Vacation rentals with a pool in Anna Maria Island
Find and book unique homes with a pool on Airbnb
Top-rated rentals with a pool in Anna Maria Island
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 Anna Maria Island rentals with a pool
House rentals with a pool
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 Bradenton
4.91 out of 5 average rating, 254 reviewsPalm Retreat Gold: Luxury Edition of #1 Rental
Sep. 12 – 19
Home in Holmes Beach
4.99 out of 5 average rating, 154 reviewsCaptain's Quarters at Spinnakers Vacation Cottages
Sep. 28 – Oct. 5
Home in Holmes Beach
4.92 out of 5 average rating, 24 reviewsBackyard Bliss Anna Maria Island
Nov. 17 – 24
Home in Anna Maria
4.94 out of 5 average rating, 18 reviewsWhispering Winds by Beach Boutique Rentals
Dec. 2 – 9
Home in Bradenton
4.83 out of 5 average rating, 18 reviews"Paradise" by the Private (Heated) Pool light!
Sep. 6 – 13
Home in Anna Maria
4.96 out of 5 average rating, 50 reviewsSteps to the Beach! Pool/spa! Golf Cart Included!!
Sep. 14 – 21
Home in Anna Maria
4.99 out of 5 average rating, 86 reviews1 block to Beach on Pine Ave! Private Heated Pool
Aug. 27 – Sep. 3
Condo rentals with a pool
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 Redington Beach
4.94 out of 5 average rating, 356 reviewsBeach Condo, Heated Pool, 2 Minute Walk to Ocean
Aug. 2 – 9
Condo in Siesta Key
4.93 out of 5 average rating, 181 reviewsSiesta key getaway!
Jul. 18 – 25
Condo in Longboat Key
4.93 out of 5 average rating, 144 reviewsBeachfront Resort, Ocean View, Pool, Tennis, Gym
Sep. 7 – 14
Condo in Bradenton
4.94 out of 5 average rating, 108 reviewsNewly remodeled cozy 2 bed/2.5 bath townhome
Sep. 19 – 26
Condo in Treasure Island
4.97 out of 5 average rating, 119 reviewsFunshine Pointe Capri - Pool on the Intercoastal!
Sep. 10 – 17
Condo in Longboat Key
4.97 out of 5 average rating, 148 reviewsSunset Views - Open May 13 & 14 - $175/nt!
Apr. 6 – 13
Condo in St. Petersburg
4.97 out of 5 average rating, 144 reviewsSea La Vie- Studio by the bay!
Jan. 20 – 27
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