Anna Maria Guest Houses

Check prices for these dates

Next weekend

In two weeks

In one month

In two months

Our top choices for Anna Maria guest houses

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

1. With Oasis Shared Backyard

Lake Maggiore Shore

Glen V.

includes taxes & fees

15 Oct - 16 Oct

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

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

Pass-a-Grille

Barbara F.

includes taxes & fees

20 Oct - 21 Oct

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

Pass-a-Grille

Melissa G

includes taxes & fees

27 Oct - 28 Oct

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

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

Whitfield Estates

Susan B.

includes taxes & fees

15 Oct - 16 Oct

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

Central Sarasota

Liz

includes taxes & fees

2 Nov - 3 Nov

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

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

Pass-a-Grille

Laura P.

includes taxes & fees

11 Nov - 12 Nov

A beach at sunset with waves and a colorful sky.

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

Historic Old Northeast

Phoebe A.

View all properties

Save an average of 15% on thousands of hotels when you're signed in

Sign in

Sign up, it's free

Top Anna Maria Hotel Reviews

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

10/10 Excellent

"Naut 2 Shabby Bungalow is one of the best places we've had the pleasure of staying on Anna Maria Island. This place is perfect for a couple's vacation. The bungalow is very clean, very well appointed and wonderfully private. Thanks so much for the use of your place, it was an amazing way to end our vacation to Anna Maria Island. We look forward to a future stay when we return. Thanks again!"

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

10/10 Excellent

"This home has it all! And it is located right on the beach on Pine Street, which is the best! The host responded right away to any questions. This is the best spot for your family! Absolute Gem!"

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"

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."

Find out more about Anna Maria