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Vacation rentals with a pool in Anna Maria

Find and book unique homes with a pool on Airbnb

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Popular amenities for Anna Maria rentals with a pool

House rentals with a pool

Guest favorite
Home in Anna Maria
4.9 out of 5 average rating, 59 reviews

Island in the Sun, luxury beach house,private pool

JamieRating, 5 stars1 month ago
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!
Top guest favorite
Home in Anna Maria
5 out of 5 average rating, 30 reviews

Shore Beats Work, Bean Point Beauty on Anna Maria

MikeRating, 5 stars2 weeks ago
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.
Superhost
Home in Anna Maria
4.82 out of 5 average rating, 17 reviews

Isla Living 3 Bed / 2 bath / Waterfront / Kayaks

Ashley MoniqueRating, 5 stars3 weeks ago
It was exactly like the photos and such a cute quaint area, very peaceful and pleasant
Top guest favorite
Home in Anna Maria
4.94 out of 5 average rating, 175 reviews

Discounted Thru July with Private Boat Dock & Pool

JacobRating, 5 stars1 month ago
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.
Top guest favorite
Home in Holmes Beach
5 out of 5 average rating, 66 reviews

Private Luxurious Ground Level Home

JemimaRating, 5 stars1 month ago
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!
Superhost
Home in Bradenton Beach
5 out of 5 average rating, 4 reviews

Casa Bonita

SonyaRating, 5 stars1 day ago
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!
Guest favorite
Home in Bradenton
4.92 out of 5 average rating, 367 reviews

Palm Retreat: #1 Top Rated Rental of Bradenton/AMI

AlejandraRating, 5 stars5 days ago
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 !!
Guest favorite
Home in Holmes Beach
4.93 out of 5 average rating, 58 reviews

Bayfront Gem Pool, Spa & walk to Anna Maria Beach

KimberlyRating, 5 stars2 weeks ago
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

Superhost
Condo in Bradenton Beach
4.76 out of 5 average rating, 220 reviews

Amazing View, Updated Beachfront Condo

TeriRating, 5 stars9 months ago
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!
Guest favorite
Condo in Holmes Beach
4.88 out of 5 average rating, 121 reviews

Steps from the beach

KellieRating, 5 stars1 week ago
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!
Guest favorite
Condo in Bradenton Beach
4.96 out of 5 average rating, 51 reviews

Next to Beach & Largest Pool on Island-258

LoriRating, 5 stars2 months ago
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!!
Top guest favorite
Condo in Bradenton
4.96 out of 5 average rating, 101 reviews

A&A's Paradise near IMG & Anna Maria beaches

AlekseyRating, 5 stars3 weeks ago
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!
Guest favorite
Condo in Bradenton Beach
4.88 out of 5 average rating, 121 reviews

Charming and Updated 1 Bedroom in Runaway Bay

MeleahRating, 5 stars1 week ago
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!
Top guest favorite
Condo in Tampa
4.95 out of 5 average rating, 302 reviews

Modern Waterfront Condo - Captivating Sunset Views

KateRating, 5 stars3 days ago
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.
Top guest favorite
Condo in Longboat Key
4.99 out of 5 average rating, 136 reviews

Condo with a View 2!

AndreiRating, 5 stars1 week ago
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.
Top guest favorite
Condo in Bradenton
4.98 out of 5 average rating, 204 reviews

Shorewalk full condo IMG Beaches Anna Maria

NicholeRating, 5 stars2 weeks ago
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!!!

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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