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

Search Cottages 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
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 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
19 Oct - 20 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, (76 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
18 Oct - 19 Oct
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
10.0 out of 10, Exceptional, (13 reviews)
"Clean and nice place"
United States
Ismael
The price is AED 314
AED 989 total
includes taxes & fees
19 Oct - 20 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
18 Oct - 19 Oct
Pet-friendly Bradenton Home 1.5 Mi to Cortez Beach
A balcony with two wooden chairs and a small round table, surrounded by white railings and palm trees.

5. 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 1,181 total
includes taxes & fees
1 Nov - 2 Nov
Sunny PaG Island rental w/bikes-just steps2beach
A pool area with a blue deck, lounge chairs, a barbecue, and a view of buildings in the background.

6. The Inn On Siesta Key

The Inn On Siesta Key
3.5 star property
Siesta Key
10.0 out of 10, Exceptional, (211 reviews)
"The property was perfect. Walk to down town and the beach. Loved the provisions for the beach which made it so convenient. Room was super clean and overall the property was well maintained."
United States
Stephen
The price is AED 835
AED 1,147 total
includes taxes & fees
18 Oct - 19 Oct
The Inn On Siesta Key
A white house with a covered porch, surrounded by a gravel driveway and various tropical plants.

7. 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
22 Oct - 23 Oct
3716 7th Ave W
A patio area with a grill, potted plants, and a building with a teal door.

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 489
AED 1,287 total
includes taxes & fees
18 Oct - 19 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 836
AED 1,748 total
includes taxes & fees
18 Oct - 19 Oct
Steps 2 Beach- Cottage w/king bd +2bikes +parking
A yellow house with a porch, a mailbox, and a number 5306 on the door.

10. 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 542
AED 1,347 total
includes taxes & fees
18 Oct - 19 Oct
Yellow Palm Cottage, Heart of Siesta Key
A room with a dining table, chairs, a television, a sofa, and a lamp.

11. BlueDolphin Cottage Walk To Siesta Beach

BlueDolphin Cottage Walk To Siesta Beach
2.5 star property
Siesta Key Village
The price is AED 598
AED 1,411 total
includes taxes & fees
19 Oct - 20 Oct
BlueDolphin Cottage Walk To Siesta Beach
A bedroom with a bed, a ceiling fan, a window with curtains, a wooden wardrobe, and a framed picture on the wall.

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

Cozy Lido Studio by Beach & St Armand's
Lido Key
The price is AED 638
AED 1,631 total
includes taxes & fees
31 Oct - 1 Nov
Cozy Lido Studio by Beach & St Armand's
A single-story house with a blue exterior, a front door, and a small porch area.

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 AED 331
AED 907 total
includes taxes & fees
19 Oct - 20 Oct
Coastal Breeze Cottage in Sunny Sarasota. Pet friendly. King size bed.
A rectangular pool with white lounge chairs and a white fence, surrounded by palm trees and a building with balconies.

14. Lido Key Casita w Pool Steps to the Beach

Lido Key Casita w Pool Steps to the Beach
Lido Key
Lido Key Casita w Pool Steps to the Beach
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 AED 526
AED 1,367 total
includes taxes & fees
18 Oct - 19 Oct
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 AED 652
AED 1,897 total
includes taxes & fees
18 Oct - 19 Oct
🐾 1 BR Beach Cottage | Pet Friendly I Unit 8
A residential house with a white fence, a palm tree, and a parked car.

17. 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 459
AED 1,236 total
includes taxes & fees
25 Oct - 26 Oct
Drift Inn A, Heated Pool, Beach and Amenities, 2-3 min walk.
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.
The price is AED 717
AED 1,459 total
includes taxes & fees
18 Oct - 19 Oct
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 AED 624
AED 1,368 total
includes taxes & fees
25 Oct - 26 Oct
Escape near Siesta Key with Hot Tub, BBQ, and Fire pit
Shared sunbathing deck by the pool, at the resort.

20. 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 AED 459
AED 1,281 total
includes taxes & fees
20 Oct - 21 Oct
Siesta Key Sanctuary -Pool-Kayaks-TikiHut-King bed
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

Driftwood at Anna Maria Island Inn

Driftwood at Anna Maria Island Inn

10/10 Excellent
"Muy limpio muy atento es staff"
Jaqueline 1-night trip
Posted 17 hours ago
Driftwood 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 9.6, 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.

Explore a world of travel with Expedia