Anna Maria Vacation Homes

A marina with boats, a bridge, and high-rise buildings.

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Our top choices for Anna Maria holiday homes

A spacious living area with a dining table, seating, a kitchen, and a view of the outdoors.

1. Tiny Tides: Adorable Cozy House!

Anna Maria

karen l.

A pool area with a white fence, palm trees, and outdoor furniture.

2. Anna Cabana B: Pool Home, AMI North End, 2 Blocks to Beach by Anna Maria Life Vacation Rentals

Anna Maria

Jaymi R.

HK$5,359 total

includes taxes & fees

8 Nov - 9 Nov

A stone building with a brick pathway, palm trees, and a stone staircase.

3. The Hideaway ~ Near Beach ~ Coastal Cottage

Anna Maria

JASON G.

HK$6,740 total

includes taxes & fees

15 Nov - 16 Nov

A beach with clear turquoise water and white sand.

4. Adorable Updated Cottage steps to the beach with pool, beach gear, bikes & grill

Anna Maria

Lewis E.

HK$5,953 total

includes taxes & fees

24 Oct - 25 Oct

A modern kitchen with white cabinets, a stainless steel refrigerator, and a microwave.

5. 3BR Cottage with Heated Pool – Walk to Beach & Pine Ave

Anna Maria

Cheryl M.

HK$6,586 total

includes taxes & fees

27 Oct - 28 Oct

6. Sassy Seagull -Charming cottage, moments from sand w/ pool, bikes & beach gear!

Anna Maria

Terry R.

HK$5,897 total

includes taxes & fees

23 Oct - 24 Oct

A yellow house with a swimming pool surrounded by palm trees and various plants.

7. Covey Cottage! Walk to Beach, Boutique Shops and City Pier

Anna Maria

Kristen D.

A spacious kitchen with a large island, pendant lighting, and a view of the outdoors.

8. Elegance ~ Near Pine Ave ~ Pool/Spa ~ Arcade

Anna Maria

"We were getting married at the Sandbar restaurant and booking this rental was perfect. A close walk or golf cart ride down the street. So convenient. And the house was perfect for the guests that stayed there, as well as having extra room for some friends to come hang out prior to the big day. Highly recommend this spot for any large groups (very reasonably priced when you consider splitting it between 7 adults/couples per room)"

Luke N.

HK$13,610 total

includes taxes & fees

11 Nov - 12 Nov

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Top Anna Maria Hotel Reviews

Charming cottage , close to beach & bay.

10/10 Excellent

"The cottage was very close to the beach, 2-3 blocks. It came equipped with a beach wagon, beach chairs, and a beach umbrella. Easy to transport all to the beach. Kitchen and bathroom were both well-stocked with essentials. Beds were comfy. We enjoyed the back screened patio for coffee each morning.Very nice cottage, very clean and comfortable. Close to lots of restaurants and shops.We very much enjoyed our 3 night stay and would recommend to other couples."

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"

LOCATION! COMPLETE REHAB Great pool, close to north bean pt., twin family rooms

10/10 Excellent

"The house was beautiful and clean! The pictures do not do it justice for how large the family room/dining room was! Great/easy walk to the beach, enjoyable pool area. Made for one fantastic family vacation."

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."

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