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
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 Bradenton Beach
5 out of 5 average rating, 46 reviewsAMI*Steps to the beach-Modern luxury POOL SPA
Home in Holmes Beach
4.97 out of 5 average rating, 128 reviewsTwin Palms: Big House Steps to Beach w/Lush Pool
Home in Holmes Beach
5 out of 5 average rating, 3 reviewsThe Wave by Beach Boutique Rentals
Home in Indian Beach-Sapphire Shores
4.92 out of 5 average rating, 103 reviewsPool Courtyard, patio w/ fire pit, 2 mls downtown
Home in Holmes Beach
4.95 out of 5 average rating, 94 reviewsThe Peachy Beach House, steps to the gulf
Home in Holmes Beach
5 out of 5 average rating, 20 reviews5 min walk to beach, private pool & spa, elevator
Home in Sarasota
5 out of 5 average rating, 57 reviewsThe Blessing House- Htd Pool/Spa, Close to Beaches
Home in Sarasota
4.82 out of 5 average rating, 225 reviewsPrivate Siesta Beach House Oasis with Heated Pool.
Condo rentals with a pool
Condo in Holmes Beach
4.87 out of 5 average rating, 114 reviewsSteps from the beach
Condo in Siesta Key
4.93 out of 5 average rating, 105 reviewsSea Shell Ocean view On Beach Walk everywhere Pool
Condo in Siesta Key
4.95 out of 5 average rating, 114 reviews2 Bed/2 Bath Condo Resort View on Siesta Key Beach
Condo in Siesta Key
4.94 out of 5 average rating, 190 reviewsSiesta key getaway!
Condo in Sarasota
4.88 out of 5 average rating, 113 reviews6 min. from Siesta Beach+heated pool+lake view
Condo in Treasure Island
4.99 out of 5 average rating, 168 reviewsSpectacular beach to bay views from this resort.
Condo in Bradenton Beach
4.86 out of 5 average rating, 103 reviewsOceanfront Condo for Beach Lovers
Condo in Indian Shores
4.94 out of 5 average rating, 155 reviews1 BR Beachfront Amazing sunsets-
Quick stats about vacation rentals with a pool in Longboat Key
Total rentals
740 properties
Nightly prices starting at
$40 before taxes and fees
Total number of reviews
6.6K reviews
Family-friendly rentals
590 properties are a good fit for families
Pet-friendly rentals
90 properties allow pets
Rentals with dedicated workspaces
230 properties have a dedicated workspace
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