Holiday 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.
Holiday 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
4.97 out of 5 average rating, 155 reviewsParadise! Steps2 Private Beach & Tropical Yard!
Home in Holmes Beach
4.95 out of 5 average rating, 160 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 Holmes Beach
4.93 out of 5 average rating, 30 reviewsBackyard Bliss Anna Maria Island
Home in Anna Maria
5.0 out of 5 average rating, 4 reviewsPirates Bay by Beach Boutique Rentals
Home in Anna Maria
4.96 out of 5 average rating, 52 reviewsSteps to the Beach! Pool/spa! Golf Cart Included!!
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
4.92 out of 5 average rating, 48 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, 126 reviewsLido-Key- Tiny Studio Holiday Cottage-A
Condo in Siesta Key
4.96 out of 5 average rating, 280 reviewsOn the Beach; Siesta Key SunBum Studio
Condo in Siesta Key
4.87 out of 5 average rating, 212 reviewsSiesta Key Beach Community!
Condo in Bradenton
4.98 out of 5 average rating, 173 reviewsShorewalk full condo IMG Beaches Anna Maria
Condo in Holmes Beach
4.93 out of 5 average rating, 143 reviewsBlanco at Sunset Villas on Anna Maria Island
Condo in Redington Beach
4.97 out of 5 average rating, 466 reviewsAmazingBeachCondo/NoCleaningFee/AwesomeAmenities
Condo in Indian Shores
4.96 out of 5 average rating, 145 reviews1 BR Beachfront! Gorgeous sunsets!
Condo in Siesta Key
4.96 out of 5 average rating, 108 reviewsSiesta Key Condo. Checkout our great rates!
Quick stats about holiday 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
$65 NZD before taxes and fees
Destinations to explore
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