House vacation rentals in Anna Maria Island

Find and book unique houses on Airbnb

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Popular amenities for Anna Maria Island house rentals

House rentals with a pool

Guest favourite
Home in Tampa
4.92 out of 5 average rating, 146 reviews

Pool Oasis | Karaoke | 5G | Theater 135" | Grill

KarenRating, 5 stars1 week ago
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.
Guest favourite
Home in Sarasota
4.97 out of 5 average rating, 58 reviews

2223 Doud Street, Sarasota, FL

MicheleRating, 5 stars2 weeks ago
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!
Guest favourite
Home in Tampa
5 out of 5 average rating, 7 reviews

(HGR) Poolside Paradise: Airbnb Retreat

MikeRating, 5 stars6 months ago
Beautiful place peaceful laid back neighborhood
Guest favourite
Home in Sarasota
4.94 out of 5 average rating, 98 reviews

Beautiful heated pool home, minutes from beaches

KatarzynaRating, 5 stars5 days ago
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.
Superhost
Home in Seminole
4.88 out of 5 average rating, 141 reviews

Huge & Heated Pool Home 5 Minutes Away from Beach!

IleaRating, 5 stars5 months ago
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.
Guest favourite
Home in Clearwater
4.88 out of 5 average rating, 172 reviews

Poolside Bliss in Clearwater! Heated-pool/Spa

CarmenRating, 5 stars6 days ago
This was a great place for me and my family. She was very kind ! Definitely would stay here again …..
Superhost
Home in Bradenton
4.87 out of 5 average rating, 289 reviews

Large 4 bedroom pool home tiki bar close to Ami

RaghuRating, 5 stars3 months ago
Great stay. This place is near to beaches in Sarasota. Host is very responsive .
Guest favourite
Home in Largo
4.95 out of 5 average rating, 134 reviews

Beautiful Heated Pool house, 10 mins to the beach!

LorettaRating, 5 stars1 month ago
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

Guest favourite
Home in Tampa
4.88 out of 5 average rating, 116 reviews

Seminole Heights Gem

JessicaRating, 5 stars3 weeks ago
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!!
Guest favourite
Home in Sarasota
4.9 out of 5 average rating, 134 reviews

Your Slice of Paradise

KArinaRating, 5 stars5 months ago
Very happy beginning to end! House is very clean and pleasant to stay. Will be returning for sure!
Superhost
Home in Bradenton
4.83 out of 5 average rating, 255 reviews

Comfortable & modern house in Central Bradenton

RosemaryRating, 5 stars1 month ago
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.
Top guest favourite
Home in Sarasota
4.94 out of 5 average rating, 162 reviews

Wood Street Retreat 4/2 Near Beaches & Downtown

LeeRating, 5 stars2 weeks ago
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!
Guest favourite
Home in Sarasota
4.93 out of 5 average rating, 68 reviews

The Happy House - Seeing is Believing!

AmberRating, 5 stars1 week ago
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.
Guest favourite
Home in Largo
4.85 out of 5 average rating, 39 reviews

The A.G.E House Minutes to West Fl. beaches

JohnRating, 5 stars1 month ago
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!
Top guest favourite
Home in Sarasota
5 out of 5 average rating, 18 reviews

Elegant Newly Remodelled Spacious HOME

RobertRating, 5 stars1 month ago
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.
Superhost
Home in Bradenton
5 out of 5 average rating, 11 reviews

Now Booking for Summer! New! Heated Pool On Canal!

MaryRating, 5 stars4 months ago
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

Superhost
Home in Largo
4.79 out of 5 average rating, 423 reviews

Spacious Home Solar-Heated Pool and Spa

WendyRating, 5 stars2 months ago
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!
Guest favourite
Home in Largo
5 out of 5 average rating, 9 reviews

Poolside Paradise, Near Beach

LindseyRating, 5 stars1 day ago
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.
Superhost
Home in Tampa
4.93 out of 5 average rating, 96 reviews

The Breeze-private (optional) heated pool house.

PhatRating, 5 stars4 months ago
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.
Top guest favourite
Home in Largo
4.95 out of 5 average rating, 113 reviews

Slice of Life, pet free heated pool 10 min 2 beach

RobertRating, 5 stars2 weeks ago
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❤️
Guest favourite
Home in Longboat Key
4.87 out of 5 average rating, 118 reviews

Summer House longboat key

DwayneRating, 5 stars1 week ago
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 😁
Guest favourite
Home in Largo
4.91 out of 5 average rating, 57 reviews

Walk to Beach Food Drinks & Shops! “The Big House”

DebbieRating, 5 stars1 month ago
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.
Guest favourite
Home in Largo
4.81 out of 5 average rating, 79 reviews

Tranquil Home. 2 minutes to Indian Rock Beach...

TerrenceRating, 5 stars1 week ago
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!
Guest favourite
Home in Siesta Key
4.92 out of 5 average rating, 115 reviews

Siesta Peace Retreat a private home rental

Isabel CristinaRating, 5 stars8 months ago
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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