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

Anna Maria Vacation Rentals

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Check prices for these dates

In two weeks
Nov 6 - Nov 8
In two months
Dec 18 - Dec 20
In three months
Jan 15 - Jan 17
In four months
Feb 12 - Feb 14

Our top choices for Anna Maria vacation homes

A covered outdoor seating area with a table and chairs, large windows, and a view of palm trees and a road.

1. Family-Friendly Duplex Near Beaches and Local Shops! - A Place In Paradise Unit

Family-Friendly Duplex Near Beaches and Local Shops! - A Place In Paradise Unit
Anna Maria
9.4 out of 10, Exceptional, (33 reviews)
"We really enjoyed our stay. The location was perfect- super close to a quiet beach, and close to restaurants and shopping on Pine street. Place was clean and comfortable and had everything we needed to enjoy the beach."
United States
Louise W.
The price is CA $166
CA $826 total
includes taxes & fees
Oct 26 - Oct 27
Family-Friendly Duplex Near Beaches and Local Shops! - A Place In Paradise Unit
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 Cabana B: Pool Home, AMI North End, 2 Blocks to Beach by Anna Maria Life Vacation Rentals
Anna Maria
9.2 out of 10, Wonderful, (63 reviews)
"Great place- close to the beach!"
United States
Jaymi R.
The price is CA $315
CA $956 total
includes taxes & fees
Nov 8 - Nov 9
Anna Cabana B: Pool Home, AMI North End, 2 Blocks to Beach by Anna Maria Life Vacation Rentals
A beach with clear turquoise water and white sand.

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

Sassy Seagull -Charming cottage, moments from sand w/ pool, bikes & beach gear!
Anna Maria
10.0 out of 10, Exceptional, (29 reviews)
"Great property!"
United States
Jessica S.
The price is CA $460
CA $1,061 total
includes taxes & fees
Nov 1 - Nov 2
Sassy Seagull -Charming cottage, moments from sand w/ pool, bikes & beach gear!
A stone building with a brick pathway, palm trees, and a stone staircase.

4. The Hideaway ~ Near Beach ~ Coastal Cottage

The Hideaway ~ Near Beach ~ Coastal Cottage
Anna Maria
10.0 out of 10, Exceptional, (3 reviews)
"Everything was great. So close to the beach a 3 min walk. We loved everything about it."
United States
JASON G.
The price is CA $349
CA $1,259 total
includes taxes & fees
Nov 15 - Nov 16
The Hideaway ~ Near Beach ~ Coastal Cottage
A coastal hotel with multiple buildings, a beach view, and a pool area.

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

Private Pool / Spa Home - Steps to Anna Maria Island Beach
Anna Maria
10.0 out of 10, Exceptional, (1 review)
"An absolute gem! This place was perfection and we couldn’t be happier. We are already planning to hopefully come back in 2 years for our next girls trip. It was immaculately clean, beautifully decorated, so close to the beach and great location for shopping/restaurants. They had everything at the property we could think of."
United States
Erin S.
The price is CA $357
CA $1,190 total
includes taxes & fees
Nov 18 - Nov 19
Private Pool / Spa Home - Steps to Anna Maria Island Beach
A beach with clear turquoise water and white sand.

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

Adorable Updated Cottage steps to the beach with pool, beach gear, bikes & grill
Anna Maria
10.0 out of 10, Exceptional, (24 reviews)
"Love these cottages, very close to the beach and restaurants!"
United States
Lewis E.
The price is CA $405
CA $986 total
includes taxes & fees
Nov 22 - Nov 23
Adorable Updated Cottage steps to the beach with pool, beach gear, bikes & grill
A modern kitchen with white cabinets, a stainless steel refrigerator, and a microwave.

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

3BR Cottage with Heated Pool – Walk to Beach & Pine Ave
Anna Maria
10.0 out of 10, Exceptional, (1 review)
"Great sister stayHouse was perfect, pool was enjoyed by us all after a day a the beachMorning and evening at the pool We will be back for our next get together"
United States
Cheryl M.
The price is CA $343
CA $1,189 total
includes taxes & fees
Oct 27 - Oct 28
3BR Cottage with Heated Pool – Walk to Beach & Pine Ave
A modern living room with a blue sofa, a TV, and a kitchen area with a white countertop and bar stools.

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

Private Home with Pool and Spa, 2 Blocks to Beach and Guest Suite!
Anna Maria
9.6 out of 10, Exceptional, (46 reviews)
"My husband and I had a great week staying here. We had everything that we needed for our stay, the house was very comfortable. We loved spending time in the pool and spa!"
United States
Jesse Z.
The price is CA $350
CA $1,214 total
includes taxes & fees
Oct 26 - Oct 27
Private Home with Pool and Spa, 2 Blocks to Beach and Guest Suite!
A wooden deck with a table and chairs overlooking a calm body of water, a dock with a boat, and a clear sky.

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

Water Front Sea Waves Cottage With Private Dock, Access To Bimini Bay
ANNA MARIA
9.6 out of 10, Exceptional, (123 reviews)
"We enjoyed our stay. Great location, and beautiful water view. Would defiantly stay again"
United States
Tina H.
The price is CA $419
CA $934 total
includes taxes & fees
Oct 26 - Oct 27
Water Front Sea Waves Cottage With Private Dock, Access To Bimini Bay
A spacious kitchen with a large island, pendant lighting, and a view of the outdoors.

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

Elegance ~ Near Pine Ave ~ Pool/Spa ~ Arcade
Anna Maria
10.0 out of 10, Exceptional, (3 reviews)
"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)"
United States
Luke N.
The price is CA $504
CA $2,429 total
includes taxes & fees
Nov 11 - Nov 12
Elegance ~ Near Pine Ave ~ Pool/Spa ~ Arcade
A modern kitchen with granite countertops, stainless steel appliances, and pendant lighting.

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

Waterfront dog-friendly home with heated private pool, dock, views, and lanai
Anna Maria
7.8 out of 10, Good, (91 reviews)
"Absolutely loved it and would love to stay there again."
United States
Marcus S.
The price is CA $394
CA $1,086 total
includes taxes & fees
Oct 26 - Oct 27
Waterfront dog-friendly home with heated private pool, dock, views, and lanai
An aerial view of a coastal area with beach, houses, and a clear blue sea.

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

Mermaid’s Purse ~ Near Beach ~ Heated Pool
Anna Maria
10.0 out of 10, Exceptional, (2 reviews)
"Perfect location and great service. Thanks for allowing us to make life long memories with our kids!"
United States
Magen S.
The price is CA $484
CA $1,261 total
includes taxes & fees
Nov 1 - Nov 2
Mermaid’s Purse ~ Near Beach ~ Heated Pool
A poolside area with lounge chairs and umbrellas, surrounded by palm trees and a wooden fence.

13. Kiwi Cottage ~ Near Beach ~ Heated Pool

Kiwi Cottage ~ Near Beach ~ Heated Pool
Anna Maria
10.0 out of 10, Exceptional, (1 review)
"Perfect location! Walking distance to beaches, shops and restaurants! The pool was an added bonus"
United States
Christopher
The price is CA $617
CA $1,368 total
includes taxes & fees
Nov 15 - Nov 16
Kiwi Cottage ~ Near Beach ~ Heated Pool
A backyard with a swimming pool, lounge chairs, and a barbecue grill.

14. 4 King Beds + Guest House • Heated Pool/Spa

4 King Beds + Guest House • Heated Pool/Spa
Anna Maria
The price is CA $459
CA $1,397 total
includes taxes & fees
Nov 15 - Nov 16
4 King Beds + Guest House • Heated Pool/Spa
A beach with clear turquoise water and white sand.

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

Flirty Flamingo Cottage Updated, moments from sand, w/pool, bikes, beach gear!
Anna Maria
10.0 out of 10, Exceptional, (40 reviews)
"Perfect beach cottage"
United States
Jane S.
The price is CA $561
CA $1,314 total
includes taxes & fees
Nov 8 - Nov 9
Flirty Flamingo Cottage Updated, moments from sand, w/pool, bikes, beach gear!
A beachfront property with a two-story house, a sandy beach, and several Adirondack chairs.

16. OCT., NOV. SPECIALS ,BEACHFRONT, PRIVATE BEACH ON THE WATERFRONT, Bring your Dog

OCT., NOV. SPECIALS ,BEACHFRONT, PRIVATE BEACH ON THE WATERFRONT, Bring your Dog
Anna Maria
9.6 out of 10, Exceptional, (218 reviews)
"Fantastic stay! Extremely clean and the location is perfect. The private beach was a great addition to our stay."
United States
Anonymous traveller
The price is CA $699
CA $1,441 total
includes taxes & fees
Nov 9 - Nov 10
OCT., NOV. SPECIALS ,BEACHFRONT, PRIVATE BEACH ON THE WATERFRONT, Bring your Dog
A modern living room with a grey sofa, a striped armchair, a coffee table, and a bookshelf.

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

Shell We Dance? Charming Bungalow with Fabulous Location and Private Pool!
Anna Maria
9.8 out of 10, Exceptional, (209 reviews)
"We had a great stay"
United States
Michelle J.
The price is CA $559
CA $1,095 total
includes taxes & fees
Oct 27 - Oct 28
Shell We Dance? Charming Bungalow with Fabulous Location and Private Pool!
A spacious kitchen with a large island, stainless steel appliances, and a chandelier.

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

AMI Oasis ~ Near Pine Ave ~ Pool & Mini Golf
Anna Maria
10.0 out of 10, Exceptional, (2 reviews)
"Great location. Nice size rooms. Pool was in the shade but very clean. All around a great stay"
United States
Kelly F.
The price is CA $635
CA $1,874 total
includes taxes & fees
Oct 26 - Oct 27
AMI Oasis ~ Near Pine Ave ~ Pool & Mini Golf
A bathroom with a white sink, a green vase, and framed artwork on the walls.

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

Seaside Magnolia ~ Near Pine Ave ~ Pool/Spa
Anna Maria
9.8 out of 10, Exceptional, (22 reviews)
"Great house! Great host!"
United States
Katie K.
The price is CA $911
CA $2,367 total
includes taxes & fees
Nov 15 - Nov 16
Seaside Magnolia ~ Near Pine Ave ~ Pool/Spa
An outdoor patio with a pool, lounge chairs, and a dining area.

20. Birdsong ~ North End ~ Private Heated Pool

Birdsong ~ North End ~ Private Heated Pool
Anna Maria
10.0 out of 10, Exceptional, (1 review)
"The property was exactly as advertised. We loved our time at this property and how clean it was. The private pool was so enjoyable and complimented our time at the beach that is just down the street during our stay."
United States
Aaron C.
The price is CA $594
CA $1,317 total
includes taxes & fees
Nov 8 - Nov 9
Birdsong ~ North End ~ Private Heated Pool
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Top Anna Maria Hotel Reviews

Charming cottage , close to beach & bay.

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!"
Chris E. 3-night trip
Posted 2 days ago
Charming cottage , close to beach & bay.

Find out more about Anna Maria

Anna Maria Vacation Homes information

Number of reviews
789
Accommodation
954 Vacation Homes
Lowest Price
CA $826
Highest Price
CA $3,593

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