Anna Maria Vacation Homes

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Our top choices for Anna Maria holiday homes

A beach with clear turquoise water and white sand.

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

Anna Maria

Jessica S.

HK$4,861 total

includes taxes & fees

1 Dec - 2 Dec

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

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

Anna Maria

Holly F.

HK$5,884 total

includes taxes & fees

2 Dec - 3 Dec

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

Anna Maria

Anne B.

HK$4,666 total

includes taxes & fees

29 Nov - 30 Nov

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

4. 3BR Cottage with Heated Pool – Walk to Beach & Pine Ave

Anna Maria

Cheryl M.

HK$5,881 total

includes taxes & fees

2 Dec - 3 Dec

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

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

Anna Maria

Jaymi R.

HK$5,097 total

includes taxes & fees

8 Nov - 9 Nov

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

6. The Hideaway ~ Near Beach ~ Coastal Cottage

Anna Maria

JASON G.

HK$6,457 total

includes taxes & fees

16 Nov - 17 Nov

A pool area with a curved pool, a blue chair, and a covered seating area.

7. Coast Is Clear ~ Pool/Hot Tub ~ Near Pine Ave

Anna Maria

Richard

HK$5,767 total

includes taxes & fees

1 Dec - 2 Dec

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

8. Kiwi Cottage ~ Near Beach ~ Heated Pool

Anna Maria

Christopher

HK$6,098 total

includes taxes & fees

28 Nov - 29 Nov

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

9. Mermaid’s Purse ~ Near Beach ~ Heated Pool

Anna Maria

Magen S.

HK$6,392 total

includes taxes & fees

29 Nov - 30 Nov

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

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

Anna Maria

Marcus S.

HK$6,435 total

includes taxes & fees

15 Nov - 16 Nov

11. Flirty Flamingo Cottage Updated, moments from sand, w/pool, bikes, beach gear!

Anna Maria

April B.

HK$6,048 total

includes taxes & fees

29 Nov - 30 Nov

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

Anna Maria

Erin V.

HK$5,744 total

includes taxes & fees

30 Nov - 1 Dec

A spacious kitchen with a large island, stainless steel appliances, and a chandelier.

13. AMI Oasis ~ Near Pine Ave ~ Pool & Mini Golf

Anna Maria

Kelly F.

HK$9,836 total

includes taxes & fees

30 Nov - 1 Dec

A spacious living room with a large sofa set, a coffee table, and a television mounted on the wall.

14. Palm Paradise ~ Near Beach ~ Heated Pool

Anna Maria

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

15. Birdsong ~ North End ~ Private Heated Pool

Anna Maria

Aaron C.

A backyard with a swimming pool, lounge chairs, and a barbecue grill.

16. 4 King Beds + Guest House • Heated Pool/Spa

Anna Maria

HK$7,434 total

includes taxes & fees

15 Nov - 16 Nov

A spacious dining area with a view of the ocean through large windows.

17. BEACHFRONT, NOV. SPECIALS PRIVATE BEACH WATERFRONT, Bring your Dog Awesome views

Anna Maria

Anonymous traveller

HK$6,994 total

includes taxes & fees

9 Nov - 10 Nov

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

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

ANNA MARIA

Tina H.

HK$5,298 total

includes taxes & fees

8 Nov - 9 Nov

A covered patio area with a curved sofa, a dining table, and chairs, featuring large windows and a view of greenery.

19. AMI Canal-Front Luxury • Heated Pool /Spa & Boat Dock

Anna Maria

Kevin D.

HK$9,504 total

includes taxes & fees

8 Dec - 9 Dec

A spacious kitchen with a large island, white cabinetry, and pendant lighting.

20. Seaside Magnolia ~ Near Pine Ave ~ Pool/Spa

Anna Maria

Katie K.

HK$12,571 total

includes taxes & fees

29 Nov - 30 Nov

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Top Anna Maria Hotel Reviews

Sunrise Garden Resort

8/10 Good

"The beach to the east is 1 minute walk away. Walkable restaurants. Beach to the west, possibly the most beautiful in all of Florida, is a 10 minute walk away or very short drive. Sand is almost like flower. The Pier was closed, (across the street) but will be a great place to fish, walk and enjoy the scenery. Nice pool, great shower, nice picnic table..."

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

10/10 Excellent

"My husband and I came to Ana Maria Island for a half week vacation. We could not have picked a better place to spend our time. The home is impeccable. There is every amenity you would ever want there and more. Everything was well maintained. It exceeded our expectations for a Vrbo home. We highly recommend it."

Luxury waterfront home with a heated pool and spa!

10/10 Excellent

"This house is beautiful and as described. The check-in, communication, and cleanliness was great. The location is perfect, we never moved our car. Easy walk to the beach, shops, restaurants. The pool and hot tub is awesome and the views with the big palm trees is really lovely. Plenty of bath and beach towels are provided. I loved everything about the Island. Very chill lowkey vibe."

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!"

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!"

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