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.

HK$4,618 total

includes taxes & fees

18 Oct - 19 Oct

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 modern living room with a blue sofa, a TV, and a kitchen area with a white countertop and bar stools.

3. Private Home with Pool and Spa, 2 Blocks to Beach and Guest Suite!

Anna Maria

Jesse Z.

HK$6,970 total

includes taxes & fees

26 Oct - 27 Oct

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

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

6. The Hideaway - Less than a block from beach!

Anna Maria

JASON G.

HK$7,108 total

includes taxes & fees

22 Oct - 23 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.

HK$6,909 total

includes taxes & fees

18 Oct - 19 Oct

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

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

Anna Maria

Marcus S.

HK$6,030 total

includes taxes & fees

18 Oct - 19 Oct

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

9. Elegance~Gorgeous! Arcade!~ Heated pool/spa~North End!

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

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

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

Anna Maria

Erin S.

HK$6,980 total

includes taxes & fees

19 Oct - 20 Oct

11. 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

An aerial view of a coastal area with beach, houses, and a clear blue sea.

12. Mermaid’s Purse~Private Pool! 40 steps to beach!

Anna Maria

Magen S.

HK$6,982 total

includes taxes & fees

19 Oct - 20 Oct

A poolside area with lounge chairs and umbrellas, surrounded by palm trees and a wooden fence.

13. Kiwi Cottage~Private Heated Pool!~Shopping close!

Anna Maria

Christopher

HK$8,201 total

includes taxes & fees

29 Oct - 30 Oct

A wooden deck with a table and chairs overlooking a calm body of water, a dock with a boat, and a clear sky.

14. Water Front Sea Waves Cottage With Private Dock, Access To Bimini Bay

ANNA MARIA

Tina H.

HK$5,173 total

includes taxes & fees

16 Oct - 17 Oct

A four-poster bed with a grey frame, a bedside table with a lamp, and a white dresser with gold handles.

15. 4 King Beds + Guest House • Heated Pool/Spa

Anna Maria

HK$6,928 total

includes taxes & fees

15 Nov - 16 Nov

A modern living room with a grey sofa, a striped armchair, a coffee table, and a bookshelf.

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

Anna Maria

Michelle J.

HK$6,081 total

includes taxes & fees

21 Oct - 22 Oct

17. Island beach cottage, Pool, bikes, beach gear, moments from the sand!

Anna Maria

Colleen D.

HK$6,628 total

includes taxes & fees

25 Oct - 26 Oct

A modern kitchen with white cabinetry, a wooden island, pendant lighting, and a patterned backsplash.

18. NEW! Meet Me At Sunset! 3 Homes from the Beach!

Anna Maria

Bobby R.

HK$9,409 total

includes taxes & fees

22 Oct - 23 Oct

An outdoor patio with a pool, lounge chairs, and a dining area.

19. Birdsong-Steps to Bean Point Beach Heated Pool!

Anna Maria

Aaron C.

HK$6,748 total

includes taxes & fees

21 Oct - 22 Oct

A bathroom with a large mirror, vanity, and a ceiling fan.

20. Hammock Dreams - Canal Home with Pool and Dock Near Beach

Anna Maria

Julie T.

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Top Anna Maria Hotel Reviews

Sunrise Garden Resort

10/10 Excellent

"The hotel was conveniently located near the beach and restaurants. The interior and exterior were immaculately clean, and the pool was a lovely feature. It was a peaceful and relaxing getaway."

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

8/10 Good

"Cute house in a great location. So close to the beach and other places on the island. Enjoyed the pool and hot tub. We had a little difficultly finding in the dark. I know that lights are a concern for the turtles at night but a motion light to help navigate getting the key would be very helpful.There is currently a beach wagon available, which I know is helpful for families."

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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