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 Holmes Beach
4.93 out of 5 average rating, 41 reviewsBackyard Bliss Anna Maria Island
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, 19 reviews5 min walk to beach, private pool & spa, elevator
Home in Holmes Beach
4.95 out of 5 average rating, 94 reviewsThe Peachy Beach House, steps to the gulf
Home in Anna Maria
4.99 out of 5 average rating, 102 reviews1 block to Beach on Pine Ave! Private Pool Oasis
Home in Sarasota
4.82 out of 5 average rating, 225 reviewsPrivate Siesta Beach House Oasis with Heated Pool.
Home in Lido Key
5 out of 5 average rating, 16 reviewsWalk to Lido Beach &St. Armands -grill/HEATED POOL
Home in Bradenton
4.89 out of 5 average rating, 104 reviewsAmazing Game Room-86°Pool/Spa-Beaches-Dog Friendly
Condo rentals with a pool
Condo in Siesta Key
4.83 out of 5 average rating, 209 reviewsNo Damage: Cozy 1BR Beach Condo on Siesta Key!
Condo in Indian Shores
4.99 out of 5 average rating, 108 reviewsTropical Beachfront Penthouse-Beach Cottages II
Condo in Sarasota
4.89 out of 5 average rating, 110 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 Siesta Key
4.93 out of 5 average rating, 222 reviewsPrivate Siesta Key Escape
Condo in Bradenton
4.95 out of 5 average rating, 149 reviewsThe Seashell Cottage with peaceful water views!
Condo in Siesta Key
4.94 out of 5 average rating, 152 reviewsSea Club 2-Relaxing Siesta Key Condo-Mermaids Rest
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
Destinations to explore
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