
House vacation rentals in Anna Maria Island
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Top-rated house rentals in Anna Maria Island
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Popular amenities for Anna Maria Island house rentals
House rentals with a pool

Pool Oasis | Karaoke | 5G | Theater 135" | Grill
We had a wonderful time. It was a quiet neighborhood. The house had everything we needed. The hosts were great on communication and always responsive. The beds were comfortable. The theater was great! They were great with reminders to put out the trash and responded quickly with any questions we had. I would highly recommend staying with them.

2223 Doud Street, Sarasota, FL
This home was perfect for our group. We loved having 3 en-suite master bedrooms. The location is great for beach(Siesta Key), waterfront restaurants and shopping. We would definitely book again!

(HGR) Poolside Paradise: Airbnb Retreat
Beautiful place peaceful laid back neighborhood

Beautiful heated pool home, minutes from beaches
Great host and house. We enjoyed the layout of the house, awesome kitchen but the most we enjoyed the outside space and pool. Very nice neighborhood for walks in the morning. Easy drive to beaches, quick drive to grocery stores and restaurants.

Huge & Heated Pool Home 5 Minutes Away from Beach!
We stayed here right after Hurricane Helene for work, had to evacute for Milton, and then came back. Mark and his crew was amazing from start to finish in accommodations and communication.

Poolside Bliss in Clearwater! Heated-pool/Spa
This was a great place for me and my family. She was very kind ! Definitely would stay here again …..

Large 4 bedroom pool home tiki bar close to Ami
Great stay. This place is near to beaches in Sarasota. Host is very responsive .

Beautiful Heated Pool house, 10 mins to the beach!
The home was exactly as described. The backyard is truly an oasis, very private and peaceful. The pool was wonderful and heated to a comfortable temperature. Grocery stores and restaurants close by. A short drive to Clearwater and St. Petersburg, Anna is a wonderful host, very pleasant, helpful and responsive.
Weekly house rentals

Seminole Heights Gem
We absolutely loved our stay in this house!! Our main priority was separate bedrooms for our teenage son and our preteen daughter to have their own space and this house was perfect!! The rooms were very good size and the master bed/bath was HUGE!!! The beds were very comfy and we loved that the fridge had ice and a water dispenser! We had a little hiccup when originally checking into the house with the passcode not working, but Hannah responded to my message almost immediately, even with it being late at night, and got us into the house in no time!! We would definitely recommend and would love to stay here again on our next trip down to Tampa!!

Your Slice of Paradise
Very happy beginning to end! House is very clean and pleasant to stay. Will be returning for sure!

Comfortable & modern house in Central Bradenton
This place really started to feel like home as we have rented long term for the last I believe, four years. We knew we could get in our car and get to the beach, eat out or visit friends because everything was nearby. The beds were super comfortable and the kitchen had everything I needed to prepare most of our meals. I loved that we had access to a washer and dryer and the back yard was very inviting just to sit in the sun. The host was very quick to respond to any questions and concerns too. We made some great memories there with pictures to prove it. Thanks Elbert.

Wood Street Retreat 4/2 Near Beaches & Downtown
We thoroughly enjoyed our stay! Wanda's place is tremendous! 4 nice bedrooms (3 queens and a king as listed) and two full baths-spacious, comfortable and very clean! Good location. Close to excellent beaches, spring training stadiums and downtown Sarasota/marina. Fair price particularly for Sarasota and spring break. Wanda was an excellent host!! Very responsive and helpful!! I would highly recommend her place!! Two thumbs up!

The Happy House - Seeing is Believing!
Very nice home. Cozy space and beds. Nice pool. Our electric went out for about 12 hours so we couldn’t see anything the last night, but they were very attentive. It wasn’t their fault at all. Other than that, wonderful stay.

The A.G.E House Minutes to West Fl. beaches
Cute place! Place was very clean, had all the amenities we needed, and comfortable. Easy to find and in peaceful neighborhood. Perfect for families or groups of 2-4 people. Ashlee was a great host and very responsive. I made the mistake of leaving a small bag behind and she worked with me to get it returned - thanks so much Ashlee I appreciate you!

Elegant Newly Remodelled Spacious HOME
We had a great one month stay! Dorina was very responsive and accommodating. We have a one year old, and they purchased a pack and play and a rocking chair for us to use doing our stay. The place was exceptionally clean! We had some minor plumbing issues (shower drain backed up), but they did everything they could and quickly took care of the issue. The hosts went the extra mile to make sure we enjoyed our stay, and we would definitely recommend booking with them.

Now Booking for Summer! New! Heated Pool On Canal!
We had an absolutely amazing stay at this beautiful home on the canal in Cortez! The property exceeded all of our expectations — it was even better than the photos. The location was perfect, offering a peaceful and scenic atmosphere while still being close to everything we needed. The home was impeccably clean, beautifully decorated, and thoughtfully equipped with everything to make our stay comfortable. Sitting by the canal in the morning with a cup of coffee was a highlight, as was watching the sunset from the spacious deck. The host was incredible — super friendly, responsive, and quick to answer any questions. Their attention to detail and care for guests truly made this experience stand out. We cannot recommend this place enough and are already planning our next trip back. If you’re looking for the perfect getaway in Bradenton, this is it!
Private house rentals

Spacious Home Solar-Heated Pool and Spa
We have stayed at this location for a few years now and is also a very nice place! Very clean, well furnished and close to the beach and our favorite places. Thanks Kenneth and Deborah!

Poolside Paradise, Near Beach
A perfect home for our family to stay at! The pool was amazing, the linens were the most comfortable I’ve ever had and the house had great amenities. Thao was responsive and helpful.

The Breeze-private (optional) heated pool house.
The house is clean and private. Nice patio and pool. Dishwasher is good. Rooms are good. The master toilet is little tight to straighten the legs. Hosts are responsive and helpful. House size is kinda small for the high pricing. Maybe it is due to the demand and the hurricane. Overall rating should be 4.5-4.8.

Slice of Life, pet free heated pool 10 min 2 beach
WOW … what a great place to stay. This house feels like home!! It is very tastefully decorated, and it’s well stocked with everything you need - including spices, soaps, pool towels, beach chairs, umbrellas, beach cart, and even an car vac and air compressor. Their effort to make our stay memorable was appreciated. If we are in the area again … we will be staying here❤️

Summer House longboat key
My family and I would like to thank Chris for allowing us to stay at his beautiful beach house that was full of all the things we needed to feel at home. Chris responded to our messages very promptly and he even checked in on us to make sure we were doing well. Thank you Chris for a great experience on Long Boat Key; my family and I are very grateful 😁

Walk to Beach Food Drinks & Shops! “The Big House”
When our crew of 4 arrived at The Big House for our 11 days stay, we were welcomed with messages and very tasty rum cakes. We felt comfortable right away in the house and in the quiet neighbourhood. The Big House is perfectly named. The house is very spacious for 2 couples to feel they have their own space and privacy. The beds are really comfortable and the warm living room has lots of furniture for everyone. The kitchen is huge and well stocked with any utensils or appliances needed to cook wonderful meals. Great to have a laundry area too. Lynne has gone above and beyond providing anything you may need for your stay. Lynne is an excellent communicator. She answered all our messages quickly and kept us in the loop on everything. We took her suggestion to go to PJs Oyster Bar for dinner one night and thoroughly enjoyed our evening. We all agree we had a wonderful stay in The Big House. If we are in Largo again, it will be the place we want to be.

Tranquil Home. 2 minutes to Indian Rock Beach...
Gisele's place was clean and just like the pictures showed. The pool area was nice with a large Weber grill and lots of chairs . There were plenty of pool rafts in the garage for our use. Grocery stores, liquor stores, and restaurants all within a short drive and some within walking distance. The neighborhood was friendly and quiet and had a Catholic church within a 2 minute walk. We would definitely consider staying again!

Siesta Peace Retreat a private home rental
Tracy's place is wonderful, and she is very attentive. She gave us lots of tips on what to do and where to go, which was a big plus. The backyard is very relaxing with a lovely spa where we enjoyed the evenings. The house was super clean, and the beds were very comfortable. If I return to Siesta Key, I will definitely stay there again.
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- Crescent Beach
- John's Pass
- Cortez Beach
- Bean Point Beach
- Lido Key Beach
- Busch Gardens Tampa Bay
- Amalie Arena
- North Beach
- Raymond James Stadium
- Clearwater Beach
- Vinoy Park
- Coquina Beach
- Curtis Hixon Waterfront Park
- Tampa Theatre
- Fort De Soto Park
- Tropicana Field
- Manasota Key Beach
- ZooTampa at Lowry Park
- Splash Harbour Water Park
- Lakewood National Golf Club
- Streamsong Resort
- River Strand Golf and Country Club
- Sand Key Beach
- Honeymoon Island State Park