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
6 Nov - 8 Nov
In two months
18 Dec - 20 Dec
In three months
15 Jan - 17 Jan
In four months
12 Feb - 14 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 AED 915
AED 2,143 total
includes taxes & fees
25 Oct - 26 Oct
Newly Renovated Sea Breeze Cottage with Private Dock, Easy Access to Bimini Bay
A two-story house with a green exterior, a blue door, and orange trim.

2. 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 AED 364
AED 782 total
includes taxes & fees
19 Nov - 20 Nov
The "Grouper"
A small, single-story house with a white exterior, a brick planter with palm trees, and a white picket fence.

3. 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 AED 261
AED 922 total
includes taxes & fees
25 Oct - 26 Oct
Cozy Private Cottage, Minutes to Anna Maria Island
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 AED 643
AED 1,234 total
includes taxes & fees
25 Oct - 26 Oct
Pet-friendly Bradenton Home 1.5 Mi to Cortez Beach
A patio with a sun lounger, a table with chairs, and an umbrella.

5. Beach View 100ft To Beach and SPA

Beach View 100ft To Beach and SPA
2.0 star property
Siesta Key Village
The price is AED 559
AED 1,366 total
includes taxes & fees
25 Oct - 26 Oct
Beach View 100ft To Beach and SPA
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, (28 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 AED 454
AED 1,173 total
includes taxes & fees
25 Oct - 26 Oct
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 AED 559
AED 1,366 total
includes taxes & fees
25 Oct - 26 Oct
Beach Tree Cottage,Walk To Beach& Siesta
A yellow house with a blue door and the number 2202.

9. Steps 2 Beach- Cottage w/king bd +2bikes +parking

Steps 2 Beach- Cottage w/king bd +2bikes +parking
Pass-a-Grille
9.6 out of 10, Exceptional, (52 reviews)
"Clean, quiet and an easy walk to the beach."
United States
Marion W.
The price is AED 664
AED 1,536 total
includes taxes & fees
26 Oct - 27 Oct
Steps 2 Beach- Cottage w/king bd +2bikes +parking
A small pink house with a white door, a blue car parked in front, and a white picket fence.

10. PinkMango Cottage Steps to Beach&Village

PinkMango Cottage Steps to Beach&Village
2.0 star property
Siesta Key Village
The price is AED 645
AED 1,463 total
includes taxes & fees
26 Oct - 27 Oct
PinkMango Cottage Steps to Beach&Village
A backyard with a wooden fence, a blue trash bin, and a hammock.

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

Coastal Breeze Cottage in Sunny Sarasota. Pet friendly. King size bed.
Desoto Lakes
Coastal Breeze Cottage in Sunny Sarasota. Pet friendly. King size bed.
A small, light blue single-story house with a front door, a garage door, and a small porch area.

12. 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.
St Pete/gulfport Tiny little small home
A yellow house with a porch, a mailbox, and a number 5306 on the door.

13. Yellow Palm Cottage, Heart of Siesta Key

Yellow Palm Cottage, Heart of Siesta Key
2.0 star property
Siesta Key Village
The price is AED 681
AED 1,504 total
includes taxes & fees
26 Oct - 27 Oct
Yellow Palm Cottage, Heart of Siesta Key
A modern house with a driveway, a tree with purple lighting, and a white car parked in front.

14. 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 AED 624
AED 1,356 total
includes taxes & fees
20 Nov - 21 Nov
Escape near Siesta Key with Hot Tub, BBQ, and Fire pit
A white house with a covered porch, surrounded by a gravel driveway and various tropical plants.

15. 3716 7th Ave W

3716 7th Ave W
3.0 star property
Bradenton
The price is AED 8,148
AED 10,746 total
includes taxes & fees
27 Oct - 28 Oct
3716 7th Ave W
A rectangular pool with white lounge chairs and a white fence, surrounded by palm trees and a building with balconies.

16. Lido Key Casita w Pool Steps to the Beach

Lido Key Casita w Pool Steps to the Beach
Lido Key
10.0 out of 10, Exceptional, (1 review)
The price is AED 545
AED 1,512 total
includes taxes & fees
4 Nov - 5 Nov
Lido Key Casita w Pool Steps to the Beach
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.
Siesta Key Sanctuary -Pool-Kayaks-TikiHut-King bed
A residential house with a white fence, a palm tree, and a parked car.

18. 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
9.6 out of 10, Exceptional, (90 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 AED 364
AED 1,106 total
includes taxes & fees
10 Nov - 11 Nov
Drift Inn A, Heated Pool, Beach and Amenities, 2-3 min walk.
A bedroom with a bed, a ceiling fan, a window with curtains, a wooden wardrobe, and a framed picture on the wall.

19. Cozy Lido Studio by Beach & St Armand's

Cozy Lido Studio by Beach & St Armand's
Lido Key
Cozy Lido Studio by Beach & St Armand's
A two-story building with a blue exterior and white railings.

20. 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
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

Tropic Isle at Anna Maria Island Inn

Tropic Isle at Anna Maria Island Inn

10/10 Excellent
"We had a wonderful stay and were pleasantly surprised by how great the overall experience was! The location was perfect, the amenities were excellent, and everything was spotless. But what truly made our stay special was the outstanding service from the staff. A special shoutout to Danelis at the front desk, who was incredibly kind, welcoming, and thoughtful. We were celebrating a birthday, and she went out of her way to leave a little surprise in our room. That personal touch truly made a difference and made us feel extra special. It’s that kind of genuine hospitality that sets a hotel apart. We’ll definitely be back and would highly recommend this hotel to anyone looking for a great stay and exceptional service!"
Eliz 1-night trip
Posted 11 hours ago
Tropic Isle at Anna Maria Island Inn

Frequently asked questions

What are the best cottages in Anna Maria Island?
There are multiple cottages in Anna Maria Island with a total average guest review rating of 9.5, so you're sure to snag a place that suits your style. Planning to stay in Bradenton Beach? Queen's Gate Resort is one property favored by travelers. This 2.5-star cottage includes amenities such as a swimming pool and a garden. 105b 12th Street South Front 2 Bedroom Apts By Redawning is another highly rated escape where you'll be close to nature. A barbecue grill and a swimming pool are two of the conveniences waiting for you at this 3-star pick in Bradenton Beach.
Why book your cottage in Anna Maria Island with Expedia?
Reserving a cottage in Anna Maria Island is as simple as entering your travel dates and choosing an ideal place for a getaway in nature. From ritzy retreats to affordable properties and cottages that feature amenities like a kitchenette, Expedia has something for all traveler styles. As for the best offers around? We've got them as well!
How can I find cheap cottages in Anna Maria Island?
With Expedia's helpful filter tool, sourcing cheap cottages in Anna Maria Island has never been simpler. To discover accommodations that'll make your hip pocket happy, tailor your search results by budget, amenities and star rating.

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