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
4.95 out of 5 average rating, 158 reviewsSea AMI
Home in Holmes Beach
4.93 out of 5 average rating, 27 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
4.91 out of 5 average rating, 46 reviewsGorgeous Bay house in AMI! 5 min walk to beach!
Home in Sarasota
5.0 out of 5 average rating, 12 reviewsWalk to Lido Beach &St. Armands -grill/HEATED POOL
Home in Sarasota
4.92 out of 5 average rating, 12 reviewsFruit /Botanical Garden Estate 2 miles to downtown
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
Condo rentals with a pool
Condo in Redington Beach
4.97 out of 5 average rating, 461 reviewsAmazingBeachCondo/NoCleaningFee/AwesomeAmenities
Condo in Siesta Key
4.96 out of 5 average rating, 276 reviewsOn the Beach; Siesta Key SunBum Studio
Condo in Indian Shores
4.96 out of 5 average rating, 143 reviews1 BR direct beachfront! Now avail. 5/11-5/22
Condo in Siesta Key
4.96 out of 5 average rating, 106 reviewsSiesta Key Condo. Checkout our great rates!
Condo in Holmes Beach
4.99 out of 5 average rating, 125 reviewsBeach Escape - Make Memories on Anna Maria Island!
Condo in Sarasota
4.96 out of 5 average rating, 122 reviewsLido-Key- Tiny Studio Holiday Cottage-A
Condo in Treasure Island
4.97 out of 5 average rating, 119 reviewsFunshine Pointe Capri - Pool on the Intercoastal!
Condo in Bradenton
4.94 out of 5 average rating, 108 reviewsNewly remodeled cozy 2 bed/2.5 bath townhome
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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