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 Longboat Key
4.9 out of 5 average rating, 106 reviewsLongboat Key Beach House
Home in Holmes Beach
4.97 out of 5 average rating, 126 reviewsTwin Palms: Big House Steps to Beach w/Lush Pool
Home in Bradenton
4.94 out of 5 average rating, 105 reviewsEndless Outdoor FUN! Pool/Spa/Golf/Games/Near IMG
Home in Holmes Beach
4.95 out of 5 average rating, 161 reviewsSea AMI
Home in Anna Maria
4.94 out of 5 average rating, 154 reviewsPrivate 30' Pool and Boat Dock - Rated best on AMI
Home in Longboat Key
5 out of 5 average rating, 8 reviewsZilli Villa, a 2,000 sf home right on the beach.
Home in Anna Maria
5 out of 5 average rating, 5 reviewsPirates Bay by Beach Boutique Rentals
Home in Holmes Beach
5 out of 5 average rating, 33 reviewsTip’Sea Turtle Anna Maria island
Condo rentals with a pool
Condo in Siesta Key
4.93 out of 5 average rating, 182 reviewsSiesta key getaway!
Condo in Siesta Key
4.96 out of 5 average rating, 280 reviewsOn the Beach; Siesta Key SunBum Studio
Condo in Indian Shores
4.96 out of 5 average rating, 146 reviews1 BR Beachfront! Gorgeous sunsets!
Condo in Holmes Beach
4.93 out of 5 average rating, 143 reviewsBlanco and Sunset Villas on Anna Maria Island
Condo in Siesta Key
4.96 out of 5 average rating, 108 reviewsSiesta Key Condo. Checkout our great rates!
Condo in Holmes Beach
4.99 out of 5 average rating, 126 reviewsBeach Escape - Make Memories on Anna Maria Island!
Condo in Treasure Island
4.98 out of 5 average rating, 125 reviewsFunshine Pointe Capri - Pool on the Intercoastal!
Condo in Bradenton
4.98 out of 5 average rating, 173 reviewsShorewalk full condo IMG Beaches Anna Maria
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
$40 before taxes and fees
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