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
Jan 25 – Feb 1
Home in Holmes Beach
4.97 out of 5 average rating, 32 reviewsUnit B updated 2/2 Shared pool! Walk to beach
Dec 1 – 8
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
Aug 26 – Sep 2
Home in Sarasota
4.92 out of 5 average rating, 12 reviewsFruit /Botanical Garden Estate 2 miles to downtown
Jan 22 – 29
Home in Holmes Beach
4.93 out of 5 average rating, 27 reviewsBackyard Bliss Anna Maria Island
Mar 7 – 14
Home in Bradenton
4.85 out of 5 average rating, 20 reviews"Paradise" by the Private (Heated) Pool light!
Aug 23 – 30
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 Redington Beach
4.97 out of 5 average rating, 460 reviewsAmazingBeachCondo/NoCleaningFee/AwesomeAmenities
Nov 23 – 30
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 Siesta Key
4.96 out of 5 average rating, 276 reviewsOn the Beach; Siesta Key SunBum Studio
Apr 3 – 10
Condo in Holmes Beach
4.99 out of 5 average rating, 125 reviewsBeach Escape - Make Memories on Anna Maria Island!
May 9 – 16
Condo in Siesta Key
4.93 out of 5 average rating, 181 reviewsSiesta key getaway!
Jul 30 – Aug 6
Condo in Bradenton
4.94 out of 5 average rating, 108 reviewsNewly remodeled cozy 2 bed/2.5 bath townhome
Sep 16 – 23
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 7 – 14
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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