An aerial view of a coastal town with a long pier extending into turquoise waters.

Search Holiday Rentals in Anna Maria Island

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
11 Sep - 13 Sep
In two months
23 Oct - 25 Oct
In three months
20 Nov - 22 Nov
In four months
18 Dec - 20 Dec

Our top choices for Anna Maria Island holiday rentals

A wooden boardwalk leading to a beach with a view of the ocean and clouds in the sky.

1. Haley's at The Anna Maria Island Inn

Haley's at The Anna Maria Island Inn
3.0 star property
Holmes Beach
8.6 out of 10, Excellent, (476 reviews)
"Very clean room and just a short walk to the beach!"
United States
Ivet
The price is 4.120.061 ₫
5.214.348 ₫ total
includes taxes & fees
26 Aug - 27 Aug
Haley's at The Anna Maria Island Inn
A two-story building with a balcony, palm trees, and outdoor seating.

2. Bridgewalk Resort

Bridgewalk Resort
3.5 star property
Bridge Street
9.4 out of 10, Exceptional, (823 reviews)
"loved it here"
United States
Hannah
The price is 7.547.524 ₫
8.528.702 ₫ total
includes taxes & fees
8 Sept - 9 Sept
Bridgewalk Resort
A modern building with a white exterior, a brick gable, and a palm tree in the foreground.

3. Pelican Post at Anna Maria Island Inn

Pelican Post at Anna Maria Island Inn
3.5 star property
Bradenton Beach
9.2 out of 10, Wonderful, (448 reviews)
"Great place to stay,"
United States
Wilson
The price is 4.500.702 ₫
5.696.087 ₫ total
includes taxes & fees
15 Sept - 16 Sept
Pelican Post at Anna Maria Island Inn
A modern bedroom with a large bed, a TV mounted on the wall, a wooden headboard, and a view of the sea through the balcony.

4. Seabreeze at Anna Maria Island Inn

Seabreeze at Anna Maria Island Inn
3.0 star property
Bradenton Beach
8.8 out of 10, Excellent, (124 reviews)
"I love how close I was to the beach"
United States
Rixie
The price is 5.086.143 ₫
6.437.023 ₫ total
includes taxes & fees
31 Aug - 1 Sept
Seabreeze at Anna Maria Island Inn
An outdoor deck with tables and chairs, a striped umbrella, and a view of the beach.

5. Alamanda Villas

Alamanda Villas
3.5 star property
Holmes Beach
8.4 out of 10, Very good, (11 reviews)
"The condo was great! Couldn’t have asked for a better place to start our first time in AMI!"
United States
Josephine
The price is 6.607.348 ₫
12.806.765 ₫ total
includes taxes & fees
20 Sept - 21 Sept
Alamanda Villas
A beach scene with waves gently lapping at the shore and the sun setting in the distance.

6. Palm Tree Villas

Palm Tree Villas
3.0 star property
Holmes Beach
9.2 out of 10, Wonderful, (174 reviews)
"It was just a beautiful stay and love to come back next year!!"
United States
Allison
The price is 3.813.719 ₫
17.487.795 ₫ total
includes taxes & fees
26 Aug - 27 Aug
Palm Tree Villas

7. Gulf to Bay Island Oasis

Gulf to Bay Island Oasis
2.0 star property
Bradenton Beach
The price is 4.946.387 ₫
15.354.097 ₫ total
includes taxes & fees
8 Sept - 9 Sept
Gulf to Bay Island Oasis
A modern kitchen with white cabinetry, a central island, pendant lighting, and a dining area with a white sofa and table.

8. 3716 7th Ave W

3716 7th Ave W
3.0 star property
Bradenton
The price is 61.633.760 ₫
80.583.811 ₫ total
includes taxes & fees
27 Aug - 28 Aug
3716 7th Ave W
A modern outdoor seating area with two blue chairs and a large potted plant.

9. Pet-friendly Bradenton Home 1.5 Mi to Cortez Beach

Pet-friendly Bradenton Home 1.5 Mi to Cortez Beach
3.0 star property
Bradenton
10.0 out of 10, Exceptional, (3 reviews)
"Very nice place to stay. Clean and a lot of amenities. We enjoyed all the little touches that went into decorating the house, giving it a beach house feel. We would definitely stay here again. "
United States
Rob
The price is 4.570.300 ₫
8.774.454 ₫ total
includes taxes & fees
31 Aug - 1 Sept
Pet-friendly Bradenton Home 1.5 Mi to Cortez Beach
A water slide in a pool area with a rocky backdrop and a small waterfall.

10. Cedar Run Resort - Roam Hospitality

Cedar Run Resort - Roam Hospitality
3.5 star property
South Bradenton
9.4 out of 10, Exceptional, (8 reviews)
"I would stay again, very accommodating"
United States
Deliondra
The price is 3.604.008 ₫
11.538.832 ₫ total
includes taxes & fees
26 Aug - 27 Aug
Cedar Run Resort - Roam Hospitality
A covered outdoor bar area with seating, a pool, and a view of the outdoors.

11. Beach House Suites by the Don CeSar

Beach House Suites by the Don CeSar
3.0 star property
Belle Vista
9.0 out of 10, Wonderful, (1,171 reviews)
"Great place to stay"
United States
Michael
The price is 4.885.753 ₫
6.703.423 ₫ total
includes taxes & fees
30 Aug - 31 Aug
Beach House Suites by the Don CeSar
A modern kitchen with white cabinets, a microwave, and an oven. There is a dining table with chairs and a decorative bowl.

12. Sarasota Family Home Private Heated Pool Relax

Sarasota Family Home Private Heated Pool Relax
2.0 star property
Whitfield Estates
2.0 out of 10, (1 review)
"Very disappointing stay Unfortunately, our experience at this property was very disappointing. The biggest issue was the air conditioning, which was not working properly during our entire stay. The first night was already very uncomfortable, but during the day it seemed to cool a little better, so we decided not to request a technician at that point. However, the second night was even worse, and the heat made it extremely difficult to sleep and enjoy our stay. We did report the problem to the...
United States
German
The price is 5.333.470 ₫
12.306.780 ₫ total
includes taxes & fees
30 Aug - 31 Aug
Sarasota Family Home Private Heated Pool Relax
An aerial view of a coastal resort area with multiple buildings, a beach, and a marina.

13. Sunset Vistas Two Bedroom Beachfront Suites

Sunset Vistas Two Bedroom Beachfront Suites
3.5 star property
Sunshine Beach
8.8 out of 10, Excellent, (3,719 reviews)
"Good spot, right on the beach."
United States
Paul
The price is 4.137.819 ₫
5.413.512 ₫ total
includes taxes & fees
20 Sept - 21 Sept
Sunset Vistas Two Bedroom Beachfront Suites
An outdoor patio with a dining table, chairs, and a sofa.

14. Mint House St. Petersburg Downtown by Kasa

Mint House St. Petersburg Downtown by Kasa
4.0 star property
Downtown St. Petersburg
9.4 out of 10, Exceptional, (980 reviews)
"Nice stay"
United States
Michelle
The price is 2.757.850 ₫
3.116.371 ₫ total
includes taxes & fees
31 Aug - 1 Sept
Mint House St. Petersburg Downtown by Kasa
A pool area with a waterfall feature, lounge chairs, and palm trees.

15. Tropical Beach Resorts

Tropical Beach Resorts
3.5 star property
South Village
9.4 out of 10, Exceptional, (5,791 reviews)
"Great place to visit!"
United States
Margaret Lai Ling
The price is 2.904.099 ₫
3.960.387 ₫ total
includes taxes & fees
27 Aug - 28 Aug
Tropical Beach Resorts
A beach with a clear sky and calm sea.

16. The Inn On Siesta Key

The Inn On Siesta Key
3.5 star property
Siesta Key
10.0 out of 10, Exceptional, (204 reviews)
"We had a wonderful stay at The Inn on Siesta Key. The Cabana was perfect for our family of 4, very clean and well equipped kitchen. The beds are very comfortable, and we enjoyed our morning coffee on the porch area. The property is fully equipped for the beach with chairs, towels, umbrellas, coolers, ice, and these great wagons to haul it all to the beach. Beaches are a short walk and amazing. The property is also a very short walk to The Village for shopping and dining. Paige checked us in and...
United States
Lisa
The price is 6.595.857 ₫
9.076.428 ₫ total
includes taxes & fees
27 Aug - 28 Aug
The Inn On Siesta Key
A modern living room with a flat-screen TV on a wooden cabinet, a grey sofa with patterned cushions, and a large window with sheer curtains.

17. SeaSpray Resort

SeaSpray Resort
4.0 star property
Siesta Key
9.6 out of 10, Exceptional, (174 reviews)
"Beautiful hotel comfortable bed nice and friendly staff!!!!"
United States
Isabel
The price is 5.382.508 ₫
6.082.417 ₫ total
includes taxes & fees
2 Sept - 3 Sept
SeaSpray Resort
A wooden boardwalk leading to a beach with clear blue water and a few people in the distance.

18. Southern PAG Beach House Bungalows

Southern PAG Beach House Bungalows
3.0 star property
Pass-a-Grille
6.0 out of 10, (2 reviews)
"Great staff and excellent location."
United States
Gregg
The price is 9.401.760 ₫
14.541.389 ₫ total
includes taxes & fees
26 Aug - 27 Aug
Southern PAG Beach House Bungalows
An outdoor patio with a grill, white chairs, and a red umbrella.

19. Hibiscus Suites - Gateway to Siesta Key

Hibiscus Suites - Gateway to Siesta Key
2.5 star property
Sarasota
8.6 out of 10, Excellent, (2,423 reviews)
"We stayed for 2 nights, the location was perfect for our needs! The beds were very comfortable and the kitchen was a added bonus!"
United States
Justine
The price is 3.322.963 ₫
3.754.948 ₫ total
includes taxes & fees
23 Sept - 24 Sept
Hibiscus Suites - Gateway to Siesta Key

20. Sun Outdoors Sarasota

Sun Outdoors Sarasota
2.5 star property
Fordville
The price is 11.752.200 ₫
13.279.987 ₫ total
includes taxes & fees
26 Aug - 27 Aug
Sun Outdoors Sarasota
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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Anna Maria Island Hotel Reviews

Silver Surf Gulf Beach Resort

Silver Surf Gulf Beach Resort

10/10 Excellent
"Everything is great here. Staff, facilities and location."
David 2-night trip
Posted 10 hours ago
Silver Surf Gulf Beach Resort