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
4.95 out of 5 average rating, 159 reviewsSea AMI
Home in Sarasota
4.9 out of 5 average rating, 111 reviews🌴🐬Bay Haven- Resort style Backyard 🏊♀️🔥 & Game Rm⚽️
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 Siesta Key
5.0 out of 5 average rating, 20 reviewsSiesta Key, Private Tropical Waterfront Pool Home
Home in Anna Maria
5.0 out of 5 average rating, 4 reviewsPirates Bay by Beach Boutique Rentals
Home in Holmes Beach
4.93 out of 5 average rating, 29 reviewsBackyard Bliss Anna Maria Island
Home in Holmes Beach
4.91 out of 5 average rating, 47 reviewsGorgeous Bay house in AMI! 5 min walk to beach!
Condo rentals with a pool
Condo in Sarasota
4.96 out of 5 average rating, 124 reviewsLido-Key- Tiny Studio Holiday Cottage-A
Condo in Bradenton
4.98 out of 5 average rating, 172 reviewsShorewalk full condo IMG Beaches Anna Maria
Condo in Siesta Key
4.96 out of 5 average rating, 278 reviewsOn the Beach; Siesta Key SunBum Studio
Condo in Holmes Beach
4.98 out of 5 average rating, 108 reviewsNEW listing on AMI! Walk to fabulous beach front!
Condo in Treasure Island
4.98 out of 5 average rating, 122 reviewsFunshine Pointe Capri - Pool on the Intercoastal!
Condo in Treasure Island
4.89 out of 5 average rating, 222 reviewsBeachfront Condo in Exclusive Resort
Condo in Holmes Beach
4.93 out of 5 average rating, 142 reviewsBlanco and Sunset Villas on Anna Maria Island
Condo in Redington Beach
4.97 out of 5 average rating, 466 reviewsAmazingBeachCondo/NoCleaningFee/AwesomeAmenities
Home rentals with a private pool
Home in Seminole
4.93 out of 5 average rating, 44 reviewsGreat 6br for All Ages/heated Pool 5 Min to Beach
Home in Tampa
4.66 out of 5 average rating, 32 reviewsLarge Tropical Estate (1.5 Acres Space)- Tampa Bay
Home in Dunedin
New place to stayNew Listing! Modern 3br | Pool | Game Room
Home in Port Charlotte
Serenity Haven: New Pool Home Near Englewood Beach
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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