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