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

Search Anna Maria Cottages

  • Bundle & Save

    Get more, spend less whenever you see Bundle & Save deals

  • OneKeyCash

    Earn OneKeyCash on all your eligible bookings

  • Upfront pricing

    We are not like the others - we include taxes and fees

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 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
Sep 23 - Sep 24
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
9.6 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
Sep 26 - Sep 27
Total with taxes and fees
The "Grouper"
A keyless entry system with a red pathway leading to a gated entrance.

3. 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)
"Very nice location. "
United States
Daniel o.
$218 nightly
The price is $243
Sep 23 - Sep 24
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
Sep 23 - Sep 24
Total with taxes and fees
Pet-friendly Bradenton Home 1.5 Mi to Cortez Beach
A yellow building with a blue door and a white staircase.

5. 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.
$271 nightly
The price is $302
Sep 23 - Sep 24
Total with taxes and fees
Pass-a-Grille Beach Getaway| Walkable| Bikes +Gear
A balcony with two wooden chairs and a small round table, surrounded by white railings and palm trees.

6. 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.
$255 nightly
The price is $285
Sep 27 - Sep 28
Total with taxes and fees
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.

7. 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
Sep 23 - Sep 24
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.

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

Coastal Breeze Cottage in Sunny Sarasota. Pet friendly. King size bed.
Desoto Lakes
$215 nightly
The price is $240
Sep 25 - Sep 26
Total with taxes and fees
Coastal Breeze Cottage in Sunny Sarasota. Pet friendly. King size bed.
A bedroom with a bed, a ceiling fan, a window with curtains, a wooden wardrobe, and a framed picture on the wall.

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

Cozy Lido Studio by Beach & St Armand's
Lido Key
$308 nightly
The price is $342
Sep 23 - Sep 24
Total with taxes and fees
Cozy Lido Studio by Beach & St Armand's
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
$304 nightly
The price is $338
Sep 24 - Sep 25
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.

11. Downtown Cottage | Walk Everywhere, Park once

Downtown Cottage | Walk Everywhere, Park once
Historic Old Northeast
10.0 out of 10, Exceptional, (11 reviews)
"Lovely accommodation close to everything. So many lovely restaurants and sights right you doorstep while sating in a darling cottage in a very quaint neighborhood. And just a short drive to lovely beaches. Highly recommend."
United States
Jennifer C.
$291 nightly
The price is $325
Sep 23 - Sep 24
Total with taxes and fees
Downtown Cottage | Walk Everywhere, Park once
A beach with tall grasses in the foreground and a sunset over the ocean.

12. 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
$271 nightly
The price is $302
Sep 23 - Sep 24
Total with taxes and fees
An oasis ACROSS THE STREET FROM 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
$479 nightly
The price is $533
Sep 23 - Sep 24
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.

14. 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.
$271 nightly
The price is $302
Sep 23 - Sep 24
Total with taxes and fees
Happy Hour ACROSS THE STREET FROM THE BEACH
A white house with a covered porch, surrounded by a gravel driveway and various tropical plants.

15. 3716 7th Ave W

3716 7th Ave W
3.0 star property
Bradenton
$2,707 nightly
The price is $3,059
Oct 4 - Oct 5
Total with taxes and fees
3716 7th Ave W
A rustic building with a sign reading "The Hut Grill" and a covered outdoor seating area.

16. 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.
$286 nightly
The price is $319
Sep 23 - Sep 24
Total with taxes and fees
Order up relaxation ACROSS The STREET FROM The BEACH :)
A patio with a table set for two, a blue umbrella, and a white fence.

17. Studio by Lido Beach w heated pool

Studio by Lido Beach w heated pool
Lido Key
$304 nightly
The price is $338
Sep 24 - Sep 25
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.

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

Coastal Studio, Walk to St Armand's or Lido Beach
Lido Key
$325 nightly
The price is $362
Oct 4 - Oct 5
Total with taxes and fees
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.

19. 🌅 Ocean View 2 Bedroom Cottage | Unit 6

🌅 Ocean View 2 Bedroom Cottage | Unit 6
Sunset Beach
$530 nightly
The price is $590
Sep 23 - Sep 24
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.

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

⭐ Sea Side 2 Bedroom 2 Bath Cottage | Unit 7
Sunset Beach
$567 nightly
The price is $632
Sep 23 - Sep 24
Total with taxes and fees
⭐ Sea Side 2 Bedroom 2 Bath Cottage | Unit 7
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

Private Home Situated Near Bean Point with Spacious Heated Pool!

Private Home Situated Near Bean Point with Spacious Heated Pool!

8/10 Good
"Great house, amazing closeness to the beach, loved the pool. Everything was clean and house was well equipped. Just wish the upstairs and downstairs connected from the inside and the air conditioner was very noisy, had trouble sleeping in the room with the king bed."
Samantha M. 2-night trip
Posted 21 hours ago
Private Home Situated Near Bean Point with Spacious Heated Pool!

Find out more about Anna Maria

Anna Maria Cottages information

Number of reviews
188
Accommodation
23 Cottages
Lowest Price
$243
Highest Price
$3,059

Frequently asked questions

How much do cottages in Anna Maria cost?
Cottages in Anna Maria range between $243 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 9.9. 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 $243 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.

Explore a world of travel with Expedia