
Vacation 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

Veselka - Canal front w private heated pool & dock
We had a fantastic time at Michael and Denzil’s place! This was our second time in AMI. We stayed for a week with 6 adults and a toddler and had more than enough space for everyone to have their own room and not feel like we were on top of each other either. The home is very comfortable, clean, and has lots of natural light. We loved that each bedroom had its own bathroom and that we were walking distance to the beach (which wasn’t very busy, it felt private). We loved the pool and backing on to the lagoon too - we did a little fishing and went for a swim everyday. We really appreciated getting a 1:00 PM check in as we were coming in from the airport with a toddler due for a nap! We would 100% book with Michael and Denzil again, we love AMI! Thank you so much!

NEW saltwater pool/spa! Amazing outdoor space!
Great place as described. Kids loved the pool and the shade by the pool is 💵💵💵.

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

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
We had an amazing stay at Kelly’s place. It’s very conveniently located next to local restaurants, mini golf, and local shops. We loved having the beach on one side and the bay on the other. If you are looking for a calm, relaxing beach look no further! We definitely would return in the future!

3BR/2BA Private Oasis: Pool, Hot Tub, Dining
I recommend this oasis it’s beautiful just like the pictures private the outside is breathtaking I was surprised on how many cool electronics was around the house from the bathroom to the oven lol but 10/10 I had a blast great way to start my 30s 🙏🏾

One Level Large Home 2 Minute Walk to the Beach!
From the minute you get there the grounds are beautifully kept, crisp and lush. Inside was immaculate and the fenced, private backyard with pool did not disappoint. Tropical landscape, a variety of comfy options for relaxing or dining and the pool was perfect! We paid extra to have it heated and it was totally worth it…especially for my young children(3 and 7) to swim and not shiver:-). This place has a nice light, airy, relaxed, indoor outdoor vibe! My parents traveled with us as well and also loved it! The very short walk to the beach was perfect and opened up to this beautiful, seemingly private beach. You could see the public beach down a bit where there were quite a few umbrellas, but no one around where we were. Very nice! The neighborhood was beautiful and quiet as well. Communicating with the host was very easy and she always responded. We had a great vacation and will definitely be back.

4 Bed 4.5 Bath Family Friendly, 3 Blocks to Gulf
Stayed here with the whole crew and it was perfect. Flow of the house is great for extended family and guests. Patrick is super responsive and helpful. I couldn't find something and he literally brought it over. Would totally stay here again.
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!

Beach Escape & Pool, steps to Beach & restaurants
Cyndi and Colin - Thank you so much for having us! We truly enjoyed the weekend to the fullest thanks to this wonderful condo. Super close to the beach, restaurants, bars, and activities. Our favorites were Island Time (drinks), Daiquiri Deck (HH 3-7 Daily), Shore on LBK, and Drift Inn (drinks, cash only). Had an incredibly scenic dinner at Waterfront Beach House on the final night, about a 1 minute walk and you can enjoy a delicious dinner right on the beach! The condo had pretty much everything you could ever need for a beach trip, with Publix accessible nearby for anything additional we needed. Colin was so incredibly accommodating by letting us check in early and check out late. The condo was perfect size for us as a couple, and could certainly accommodate a couple small kids as well. We will absolutely be back in the area soon and will be booking with Colin and Cyndi again!

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
Totally exceeded my expectations!!! Rosana was amazing! Her condo was exquisite. Loved the personal touches and hospitality that was extended. Can't wait to come back!!!

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!!!

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.
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$27,197 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