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Holiday 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

Top Guest favourite
Home in Bradenton
5 out of 5 average rating, 32 reviews

Just 5 miles to Anna Maria Island Beaches + IMG!

AddisonRating, 5 stars4 days ago
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!
Top Guest favourite
Home in Anna Maria
5 out of 5 average rating, 36 reviews

Veselka - Canal front w private heated pool & dock

CarrieRating, 5 stars2 weeks ago
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!
Guest favourite
Home in Holmes Beach
4.96 out of 5 average rating, 182 reviews

Be an AMI

JessicaRating, 5 stars2 weeks ago
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 .
Top Guest favourite
Home in Holmes Beach
5 out of 5 average rating, 36 reviews

Wk of 6/29 now avail at last minute SALE rate!

ChristiRating, 5 stars6 days ago
Wonderful home in Anna Maria! Very close to the beach, pool was a nice break from the sun and many beach and pool supplies! Mark was gracious and allowed us to check in earlier as well- this was a life saver with the kids and heat! Would stay again!
Guest favourite
Home in Bradenton
5 out of 5 average rating, 6 reviews

HeatPool~Pickleball~Mini-Golf~4 Kings+Kids Suite!

CarolRating, 5 stars4 days ago
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!
Top Guest favourite
Home in Bradenton
5 out of 5 average rating, 38 reviews

Heated Pool |Game Room|SmartTVs|King Beds|Sleeps14

BeckyRating, 5 stars1 week ago
We had a wonderful stay at this beautiful home. This home is super clean, well styled, and spacious. The backyard oasis is amazing - very private and quiet. The location is great; the home is close to all amenities as well as the beach. Communication with the host was exceptional. Dana is super responsive and very friendly and accommodating. I highly recommend booking this home!
Top Guest favourite
Home in Bradenton Beach
5 out of 5 average rating, 22 reviews

Luxe! / Beach Access & Trolley/ Restaurants!

TerryRating, 5 stars2 weeks ago
This location was awesome for our family vacation. We had 8 people and we had plenty of room. The outdoor area was relaxing. It was a comfortable house for both adults and kids. The proximity to the beach is great. We really appreciated the beach chairs, toys, cooler and umbrella. Hated to leave!
Top Guest favourite
Home in Holmes Beach
5 out of 5 average rating, 45 reviews

Perfect Hideaway- Post Storms Better Than Ever!

PixyRating, 5 stars3 weeks ago
Rebecca’s place was perfect for our family vacation of two young children, two parents and two grandparents. Her house sits on a dead end street just a few blocks from the beach. We found everything we needed for a few meals at home, and having a washer and dryer was convenient. The kicker was the outdoor pool, which we loved. We would easily recommend her place to anyone who wants a beautiful place to spend vacation.

Condo rentals with a pool

Guest favourite
Condo in Anna Maria
4.86 out of 5 average rating, 29 reviews

Resort-Style Ground Floor Suite Heated Pool/Spa

CandiceRating, 5 stars2 weeks ago
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.
Top Guest favourite
Condo in Holmes Beach
5 out of 5 average rating, 54 reviews

Hello Sunshine! BeachView Condo on Anna Maria Isl.

StephieRating, 5 stars1 week ago
We loved our stay at Hello Sunshine ☀️!! Anna Maria Island is very special to us and we are so glad we found this place. It is very close to the beach and all the shops and restaurants. The place was cozy, clean and comfortable, we felt right at home. Thank you for sharing it with us, we will be definitely rent again in the future.
Top Guest favourite
Condo in Bradenton
4.96 out of 5 average rating, 102 reviews

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

AmyRating, 5 stars3 weeks ago
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!!!!
Top Guest favourite
Condo in Holmes Beach
5 out of 5 average rating, 6 reviews

Gulf Place ~ Anna Maria Island, Beach, Pool, Tenni

VanessaRating, 5 stars5 months ago
What a wonderful stay we had here in Anna Maria! The condo was well located on the island and just a short golf cart away from shops and restaurants. We could hear, see, and feel the ocean and sea breeze from the Condo porch. The pool is large and warm. The beach is beautiful and you can walk as long as you want to along the ocean. The unit was clean, well stocked etc. Really my only wish was that the check in process was just through digital combo. We had to stop by a rental office to get an envelope and it seemed a little unnecessary. Not a huge deal, but it kept our concierge from being able to stock our unit ahead of us in the end. If we had just been sent the instructions and combo code ( which was written on the envelope and easily could have been messaged digitally) it would have shamed us some hassle. That didn't spoil our trip though! We loved it. We definitely would rent this unit again. Thank you so much!
Top Guest favourite
Condo in Longboat Key
4.98 out of 5 average rating, 186 reviews

Condo with a View 1: Open Friday Night!

AbigailRating, 5 stars1 week ago
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. 🌴🌊💛
Top Guest favourite
Condo in Tampa
4.95 out of 5 average rating, 302 reviews

Modern Waterfront Condo - Captivating Sunset Views

KateRating, 5 stars1 week 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 favourite
Condo in Holmes Beach
4.99 out of 5 average rating, 137 reviews

Beach Escape - Make Memories on Anna Maria Island

GinaRating, 5 stars1 month ago
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.
Top Guest favourite
Condo in Bradenton
4.98 out of 5 average rating, 206 reviews

Shorewalk full condo IMG Beaches Anna Maria

FrankRating, 5 stars5 days ago
I've stayed in Shorewalk 4 different times now, but you're place has been the best, by far. Super clean and accommodating. Great communication and always quick to respond. Thank you!

Quick stats about holiday rentals with a pool in Anna Maria

  • Total rentals

    410 properties

  • Nightly prices starting at

    $202 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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