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

Holiday Homes in Anna Maria

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Check prices for these dates

In two weeks
30 Oct - 1 Nov
In two months
11 Dec - 13 Dec
In three months
8 Jan - 10 Jan
In four months
5 Feb - 7 Feb

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!

Tiny Tides: Adorable Cozy House!
Anna Maria
9.4 out of 10, Exceptional, (6 reviews)
"The weather and peacefulness of the island. "
United States
karen l.
The price is €527
includes taxes & fees
18 Oct - 19 Oct
Tiny Tides: Adorable Cozy House!
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 €620
includes taxes & fees
8 Nov - 9 Nov
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. 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, (23 reviews)
"Love these cottages, very close to the beach and restaurants!"
United States
Lewis E.
The price is €682
includes taxes & fees
24 Oct - 25 Oct
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.

4. 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 €744
includes taxes & fees
27 Oct - 28 Oct
3BR Cottage with Heated Pool – Walk to Beach & Pine Ave
A stone building with a brick pathway, palm trees, and a stone staircase.

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

The Hideaway - Less than a block from beach!
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 €809
includes taxes & fees
15 Oct - 16 Oct
The Hideaway - Less than a block from beach!
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

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.
Waterfront dog-friendly home with heated private pool, dock, views, and lanai
A coastal hotel with multiple buildings, a beach view, and a pool area.

7. 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 €796
includes taxes & fees
19 Oct - 20 Oct
Private Pool / Spa Home - Steps to Anna Maria Island Beach
A beach with clear turquoise water and white sand.

8. 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)
"Cottage 107 was ver clean, comfortable, and had everything we needed. The property was quiet and very family friendly. The beach, just a very short half block walk, is gorgeous. We had a wonderful time!"
United States
Terry R.
Sassy Seagull -Charming cottage, moments from sand w/ pool, bikes & beach gear!
A poolside area with lounge chairs and umbrellas, surrounded by palm trees and a wooden fence.

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

Kiwi Cottage~Private Heated Pool!~Shopping close!
Anna Maria
10.0 out of 10, Exceptional, (1 review)
The price is €827
includes taxes & fees
20 Oct - 21 Oct
Kiwi Cottage~Private Heated Pool!~Shopping close!
A modern living room with a grey sofa, a striped armchair, a coffee table, and a bookshelf.

10. 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.
Shell We Dance? Charming Bungalow with Fabulous Location and Private Pool!
A four-poster bed with a grey frame, a bedside table with a lamp, and a white dresser with gold handles.

11. 4 King Beds + Guest House • Heated Pool/Spa

4 King Beds + Guest House • Heated Pool/Spa
Anna Maria
The price is €897
includes taxes & fees
26 Oct - 27 Oct
4 King Beds + Guest House • Heated Pool/Spa
A wooden deck with a table and chairs overlooking a calm body of water, a dock with a boat, and a clear sky.

12. 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 €606
includes taxes & fees
14 Oct - 15 Oct
Water Front Sea Waves Cottage With Private Dock, Access To Bimini Bay
A bathroom with a large mirror, vanity, and a ceiling fan.

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

Hammock Dreams - Canal Home with Pool and Dock Near Beach
Anna Maria
9.6 out of 10, Exceptional, (17 reviews)
"Very happy with accommodation."
United States
Julie T.
Hammock Dreams - Canal Home with Pool and Dock Near Beach
An outdoor patio with a pool, lounge chairs, and a dining area.

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

Birdsong-Steps to Bean Point Beach 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.
Birdsong-Steps to Bean Point Beach Heated Pool!
An aerial view of a coastal area with beach, houses, and a clear blue sea.

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

Mermaid’s Purse~Private Pool! 40 steps to beach!
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 €838
includes taxes & fees
10 Nov - 11 Nov
Mermaid’s Purse~Private Pool! 40 steps to beach!
A beach with clear turquoise water and white sand.

16. 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 €861
includes taxes & fees
14 Oct - 15 Oct
Flirty Flamingo Cottage Updated, moments from sand, w/pool, bikes, beach gear!
A spacious kitchen with a large island, stainless steel appliances, and a chandelier.

17. Pine Avenue next door!~Heated pool~Steps to Beach

Pine Avenue next door!~Heated pool~Steps to Beach
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 €1,240
includes taxes & fees
15 Oct - 16 Oct
Pine Avenue next door!~Heated pool~Steps to Beach
A spacious kitchen with a large island, white cabinetry, and pendant lighting.

18. Seaside Magnolia~1 Block to Pine Ave, Heated Pool!

Seaside Magnolia~1 Block to Pine Ave, Heated Pool!
Anna Maria
9.8 out of 10, Exceptional, (22 reviews)
"Great house! Great host!"
United States
Katie K.
The price is €1,591
includes taxes & fees
19 Oct - 20 Oct
Seaside Magnolia~1 Block to Pine Ave, Heated Pool!
A spacious living area with a blue sofa, a dining table with chairs, and a view of a swimming pool through large sliding glass doors.

19. Private Duplex with Beautiful Updates and Heated Pool! 1 Minute from the Beach!

Private Duplex with Beautiful Updates and Heated Pool! 1 Minute from the Beach!
Anna Maria
8.0 out of 10, Very good, (9 reviews)
"The location is amazing and pool felt so relaxing! We had a great stay and really enjoyed this property!"
United States
Andrea P.
Private Duplex with Beautiful Updates and Heated Pool! 1 Minute from the Beach!
A beach with clear turquoise water and white sand.

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

Island beach cottage, Pool, bikes, beach gear, moments from the sand!
Anna Maria
9.8 out of 10, Exceptional, (50 reviews)
"Condo was very close to beach and clean."
United States
Colleen D.
The price is €753
includes taxes & fees
25 Oct - 26 Oct
Island beach cottage, Pool, bikes, beach gear, moments from the sand!
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

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

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!"
Jason G. 3-night trip
Posted 19 hours ago
Naut 2 Shabby Bungalow - A sweet and cozy getaway on Pine Avenue!

Find out more about Anna Maria

Anna Maria Holiday Homes information

Number of reviews
570
Accommodation
957 Holiday Homes
Lowest Price
€527
Highest Price
€1,591