Anna Maria Island vacation rentals with pools

We found 106 vacation rentals waiting for you.

Find your ultimate splash pad

From plunge pools for a quick dip to infinity pools with a view, here are the Anna Maria Island vacation homes where you can dive in, cool off, and catch some sun.

Top-rated Anna Maria Island rentals with pools

Our guests have spoken. Explore their favorite and top-rated homes on Anna Maria Island with refreshing pools, sun-splashed decks, and poolside seating.

Explore All Vacation Rentals With Pools

Recent guest reviews

Condo

This rental was absolutely fabulous. Definitely recommend
elizabeth C. | Jul 2026

Condo

Our first time to the Island. We spent the week in Unit A and the views were remarkable, the proximity to the beach, Bridge Street shopping and trolley stops was the best. The house was very well kept up and clean. We did call ahead to see if toys etc. were on site and were told no. But we were pleased to find pool toys, a beach tent and beach chairs. Even a pack n play for the infant was tucked away in the closet. All were a pleasant surprise! No beach towels but plenty of pool towels were present. The neighbors in unit B were kind. The covered pool was the best. Would return again for sure. Thanks!
Richard M. | Jul 2026

Condo

My husband and I found that it was the perfect space for us to spend a few days exploring the island. Space was nicely decorated and spacious. The location is walkable to both the Bay and the Ocean as well as lots of nice restaurants and shops. There is a trolley stop a block away that will take you around the island. Pool was also nice and very clean.
Jen C. | Jul 2026

House

We recently returned from a five-night stay, our first visit to AMI. The home is in a great, residential location about two blocks from a stretch of beach that is both gorgeous and quiet. Pine Avenue isn't far. We rode bikes there daily (highly recommend renting). Publix is about a 10-15 minute drive depending on traffic. We are really glad we settled on this area. It's quiet, safe and also provided easy access to Bean Point and other sites. As for the home itself, it's spacious and clean. We brought our son and three of his friends. We loved the fact that the primary bedroom was down a long hall. We never heard them once late at night. The pool is lovely and overlooks a canal with dock that's perfect for fishing. We had an issue with the AC when we arrived. We texted the local Vacasa team and they took care of it right away. A few things to note about that may be helpful: There is a blender, toaster, some spices, salt, pepper and a little bit of olive oil in the kitchen. We definitely had to stock up on other essentials, like foil, sandwich bags, etc. Towels, beach chairs, small umbrellas, floats and sand toys are provided, though the chairs are a little dated. All-in-all we loved the home and would definitely return!
Shannon F. | Jul 2026
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FAQ

Our vacation rentals offer both private and shared pools. Each property’s listing description will specify whether the pool offered is private or shared.

Every home is stocked with plenty of towels. However, the availability of pool towels varies by property.

Some pools are heated, and there may be an additional fee for this service. You can find more information about heating fees in the property description.

Yes, pool maintenance is included during your stay. We ensure that pools and hot tubs are regularly cleaned and maintained to provide an optimal experience. If you encounter any issues with the pool during your stay, contact our Guest Experience team immediately.

Many of our properties include lounge chairs, umbrellas, or shaded areas by the pool, but this can vary. Check the property details and listing photos for specific details.

Generally, food and drinks are allowed by—but not in—the pool. However, to be safe, it’s best not to use glass or china in the pool area.

Pool toys, floaties, or inflatables are typically not provided. You may want to bring your own, if needed.

Some properties include a poolside grill or outdoor kitchen area, but this is not standard across all rentals. Check the property listing for details.

We have a good neighbor policy that includes quiet hours from 10 p.m. to 8 a.m. In addition, certain communities have noise policies in place. Unauthorized parties are not allowed, and excessive noise can lead to intervention and removal from a property.

If you encounter any issues with the pool during your stay, contact our Guest Experience team immediately. Your local Vacasa team will work to resolve the problem as quickly as possible.

Not all pools are open all year round. Some pools—depending on the destination—are seasonal only. Read the listing description for specific operating times for the pool.

More ways to stay on Anna Maria Island

Dog-friendly
Hot tub
Internet
Ocean view
Oceanfront
Water view
Waterfront
A/C

Nearby destinations

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Florida Gulf Coast
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