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
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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
Sep 20 – 27
Home in Sarasota
4.9 out of 5 average rating, 107 reviews🌴🐬Bay Haven- Resort style Backyard 🏊♀️🔥 & Game Rm⚽️
Nov 5 – 12
Home in Sarasota
4.91 out of 5 average rating, 11 reviewsFruit /Botanical Garden Estate 2 miles to downtown
Jan 20 – 27
Home in Holmes Beach
4.93 out of 5 average rating, 27 reviewsBackyard Bliss Anna Maria Island
Mar 5 – 12
Home in Longboat Key
5.0 out of 5 average rating, 7 reviewsZilli Villa, a 2,000 sf home right on the beach.
Apr 26 – May 3
Home in Anna Maria
5.0 out of 5 average rating, 3 reviewsPirates Bay by Beach Boutique Rentals
Oct 24 – 31
Home in Sarasota
5.0 out of 5 average rating, 12 reviewsWalk to Lido Beach &St. Armands -grill/HEATED POOL
Aug 10 – 17
Home in Anna Maria
4.96 out of 5 average rating, 52 reviewsSteps to the Beach! Pool/spa! Golf Cart Included!!
Dec 10 – 17
Condo rentals with a pool
Condo in Sarasota
4.96 out of 5 average rating, 121 reviewsLido-Key- Tiny Studio Holiday Cottage-A
Dec 1 – 8
Condo in Redington Beach
4.97 out of 5 average rating, 459 reviewsAmazingBeachCondo/NoCleaningFee/AwesomeAmenities
Nov 9 – 16
Condo in Tierra Verde
4.96 out of 5 average rating, 238 reviewsNatural Beauty on Tierra Verde, Waterfront Condo
May 26 – 31
Condo in Siesta Key
4.96 out of 5 average rating, 276 reviewsOn the Beach; Siesta Key SunBum Studio
Mar 4 – 11
Condo in Holmes Beach
4.99 out of 5 average rating, 125 reviewsBeach Escape - Make Memories on Anna Maria Island!
Apr 27 – May 4
Condo in Holmes Beach
4.98 out of 5 average rating, 108 reviewsNEW listing on AMI! Walk to fabulous beach front!
Jun 22 – 29
Condo in Indian Shores
4.96 out of 5 average rating, 143 reviews1 BR direct beachfront! Now avail. 8/29-9/11.
Dec 10 – 17
Condo in Siesta Key
4.96 out of 5 average rating, 105 reviewsSiesta Key Condo. Checkout our great rates!
Oct 14 – 21
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
Destinations to explore
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