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

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Check prices for these dates

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

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)
"Very nice property! Clean and lovely water view!"
United States
Sadie E.
$523 nightly
The price is $583
Oct 1 - Oct 2
Total with taxes and fees
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, (52 reviews)
"Pleasantly surprised how great this place was - awesome backyard setup and incredible location "
United States
Cyrus M.
$813 nightly
The price is $907
Oct 3 - Oct 4
Total with taxes and fees
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.
$820 nightly
The price is $914
Oct 24 - Oct 25
Total with taxes and fees
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.
$191 nightly
The price is $213
Oct 1 - Oct 2
Total with taxes and fees
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
$196 nightly
The price is $218
Oct 1 - Oct 2
Total with taxes and fees
Cozy Private Cottage, Minutes to Anna Maria Island
A small, single-story mobile home with a front porch, a small attached garage, and a clock tower.

6. 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.
$350 nightly
The price is $390
Oct 5 - Oct 6
Total with taxes and fees
Bridge Street Beach House | Wi-Fi | Center of All
A patio with two blue lounge chairs, a potted plant, and a gravel area.

7. 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
Oct 1 - Oct 2
Total with taxes and fees
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.

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.
$312 nightly
The price is $348
Oct 7 - Oct 8
Total with taxes and fees
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, (31 reviews)
"Such a great place to stay at a beautiful location! Will be back for sure!"
United States
Erin W.
$324 nightly
The price is $361
Oct 4 - Oct 5
Total with taxes and fees
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
$2,707 nightly
The price is $3,059
Oct 18 - Oct 19
Total with taxes and fees
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.
$331 nightly
The price is $369
Oct 1 - Oct 2
Total with taxes and fees
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
$210 nightly
The price is $235
Oct 15 - Oct 16
Total with taxes and fees
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
$306 nightly
The price is $340
Oct 1 - Oct 2
Total with taxes and fees
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.
$309 nightly
The price is $344
Oct 4 - Oct 5
Total with taxes and fees
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
$297 nightly
The price is $331
Oct 5 - Oct 6
Total with taxes and fees
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
$479 nightly
The price is $533
Oct 1 - Oct 2
Total with taxes and fees
🐾 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.
$286 nightly
The price is $319
Oct 1 - Oct 2
Total with taxes and fees
Happy Hour ACROSS THE STREET FROM THE BEACH
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
$286 nightly
The price is $319
Oct 1 - Oct 2
Total with taxes and fees
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.
$288 nightly
The price is $321
Oct 5 - Oct 6
Total with taxes and fees
Order up relaxation 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
$530 nightly
The price is $590
Oct 1 - Oct 2
Total with taxes and fees
🌅 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.
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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 2 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
401
Accommodation
23 Cottages
Lowest Price
$213
Highest Price
$3,059

Frequently asked questions

How much do cottages in Anna Maria cost?
Cottages in Anna Maria range between $213 and $3,059 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 $213 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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