A marina with boats, a bridge, and high-rise buildings.

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Check prices for these dates

In two weeks
Nov 27 - Nov 29
In two months
Jan 8 - Jan 10
In three months
Feb 5 - Feb 7
In four months
Mar 5 - Mar 7

Our top choices for Anna Maria 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)
"Has a beautiful view of the bay right behind the houseNeighbors were very friendly,has a new house being built next door but it still was quaint beach was in walking distance. Definitely a must do again."
United States
Terrence H.
$536 nightly
The price is $598
Nov 15 - Nov 16
Total with taxes and fees
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
9.4 out of 10, Exceptional, (80 reviews)
"Perfect spot"
United States
Canyon L.
$182 nightly
The price is $204
Nov 15 - Nov 16
Total with taxes and fees
The "Grouper"
A small, single-story house with a white exterior, surrounded by a white fence, and a gravel driveway with red tiles.

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
$217 nightly
The price is $243
Nov 15 - Nov 16
Total with taxes and fees
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
$297 nightly
The price is $336
Nov 16 - Nov 17
Total with taxes and fees
Pet-friendly Bradenton Home 1.5 Mi to Cortez Beach
A covered porch with a sign reading "BEACH HOUSE," outdoor seating, a grill, and a view of the water.

5. 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.
$455 nightly
The price is $455
Nov 23 - Nov 24
Total with taxes and fees
Bridge Street Pier Beach House + Dog-friendly
A yellow building with a blue door and a white staircase.

6. Beach Getaway Near Rays, Bikes & Gear

Beach Getaway Near Rays, 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.
$284 nightly
The price is $318
Nov 15 - Nov 16
Total with taxes and fees
Beach Getaway Near Rays, Bikes & Gear
A wooden deck with a white railing, a wicker sofa with cushions, and a small round table.

7. Sunny Island Rental, Bikes, Steps2Beach

Sunny Island Rental, Bikes, 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.
$324 nightly
The price is $364
Nov 22 - Nov 23
Total with taxes and fees
Sunny Island Rental, Bikes, Steps2Beach
A yellow house with a blue door and the number 2202.

8. Steps 2 Beach Cottage, King Bed, Bikes

Steps 2 Beach Cottage, King Bed, Bikes
Pass-a-Grille
9.6 out of 10, Exceptional, (52 reviews)
"Excellent location, property and adorable place!"
United States
Meredith S.
$375 nightly
The price is $420
Dec 6 - Dec 7
Total with taxes and fees
Steps 2 Beach Cottage, King Bed, Bikes
A backyard with a tree, a wooden fence, a blue shed, and a house with a door.

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

Coastal Breeze Cottage in Sunny Sarasota. Pet friendly. King size bed.
Desoto Lakes
$216 nightly
The price is $242
Dec 2 - Dec 3
Total with taxes and fees
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.

10. 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.
$316 nightly
The price is $354
Nov 15 - Nov 16
Total with taxes and fees
St Pete/gulfport Tiny little small home
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
$2,731 nightly
The price is $3,086
Nov 16 - Nov 17
Total with taxes and fees
3716 7th Ave W
A building with a tiled roof, a door, and two windows with shutters. There are two white chairs outside.

12. 🐾 1 BR Beach Cottage | Pet Friendly I Unit 8

🐾 1 BR Beach Cottage | Pet Friendly I Unit 8
Sunset Beach
$430 nightly
The price is $482
Nov 15 - Nov 16
Total with taxes and fees
🐾 1 BR Beach Cottage | Pet Friendly I Unit 8
A patio with a table set for two, a blue umbrella, and a white fence.

13. Lido Beach Studio with Heated Pool

Lido Beach Studio with Heated Pool
Lido Key
10.0 out of 10, Exceptional, (1 review)
"Wonderful place!!"
United States
Lorraine B.
$360 nightly
The price is $403
Nov 26 - Nov 27
Total with taxes and fees
Lido Beach Studio with Heated Pool
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
10.0 out of 10, Exceptional, (2 reviews)
"Alex was very quick to reply to my questions. Room was exactly as pictured!"
United States
Felecia P.
$361 nightly
The price is $404
Nov 18 - Nov 19
Total with taxes and fees
Lido Key Casita w Pool Steps to the Beach
A well-maintained garden with artificial grass, palm trees, and a pathway leading to a building with a light-colored facade.

15. Downtown | Walk Everywhere, Park Once

Downtown | Walk Everywhere, Park Once
Historic Old Northeast
10.0 out of 10, Exceptional, (13 reviews)
"Nice place. Nice location."
United States
Betsy D.
$337 nightly
The price is $377
Nov 16 - Nov 17
Total with taxes and fees
Downtown | Walk Everywhere, Park Once
A patio with a table set for two, a blue umbrella, and a white fence with plants.

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

Cozy Lido Studio by Beach & St Armand's
Lido Key
$359 nightly
The price is $402
Nov 22 - Nov 23
Total with taxes and fees
Cozy Lido Studio by Beach & St Armand's
A house with a red door, a blue chair, and palm trees in the yard.

17. 🌅 Ocean View 2 Bedroom Cottage | Unit 6

🌅 Ocean View 2 Bedroom Cottage | Unit 6
Sunset Beach
$473 nightly
The price is $530
Nov 15 - Nov 16
Total with taxes and fees
🌅 Ocean View 2 Bedroom Cottage | Unit 6
A building with a red-tiled roof, a blue door, and a 'NO PARKING' sign.

18. ⭐ Sea Side 2 Bedroom 2 Bath Cottage | Unit 7

⭐ Sea Side 2 Bedroom 2 Bath Cottage | Unit 7
Sunset Beach
$516 nightly
The price is $578
Nov 15 - Nov 16
Total with taxes and fees
⭐ Sea Side 2 Bedroom 2 Bath Cottage | Unit 7
A kitchen with white cabinets, a microwave, an oven, a sink, and a coffee maker.

19. 🏖️ Beach Suite Collection I Pet Friendly

🏖️ Beach Suite Collection I Pet Friendly
Sunset Beach
$758 nightly
The price is $849
Nov 15 - Nov 16
Total with taxes and fees
🏖️ Beach Suite Collection I Pet Friendly
A house with a red door, a blue chair, and palm trees in the yard.

20. 🌴 Beach Escape Collection | Sleeps Up to 8

🌴 Beach Escape Collection | Sleeps Up to 8
Sunset Beach
$801 nightly
The price is $897
Nov 22 - Nov 23
Total with taxes and fees
🌴 Beach Escape Collection | Sleeps Up to 8
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 Hotel Reviews

Duplex on North End of Anna Maria Island! With Pool and Grill

Duplex on North End of Anna Maria Island! With Pool and Grill

10/10 Excellent
"We loved our stay at this condo! It was very clean, comfortable, and had everything our family needed. We especially liked the updated feel and the layout, which worked perfectly for us. The location was convenient to Bean Point, several of our favorite restaurants, and great ice cream spots. The heated pool was a wonderful bonus and was always clean. We’d definitely stay here again!"
michael r. 3-night trip
Posted 6 hours ago
Duplex on North End of Anna Maria Island! With Pool and Grill

Find out more about Anna Maria

Anna Maria Cottages information

Number of reviews
385
Accommodation
23 Cottages
Lowest Price
$204
Highest Price
$3,086

Frequently asked questions

How much do cottages in Anna Maria cost?
Cottages in Anna Maria range between $204 and $3,086 per night. These stays offer a chance to reconnect with nature — at a price you can afford. These prices were 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.
What are the best cottages in Anna Maria?
There are multiple cottages in Anna Maria with a total average guest review rating of 9.8. Queen's Gate Resort is a superb place to rest and unwind between adventures. This 2.5-star cottage also features a garden and pool sun loungers. 105b 12th Street South Front 2 Bedroom Apts By Redawning is another popular pick with travelers in this area. It has a 3-star rating and amenities including a barbecue grill and a swimming pool.
How many cottages are there in Anna Maria?
You can choose from 23 cottages in Anna Maria. No matter if you're traveling with the family or planning a retreat with close friends, Expedia will help you find the perfect property to enjoy nature's beauty.
What are the best cheap cottages in Anna Maria?
With cottages starting from just $204 per night, you can afford to stay a little longer in Anna Maria! One escape that's easy on the pocket is Queen's Gate Resort. Amenities here include a swimming pool and a barbecue grill. Another cost-effective pick where you can get back in touch with nature is Pool Party North - 2 Bedroom Cottage. A barbecue grill and clothes washing facilities are two of the conveniences here. If you're sightseeing in Anna Maria and want to stay within your budget, there are loads of fun and free attractions to put on your to-do list. Anna Maria Beach and Coquina Beach are favorites. 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?
Get cozy at Queen's Gate Resort, a 2.5-star cottage just a short drive from downtown. Conveniences here include a nearby beach and beach umbrellas. Another family-friendly option where you can swap the concrete jungle for wide open spaces is 105b 12th Street South Front 2 Bedroom Apts By Redawning. A barbecue grill and WiFi help make this 3-star cottage a hit with guests. Once you've checked in and unpacked your things, there are tons of family-friendly attractions to visit in and around Anna Maria. Anna Maria Beach and Coquina Beach are two popular options.
Why book your cottage in Anna Maria with Expedia?
Expedia has some great cottages in Anna Maria, so get ready for a memorable stay close to nature. If you're sticking to a budget, select how much you'd like to spend and the star rating of your property. Or, try out our filters to search for cottages with a kitchen or a pool. We'll help you find the right place whatever your trip looks like.
How can I find cheap cottages in Anna Maria?
With Expedia's helpful filter tool, getting your hands on cheap cottages in Anna Maria has never been simpler. To discover accommodations that'll make your wallet smile, narrow your search by star rating, amenities and budget.
What is there to do in Anna Maria near my cottage?
Anna Maria has enough sights and experiences to keep you entertained for weeks, starting with Anna Maria Island Museum and Historical Park. Bean Point Beach, Palmetto Avenue Beach and Island Players are other popular attractions. If you're in town a while, Bayfront Park and Historic Green Village will cap off your itinerary nicely.

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