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 Anna Maria
5 out of 5 average rating, 22 reviewsVeselka - Canal front w private heated pool & dock
Home in Sarasota
4.95 out of 5 average rating, 194 reviewsThe Oasis-Heated Private Pool Hot Tub-5mi to beach
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
4.95 out of 5 average rating, 94 reviewsThe Peachy Beach House, steps to the gulf
Home in Lido Key
5 out of 5 average rating, 15 reviewsWalk to Lido Beach &St. Armands -grill/HEATED POOL
Home in Holmes Beach
4.87 out of 5 average rating, 103 reviewsNew Golf cart + 4bd/3b w pool/2100 sq ft home
Home in Siesta Key
4.96 out of 5 average rating, 23 reviewsSiesta Key~Private Home with Private Pool and Spa
Condo rentals with a pool
Condo in Siesta Key
4.82 out of 5 average rating, 205 reviewsNo Damage: Cozy 1BR Beach Condo on Siesta Key!
Condo in Siesta Key
4.96 out of 5 average rating, 112 reviews2 Bed/2 Bath Condo Resort View on Siesta Key Beach
Condo in Siesta Key
4.94 out of 5 average rating, 189 reviewsSiesta key getaway!
Condo in Sarasota
4.85 out of 5 average rating, 137 reviewsSiesta Key Ground Floor Condo 2BR On Trolley Line
Condo in Sarasota
4.89 out of 5 average rating, 109 reviews6 min. from Siesta Beach+heated pool+lake view
Condo in Bradenton Beach
4.87 out of 5 average rating, 114 reviewsCharming and Updated 1 Bedroom in Runaway Bay
Condo in Bradenton Beach
4.86 out of 5 average rating, 103 reviewsOceanfront Condo for Beach Lovers
Condo in Holmes Beach
4.85 out of 5 average rating, 143 reviewsAnna Maria Island-just a few steps to the beach
Home rentals with a private pool
Home in Palmetto
Sunny Palmetto Oasis: 4br Home with Private Pool
Home in Dunedin
4.5 out of 5 average rating, 8 reviewsNew Listing! Modern 3br | Pool | Game Room
Home in Seminole
4.94 out of 5 average rating, 53 reviewsGreat 6br for All Ages/heated Pool 5 Min to Beach
Home in Tampa
4.68 out of 5 average rating, 37 reviewsLarge Tropical Estate (1.5 Acres Space)- Tampa Bay
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
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