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

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Check prices for these dates

In two weeks
13 Nov - 15 Nov
In two months
25 Dec - 27 Dec
In three months
22 Jan - 24 Jan
In four months
19 Feb - 21 Feb

Our top choices for Anna Maria Island cottages

A balcony with wicker furniture, a grill, and a view of a marina with boats and greenery.

1. Newly Renovated Sea Breeze Cottage with Private Dock, Easy Access to Bimini Bay

Newly Renovated Sea Breeze Cottage with Private Dock, Easy Access to Bimini Bay
Anna Maria
9.6 out of 10, Exceptional, (129 reviews)
"Place is great and clean. Love how smooth everything was. Jenny is easy to communicate as well"
United States
Natalia D.
The price is AU$816
includes taxes & fees
30 Oct - 31 Oct
Newly Renovated Sea Breeze Cottage with Private Dock, Easy Access to Bimini Bay
A covered porch with a sign reading "BEACH HOUSE," outdoor seating, a grill, and a view of the water.

2. Bridge Street Pier Beach House + Dog-friendly

Bridge Street Pier Beach House + Dog-friendly
Bridge Street
9.6 out of 10, Exceptional, (38 reviews)
"Great place! Perfect location to the beach and shops "
United States
Michelle R.
The price is AU$685
includes taxes & fees
23 Nov - 24 Nov
Bridge Street Pier Beach House + Dog-friendly
A two-story house with a green exterior, a blue door, and orange trim.

3. The "Grouper"

The "Grouper"
Sunny Shores
9.6 out of 10, Exceptional, (78 reviews)
"We enjoyed our stay, close to shops and beach!"
United States
Savannah S.
The price is AU$305
includes taxes & fees
30 Oct - 31 Oct
The "Grouper"
A patio with two blue lounge chairs, a potted plant, and a gravel area.

4. 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 AU$477
includes taxes & fees
31 Oct - 1 Nov
Pet-friendly Bradenton Home 1.5 Mi to Cortez Beach
A small, single-story house with a white exterior, a brick planter with palm trees, and a white picket fence.

5. Cozy Private Cottage, Minutes to Anna Maria Island

Cozy Private Cottage, Minutes to Anna Maria Island
Bradenton
9.8 out of 10, Exceptional, (14 reviews)
"Clean and nice place"
United States
Ismael
The price is AU$418
includes taxes & fees
1 Nov - 2 Nov
Cozy Private Cottage, Minutes to Anna Maria Island
A balcony with two wooden chairs and a small round table, surrounded by white railings and palm trees.

6. Sunny PaG Island rental w/bikes-just steps2beach

Sunny PaG Island rental w/bikes-just steps2beach
Pass-a-Grille
9.4 out of 10, Exceptional, (29 reviews)
"Wonderful place to stay. Great location to the beach, restaurants and shopping. If you want a peaceful getaway highly recommend."
United States
Janise W.
The price is AU$445
includes taxes & fees
1 Nov - 2 Nov
Sunny PaG Island rental w/bikes-just steps2beach
A yellow building with a blue door and a white staircase.

7. Rays Baseball close! Beach Getaway| Bikes +Gear

Rays Baseball close! Beach Getaway| Bikes +Gear
Pass-a-Grille
9.8 out of 10, Exceptional, (34 reviews)
"We love staying at this nice cozy beach house! It's so close to the beach.And such a nice quiet location!"
United States
Cathy P.
Rays Baseball close! Beach Getaway| Bikes +Gear
An outdoor patio with green metal chairs and tables, a red umbrella, and a building with balconies in the background.

8. Beach Tree Cottage,Walk To Beach& Siesta

Beach Tree Cottage,Walk To Beach& Siesta
2.0 star property
Siesta Key Village
The price is AU$490
includes taxes & fees
2 Nov - 3 Nov
Beach Tree Cottage,Walk To Beach& Siesta
A small pink house with a white door, a blue car parked in front, and a white picket fence.

9. PinkMango Cottage Steps to Beach&Village

PinkMango Cottage Steps to Beach&Village
2.0 star property
Siesta Key Village
The price is AU$547
includes taxes & fees
2 Nov - 3 Nov
PinkMango Cottage Steps to Beach&Village
A patio with a sun lounger, a table with chairs, and an umbrella.

10. Beach View 100ft To Beach and SPA

Beach View 100ft To Beach and SPA
2.0 star property
Siesta Key Village
The price is AU$558
includes taxes & fees
1 Nov - 2 Nov
Beach View 100ft To Beach and SPA
A white house with a covered porch, surrounded by a gravel driveway and various tropical plants.

11. 3716 7th Ave W

3716 7th Ave W
3.0 star property
Bradenton
The price is AU$4,378
includes taxes & fees
9 Nov - 10 Nov
3716 7th Ave W
A small, single-story building with a porch, surrounded by tropical vegetation.

12. BlueDolphin Cottage Walk To Siesta Beach

BlueDolphin Cottage Walk To Siesta Beach
2.5 star property
Siesta Key Village
The price is AU$568
includes taxes & fees
2 Nov - 3 Nov
BlueDolphin Cottage Walk To Siesta Beach
A backyard with a tree, a wooden fence, a blue shed, and a house with a door.

13. Coastal Breeze Cottage in Sunny Sarasota. Pet friendly. King size bed.

Coastal Breeze Cottage in Sunny Sarasota. Pet friendly. King size bed.
Desoto Lakes
The price is AU$358
includes taxes & fees
24 Nov - 25 Nov
Coastal Breeze Cottage in Sunny Sarasota. Pet friendly. King size bed.
A yellow house with a porch, a mailbox, and a number 5306 on the door.

14. Yellow Palm Cottage, Heart of Siesta Key

Yellow Palm Cottage, Heart of Siesta Key
2.0 star property
Siesta Key Village
The price is AU$633
includes taxes & fees
1 Nov - 2 Nov
Yellow Palm Cottage, Heart of Siesta Key
A small, light blue single-story house with a front door, a garage door, and a small porch area.

15. St Pete/gulfport Tiny little small home

St Pete/gulfport Tiny little small home
St. Petersburg
10.0 out of 10, Exceptional, (4 reviews)
"Really nice place to stay and host communication was excellent "
United States
Susan D.
The price is AU$515
includes taxes & fees
31 Oct - 1 Nov
St Pete/gulfport Tiny little small home
A building with a tiled roof, a door, and two windows with shutters. There are two white chairs outside.

16. 🐾 1 BR Beach Cottage | Pet Friendly I Unit 8

🐾 1 BR Beach Cottage | Pet Friendly I Unit 8
Sunset Beach
The price is AU$717
includes taxes & fees
1 Nov - 2 Nov
🐾 1 BR Beach Cottage | Pet Friendly I Unit 8
Shared sunbathing deck by the pool, at the resort.

17. Siesta Key Sanctuary -Pool-Kayaks-TikiHut-King bed

Siesta Key Sanctuary -Pool-Kayaks-TikiHut-King bed
Siesta Key
9.6 out of 10, Exceptional, (8 reviews)
"The most well maintained property I've ever stayed."
United States
Russ H.
The price is AU$487
includes taxes & fees
10 Nov - 11 Nov
Siesta Key Sanctuary -Pool-Kayaks-TikiHut-King bed
A two-story building with a blue exterior and white railings.

18. Siesta Key Beachside Getaway Cottage Walking Distance to Beach and Village

Siesta Key Beachside Getaway Cottage Walking Distance to Beach and Village
Sarasota
9.2 out of 10, Wonderful, (192 reviews)
"Loved the location of this property! The property manager was easy to contact and the property was exactly as shown in the pictures. Would stay here again!"
United States
Tracie B.
Siesta Key Beachside Getaway Cottage Walking Distance to Beach and Village
A modern house with a driveway, a tree with purple lighting, and a white car parked in front.

19. Escape near Siesta Key with Hot Tub, BBQ, and Fire pit

Escape near Siesta Key with Hot Tub, BBQ, and Fire pit
Sarasota
8.4 out of 10, Very good, (10 reviews)
"The house was truly lovely, and the hosts were exceptionally caring, kind, and attentive in their communication. It was wonderful to be so close to the beach, with stores conveniently nearby, making the stay feel comfortable and welcoming."
United States
Kandra R.
The price is AU$529
includes taxes & fees
30 Oct - 31 Oct
Escape near Siesta Key with Hot Tub, BBQ, and Fire pit
A residential house with a white fence, a palm tree, and a parked car.

20. Drift Inn A, Heated Pool, Beach and Amenities, 2-3 min walk.

Drift Inn A, Heated Pool, Beach and Amenities, 2-3 min walk.
South Village
9.8 out of 10, Exceptional, (91 reviews)
"Would definitely stay here again. Great location and great house! Owner was quick and helpful with communication."
United States
Clarissa S.
The price is AU$428
includes taxes & fees
3 Nov - 4 Nov
Drift Inn A, Heated Pool, Beach and Amenities, 2-3 min walk.
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 Island Hotel Reviews

Pelican Post at Anna Maria Island Inn

Pelican Post at Anna Maria Island Inn

10/10 Excellent
"Location was perfect"
Amylynn 4-night trip
Posted 12 hours ago
Pelican Post at Anna Maria Island Inn

Find out more about Anna Maria Island

Anna Maria Island Cottages information

Number of reviews
616
Accommodation
59 Cottages
Lowest Price
AU$305
Highest Price
AU$4,378

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