Vacation rentals with a pool in Longboat Key
Find and book unique homes with a pool on Airbnb
Top-rated rentals with a pool in Longboat Key
Guests agree: these homes with a pool are highly rated for location, cleanliness, and more.
Vacation rentals for every style
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Popular amenities for Longboat Key rentals with a pool
House rentals with a pool
Home in Bradenton Beach
4.97 out of 5 average rating, 153 reviewsParadise! Steps2 Private Beach & Tropical Yard!
Dec. 7 – 14
Home in Holmes Beach
4.95 out of 5 average rating, 158 reviewsSet AMI
Nov. 11 – 18
Home in Sarasota
4.91 out of 5 average rating, 11 reviewsFruit /Botanical Garden Estate 2 miles to downtown
May 6 – 13
Home in Longboat Key
5.0 out of 5 average rating, 7 reviewsZilli Villa, a 2,000 sf home right on the beach.
Dec. 7 – 14
Home in Sarasota
5.0 out of 5 average rating, 12 reviewsWalk to Lido Beach &St. Armands -grill/HEATED POOL
Nov. 12 – 19
Home in Anna Maria
5.0 out of 5 average rating, 3 reviewsPirates Bay by Beach Boutique Rentals
Aug. 14 – 21
Home in Anna Maria
4.99 out of 5 average rating, 78 reviewsCHARMING HOUSE W/HEATED POOL,STEPS TO BEACH UNIT B
Aug. 27 – Sep. 3
Home in Holmes Beach
4.92 out of 5 average rating, 25 reviewsBackyard Bliss Anna Maria Island
Jul. 7 – 14
Condo rentals with a pool
Condo in Redington Beach
4.97 out of 5 average rating, 459 reviewsAmazingBeachCondo/NoCleaningFee/AwesomeAmenities
Nov. 9 – 16
Condo in Siesta Key
4.83 out of 5 average rating, 236 reviewsSiesta Key 1/1 King bed “Sunset Suite” Pool Kayaks
Condo in Siesta Key
4.96 out of 5 average rating, 276 reviewsOn the Beach; Siesta Key SunBum Studio
Nov. 13 – 20
Condo in Tierra Verde
4.96 out of 5 average rating, 237 reviewsNatural Beauty on Tierra Verde, Waterfront Condo
Apr. 2 – 9
Condo in Holmes Beach
4.99 out of 5 average rating, 125 reviewsBeach Escape - Make Memories on Anna Maria Island!
Apr. 20 – 27
Condo in Holmes Beach
4.98 out of 5 average rating, 108 reviewsNEW listing on AMI! Walk to fabulous beach front!
Dec. 21 – 28
Condo in Indian Shores
4.96 out of 5 average rating, 143 reviews1 BR direct beachfront! Now avail. 8/29-9/11.
Dec. 10 – 17
Condo in Sarasota
4.92 out of 5 average rating, 122 reviewsBeachside Siesta Key Cottage steps from the ocean
May 28 – Jun. 2
Quick stats about vacation rentals with a pool in Longboat Key
Total rentals
650 properties
Rentals with dedicated workspaces
220 properties have a dedicated workspace
Pet-friendly rentals
80 properties allow pets
Family-friendly rentals
490 properties are a good fit for families
Total number of reviews
6.6K reviews
Nightly prices starting at
$55 CAD before taxes and fees
Destinations to explore
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