community Fisherman's Cove
- rental type Condo
- sleeps 6
- baths 2
- rates (USD)
$1,020
- $1,645
/wk
-
$100 off = $635 per week
- bedrooms 2
- community Bay Oaks Condominium
- rental type Condo
- sleeps 6
- baths 2½
- rates (USD)
$735
- $810
/wk
$2,100 - $3,500 /mth
-
Internet, 40 movies, beach equipment,...
($150)
- bedrooms 2
- community Sarasota- By-The-Sea
- rental type Villa
- sleeps 6
- baths 1
- rates (USD)
$600
- $1,200
/wk
$2,300 - $4,700 /mth
-
10% off = $495 per week
- bedrooms 1
- community
- rental type Condo
- sleeps 4
- baths 1
- rates (USD)
$500
- $870
/wk
-
$100 off = $600 per week
- bedrooms 2
- community Pepper Tree Bay
- rental type Condo
owner badge
- sleeps 6
- baths 2
- rates (USD)
$700
- $1,000
/wk
$2,400 - $4,000 /mth
-
5% off = $712 per week
- bedrooms 2
- community White Sands Village
- rental type Condo
- sleeps 6
- baths 2
- rates (USD)
$450
- $925
/wk
$1,600 - $3,600 /mth
-
$70 off = $980 per week
-
Free WiFi, Free Laundry Room, Free Beach...
($150)
- bedrooms 2
- community Sarasota By The Sea
- rental type Villa
- sleeps 4
- baths 1
- rates (USD)
$700
- $1,200
/wk
-
10% off = $1,615 per week
- bedrooms 1
- community
- rental type Condo
owner badge
- sleeps 4
- baths 1
- rates (USD)
$125
- $400
/nt
$695 - $1,795 /wk
-
10% off = $1,255 per week
- bedrooms 2
- community
- rental type Condo
owner badge
- sleeps 6
- baths 1½
- rates (USD)
$95
- $250
/nt
$595 - $1,395 /wk
$1,995 - $3,995 /mth
-
10% off = $4,050 per month
- bedrooms 2
- community
- rental type Condo
owner badge
- sleeps 6
- baths 2
- rates (USD)
$93
- $322
/nt
$1,295 - $2,295 /wk
$2,495 - $4,500 /mth
-
10% off = $1,795 per week
- bedrooms 2
- community
- rental type Condo
owner badge
- sleeps 6
- baths 2
- rates (USD)
$150
- $400
/nt
$795 - $1,995 /wk
$2,995 - $5,995 /mth
-
10% off = $1,435 per week
- bedrooms 2
- community
- rental type House
owner badge
- sleeps 6
- baths 2
- rates (USD)
$150
- $350
/nt
$650 - $1,595 /wk
$2,495 - $4,995 /mth
-
10% off = $1,435 per week
- bedrooms 2
- community
- rental type Condo
owner badge
- sleeps 6
- baths 2
- rates (USD)
$150
- $350
/nt
$650 - $1,595 /wk
$2,495 - $4,995 /mth
-
10% off = $5,850 per month
- bedrooms 2
- community
- rental type Condo
owner badge
- sleeps 6
- baths 2
- rates (USD) $2,495 - $6,500 /mth
-
10% off = $5,850 per month
- bedrooms 2
- community
- rental type Condo
owner badge
- sleeps 6
- baths 2
- rates (USD) $2,495 - $6,500 /mth
-
10% off = $1,615 per week
- bedrooms 3
- community
- rental type House
owner badge
- sleeps 10
- baths 2
- rates (USD)
$150
- $400
/nt
$795 - $1,995 /wk
$3,500 - $4,500 /mth
- bedrooms 1
- community White Sands Village
- rental type Condo
- sleeps 4
- baths 1
- rates (USD)
$363
- $700
/wk
$1,300 - $3,200 /mth
- bedrooms 1
- community Sunset Royale
- rental type Condo
owner badge
- sleeps 2
- baths 1
- rates (USD)
$499
- $999
/wk
- bedrooms 2
- community Gulf Haven
- rental type Villa
owner badge
- sleeps 4
- baths 2
- rates (USD) $3,300 - $4,800 /mth
- bedrooms 1
- community Siesta Key Village
- rental type Apartment
owner badge
- sleeps 4
- baths 1
- rates (USD)
$600
- $825
/wk
- bedrooms 1
- community
- rental type Condo
- sleeps 6
- baths 1
- rates (USD)
$1,075
- $1,075
/wk
- bedrooms 1
- community Siesta Key
- rental type Condo
- sleeps 4
- baths 1
- rates (USD)
$700
- $1,000
/wk
- bedrooms 2
- community Navarra on the Key
- rental type Villa
- sleeps 5
- baths 1
- rates (USD)
$1,050
- $1,250
/wk
$3,600 - $4,500 /mth
- bedrooms 2
- community Peppertree Bay
- rental type Condo
- sleeps 6
- baths 2
- rates (USD) $2,200 - $3,990 /mth
- bedrooms 2
- community Fisherman's Cove
- rental type Condo
- sleeps 6
- baths 2
- rates (USD)
$1,045
- $1,645
/wk
- bedrooms 2
- community Fisherman's Cove
- rental type Condo
owner badge
- sleeps 6
- baths 2
- rates (USD)
$1,045
- $1,645
/wk
- bedrooms 3
- community Fisherman's Cove
- rental type Condo
- sleeps 8
- baths 2
- rates (USD)
$1,545
- $2,095
/wk
- bedrooms 3
- community Fisherman's Cove
- rental type Condo
owner badge
- sleeps 8
- baths 2
- rates (USD)
$1,545
- $2,095
/wk
- bedrooms 1
- community Fisherman's Cove
- rental type Condo
- sleeps 4
- baths 1
- rates (USD)
$790
- $1,290
/wk
- bedrooms 4
- community Seista Key Village
- rental type Townhome
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- sleeps 12
- baths 3½
- rates (USD)
$2,120
- $2,945
/wk
- bedrooms 3
- community
- rental type Villa
owner badge
- sleeps 8
- baths 3
- rates (USD)
$600
- $2,050
/wk
- bedrooms 1
- community Siesta Key Village
- rental type Villa
owner badge
- sleeps 4
- baths 1
- rates (USD)
$625
- $900
/wk
- bedrooms 2
- community Siesta Breakers
- rental type Condo
- sleeps 6
- baths 2
- rates (USD)
$1,288
- $1,911
/wk
- bedrooms 1
- community Sunset Royale
- rental type Condo
owner badge
- sleeps 3
- baths 1
- rates (USD)
$100
- $157
/nt
$699 - $1,099 /wk
- bedrooms 2
- community Palm Bay Club
- rental type Condo
- sleeps 6
- baths 2
- rates (USD)
$1,075
- $1,950
/wk
- bedrooms 2
- community Fisherman's Cove
- rental type Condo
- sleeps 6
- baths 2
- rates (USD)
$1,045
- $1,645
/wk
- bedrooms 2
- community Palm Bay Club #310
- rental type Condo
owner badge
- sleeps 6
- baths 2
- rates (USD)
$135
- $250
/nt
$850 - $1,600 /wk
$3,400 - $4,800 /mth
- bedrooms 3
- community Sarasota Beach
- rental type House
owner badge
- sleeps 9
- baths 2½
- rates (USD)
$220
- $350
/nt
$2,000 - $2,500 /wk
$6,800 - $6,800 /mth
- bedrooms 2
- community Peppertree Bay
- rental type Condo
- sleeps 6
- baths 2
- rates (USD) $2,800 - $4,600 /mth
- bedrooms 0
- community Casa Mar
- rental type Studio
- sleeps 3
- baths 1
- rates (USD)
$595
- $756
/wk
$1,200 - $2,722 /mth
- bedrooms 3
- community Siesta Key Village
- rental type Apartment
- sleeps 10
- baths 3
- rates (USD)
$1,350
- $1,845
/wk
- bedrooms 2
- community Siesta Village
- rental type Apartment
owner badge
- sleeps 6
- baths 2
- rates (USD)
$885
- $1,210
/wk
- bedrooms 2
- community Crescent Arms
- rental type Condo
- sleeps 6
- baths 2
- rates (USD)
$1,325
- $1,725
/wk
- bedrooms 3
- community Siesa Key Beach
- rental type Townhome
- sleeps 8
- baths 2½
- rates (USD)
$1,495
- $2,045
/wk
- bedrooms 3
- community
- rental type Townhome
owner badge
- sleeps 8
- baths 2½
- rates (USD)
$1,400
- $2,050
/wk
- bedrooms 2
- community
- rental type House
- sleeps 6
- baths 2½
- rates (USD)
$1,275
- $1,600
/wk
- bedrooms 2
- community Midnight Cove II
- rental type Condo
owner badge
- sleeps 4
- baths 1½
- rates (USD)
$700
- $1,200
/wk
$1,000 - $4,450 /mth
- bedrooms 2
- community Palm Bay Club
- rental type Condo
owner badge
- sleeps 6
- baths 2
- rates (USD)
$850
- $1,600
/wk
- bedrooms 1
- community
- rental type Apartment
- sleeps 4
- baths 1
- rates (USD)
$99
- $199
/nt
- 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
- bedrooms 2
- community Sunset Royale
- rental type Condo
- sleeps 4
- baths 2
- rates (USD)
$599
- $1,165
/wk
- bedrooms 2
- community Midnight Cove I
- rental type Condo
owner badge
- sleeps 6
- baths 2
- rates (USD)
$600
- $1,200
/wk
- bedrooms 2
- community Sunset Royale # 314
- rental type Condo
owner badge
- sleeps 5
- baths 2
- rates (USD)
$114
- $189
/nt
$799 - $1,325 /wk
- bedrooms 3
- community
- rental type Villa
- sleeps 8
- baths 4½
- rates (USD)
$2,890
- $2,890
/wk
$6,500 - $6,500 /mth
- bedrooms 2
- community Casa Blanca
- rental type Villa
- sleeps 6
- baths 1
- rates (USD)
$120
- $160
/nt
$820 - $1,120 /wk
- bedrooms 2
- community Seashell Condos
- rental type Condo
owner badge
- sleeps 6
- baths 2
- rates (USD)
$150
- $250
/nt
$1,050 - $1,650 /wk
- bedrooms 2
- community Island Reef Condo
- rental type Condo
- sleeps 4
- baths 2
- rates (USD) $4,000 - $5,600 /mth
- bedrooms 2
- community Siesta Key Beach
- rental type Condo
owner badge
- sleeps 5
- baths 1½
- rates (USD)
$215
- $285
/nt
$1,495 - $1,995 /wk
$4,995 - $6,995 /mth
- bedrooms 2
- community Beach Way
- rental type Condo
- sleeps 4
- baths 2
- rates (USD) $5,000 - $5,000 /mth
- bedrooms 3
- community
- rental type House
- sleeps 6
- baths 2
- rates (USD)
$1,500
- $2,000
/wk
$3,750 - $5,000 /mth
- bedrooms 4
- community
- rental type Hotel
- sleeps 14
- baths 4
- rates (USD)
$105
- $150
/nt
$544 - $1,118 /wk
$2,067 - $4,248 /mth
- bedrooms 20
- community
- rental type Hotel
- sleeps 30
- baths 15½
- rates (USD)
$85
- $210
/nt
$404 - $1,521 /wk
$1,535 - $5,779 /mth
- bedrooms 1
- community
- rental type Condo
- sleeps 4
- baths 1
- rates (USD)
$110
- $135
/nt
$713 - $972 /wk
$2,790 - $3,693 /mth
- bedrooms 6
- community
- rental type Condo
- sleeps 20
- baths 6
- rates (USD)
$110
- $180
/nt
$544 - $1,118 /wk
$2,067 - $4,248 /mth
- bedrooms 2
- community House of Sun Condos
- rental type Condo
- sleeps 6
- baths 2
- rates (USD)
$150
- $250
/nt
$1,050 - $1,650 /wk
- bedrooms 2
- community Midnight Cove II
- rental type Condo
owner badge
- sleeps 6
- baths 1½
- rates (USD)
$650
- $1,150
/wk
- bedrooms 3
- community Twin Oak Park
- rental type House
owner badge
- sleeps 8
- baths 3
- rates (USD)
$1,600
- $2,000
/wk
$4,500 - $5,000 /mth
- bedrooms 3
- community
- rental type Villa
- sleeps 8
- baths 2
- rates (USD)
$1,600
- $2,950
/wk
$6,400 - $11,900 /mth
- bedrooms 4
- community Siesta Bayfront
- rental type House
- sleeps 10
- baths 2
- rates (USD)
$1,800
- $2,200
/wk
$5,700 - $7,000 /mth
- bedrooms 2
- community
- rental type House
owner badge
- sleeps 4
- baths 1
- rates (USD)
$950
- $1,250
/wk
- bedrooms 3
- community
- rental type House
owner badge
- sleeps 8
- baths 2
- rates (USD)
$1,150
- $1,550
/wk
- bedrooms 2
- community Vista Hermosa
- rental type Villa
owner badge
- sleeps 4
- baths 2
- rates (USD)
$575
- $900
/wk
- bedrooms 2
- community Our House at Beach
- rental type Condo
owner badge
- sleeps 6
- baths 2
- rates (USD)
$910
- $1,240
/wk
- bedrooms 2
- community Fisherman's Cove
- rental type Condo
owner badge
- sleeps 6
- baths 2
- rates (USD)
$1,020
- $1,645
/wk
- bedrooms 2
- community El Presidente
- rental type Condo
- sleeps 6
- baths 2
- rates (USD)
$1,150
- $1,975
/wk
- bedrooms 2
- community Midnight Cove
- rental type Condo
- sleeps 4
- baths 2
- rates (USD)
$1,200
- $1,600
/wk
- bedrooms 2
- community
- rental type Townhome
- sleeps 4
- baths 2
- rates (USD)
$200
- $400
/nt
$2,000 - $3,000 /wk
$5,000 - $7,000 /mth
- bedrooms 2
- community Siesta Dunes
- rental type Condo
owner badge
- sleeps 6
- baths 2
- rates (USD)
$1,325
- $1,795
/wk
- bedrooms 2
- community Anchorage
- rental type Condo
- sleeps 5
- baths 2
- rates (USD)
$852
- $1,226
/wk
- bedrooms 1
- community Mira Mar
- rental type Apartment
owner badge
- sleeps 4
- baths 1
- rates (USD)
$125
- $145
/nt
$799 - $799 /wk
$1,700 - $2,800 /mth
- bedrooms 1
- community
- rental type House
- sleeps 4
- baths 1
- rates (USD)
$125
- $199
/nt
$749 - $1,199 /wk
$1,700 - $2,800 /mth
- bedrooms 2
- community Crescent Arms
- rental type Condo
owner badge
- sleeps 6
- baths 2
- rates (USD)
$995
- $1,950
/nt
$995 - $1,850 /wk
- bedrooms 2
- community Siesta Key
- rental type Condo
- sleeps 6
- baths 2
- rates (USD)
$850
- $1,325
/wk
$2,550 - $5,035 /mth
- bedrooms 3
- community
- rental type Villa
owner badge
- sleeps 10
- baths 2½
- rates (USD)
$1,250
- $1,900
/wk
$3,600 - $6,000 /mth
- bedrooms 2
- community Sunset Royale
- rental type Condo
owner badge
- sleeps 6
- baths 2
- rates (USD)
$114
- $189
/nt
$799 - $1,325 /wk
- bedrooms 4
- community Aloha Kai
- rental type Villa
owner badge
- sleeps 8
- baths 2
- rates (USD)
$1,995
- $3,095
/wk
- bedrooms 2
- community
- rental type House
- sleeps 4
- baths 2
- rates (USD)
$800
- $1,200
/wk
$3,400 - $4,000 /mth
- bedrooms 2
- community Peppertree Bay
- rental type Condo
- sleeps 4
- baths 2
- rates (USD) $2,300 - $3,900 /mth
- bedrooms 2
- community Fisherman's Cove
- rental type Condo
- sleeps 6
- baths 2
- rates (USD)
$1,020
- $1,650
/wk
- bedrooms 2
- community Midnight Cove
- rental type Condo
owner badge
- sleeps 4
- baths 1½
- rates (USD)
$560
- $1,492
/wk
$1,895 - $3,821 /mth
- bedrooms 2
- community Siesta Breakers
- rental type Condo
owner badge
- sleeps 6
- baths 2
- rates (USD)
$840
- $2,140
/wk
$2,939 - $5,605 /mth
- bedrooms 2
- community Midnight Cove
- rental type Condo
owner badge
- sleeps 4
- baths 1½
- rates (USD)
$560
- $1,491
/wk
$1,895 - $3,590 /mth
- bedrooms 2
- community Gulf Haven
- rental type Villa
- sleeps 5
- baths 2
- rates (USD) $2,600 - $4,300 /mth
- bedrooms 4
- community
- rental type House
- sleeps 11
- baths 2
- rates (USD)
$395
- $495
/nt
- bedrooms 3
- community
- rental type House
owner badge
- sleeps 6
- baths 2
- rates (USD)
$1,500
- $2,100
/wk
$4,800 - $6,700 /mth
- bedrooms 3
- community Siesta Isles
- rental type House
- sleeps 6
- baths 2
- rates (USD) $3,000 - $4,500 /mth
- bedrooms 2
- community Crescent Royale
- rental type Condo
- sleeps 4
- baths 2
- rates (USD)
$1,100
- $1,550
/wk
$4,200 - $5,500 /mth
- bedrooms 4
- community
- rental type House
- sleeps 10
- baths 3
- rates (USD)
$1,800
- $2,200
/wk
$5,700 - $7,000 /mth
- bedrooms 2
- community Sea Shell Condos
- rental type Condo
- sleeps 6
- baths 2
- rates (USD)
$140
- $240
/nt
$895 - $1,695 /wk
$3,180 - $6,780 /mth
- bedrooms 2
- community Peppertree Bay
- rental type Condo
- sleeps 4
- baths 2
- rates (USD) $2,595 - $3,995 /mth
- bedrooms 2
- community Peppertree
- rental type Condo
- sleeps 5
- baths 2
- rates (USD)
$875
- $1,150
/wk
$3,500 - $4,600 /mth
- bedrooms 2
- community La Siesta
- rental type Condo
- sleeps 6
- baths 2
- rates (USD)
$825
- $1,210
/wk
- bedrooms 2
- community Island Reef
- rental type Condo
- sleeps 6
- baths 2
- rates (USD)
$200
- $350
/nt
$1,400 - $1,500 /wk
$2,800 - $4,500 /mth
- bedrooms 3
- community
- rental type House
owner badge
- sleeps 6
- baths 2
- rates (USD)
$240
- $300
/nt
$1,400 - $1,600 /wk
$4,800 - $6,500 /mth
- bedrooms 1
- community Sea Winds
- rental type Condo
- sleeps 4
- baths 1
- rates (USD)
$400
- $775
/wk
- bedrooms 2
- community Cozy Cove
- rental type Condo
owner badge
- sleeps 4
- baths 2½
- rates (USD)
$96
- $164
/nt
$675 - $1,150 /wk
- bedrooms 2
- community La Siesta
- rental type Condo
owner badge
- sleeps 6
- baths 1
- rates (USD)
$800
- $1,110
/wk
- bedrooms 3
- community
- rental type House
- sleeps 7
- baths 2½
- rates (USD)
$1,000
- $1,250
/wk
- bedrooms 2
- community Harbor Tower
- rental type Condo
- sleeps 4
- baths 2
- rates (USD)
$1,095
- $1,100
/wk
- bedrooms 2
- community LaSiesta
- rental type Condo
- sleeps 4
- baths 1
- rates (USD)
$755
- $1,110
/wk
- bedrooms 1
- community
- rental type Condo
- sleeps 4
- baths 1
- rates (USD)
$655
- $959
/wk
- bedrooms 2
- community Navarra On The Key
- rental type Villa
- sleeps 6
- baths 1
- rates (USD)
$160
- $240
/nt
$800 - $1,100 /wk
$2,500 - $3,800 /mth
- bedrooms 2
- community Whispering Sands
- rental type Condo
- sleeps 4
- baths 2
- rates (USD) $3,600 - $5,800 /mth
- bedrooms 2
- community Vista Hermosa
- rental type Condo
- sleeps 5
- baths 2
- rates (USD)
$650
- $1,000
/wk
- bedrooms 0
- community Casa Mar
- rental type Studio
- sleeps 5
- baths 1
- rates (USD)
$675
- $800
/wk
$1,200 - $2,800 /mth
- bedrooms 2
- community Siesta Key
- rental type Condo
- sleeps 8
- baths 2
- rates (USD)
$750
- $1,350
/wk
- bedrooms 3
- community Crescent Royale
- rental type Condo
- sleeps 8
- baths 3
- rates (USD)
$246
- $304
/nt
$1,722 - $2,131 /wk
- bedrooms 2
- community Jamaica Royale
- rental type Condo
- sleeps 6
- baths 2
- rates (USD)
$1,568
- $1,960
/wk
- bedrooms 3
- community
- rental type Cottage
owner badge
- sleeps 6
- baths 2
- rates (USD)
$100
- $180
/nt
$800 - $1,200 /wk
$3,500 - $4,000 /mth
- bedrooms 2
- community FIshermans Cove
- rental type Condo
- sleeps 6
- baths 2
- rates (USD)
$950
- $1,650
/wk
- bedrooms 2
- community
- rental type Condo
owner badge
- sleeps 6
- baths 2
- rates (USD)
$650
- $1,000
/wk
- bedrooms 2
- community
- rental type House
- sleeps 4
- baths 1
- rates (USD)
$130
- $170
/nt
$650 - $900 /wk
$1,900 - $2,300 /mth
- bedrooms 2
- community Casa Blanca
- rental type Villa
- sleeps 6
- baths 2
- rates (USD)
$880
- $1,250
/wk
- bedrooms 2
- community 0
- rental type Condo
owner badge
- sleeps 6
- baths 2
- rates (USD)
$799
- $1,325
/wk
- bedrooms 2
- community Midnight Cove II
- rental type Condo
- sleeps 4
- baths 1½
- rates (USD)
$700
- $1,100
/wk
- bedrooms 2
- community Fisherman's Cove
- rental type Condo
- sleeps 6
- baths 2
- rates (USD)
$145
- $235
/nt
$1,020 - $1,650 /wk
$3,468 - $6,251 /mth
- bedrooms 2
- community Siesta Dunes
- rental type Condo
owner badge
- sleeps 6
- baths 2
- rates (USD)
$1,080
- $1,494
/wk
- bedrooms 2
- community Vista Hermosa
- rental type Condo
- sleeps 6
- baths 2
- rates (USD)
$650
- $950
/wk
- bedrooms 2
- community Excelsior Beach
- rental type Condo
- sleeps 4
- baths 2
- rates (USD)
$900
- $1,380
/wk
$3,600 - $5,520 /mth
- bedrooms 2
- community
- rental type Condo
- sleeps 5
- baths 2
- rates (USD)
$150
- $250
/nt
$800 - $1,400 /wk
$2,800 - $5,320 /mth
- bedrooms 1
- community La Siesta Condos
- rental type Condo
- sleeps 3
- baths 1
- rates (USD)
$715
- $1,210
/wk
- bedrooms 3
- community Twin Oak Pond
- rental type House
owner badge
- sleeps 7
- baths 3½
- rates (USD)
$1,500
- $2,000
/wk
$4,500 - $5,500 /mth
- bedrooms 2
- community Casa Blanca
- rental type Villa
owner badge
- sleeps 4
- baths 2
- rates (USD)
$125
- $195
/nt
$880 - $1,267 /wk
$2,640 - $4,920 /mth
- bedrooms 2
- community The Moorings
- rental type Condo
- sleeps 4
- baths 2
- rates (USD)
$900
- $1,200
/wk
$2,100 - $3,950 /mth
- bedrooms 2
- community Midnight Cove II
- rental type Condo
owner badge
- sleeps 4
- baths 1½
- rates (USD)
$750
- $1,115
/wk
- bedrooms 2
- community Fisherman's Cove
- rental type Condo
- sleeps 6
- baths 2
- rates (USD)
$1,000
- $1,650
/wk
- bedrooms 2
- community House of the Sun
- rental type House
- sleeps 6
- baths 2
- rates (USD)
$1,400
- $2,000
/wk
- bedrooms 3
- community Gulf & Bay Club Bays
- rental type Townhome
- sleeps 6
- baths 2
- rates (USD)
$1,225
- $1,975
/wk
$3,300 - $5,000 /mth
- bedrooms 2
- community White Sands Village
- rental type Condo
- sleeps 6
- baths 2
- rates (USD)
$450
- $950
/wk
$1,600 - $3,600 /mth
- bedrooms 2
- community Gulf and Bay Bayside
- rental type Townhome
- sleeps 6
- baths 2
- rates (USD)
$895
- $1,231
/wk
- bedrooms 2
- community sunrise cove yacht
- rental type Condo
- sleeps 4
- baths 2
- rates (USD)
$80
- $178
/nt
$480 - $1,640 /wk
$2,268 - $4,200 /mth
- bedrooms 2
- community Siesta Key
- rental type Condo
- sleeps 6
- baths 2
- rates (USD) $2,500 - $4,000 /mth
- bedrooms 2
- community PepperTree Bay
- rental type Condo
- sleeps 4
- baths 2
- rates (USD)
$1,200
- $1,400
/wk
$3,750 - $5,000 /mth
- bedrooms 2
- community Crescent Royale
- rental type Condo
- sleeps 4
- baths 2
- rates (USD)
$913
- $1,335
/wk
- bedrooms 2
- community Sunset Royale Assoc.
- rental type Condo
- sleeps 6
- baths 2
- rates (USD)
$799
- $1,325
/wk
- bedrooms 1
- community Sunset Royale
- rental type Condo
- sleeps 4
- baths 1
- rates (USD)
$799
- $1,099
/wk
- bedrooms 1
- community Sunset Royale Assoc.
- rental type Condo
- sleeps 4
- baths 1
- rates (USD)
$799
- $1,099
/wk
- bedrooms 1
- community Sunset Royale Assoc.
- rental type Condo
- sleeps 4
- baths 1
- rates (USD)
$799
- $1,099
/wk
- bedrooms 2
- community Island Reef
- rental type Condo
- sleeps 6
- baths 2
- rates (USD) $1,600 - $3,200 /mth
- bedrooms 2
- community Whispering Sands
- rental type Condo
- sleeps 4
- baths 2
- rates (USD) $2,000 - $3,500 /mth
- bedrooms 2
- community Island Reef
- rental type Condo
- sleeps 6
- baths 2
- rates (USD) $2,500 - $5,000 /mth
- bedrooms 2
- community Our House @the Beach
- rental type Condo
- sleeps 6
- baths 2
- rates (USD)
$965
- $1,395
/wk
- bedrooms 3
- community
- rental type House
- sleeps 6
- baths 2
- rates (USD)
$1
- $1
/nt
$1,500 - $1,500 /wk
$5,300 - $5,300 /mth
- bedrooms 2
- community Siesta Sands
- rental type Condo
- sleeps 6
- baths 2
- rates (USD)
$1,250
- $2,175
/wk
- bedrooms 2
- community Siesta Sands
- rental type House
- sleeps 6
- baths 2
- rates (USD)
$1,250
- $2,175
/wk
- bedrooms 2
- community Siesta Sands
- rental type Condo
- sleeps 6
- baths 2
- rates (USD)
$1,250
- $2,175
/wk
- bedrooms 1
- community La Siesta
- rental type Condo
- sleeps 4
- baths 1
- rates (USD)
$650
- $1,010
/wk
$2,700 - $3,975 /mth
- bedrooms 2
- community Crystal Sands
- rental type Condo
- sleeps 6
- baths 2
- rates (USD)
$240
- $400
/nt
$1,300 - $2,100 /wk
- bedrooms 2
- community Crystal Sands
- rental type Condo
- sleeps 6
- baths 2
- rates (USD)
$1,300
- $2,100
/wk
- 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
- bedrooms 2
- community Peppertree Bay
- rental type Condo
- sleeps 5
- baths 2
- rates (USD)
$850
- $1,200
/wk
$2,500 - $4,200 /mth
- bedrooms 2
- community Crescent Arms
- rental type Condo
- sleeps 4
- baths 2
- rates (USD)
$850
- $1,495
/wk
- bedrooms 0
- community Twin Palms
- rental type Studio
- sleeps 2
- baths 1
- rates (USD)
$595
- $800
/wk
$1,100 - $2,550 /mth
- bedrooms 1
- community Horizons West
- rental type Condo
- sleeps 4
- baths 1
- rates (USD)
$1,430
- $1,430
/wk
- bedrooms 2
- community Gulf Haven
- rental type Villa
- sleeps 6
- baths 2
- rates (USD)
$1,000
- $1,400
/wk
$3,000 - $4,600 /mth
- bedrooms 1
- community Gulf and Bay Bayside
- rental type Condo
- sleeps 4
- baths 1½
- rates (USD)
$749
- $1,059
/wk
- bedrooms 2
- community Casa Mar
- rental type Condo
- sleeps 4
- baths 1
- rates (USD)
$1,150
- $1,300
/wk
- bedrooms 1
- community
- rental type Cottage
- sleeps 35
- baths 9
- rates (USD)
$70
- $299
/nt
$350 - $1,799 /wk
$1,200 - $7,196 /mth
- bedrooms 3
- community Navarra on the Key
- rental type Condo
- sleeps 6
- baths 2
- rates (USD)
$125
- $190
/nt
$850 - $1,300 /wk
$2,400 - $4,500 /mth
- bedrooms 2
- community
- rental type House
- sleeps 4
- baths 2
- rates (USD) $2,800 - $4,000 /mth
- bedrooms 2
- community
- rental type Condo
- sleeps 6
- baths 2
- rates (USD) $3,500 - $6,000 /mth
- bedrooms 2
- community Siesta Breakers
- rental type Condo
- sleeps 5
- baths 2
- rates (USD)
$1,200
- $1,800
/wk
- bedrooms 2
- community Anchorage
- rental type Condo
- sleeps 6
- baths 2
- rates (USD)
$975
- $1,395
/wk
- bedrooms 2
- community Siesta Key
- rental type Condo
- sleeps 6
- baths 2
- rates (USD) $2,000 - $4,500 /mth
- bedrooms 2
- community Excelsior
- rental type Condo
- sleeps 6
- baths 2
- rates (USD)
$900
- $1,400
/wk
- bedrooms 3
- community Crescent Siesta Key
- rental type Condo
- sleeps 6
- baths 2
- rates (USD)
$265
- $285
/nt
$1,950 - $2,000 /wk
- bedrooms 3
- community Black Burn Harbor
- rental type Condo
- sleeps 6
- baths 2
- rates (USD) $1,500 - $3,500 /mth
- bedrooms 2
- community Crescent Arms
- rental type Condo
- sleeps 5
- baths 2
- rates (USD)
$1,250
- $1,700
/wk
- bedrooms 2
- community Beach Villas
- rental type Condo
- sleeps 6
- baths 2
- rates (USD)
$1,350
- $1,850
/wk
- bedrooms 2
- community Siesta Sands
- rental type House
- sleeps 6
- baths 2
- rates (USD)
$85
- $400
/nt
$950 - $2,200 /wk
- bedrooms 2
- community Midnight Cove II
- rental type Condo
- sleeps 4
- baths 1½
- rates (USD)
$700
- $1,050
/wk
- bedrooms 3
- community
- rental type House
- sleeps 8
- baths 2
- rates (USD)
$1,150
- $1,750
/wk
$3,750 - $5,250 /mth
- bedrooms 2
- community Gulf Haven
- rental type Villa
- sleeps 6
- baths 2
- rates (USD) $2,770 - $4,515 /mth
- bedrooms 2
- community Sarasota by the Sea
- rental type Condo
owner badge
- sleeps 5
- baths 1
- rates (USD)
$625
- $1,450
/wk
- bedrooms 0
- community
- rental type Studio
- sleeps 50
- baths 1
- rates (USD)
$70
- $349
/nt
$349 - $2,099 /wk
$1,200 - $8,396 /mth
- bedrooms 0
- community Siesta Key
- rental type Studio
- sleeps 50
- baths 1
- rates (USD)
$79
- $349
/nt
$399 - $2,099 /wk
$1,399 - $8,396 /mth
- bedrooms 2
- community Siesta Beach House
- rental type Condo
- sleeps 5
- baths 1
- rates (USD)
$117
- $135
/nt
$600 - $900 /wk
- bedrooms 2
- community Polynesian Gardens
- rental type House
- sleeps 4
- baths 1½
- rates (USD) $3,200 - $3,200 /mth
- bedrooms 2
- community Calini Beach Club
- rental type Condo
- sleeps 6
- baths 2
- rates (USD)
$120
- $260
/nt
$800 - $1,700 /wk
- bedrooms 2
- community Fisherman's Cove
- rental type Condo
- sleeps 6
- baths 2
- rates (USD)
$183
- $279
/nt
$790 - $1,600 /wk
$3,160 - $6,400 /mth
- bedrooms 2
- community Peppertree Bay
- rental type Condo
- sleeps 6
- baths 2
- rates (USD) $3,900 - $4,200 /mth
- bedrooms 2
- community Peppertree Bay
- rental type Condo
- sleeps 4
- baths 2
- rates (USD) $3,000 - $4,500 /mth
- bedrooms 3
- community Hyatt Siesta Key
- rental type Condo
- sleeps 6
- baths 3
- rates (USD)
$630
- $770
/nt
$3,225 - $4,130 /wk
- bedrooms 3
- community
- rental type Townhome
- sleeps 6
- baths 3½
- rates (USD)
$120
- $415
/nt
$700 - $2,900 /wk
- 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
- bedrooms 5
- community Island House
- rental type Condo
- sleeps 12
- baths 4
- rates (USD)
$358
- $572
/nt
$2,500 - $4,000 /wk





