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

Search Anna Maria Island Cottage Rentals

  • 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
Oct 9 - Oct 11
In two months
Nov 20 - Nov 22
In three months
Dec 18 - Dec 20
In four months
Jan 15 - Jan 17

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)
"Very nice property! Clean and lovely water view!"
United States
Sadie E.
The price is ￥39,409
￥92,322 total
includes taxes & fees
Sep 25 - Sep 26
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, (75 reviews)
"We enjoyed our stay, close to shops and beach!"
United States
Savannah S.
The price is ￥15,588
￥33,533 total
includes taxes & fees
Sep 26 - Sep 27
The "Grouper"
A patio with two blue lounge chairs, a potted plant, and a gravel area.

3. 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 ￥27,554
￥52,900 total
includes taxes & fees
Sep 27 - Sep 28
Pet-friendly Bradenton Home 1.5 Mi to Cortez Beach
A modern living room with a television, wooden entertainment unit, beige sofa, and a large potted plant.

4. 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 ￥14,955
￥44,381 total
includes taxes & fees
Oct 1 - Oct 2
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.

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

Sunny PaG Island rental w/bikes-just steps2beach
Pass-a-Grille
9.2 out of 10, Wonderful, (27 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 ￥18,043
￥45,174 total
includes taxes & fees
Sep 27 - Sep 28
Sunny PaG Island rental w/bikes-just steps2beach
A white house with a covered porch, surrounded by a gravel driveway and various tropical plants.

6. 3716 7th Ave W

3716 7th Ave W
3.0 star property
Bradenton
The price is ￥354,841
￥467,256 total
includes taxes & fees
Oct 4 - Oct 5
3716 7th Ave W
A single-story house with a blue exterior, a front door, and a small porch area.

7. 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 ￥14,244
￥37,146 total
includes taxes & fees
Sep 25 - Sep 26
Coastal Breeze Cottage in Sunny Sarasota. Pet friendly. King size bed.
A patio with a table set for two, a blue umbrella, and a white fence.

8. Studio by Lido Beach w heated pool

Studio by Lido Beach w heated pool
Lido Key
The price is ￥14,798
￥51,977 total
includes taxes & fees
Oct 1 - Oct 2
Studio by Lido Beach w heated pool
A yellow house with a white door and number 5306.

9. Yellow Palm Cottage steps from the beach

Yellow Palm Cottage steps from the beach
Siesta Key Village
10.0 out of 10, Exceptional, (2 reviews)
"This place was so cute and quaint! It was just a short walk to the village and to the beach. The grounds were beautiful! A little oasis in the backyard. . Would stay here again!!!"
United States
Tami B.
Yellow Palm Cottage steps from the beach
A rectangular pool with white lounge chairs and a white fence, surrounded by palm trees and a building with balconies.

10. Lido Key Casita w Pool Steps to the Beach

Lido Key Casita w Pool Steps to the Beach
Lido Key
The price is ￥14,722
￥53,283 total
includes taxes & fees
Sep 28 - Sep 29
Lido Key Casita w Pool Steps to the Beach
A hammock tied between two palm trees, a pink building with a red roof, and a bush with red flowers.

11. Pink Mango Cottage steps from the beach

Pink Mango Cottage steps from the beach
Siesta Key Village
10.0 out of 10, Exceptional, (1 review)
The price is ￥15,762
￥88,104 total
includes taxes & fees
Sep 30 - Oct 1
Pink Mango Cottage steps from the beach
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.
The price is ￥22,531
￥58,132 total
includes taxes & fees
Sep 26 - Sep 27
St Pete/gulfport Tiny little small home
A small, single-story building with a blue roof and yellow walls, surrounded by a white picket fence and palm trees.

13. Blue Dolphin Cottage steps from the beach

Blue Dolphin Cottage steps from the beach
Siesta Key Village
The price is ￥20,121
￥96,600 total
includes taxes & fees
Sep 25 - Sep 26
Blue Dolphin Cottage steps from the beach
A bedroom with a bed, a ceiling fan, a window with curtains, a wooden wardrobe, and a framed picture on the wall.

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

Cozy Lido Studio by Beach & St Armand's
Lido Key
The price is ￥18,802
￥59,034 total
includes taxes & fees
Oct 17 - Oct 18
Cozy Lido Studio by Beach & St Armand's
A building with a tiled roof, a door, and two windows with shutters. There are two white chairs outside.

15. 🐾 1 BR Beach Cottage | Pet Friendly I Unit 8

🐾 1 BR Beach Cottage | Pet Friendly I Unit 8
Sunset Beach
The price is ￥29,758
￥83,995 total
includes taxes & fees
Sep 27 - Sep 28
🐾 1 BR Beach Cottage | Pet Friendly I Unit 8
A residential house with a white fence, a palm tree, and a parked car.

16. 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 ￥15,588
￥47,404 total
includes taxes & fees
Oct 6 - Oct 7
Drift Inn A, Heated Pool, Beach and Amenities, 2-3 min walk.

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 ￥15,827
￥48,351 total
includes taxes & fees
Sep 30 - Oct 1
Siesta Key Sanctuary -Pool-Kayaks-TikiHut-King bed
A beach with tall grasses in the foreground and a sunset over the ocean.

18. An oasis ACROSS THE STREET FROM THE BEACH :)

An oasis ACROSS THE STREET FROM THE BEACH :)
Sunshine Beach
10.0 out of 10, Exceptional, (16 reviews)
"Perfect location, quiet, and close to the beach. Looking forward to coming back again. "
Canada
Richard
The price is ￥22,043
￥47,581 total
includes taxes & fees
Sep 27 - Sep 28
An oasis ACROSS THE STREET FROM THE BEACH :)
A rustic building with a sign reading "The Hut Grill" and a covered outdoor seating area.

19. Order up relaxation ACROSS The STREET FROM The BEACH :)

Order up relaxation ACROSS The STREET FROM The BEACH :)
Sunshine Beach
10.0 out of 10, Exceptional, (34 reviews)
"Perfect location, perfect accommodations! Will be staying here again."
United States
Billy H.
The price is ￥24,090
￥50,209 total
includes taxes & fees
Sep 27 - Sep 28
Order up relaxation ACROSS The STREET FROM The BEACH :)
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)
"Right across the beach Less then 5 minutes Good space - rooms nice ad clean "
United States
ASHISH
The price is ￥38,846
￥70,897 total
includes taxes & fees
Oct 2 - Oct 3
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.
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

Haley's at The Anna Maria Island Inn

Haley's at The Anna Maria Island Inn

10/10 Excellent
"Beautiful room that is well located! Staff and check in was great as well! Very clean and comfortable! Will stay here again!"
Aundrea L 4-night trip
Posted less than an hour ago
Haley's at The Anna Maria Island Inn

Find out more about Anna Maria Island

Anna Maria Island Cottages information

Number of reviews
491
Accommodation
59 Cottages
Lowest Price
￥37,146
Highest Price
￥467,256

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 9.8, 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.
What are the best cheap cottages in Anna Maria Island?
With cottages starting at only ￥37,146 per night, you can afford an extra couple of nights in Anna Maria Island for outdoor fun. If Bradenton Beach is on your travel radar, book a room at Queen's Gate Resort. A garden and a swimming pool help make this option an excellent choice. You'll also find inexpensive cottages in Holmes Beach. Take deep, calming breaths in nature during your stay at Queen's Gate Resort and take advantage of conveniences like pool sun loungers and a garden. If you're exploring Anna Maria Island and want to save money, there are many fabulous free attractions to put on your itinerary. Anna Maria Beach and Coquina Beach are always popular with visitors. This price was available on Expedia within the past 7 days, for a hotel booking with a check-in date within the next year. Prices reflect current offers and availability is subject to change. Additional terms may apply.
Are there any family-friendly cottages in Anna Maria Island?
There are indeed. Whether it's in one of Anna Maria Island's busy cities or way out in nature, the cozy charm of a cottage is perfect for vacationing families. If Bradenton Beach is on your radar, book a stay at Queen's Gate Resort. This 2.5-star option offers a nearby beach and a barbecue grill. Another superb choice is 105b 12th Street South Front 2 Bedroom Apts By Redawning. Also in Bradenton Beach, this family-friendly cottage has a 3-star rating and includes WiFi and a barbecue grill. You'll find plenty of awesome things to do with the family in Bradenton Beach. Anna Maria Beach and Coquina Beach promise a fantastic day out.
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