
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!

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 .

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

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!

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

Luxe! / Beach Access & Trolley/ Restaurants!
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!

Perfect Hideaway- Post Storms Better Than Ever!
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

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.

Hello Sunshine! BeachView Condo on Anna Maria Isl.
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.

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!!!!

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

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. 🌴🌊💛

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.

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.

Shorewalk full condo IMG Beaches Anna Maria
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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- 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