Holiday 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.
Holiday rentals for every style
Get the amount of space that is right for you
Popular amenities for Longboat Key rentals with a pool
House rentals with a pool
Home in Holmes Beach
4.95 out of 5 average rating, 158 reviewsSea AMI
Home in Holmes Beach
4.93 out of 5 average rating, 28 reviewsBackyard Bliss Anna Maria Island
Home in Longboat Key
5.0 out of 5 average rating, 7 reviewsZilli Villa, a 2,000 sf home right on the beach.
Home in Holmes Beach
4.95 out of 5 average rating, 78 reviewsBreezy Harbor AMI pool retreat near the Beach
Home in Anna Maria
5.0 out of 5 average rating, 3 reviewsPirates Bay by Beach Boutique Rentals
Home in Sarasota
4.92 out of 5 average rating, 13 reviewsFruit /Botanical Garden Estate 2 miles to downtown
Home in Sarasota
5.0 out of 5 average rating, 38 reviewsThe Blessing House- Htd Pool/Spa, Close to Beaches
Home in Bradenton
4.86 out of 5 average rating, 22 reviews"Paradise" by the Private (Heated) Pool light!
Apartment rentals with a pool
Apartment in Redington Beach
4.97 out of 5 average rating, 463 reviewsAmazingBeachCondo/NoCleaningFee/AwesomeAmenities
Apartment in Holmes Beach
4.98 out of 5 average rating, 108 reviewsNEW listing on AMI! Walk to fabulous beach front!
Apartment in Siesta Key
4.96 out of 5 average rating, 276 reviewsOn the Beach; Siesta Key SunBum Studio
Apartment in Englewood
4.93 out of 5 average rating, 116 reviewsDiscounted Ground Floor Beach Studio on the Gulf!
Apartment in Tampa
4.95 out of 5 average rating, 219 reviewsModern Waterfront Condo - Captivating Sunset Views
Apartment in Treasure Island
4.98 out of 5 average rating, 121 reviewsFunshine Pointe Capri - Pool on the Intercoastal!
Apartment in Siesta Key
4.93 out of 5 average rating, 181 reviewsSiesta key getaway!
Apartment in Redington Beach
4.93 out of 5 average rating, 137 reviewsQuiet, Beachy Poolside Studio/1 Min Walk to Beach
Quick stats about holiday 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
£32 before taxes and fees
Destinations to explore
- Anna Maria Island Holiday rentals
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