Anna Maria Island, FL Cottages from AED 288

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Our top choices for Anna Maria Island 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.

AED 2,196 total

includes taxes & fees

8 Nov - 9 Nov

A covered outdoor area with wooden flooring, white rocking chairs with blue cushions, and a blue and white striped rug.

2. Adorable Cottage with Covered Balconies and Private Pool

Anna Maria

Mary C.

AED 4,223 total

includes taxes & fees

12 Nov - 13 Nov

A covered porch with a sign reading "BEACH HOUSE," outdoor seating, a grill, and a view of the water.

3. Bridge Street Pier Beach House + Dog-friendly

Bridge Street

Michelle R.

AED 1,724 total

includes taxes & fees

23 Nov - 24 Nov

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

4. The "Grouper"

Sunny Shores

Canyon L.

AED 749 total

includes taxes & fees

8 Nov - 9 Nov

A patio with two blue lounge chairs, a potted plant, and a gravel area.

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

Bradenton

Rob

AED 1,234 total

includes taxes & fees

16 Nov - 17 Nov

A small, single-story house with a white exterior, a brick planter with palm trees, and a white picket fence.

6. Cozy Private Cottage, Minutes to Anna Maria Island

Bradenton

Ismael

AED 897 total

includes taxes & fees

10 Nov - 11 Nov

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

7. Beach Getaway Near Rays, Bikes & Gear

Pass-a-Grille

Cathy P.

AED 1,197 total

includes taxes & fees

1 Dec - 2 Dec

A balcony with two wooden chairs and a small round table, surrounded by white railings and palm trees.

8. Sunny Island Rental, Bikes, Steps2Beach

Pass-a-Grille

Janise W.

AED 1,173 total

includes taxes & fees

10 Nov - 11 Nov

A yellow house with a porch, a mailbox, and a number 5306 on the door.

9. Yellow Palm Cottage, Heart of Siesta Key

Siesta Key Village

AED 1,660 total

includes taxes & fees

9 Nov - 10 Nov

An outdoor patio with green metal chairs and tables, a red umbrella, and a building with balconies in the background.

10. Beach Tree Cottage,Walk To Beach& Siesta

Siesta Key Village

AED 1,325 total

includes taxes & fees

9 Nov - 10 Nov

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

11. 3716 7th Ave W

Bradenton

AED 11,333 total

includes taxes & fees

9 Nov - 10 Nov

A pool area with a blue deck, lounge chairs, a barbecue, and a view of buildings in the background.

12. The Inn On Siesta Key

Siesta Key

"Thank you Paige & Gabe! My husband & I had a wonderful stay last week in The Nook at your beautiful Inn. Absolutely loved the old Florida charm and perfect location. Your Inn is immaculately kept as well as comfortable. We especially loved our private patio with the fire pit at The Nook. The location of The Inn could not be more perfect being less than a 5 minute walk across the street to Siesta Key beach as well as a short 10 minute walk to town with all the restaurants & shops. Thanks again...

Karen Jean

AED 1,323 total

includes taxes & fees

8 Nov - 9 Nov

A patio with a sun lounger, a table with chairs, and an umbrella.

13. Beach View 100ft To Beach and SPA

Siesta Key Village

AED 1,497 total

includes taxes & fees

11 Nov - 12 Nov

A small, single-story building with a porch, surrounded by tropical vegetation.

14. BlueDolphin Cottage Walk To Siesta Beach

Siesta Key Village

AED 1,493 total

includes taxes & fees

9 Nov - 10 Nov

A backyard with a tree, a wooden fence, a blue shed, and a house with a door.

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

Desoto Lakes

AED 889 total

includes taxes & fees

24 Nov - 25 Nov

A rectangular pool with white lounge chairs and a white fence, surrounded by palm trees and a building with balconies.

16. Lido Key Casita w Pool Steps to the Beach

Lido Key

Felecia P.

AED 1,458 total

includes taxes & fees

18 Nov - 19 Nov

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

17. Lido Beach Studio with Heated Pool

Lido Key

Lorraine B.

AED 1,458 total

includes taxes & fees

12 Nov - 13 Nov

A small, light blue single-story house with a front door, a garage door, and a small porch area.

18. St Pete/gulfport Tiny little small home

St. Petersburg

Susan D.

AED 1,301 total

includes taxes & fees

7 Nov - 8 Nov

A building with a tiled roof, a door, and two windows with shutters. There are two white chairs outside.

19. 🐾 1 BR Beach Cottage | Pet Friendly I Unit 8

Sunset Beach

AED 1,809 total

includes taxes & fees

8 Nov - 9 Nov

A modern kitchen with white cabinets, a built-in oven, and a microwave. There is a dining area with a wooden table set for two, blue plates, and wine glasses. A ceiling fan is visible in the living room area.

20. Siesta Key Beachside Getaway Cottage Walking Distance to Beach and Village

Sarasota

Tracie B.

AED 1,444 total

includes taxes & fees

13 Nov - 14 Nov

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Learn more about Anna Maria Island

Pristine white beaches and turquoise waters beckon you to this laid-back Gulf Coast paradise. Rent a bike to explore charming Pine Avenue, then watch the sunset at Bean Point's secluded shore.

See all hotels in Anna Maria Island

An aerial view of a coastal town with a long pier extending into turquoise waters.

Top reviews in Anna Maria Island

The Inn On Siesta Key

Siesta Key

10/10 Excellent

We just finished our fall break getaway at The Inn On Siesta Key, and we absolutely loved it! The owners are so friendly and accommodating, staying here was the best choice we could have made. We stayed in the Cottage, and it was awesome, so inviting and cozy, and perfect for our family of 4. The great service started on our check in day. We arrived very early, as we had taken an early morning flight into Sarasota. Paige gave us an introduction to the property and let us change in the Cottage,...

Steven

Pet-friendly Bradenton Home 1.5 Mi to Cortez Beach

Bradenton

10/10 Excellent

My wife and I were with another couple on a birthday celebration and needed a place near Palma Sol Bay where we had reservations to ride the horses in the water. The location turned out to be perfect in all respects as it offered alternative options to get to specific locations throughout the area and it was within 30 minutes of everything even if traffic was heavy. The place was very clean and offered a small kitchen, two full bathrooms and two bedrooms (one queen, one king) and two couches...

Jeffrey

A single-story house with a front porch, a small deck, and a garage.

Unwind Poolside + Walk to Beach! Sarasota Retreat

South Village

8/10 Good

The location of the property was excellent. The home was clean and had everything we needed to prepare breakfast in the morning. The 3 bedrooms and 3 bathrooms made it easy for the six of us wash up and get ready for dinner after a fun fill day at the walkable beach. Beach was great. Having a pool at the property was great for the 2 youngsters. We also made use of the wagon that was available to carry items to the beach., The property is nothing fancy but a great value for the money.

Eleuterio

Frequently Asked Questions

What are the best cottages in Anna Maria Island?

There are multiple cottages in Anna Maria Island with a total average guest review rating of 0, so you're sure to snag a place that suits your style. Planning to stay in Bradenton Beach? Queen's Gate Resort is one property favored by travelers. This 2.5-star cottage includes amenities such as a swimming pool and a garden. 105b 12th Street South Front 2 Bedroom Apts By Redawning is another highly rated escape where you'll be close to nature. A barbecue grill and a swimming pool are two of the conveniences waiting for you at this 3-star pick in Bradenton Beach.

Why book your cottage in Anna Maria Island with Expedia?

Reserving a cottage in Anna Maria Island is as simple as entering your travel dates and choosing an ideal place for a getaway in nature. From ritzy retreats to affordable properties and cottages that feature amenities like a kitchenette, Expedia has something for all traveler styles. As for the best offers around? We've got them as well!

How can I find cheap cottages in Anna Maria Island?

With Expedia's helpful filter tool, sourcing cheap cottages in Anna Maria Island has never been simpler. To discover accommodations that'll make your hip pocket happy, tailor your search results by budget, amenities and star rating.

Room 1

Change your mind

Treat yourself

Be picky

Find vacation rentals that suit your style

Check prices for these dates

Our top choices for Anna Maria Island cottages

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

2. Adorable Cottage with Covered Balconies and Private Pool