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

Search Anna Maria Cottage Rentals from CA $300

  • 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 cottages

A coastal residential area with houses, a river, and a beach.

1. Adorable Cottage with Covered Balconies and Private Pool

Adorable Cottage with Covered Balconies and Private Pool
Anna Maria
9.8 out of 10, Exceptional, (51 reviews)
"Pleasantly surprised how great this place was - awesome backyard setup and incredible location "
United States
Cyrus M.
The price is CA $359
CA $1,311 total
includes taxes & fees
Oct 25 - Oct 26
Adorable Cottage with Covered Balconies and Private Pool
A balcony with wicker furniture, a grill, and a view of a marina with boats and greenery.

2. 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 CA $352
CA $835 total
includes taxes & fees
Sep 28 - Sep 29
Newly Renovated Sea Breeze Cottage with Private Dock, Easy Access to Bimini Bay
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 CA $428
CA $1,311 total
includes taxes & fees
Oct 24 - Oct 25
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 CA $140
CA $300 total
includes taxes & fees
Sep 29 - Sep 30
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 CA $87
CA $341 total
includes taxes & fees
Sep 29 - Sep 30
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 CA $247
CA $475 total
includes taxes & fees
Sep 28 - Sep 29
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 CA $267
CA $560 total
includes taxes & fees
Oct 5 - Oct 6
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 CA $161
CA $416 total
includes taxes & fees
Sep 30 - Oct 1
Sunny PaG Island rental w/bikes-just steps2beach
A small, light blue single-story house with a front door, a garage door, and a small porch area.

9. 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 CA $202
CA $528 total
includes taxes & fees
Sep 28 - Sep 29
St Pete/gulfport Tiny little small home
A single-story house with a blue exterior, a front door, and a small porch area.

10. 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 CA $127
CA $332 total
includes taxes & fees
Oct 12 - Oct 13
Coastal Breeze Cottage in Sunny Sarasota. Pet friendly. King size bed.
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
The price is CA $3,037
CA $4,024 total
includes taxes & fees
Oct 5 - Oct 6
3716 7th Ave W
A rectangular pool with white lounge chairs and a white fence, surrounded by palm trees and a building with balconies.

12. Lido Key Casita w Pool Steps to the Beach

Lido Key Casita w Pool Steps to the Beach
Lido Key
The price is CA $132
CA $484 total
includes taxes & fees
Sep 28 - Sep 29
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.

13. 🐾 1 BR Beach Cottage | Pet Friendly I Unit 8

🐾 1 BR Beach Cottage | Pet Friendly I Unit 8
Sunset Beach
The price is CA $267
CA $754 total
includes taxes & fees
Sep 28 - Sep 29
🐾 1 BR Beach Cottage | Pet Friendly I Unit 8
A patio with a table set for two, a blue umbrella, and a white fence.

14. Studio by Lido Beach w heated pool

Studio by Lido Beach w heated pool
Lido Key
The price is CA $132
CA $484 total
includes taxes & fees
Oct 1 - Oct 2
Studio by Lido Beach w heated pool
A beach with tall grasses in the foreground and a sunset over the ocean.

15. 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 CA $216
CA $451 total
includes taxes & fees
Sep 28 - Sep 29
An oasis ACROSS THE STREET FROM THE BEACH :)
A bedroom with a large bed, multiple pillows, and a wall-mounted artwork of tropical leaves.

16. 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 CA $198
CA $429 total
includes taxes & fees
Sep 28 - Sep 29
Happy Hour ACROSS THE STREET FROM THE BEACH
A rustic building with a sign reading "The Hut Grill" and a covered outdoor seating area.

17. 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.
Order up relaxation ACROSS The STREET 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.

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

Cozy Lido Studio by Beach & St Armand's
Lido Key
The price is CA $168
CA $525 total
includes taxes & fees
Oct 17 - Oct 18
Cozy Lido Studio by Beach & St Armand's
A bathroom with a toilet, a glass-enclosed shower, and a framed picture on the wall.

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

Coastal Studio, Walk to St Armand's or Lido Beach
Lido Key
The price is CA $151
CA $504 total
includes taxes & fees
Oct 4 - Oct 5
Coastal Studio, Walk to St Armand's or Lido 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 CA $401
CA $834 total
includes taxes & fees
Sep 29 - Sep 30
🌅 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
"Loved this place- would stay again. Really made it a great trip!"
Gavin H. 4-night trip
Posted 1 day 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
399
Accommodation
23 Cottages
Lowest Price
CA $300
Highest Price
CA $4,024

Frequently asked questions

How much do cottages in Anna Maria cost?
Cottages in Anna Maria range between CA $300 and CA $4,024 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 travellers 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 CA $300 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 favourites. 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.

Explore a world of travel with Expedia