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

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

Anna Maria

Jaymi R.

HK$5,388 total

includes taxes & fees

8 Nov - 9 Nov

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

2. The Hideaway ~ Near Beach ~ Coastal Cottage

Anna Maria

JASON G.

HK$7,250 total

includes taxes & fees

3 Nov - 4 Nov

A coastal hotel with multiple buildings, a beach view, and a pool area.

3. Private Pool / Spa Home - Steps to Anna Maria Island Beach

Anna Maria

Erin S.

HK$7,287 total

includes taxes & fees

28 Nov - 29 Nov

A covered porch with teal chairs and white benches, large windows, and a view of the outside.

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

Anna Maria

Jessica S.

HK$5,942 total

includes taxes & fees

1 Nov - 2 Nov

A spacious living room with hardwood floors, a ceiling fan, and a large window with blinds.

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

Anna Maria

Anne B.

HK$4,670 total

includes taxes & fees

29 Nov - 30 Nov

A modern kitchen with granite countertops, stainless steel appliances, and pendant lighting.

6. Waterfront dog-friendly home with heated private pool, dock, views, and lanai

Anna Maria

Marcus S.

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

7. 3BR Cottage with Heated Pool – Walk to Beach & Pine Ave

Anna Maria

Cheryl M.

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$14,748 total

includes taxes & fees

29 Nov - 30 Nov

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Top Anna Maria Hotel Reviews

Duplex on North End of Anna Maria Island! With Pool and Grill

10/10 Excellent

"They stay at the property was really pleasant, unit was very clean and the phone call received to check on us with our stay and any problems is an exceptional touch of great management. Overall our stay was very enjoyable and look forward to a rebook in the future on our next trip."

Charming cottage , close to beach & bay.

10/10 Excellent

"Very nicely appointed pet friendly cottage that was perfect for us! The location is excellent, as it's within walking distance to the beach, gulf side, shops, restaurants and other amenities on the north end of AMI. The unit is stocked with everything you need in the kitchen, bathroom and items for the beach. We loved it! Kobe loved it!"

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

10/10 Excellent

"Fantastic property and location. Perfect setting for a couple. The patio is completely private and set back. It's also a great buffer from the sun and wind, the pictures can't even capture how nice and relaxing that spot is. Close to so many great beaches, shops and restaurants. Cannot wait to come back!"

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

10/10 Excellent

"I was so impressed with this house. The pics just don’t do it justice. Very short walk to the beach, lots of extras (beach toys, beach chairs and umbrellas), tons of storage and space. Loved everything about this house. The back yard was perfect for a break from the sun, with the hammock and chaise lounges."

Naut 2 Shabby Cottage-Awesome Pool Area, Pine Ave location close to everything

10/10 Excellent

"Great location! Very private pool area. We love Anna Marie Island! We would definitely stay at this location and house again. Try bakery next door yummy baked goods! And the ice cream store just a couple doors down had fabulous ice cream!! And always a must for us is the Waterfront restaurant, which is soo close!! We loved our little getaway!"

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"

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