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 Bradenton Beach
4.97 out of 5 average rating, 153 reviewsParadise! Steps2 Private Beach & Tropical Yard!
Dec 7 – 14
Home in Bradenton
4.87 out of 5 average rating, 205 reviewsSunny Oasis Near Beaches With Pool
May 6 – 13
Home in Tampa
4.97 out of 5 average rating, 107 reviewsDowntown Tampa Pool House! Walk to Armature Works!
Dec 15 – 22
Home in Holmes Beach
4.95 out of 5 average rating, 158 reviewsSea AMI
Nov 22 – 29
Home in Anna Maria
4.93 out of 5 average rating, 152 reviewsPrivate 30' Pool and Boat Dock - Rated best on AMI
Nov 6 – 13
Home in Longboat Key
5.0 out of 5 average rating, 7 reviewsZilli Villa, a 2,000 sf home right on the beach.
Dec 7 – 14
Home in Holmes Beach
4.92 out of 5 average rating, 24 reviewsBackyard Bliss Anna Maria Island
Nov 10 – 17
Home in Sarasota
5.0 out of 5 average rating, 12 reviewsWalk to Lido Beach &St. Armands -grill/HEATED POOL
Sep 10 – 17
Condo rentals with a pool
Condo in Tierra Verde
4.96 out of 5 average rating, 237 reviewsNatural Beauty on Tierra Verde, Waterfront Condo
Dec 14 – 21
Condo in Siesta Key
4.96 out of 5 average rating, 275 reviewsOn the Beach; Siesta Key SunBum Studio
Mar 9 – 16
Condo in Holmes Beach
4.96 out of 5 average rating, 116 reviewsBeautiful beachfront condo for perfect vacation
Jul 20 – 27
Condo in Indian Shores
4.96 out of 5 average rating, 143 reviews1 BR direct beachfront! Now avail. 8/29-9/11.
Dec 4 – 11
Condo in Holmes Beach
4.99 out of 5 average rating, 125 reviewsBeach Escape - Make Memories on Anna Maria Island!
Apr 20 – 27
Condo in Tampa
4.94 out of 5 average rating, 215 reviewsModern Waterfront Condo - Captivating Sunset Views
Jun 10 – 17
Condo in Sarasota
4.92 out of 5 average rating, 122 reviewsBeachside Siesta Key Cottage steps from the ocean
Jul 17 – 24
Condo in Bradenton
4.94 out of 5 average rating, 108 reviewsNewly remodeled cozy 2 bed/2.5 bath townhome
Sep 19 – 26
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
€ 37 before taxes and fees
Destinations to explore
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