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

Search Anna Maria Cottages

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Save instantly and earn perks with One Key
    Learn about One Key

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
16 Oct - 18 Oct
In two months
27 Nov - 29 Nov
In three months
25 Dec - 27 Dec
In four months
22 Jan - 24 Jan

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)
"Place is great and clean. Love how smooth everything was. Jenny is easy to communicate as well"
United States
Natalia D.
The price is £452
includes taxes & fees
4 Oct - 5 Oct
Newly Renovated Sea Breeze Cottage with Private Dock, Easy Access to Bimini Bay
A coastal residential area with houses, a river, and a beach.

2. Adorable Cottage with Covered Balconies and Private Pool

Adorable Cottage with Covered Balconies and Private Pool
Anna Maria
9.8 out of 10, Exceptional, (53 reviews)
"Pleasantly surprised how great this place was - awesome backyard setup and incredible location "
United States
Cyrus M.
The price is £690
includes taxes & fees
25 Oct - 26 Oct
Adorable Cottage with Covered Balconies and Private Pool
A covered outdoor area with wicker furniture, a glass table, and a view of a residential street.

3. Beautiful Condo on Pine Ave, 2 Blocks to Beach

Beautiful Condo on Pine Ave, 2 Blocks to Beach
Anna Maria
8.8 out of 10, Excellent, (29 reviews)
"Nice place, a little noisy in the morning but a good convenient location for a girls trip. It was clean and beds were decent. The water pressure was not great but that being said, I would stay here again!"
United States
Amy H.
The price is £682
includes taxes & fees
24 Oct - 25 Oct
Beautiful Condo on Pine Ave, 2 Blocks to Beach
A two-story house with a green exterior, a blue door, and orange trim.

4. 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 £166
includes taxes & fees
8 Oct - 9 Oct
The "Grouper"
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
10.0 out of 10, Exceptional, (13 reviews)
"Clean and nice place"
United States
Ismael
The price is £178
includes taxes & fees
4 Oct - 5 Oct
Cozy Private Cottage, Minutes to Anna Maria Island
A patio with two blue lounge chairs, a potted plant, and a gravel area.

6. 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 £254
includes taxes & fees
4 Oct - 5 Oct
Pet-friendly Bradenton Home 1.5 Mi to Cortez Beach
A small, single-story mobile home with a front porch, a small attached garage, and a clock tower.

7. Bridge Street Beach House | Wi-Fi | Center of All

Bridge Street Beach House | Wi-Fi | Center of All
Bridge Street
10.0 out of 10, Exceptional, (5 reviews)
"Great location, clean accommodations, good communication with host. ..."
United States
leslie m.
The price is £314
includes taxes & fees
26 Oct - 27 Oct
Bridge Street Beach House | Wi-Fi | Center of All
A balcony with two wooden chairs and a small round table, surrounded by white railings and palm trees.

8. 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 £270
includes taxes & fees
7 Oct - 8 Oct
Sunny PaG Island rental w/bikes-just steps2beach
A yellow building with a blue door and a white staircase.

9. Pass-a-Grille Beach Getaway| Walkable| Bikes +Gear

Pass-a-Grille Beach Getaway| Walkable| Bikes +Gear
Pass-a-Grille
9.8 out of 10, Exceptional, (33 reviews)
"Such a great place to stay at a beautiful location! Will be back for sure!"
United States
Erin W.
The price is £281
includes taxes & fees
4 Oct - 5 Oct
Pass-a-Grille Beach Getaway| Walkable| Bikes +Gear
A white house with a covered porch, surrounded by a gravel driveway and various tropical plants.

10. 3716 7th Ave W

3716 7th Ave W
3.0 star property
Bradenton
The price is £2,096
includes taxes & fees
12 Oct - 13 Oct
3716 7th Ave W
A small, light blue single-story house with a front door, a garage door, and a small porch area.

11. 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 £287
includes taxes & fees
4 Oct - 5 Oct
St Pete/gulfport Tiny little small home
A single-story house with a blue exterior, a front door, and a small porch area.

12. 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 £205
includes taxes & fees
12 Oct - 13 Oct
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.

13. Studio by Lido Beach w heated pool

Studio by Lido Beach w heated pool
Lido Key
The price is £289
includes taxes & fees
16 Oct - 17 Oct
Studio by Lido Beach w heated pool
A bathroom with a toilet, a glass-enclosed shower, and a framed picture on the wall.

14. Coastal Studio, Walk to St Armand's or Lido Beach

Coastal Studio, Walk to St Armand's or Lido Beach
Lido Key
10.0 out of 10, Exceptional, (1 review)
"5 Stars: This cozy studio was exactly what we were looking for. Alexander was pleasant and friendly, the check in/check out process was easy. The location was fabulous- perhaps slightly too far to walk to St.Armand’s , but a quick ride on the rentable VEO bikes/scooters. The accommodations were clean, and beachy. We did not have an opportunity to use the pool, so I do have any objective comments for the pool. If we are in the area again, we would definitely stay here again!"
United States
lisa o.
The price is £263
includes taxes & fees
4 Oct - 5 Oct
Coastal Studio, Walk to St Armand's or Lido Beach
A rectangular pool with white lounge chairs and a white fence, surrounded by palm trees and a building with balconies.

15. Lido Key Casita w Pool Steps to the Beach

Lido Key Casita w Pool Steps to the Beach
Lido Key
The price is £253
includes taxes & fees
5 Oct - 6 Oct
Lido Key Casita w Pool Steps to the Beach
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 £401
includes taxes & fees
4 Oct - 5 Oct
🐾 1 BR Beach Cottage | Pet Friendly I Unit 8
A bedroom with a large bed, multiple pillows, and a wall-mounted artwork of tropical leaves.

17. Happy Hour ACROSS THE STREET FROM THE BEACH

Happy Hour ACROSS THE STREET FROM THE BEACH
Sunshine Beach
10.0 out of 10, Exceptional, (12 reviews)
"Super accommodating, clean, and perfect location from the beach. The Happy Hour is the perfect home away from home."
United States
Morgan M.
The price is £248
includes taxes & fees
4 Oct - 5 Oct
Happy Hour ACROSS THE STREET FROM THE BEACH
A rustic building with a sign reading "The Hut Grill" and a covered outdoor seating area.

18. 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 £244
includes taxes & fees
5 Oct - 6 Oct
Order up relaxation ACROSS The STREET FROM The BEACH :)
A beach with tall grasses in the foreground and a sunset over the ocean.

19. 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 £243
includes taxes & fees
5 Oct - 6 Oct
An oasis ACROSS THE STREET FROM THE BEACH :)
A house with a red door, a blue chair, and palm trees in the yard.

20. 🌅 Ocean View 2 Bedroom Cottage | Unit 6

🌅 Ocean View 2 Bedroom Cottage | Unit 6
Sunset Beach
The price is £443
includes taxes & fees
15 Oct - 16 Oct
🌅 Ocean View 2 Bedroom Cottage | Unit 6
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 Hotel Reviews

Naut 2 Shabby Bungalow - A sweet and cozy getaway on Pine Avenue!

Naut 2 Shabby Bungalow - A sweet and cozy getaway on Pine Avenue!

10/10 Excellent
"This cozy Bungalow is nestled behind the cottage off of Pine Street. Perfect quiet location and very close to restaurants, shopping and a close walk to the beach. The Bungalow was well equipped. We loved that it had a private patio area, beach equipment and a washer and dryer for our use. I would definitely stay here again."
Eric P. 3-night trip
Posted 5 days ago
Naut 2 Shabby Bungalow - A sweet and cozy getaway on Pine Avenue!

Find out more about Anna Maria

Anna Maria Cottages information

Number of reviews
349
Accommodation
19 Cottages
Lowest Price
£166
Highest Price
£2,096

Frequently asked questions

How much do cottages in Anna Maria cost?
Cottages in Anna Maria range between £166 and £2,096 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?
Select from multiple cottages in Anna Maria with a total average guest review rating of 9.8. Queen's Gate Resort is an ideal place to relax and recharge between adventures. This 2.5-star cottage also features a barbecue grill and a garden. 105b 12th Street South Front 2 Bedroom Apts By Redawning is another leading option with visitors to this area. It has a 3-star rating and amenities including a swimming pool and a barbecue grill.
How many cottages are there in Anna Maria?
You can choose from 19 cottages in Anna Maria. No matter if you're travelling 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?
Cottages start from only £166 per night, so your Anna Maria escape doesn't have to stretch your finances! Queen's Gate Resort is a top wallet-friendly pick and features loads of amenities, including a barbecue grill and a swimming pool. Pool Party North - 2 Bedroom Cottage is another one of our popular cheap cottages. Conveniences here include a barbecue grill and clothes washing facilities. If you're exploring Anna Maria and want to save money, there are plenty of free attractions to put on your itinerary. Florida Maritime Museum at Cortez and Anna Maria Island Museum and Historical Park 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?
A trip with your group in Anna Maria is a breeze at Queen's Gate Resort. With amenities such as a nearby beach and laundry facilities, you'll find all the necessary comforts at this 2.5-star cottage. 105b 12th Street South Front 2 Bedroom Apts By Redawning is another family-friendly option where you and the rest of your crew can escape the relentless pace of life in the city. This cottage has a 3-star rating and conveniences including WiFi and a barbecue grill. Anna Maria boasts an array of family-friendly attractions to explore when the kids are getting restless. Florida Maritime Museum at Cortez and Anna Maria Island Museum and Historical Park guarantee a fun day out for visitors of all ages.
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 accommodation 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.