
Vacation rentals with a pool in Anna Maria
Find and book unique homes with a pool on Airbnb
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

Island in the Sun, luxury beach house,private pool
Had the absolute best stay here! Everything was perfect, from the interior design to the location. The pool was great with lots of privacy in the backyard. The house was spacious, each bedroom having a king and its own bathroom. My son loved that. We would love to stay here again!

Shore Beats Work, Bean Point Beauty on Anna Maria
Best family vacation yet. What made this Airbnb unforgettable was the small details that the host takes care of. All the pool/ocean toys were pre-inflated, a delicious welcome basket, small beach bags for my kids to collect seashells. We're already planning on booking for next summer.

Isla Living 3 Bed / 2 bath / Waterfront / Kayaks
It was exactly like the photos and such a cute quaint area, very peaceful and pleasant

Discounted Thru July with Private Boat Dock & Pool
Just want to begin by saying how appreciative I was of Michelle and her husband. They were super responsive and attentive to all of our requests/questions. We have stayed at numerous high-class locations and this was by far my favorite. The price compared to nearby locations was worth every dollar. The home was very welcoming, modern, and just overall paradise. Absolutely loved the swimming pool and dock right off of the back of the house. The space was very well designed. The location was within 15 minutes of everything we could have asked for out of the island. 11/10 I would recommend to anyone looking to have an amazing, peaceful retreat.

Private Luxurious Ground Level Home
Wonderful stay at this special home. Excellent location. Perfectly laid out and well designed home. Really appreciated the separate patio area to the pool area which was very safe with kids. Walk to coffee, restaurants and beach. Quick golf cart ride around the island. 10/10 recommend!

Casa Bonita
Our stay at Casa Bonita was truly a five star experience. The location was great, just steps from the beach access crossing and bridge street where we enjoyed, shops, dining and drinks. No ubers needed! The actual space itself exceeded our expectations. There is plenty of space for lounging inside and out. The pool area offered shading and full sun areas, with games and a bathroom/shower located outside for easy rinsing off. The garage had everything we needed for the perfect beach trip including towels, floats and a wagon. Kitchen and bedrooms were very clean with all of the essentials. And our host Kelly was very responsive with anything we needed. We will certainly be back to Casa Bonita!

Palm Retreat: #1 Top Rated Rental of Bradenton/AMI
Great place to stay !! The house is beautiful, it’s in a great location and I love the pool area, I had so much fun with my friends on this trip and we’re planning to come back !!

Bayfront Gem Pool, Spa & walk to Anna Maria Beach
Second time staying at Christy’s bay front home. The views are amazing. I don’t think you’ll find a better view while you take a shower from the master bath! House has everything you need for the beach. The kayaks, and paddle boards are a favorite for our family. The walk to the beach is not that far, and the section of the beach that you access usually isn’t that crowded, which is nice. Definitely recommend staying here.
Condo rentals with a pool

Amazing View, Updated Beachfront Condo
Very quaint little town. We brought the bikes and were able to bike everywhere. Very peaceful with minimal crowds. Hit the spot on the get away we wanted. Thanks!

Steps from the beach
This condo was perfect for our family. She had everything we needed to make our vacation perfect. We really appreciated the beach chairs, beach towels and beach toys. The condo was very clean! It was perfectly located on a dead-end street, so it was very quiet and peaceful. Centrally located to restaurants and a Publix within walking distance. Just a short walk to the beach! The pool was one of our favorite amenities. Monika’s place made our first trip to Anna Maria amazing and memorable. Thank you, Monika!

Next to Beach & Largest Pool on Island-258
The condo was one of the best we’ve ever stayed at (and we’ve rented a lot!). Very clean and comfortable, and decorated nicely. Everything was provided. Nice location right across the street from the beach to see beautiful sunsets. And if we didn’t want to go to the beach, we could see the sunset perfectly right outside the front door! Great restaurants that we could walk to. Great vacation!!

A&A's Paradise near IMG & Anna Maria beaches
We truly loved staying at this beautiful condo! It was super-super clean, modern-designed, had everything we needed, and even much more! Full spectrum of laundry/cleaning/bathroom supplies in abundance. The space is very cozy, stylish, and the location was really convenient - walking distance to Publix, good restaurants, and other useful places. Andrew and Angel are great hosts and kindest people! Responded immediately and positively to all our questions. Can’t wait to get back and stay here again! We feel lucky to find this place! Thank you Angel and Andrew!

Charming and Updated 1 Bedroom in Runaway Bay
My fiancé and I really enjoyed our stay at David’s place in Bradenton! The space was super clean and had everything I needed for a comfortable stay. Communication was excellent throughout; the host was responsive, helpful, and always timely with their messages. One of the best parts was the beach access—super convenient, and the place was stocked with everything from a beach cart, umbrellas, chairs, and beach towels etc. which made days at the beach so easy. There were also a few great local tips provided, which I definitely took advantage of. Honestly, I wouldn’t change a thing. I’d absolutely stay here again and highly recommend it to anyone visiting the area. Thank you for a wonderful stay!

Modern Waterfront Condo - Captivating Sunset Views
Rosana was an excellent host- very responsive, kind, and accommodating. Fun location on the bay with a great view, pool with towel service, and bar/grill with great burgers. Fire pit on the little beach at night with great view of sunset. The unit is in a quiet location within the complex with a view of the beach and bay. The trade-off is that the unit is a bit far from the elevator (though close to stairs). Great experience overall.

Condo with a View 2!
Heidi and her place is the the most organized and best operated Airbnb we stayed at. Starting with communication from the moment we booked to very last detail. The place has everything you will ever need, very clean. Beach is right out of the door, pool is great and plenty of floaties, boogie boards and toys for kids. Heidi ordered new pack n’play for our infant, left drinks in the fridge and first morning surprised us with muffins and juice left at our door. Plenty of recommendations and very friendly communication through out the stay and beyond.

Shorewalk full condo IMG Beaches Anna Maria
This was a great place and had everything you needed! My family really enjoyed it and the host was amazing to work with and responded back really fast! I would go back here!! Also the beach, omg it’s beautiful!! White sandy beaches, beautiful blue water, we even found whole sand dollars!! Worth checking out and staying!!!
Home rentals with a private pool

New! Beautiful Pool Home Near Siesta Key Beach
It was a short stay for us, but it was exactly what we needed! The house was fully stocked with necessities. Instructions were very clear, not overwhelming. The neighborhood is nice, very close to supermarkets, shopping, restaurants, coffe shops, beach, and local areas whether you want a casual night out or a party night out! Great location😉

Great 6br for All Ages/heated Pool 5 Min to Beach
Place was amazing! I would give 6 stars if I could! Check in and check out were easy and host always responded very quickly to any messages! Will definitely stay here again and recommend it to anyone else! The house is also a lot bigger in person! Thanks again guys, I loved your place!

Sunny Palmetto Oasis: 4br Home with Private Pool
Thank you RedAwning Rental for the stay in Palmetto!

Comfy Home W/ Heated Pool Near Siesta Key Beach
Quick stats about vacation rentals with a pool in Anna Maria
Total rentals
410 properties
Nightly prices starting at
G$27,189 GYD 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
- Dunedin Beach
- Anna Maria Public Beach
- Crescent Beach
- John's Pass
- Turtle Beach
- Caspersen Beach
- Bean Point Beach
- Busch Gardens Tampa Bay
- Raymond James Stadium
- Cortez Beach
- Lido Key Beach
- Amalie Arena
- Coquina Beach
- Gulfport Beach Recreation Area
- Vinoy Park
- North Beach
- Fort De Soto Park
- Manasota Key Beach
- Tampa Theatre
- Jannus Live
- Curtis Hixon Waterfront Park
- ZooTampa at Lowry Park