Anna Maria Guest Houses

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Our top choices for Anna Maria guest houses

An aerial view of a coastal town with a long sandy beach, a marina, and residential buildings.

1. A Hidden Gem Steps to Pass-a-Grille Beach-Dog Ok!

Pass-a-Grille

Melissa G

HK$3,403 total

includes taxes & fees

27 Oct - 28 Oct

2. Charming Cottage in Pass-A-Grille Beach, Dogs Ok

Pass-a-Grille

Barbara F.

HK$2,305 total

includes taxes & fees

13 Oct - 14 Oct

A beach with a sandy shore, a few people, and buildings in the background.

3. Charming PaG Studio & Sunsets +Steps 2 Sand +Bikes

Pass-a-Grille

Laura P.

HK$2,085 total

includes taxes & fees

7 Nov - 8 Nov

A wooden outdoor bar area with a clear view of the backyard, including a wooden fence, palm trees, and a small pool.

4. With Oasis Shared Backyard

Lake Maggiore Shore

Glen V.

HK$1,168 total

includes taxes & fees

9 Oct - 10 Oct

A marina with boats docked, a wooden dock, and a clear sky.

5. ALL BRAND-NEW Waterfront room-Heated Pool, Tiki Bar, Gym

Whitfield Estates

Susan B.

HK$1,686 total

includes taxes & fees

9 Oct - 10 Oct

A wooden boardwalk leading to a sandy beach with palm trees and greenery.

6. Steps to Beach, Heated Pool, 2 Queen Beds, 2BA

Madeira Beach

HK$2,476 total

includes taxes & fees

13 Oct - 14 Oct

A beach at sunset with waves and a colorful sky.

7. Stylish Retreat| Walk 2Dtwn+beach |Bikes+Patio

Historic Old Northeast

Phoebe A.

HK$1,540 total

includes taxes & fees

13 Oct - 14 Oct

8. Coolest Downtown Neighborhood - Ebikes, Beach Gear, Kayaks, Pickleball

Central Sarasota

Liz

HK$1,462 total

includes taxes & fees

14 Oct - 15 Oct

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Top Anna Maria Hotel Reviews

Charming cottage , close to beach & bay.

8/10 Good

"Cute and very clean little cottage"

Shell We Dance? Charming Bungalow with Fabulous Location and Private Pool!

10/10 Excellent

"We truly couldn’t have picked a more perfect place to celebrate our anniversary than **Shell We Dance at Bean Point**.From the moment we arrived, the cottage just felt special. It was charming, comfortable, beautifully cared for, and had that relaxed Anna Maria Island feel we were hoping for. The backyard and pool area were amazing — private, peaceful, and the perfect place to relax together.The location was absolutely incredible. Being so close to Bean Point (Our pup was originally named Bean Point when we adopted him) gave us some of our favorite memories from the trip — watching the sunrise and sunset, riding bikes around the island, walking the beach, BBQ'ing by pool, and the peace and quiet this time of year!! It was simple, peaceful, romantic, and exactly what we wanted for our anniversary getaway.We also want to give a special thank you to Goose, the Property Manager, and to the owners, Don and Sally. The customer service from beginning to end was exceptional. Everyone was welcoming, responsive, and genuinely cared about making our stay memorable. Allowing us to check in early at no additional charge for our anniversary was such a thoughtful gesture and one we truly appreciated.This was much more than just a place to stay — it became part of a really special anniversary for us. We left with some wonderful memories and are already talking about coming back.Thank you, Goose, Don, and Sally, for helping make our stay so special. Bill and Jess"

Naut 2 Shabby Bungalow - A sweet and cozy getaway on Pine Avenue!

10/10 Excellent

"This cozy Bungalow is nestled behind the cottage off of Pine Street. Perfect quiet location and very close to restaurants, shopping and a close walk to the beach. The Bungalow was well equipped. We loved that it had a private patio area, beach equipment and a washer and dryer for our use. I would definitely stay here again."

The Sunset Place- Unbeatable location. Gorgeous Sunsets. Updated Coastal Gem

10/10 Excellent

"The property was very nice although I wish I would have realized that all bedrooms were on the second floor if someone is unable to do stairs, that’s an important item to add in the description. Also, it appeared that you could walk straight out the door to the beach that was not exactly correct although it was a short walk it was not directly out the back door."

The Ballyhoo on Bean Point, 200 feet to a beautiful bayside beach and views!

10/10 Excellent

"We liked everything. The staff was very skilled in customer service and we especially liked the gentleman who checked us in when we got there. We spoke with him a few times and he was very professional and personable every time."

Kingfish: Canalfront Paddleboards Putt Putt Heated Pool *Hot Tub

10/10 Excellent

"We had an absolute blast staying at Kingfish for our vacation! The house very clean and was the perfect "chill" spot for our large family. Mornings were super relaxing - sunshine, island breeze and plenty of space for everyone to get around before heading to the beach. After a day in the sand or around the island, it was nice coming back to the pool area for swimming, ping pong, darts and just hanging out. It felt like a home away from home!The neighborhood was quiet and laid-back, which we loved. It didn't feel touristy at all - it was great staying in a local spot where we could unwind without noise or crowds. The host was very accommodating and communicated well, which made everything easy from check in to check out. Our only small complaints were that the dining chairs weren't super comfortable for family meals or game nights, and the hot tub didn't quite work as expected (though it was too hot to miss it). Some of the bathrooms could use an update, but honestly, everything else about the property outweighed those minor inconveniences.Overall, we had a fun, comfortable stay and would definitely come back. Highly recommend this property for large groups looking for a relaxing trip!"

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