Anna Maria, FL Cottage Rentals from $204

Q: 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.

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

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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

Anna Maria

Terrence H.

$536 nightly

Nov 14 - Nov 15

Total with taxes and fees

A two-story house with a green exterior, a blue door, and orange trim.

2. The "Grouper"

Sunny Shores

Canyon L.

$182 nightly

Nov 15 - Nov 16

Total with taxes and fees

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

Bradenton

Ismael

$217 nightly

Nov 15 - Nov 16

Total with taxes and fees

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

Bradenton

Rob

$297 nightly

Nov 16 - Nov 17

Total with taxes and fees

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

Michelle R.

$460 nightly

Nov 23 - Nov 24

Total with taxes and fees

A yellow building with a blue door and a white staircase.

6. Beach Getaway Near Rays, Bikes & Gear

Pass-a-Grille

Cathy P.

$284 nightly

Nov 15 - Nov 16

Total with taxes and fees

A wooden deck with a white railing, a wicker sofa with cushions, and a small round table.

7. Sunny Island Rental, Bikes, Steps2Beach

Pass-a-Grille

Janise W.

$324 nightly

Nov 22 - Nov 23

Total with taxes and fees

A yellow house with a blue door and the number 2202.

8. Steps 2 Beach Cottage, King Bed, Bikes

Pass-a-Grille

Meredith S.

$367 nightly

Dec 6 - Dec 7

Total with taxes and fees

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.

Desoto Lakes

$216 nightly

Dec 2 - Dec 3

Total with taxes and fees

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. Petersburg

Susan D.

$316 nightly

Nov 14 - Nov 15

Total with taxes and fees

A white house with a covered porch, surrounded by a gravel driveway and various tropical plants.

11. 3716 7th Ave W

Bradenton

$2,542 nightly

Dec 13 - Dec 14

Total with taxes and fees

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

Sunset Beach

$430 nightly

Nov 15 - Nov 16

Total with taxes and fees

A patio with a table set for two, a blue umbrella, and a white fence.

13. Lido Beach Studio with Heated Pool

Lido Key

Lorraine B.

$360 nightly

Nov 26 - Nov 27

Total with taxes and fees

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

Felecia P.

$361 nightly

Nov 18 - Nov 19

Total with taxes and fees

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

Historic Old Northeast

Betsy D.

$337 nightly

Nov 16 - Nov 17

Total with taxes and fees

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

Lido Key

$360 nightly

Nov 29 - Nov 30

Total with taxes and fees

A house with a red door, a blue chair, and palm trees in the yard.

17. 🌅 Ocean View 2 Bedroom Cottage | Unit 6

Sunset Beach

$473 nightly

Nov 15 - Nov 16

Total with taxes and fees

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

Sunset Beach

$516 nightly

Nov 15 - Nov 16

Total with taxes and fees

A kitchen with white cabinets, a microwave, an oven, a sink, and a coffee maker.

19. 🏖️ Beach Suite Collection I Pet Friendly

Sunset Beach

$758 nightly

Nov 15 - Nov 16

Total with taxes and fees

20. 🌴 Beach Escape Collection | Sleeps Up to 8

Sunset Beach

$801 nightly

Nov 22 - Nov 23

Total with taxes and fees

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Top Anna Maria Hotel Reviews

Beautiful North end Pool Home with Gulf Views, Heated pool, steps to beach

8/10 Good

"We enjoyed our stay! It is a beautiful, modern home with very close access to a wonderful beach, and there are plenty of bath and beach towels available for use. Overall, it was a great stay, with just a couple of things future guests should keep in mind. Only a small starter supply of essentials—like paper towels, dish soap, trash bags, and toilet paper—is provided, so you will definitely want to plan on picking up extras for a longer stay. Additionally, the cookware is in much need of an upgrade, which made cooking for six challenging. We also found the largest frying pan in the lower cupboard—it had been used and was badly burnt, charred in fact. It seemed like no one had even tried to clean it."

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

10/10 Excellent

"The bungalow was such a perfect place for a little getaway. The location is amazing as it’s close to shops and eateries. It is nicely tucked off the Main Street, which made it nice & quiet. It’s across the street from the farmers market (at the church) which operates from Oct-May, every Tuesday. I would highly recommend it."

Sunrise Garden Resort

8/10 Good

"The beach to the east is 1 minute walk away. Walkable restaurants. Beach to the west, possibly the most beautiful in all of Florida, is a 10 minute walk away or very short drive. Sand is almost like flower. The Pier was closed, (across the street) but will be a great place to fish, walk and enjoy the scenery. Nice pool, great shower, nice picnic table..."

Luxury waterfront home with a heated pool and spa!

10/10 Excellent

"This house is beautiful and as described. The check-in, communication, and cleanliness was great. The location is perfect, we never moved our car. Easy walk to the beach, shops, restaurants. The pool and hot tub is awesome and the views with the big palm trees is really lovely. Plenty of bath and beach towels are provided. I loved everything about the Island. Very chill lowkey vibe."

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

10/10 Excellent

"They stay at the property was really pleasant, unit was very clean and the phone call received to check on us with our stay and any problems is an exceptional touch of great management. Overall our stay was very enjoyable and look forward to a rebook in the future on our next trip."

Find out more about Anna Maria

Anna Maria Cottages information

Number of reviews	384
Accommodation	23 Cottages
Lowest Price	$204
Highest Price	$2,872

Frequently asked questions

How much do cottages in Anna Maria cost?

Cottages in Anna Maria range between $204 and $2,872 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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Things to do in Anna Maria Island

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Upfront pricing

Check prices for these dates

Our top choices for Anna Maria cottages

1. Newly Renovated Sea Breeze Cottage with Private Dock, Easy Access to Bimini Bay

2. The "Grouper"

3. Cozy Private Cottage, Minutes to Anna Maria Island

4. Pet-friendly Bradenton Home 1.5 Mi to Cortez Beach

5. Bridge Street Pier Beach House + Dog-friendly

6. Beach Getaway Near Rays, Bikes & Gear

7. Sunny Island Rental, Bikes, Steps2Beach

8. Steps 2 Beach Cottage, King Bed, Bikes

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

10. St Pete/gulfport Tiny little small home

11. 3716 7th Ave W

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

13. Lido Beach Studio with Heated Pool

14. Lido Key Casita w Pool Steps to the Beach

15. Downtown | Walk Everywhere, Park Once

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

17. 🌅 Ocean View 2 Bedroom Cottage | Unit 6

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

19. 🏖️ Beach Suite Collection I Pet Friendly

20. 🌴 Beach Escape Collection | Sleeps Up to 8

Find vacation rentals that suit your style

Top Anna Maria Hotel Reviews

Beautiful North end Pool Home with Gulf Views, Heated pool, steps to beach

Find out more about Anna Maria

Anna Maria Cottages information

Frequently asked questions

Explore a world of travel with Expedia