
Holiday rentals with a pool in Anna Maria
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Top-rated rentals with a pool in Anna Maria
Guests agree: These homes with a pool are highly rated for location, cleanliness and more.
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Popular amenities for Anna Maria rentals with a pool
House rentals with a pool

Just 5 miles to Anna Maria Island Beaches + IMG!
This is a wonderful house. The pool and hot tub plus the close proximity to the beach helped make it a great vacation. Highly recommend. Thank you!

AMI Du Soleil | Steps to the Beach, Heated Pool
Stellar location very close to the beach and multiple great restaurants and shops. Our kids had no problem going off on their own for coffee or food. Beds were super comfortable. Host was very responsive when we reached out with questions.

Veselka - Canal front w private heated pool & dock
We had an amazing week at Michael and Denzel’s home! It was actually better than the pictures with enough space for everyone to feel right at home. The layout was perfect for two families. The home is spotless and extremely well stocked. The island is beautiful and we enjoyed the pool everyday! Highly recommend this home. It will exceed your expectations in every way!

Be an AMI
We loved Amy’s place . Walkable to so many fun things , including the boat ramp if you do any excursions. We rented a golf cart and it was awesome and a short ride to Bean Point. The place is equipped with everything you need and more - the beach Chairs and umbrella really were nice to have. We loved the spa pool and it was so nice to dip in that after a long day at the beach. We loved AMI and hope to come back again. If your looking for a great place to- you have found it .

NEW saltwater pool/spa! Amazing outdoor space!
House was very clean and spacious. The outdoor space was great, and the house has lots of amenities that came in handy

Wk of 6/29 now avail at last minute SALE rate!
The listing says it is just a few steps from the beach and that is true! It was so easy to go back and forth and with 4 kids and beach items that was very important. The house was beautiful and spotless. We felt right at home and we loved every second of our stay! Thanks Mark for helping us make a special family vacation!

HeatPool~Pickleball~Mini-Golf~4 Kings+Kids Suite!
Loved our stay! The house was super clean and just like the photos — maybe even nicer in person. Everything went really smoothly, and communication with the hosts was super easy and clear. Would 100% come back!

Anna Maria Chateau. Private Home With Heated Pool.
Amy's beautiful oasis on Anna Maria Island was the perfect spot for a relaxed, beach vacation! We had a mellow bachelorette party spent on the beach at Bean Point during the day and spent our evenings eating home-cooked dinners on the beautiful porch at Amy's before a nighttime pool dip to cool off. Can't recommend this spot enough!
Condo rentals with a pool

Foxtail Palm: *Location *Pool *Steps to Beach
We absolutely loved staying here. It was maybe a 2 minute walk to the beach. They also have everything you could need for your time at the beach. The beach chairs, umbrella, wagon, and beach towels made it easy to load up and go to the beach everyday. Nick & Jay were super responsive and extremely helpful when we had a little problem. I can’t recommend their place enough and we hope to be back one day.

850 Sqft - 1 Bedroom 1.5 Bath (GULF FACING!) Condo
We enjoyed our stay at Cody's place immensely! Perfect location right on the beach with a gorgeous view.

Resort-Style Ground Floor Suite Heated Pool/Spa
We had a great stay at the turtle suite! Perfect getaway for a couple. Very family friendly atmosphere all over the island. The kayaks were a fun perk as well as having our very own pool. Had great neighbors during our entire stay. The house was very clean and was within walking distance to the beach, restaurants and shops. Would definitely recommend this property.

Beach Escape & Pool, steps to Beach & restaurants
Location was perfect!!!! Being so close to the beaches AND having shopping and food options nearby was the best!! Colin was very communicative and even gave a proactive option for an extra night. Thank you for being accommodating and very responsive!

A&A's Paradise near IMG & Anna Maria beaches
This was the most clean, most relaxing, most safe feeling place we've ever stayed in through Airbnb!! Thank you so much for such a wonderful experience. We would recommend 10/10 to anyone!!!!

Condo with a View 1: Open Friday Night!
This condo was everything I needed and more! The location? Absolutely perfect—the beach is literally your backyard. Waking up to that ocean view the next morning was a dream. Restaurants and activities were just minutes away, which made everything so easy and fun. Heidi, the host, went above and beyond. Her communication was fast, kind, and incredibly thoughtful. She even surprised us with a delicious key lime pie and orange juice waiting for us after jet skiing—such a sweet and personal touch! I truly have no complaints. Everything about this stay was peaceful, beautiful, and seamless. I’d absolutely recommend this spot to anyone looking for a relaxing and magical beach getaway. 🌴🌊💛

Waterfront condo on top floor @ Boca Ciega Resort
The condo was just what we were looking for. The kitchen was equipped with the basics and the view was wonderful. Tamara was friendly, responsive, and a great host. Would stay at her place again!

Beach Escape - Make Memories on Anna Maria Island
Jean & Mike's beach condo on Anna Maria Island was a wonderful get-away for us after a very long winter. We loved the beach decor and all the little things that made us feel welcome and comfortable. It had everything we needed for an awesome beach vacation - chairs, umbrella, towels and a cool beach cart to carry our stuff. The pristine beach was only about 300 steps away. The condo itself had everything we needed. The bed and couches were comfy; the master bath spacious; the kitchen well-equipped. We enjoyed eating on the screened porch that overlooked a small park and being able to walk to nearby stores and restaurants. We loved watching the sunset from "our" beach or at the AMI Beach Cafe down the beach while listening to live music. Jean was a great host. She responded quickly to our questions and had plenty of recommendations on things to do and places to eat. Jean & Mike's place is one of the best AirBnBs we've stayed at and will definitely consider it the next time we visit AMI.
Quick stats about holiday rentals with a pool in Anna Maria
Total rentals
410 properties
Nightly prices starting at
$201 AUD before taxes and fees
Total number of reviews
6K reviews
Family-friendly rentals
380 properties are a good fit for families
Pet-friendly rentals
130 properties allow pets
Rentals with dedicated workspaces
160 properties have a dedicated workspace
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- Anna Maria Island
- Siesta Beach
- Anna Maria Public Beach
- Dunedin Beach
- Crescent Beach
- John's Pass
- Turtle Beach
- Caspersen Beach
- Bean Point Beach
- Raymond James Stadium
- Busch Gardens Tampa Bay
- Cortez Beach
- Lido Key Beach
- Amalie Arena
- Coquina Beach
- Gulfport Beach Recreation Area
- North Beach
- Fort De Soto Park
- Manasota Key Beach
- Vinoy Park
- Jannus Live
- Tampa Theatre
- ZooTampa at Lowry Park
- Curtis Hixon Waterfront Park