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

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Check prices for these dates

In two weeks
20 Nov - 22 Nov
In two months
1 Jan - 3 Jan
In three months
29 Jan - 31 Jan
In four months
26 Feb - 28 Feb

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

Newly Renovated Sea Breeze Cottage with Private Dock, Easy Access to Bimini Bay
Anna Maria
9.6 out of 10, Exceptional, (129 reviews)
"Has a beautiful view of the bay right behind the houseNeighbors were very friendly,has a new house being built next door but it still was quaint beach was in walking distance. Definitely a must do again."
United States
Terrence H.
The price is €522
includes taxes & fees
5 Nov - 6 Nov
Newly Renovated Sea Breeze Cottage with Private Dock, Easy Access to Bimini Bay
A covered porch with a sign reading "BEACH HOUSE," outdoor seating, a grill, and a view of the water.

2. Bridge Street Pier Beach House + Dog-friendly

Bridge Street Pier Beach House + Dog-friendly
Bridge Street
9.6 out of 10, Exceptional, (38 reviews)
"Great place! Perfect location to the beach and shops "
United States
Michelle R.
The price is €431
includes taxes & fees
23 Nov - 24 Nov
Bridge Street Pier Beach House + Dog-friendly
A beachfront property with a two-story building, a covered porch, and signs indicating no beach parking.

3. Beautiful Guest House Near the Beach with Private Pool!

Beautiful Guest House Near the Beach with Private Pool!
Anna Maria
9.0 out of 10, Wonderful, (39 reviews)
"House was in great condition and very comfortable. Ideal location! "
United States
Scott B.
Beautiful Guest House Near the Beach with Private Pool!
A two-story house with a green exterior, a blue door, and orange trim.

4. The "Grouper"

The "Grouper"
Sunny Shores
9.4 out of 10, Exceptional, (79 reviews)
"We enjoyed our stay, close to shops and beach!"
United States
Savannah S.
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
9.8 out of 10, Exceptional, (14 reviews)
"Clean and nice place"
United States
Ismael
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 €300
includes taxes & fees
16 Nov - 17 Nov
Pet-friendly Bradenton Home 1.5 Mi to Cortez Beach
An outdoor patio with green metal chairs and tables, a red umbrella, and a building with balconies in the background.

7. Beach Tree Cottage,Walk To Beach& Siesta

Beach Tree Cottage,Walk To Beach& Siesta
2.0 star property
Siesta Key Village
Beach Tree Cottage,Walk To Beach& Siesta
A patio with a sun lounger, a table with chairs, and an umbrella.

8. Beach View 100ft To Beach and SPA

Beach View 100ft To Beach and SPA
2.0 star property
Siesta Key Village
10.0 out of 10, Exceptional, (1 review)
The price is €362
includes taxes & fees
5 Nov - 6 Nov
Beach View 100ft To Beach and SPA
A small pink house with a white door, a blue car parked in front, and a white picket fence.

9. PinkMango Cottage Steps to Beach&Village

PinkMango Cottage Steps to Beach&Village
2.0 star property
Siesta Key Village
The price is €358
includes taxes & fees
5 Nov - 6 Nov
PinkMango Cottage Steps to Beach&Village
A balcony with two wooden chairs and a small round table, surrounded by white railings and palm trees.

10. 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, (29 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 €291
includes taxes & fees
10 Nov - 11 Nov
Sunny PaG Island rental w/bikes-just steps2beach
A small, single-story building with a porch, surrounded by tropical vegetation.

11. BlueDolphin Cottage Walk To Siesta Beach

BlueDolphin Cottage Walk To Siesta Beach
2.5 star property
Siesta Key Village
The price is €374
includes taxes & fees
6 Nov - 7 Nov
BlueDolphin Cottage Walk To Siesta Beach
A yellow house with a porch, a mailbox, and a number 5306 on the door.

12. Yellow Palm Cottage, Heart of Siesta Key

Yellow Palm Cottage, Heart of Siesta Key
2.0 star property
Siesta Key Village
The price is €410
includes taxes & fees
8 Nov - 9 Nov
Yellow Palm Cottage, Heart of Siesta Key
A yellow building with a blue door and a white staircase.

13. Rays Baseball close! Beach Getaway| Bikes +Gear

Rays Baseball close! Beach Getaway| Bikes +Gear
Pass-a-Grille
9.8 out of 10, Exceptional, (34 reviews)
"We love staying at this nice cozy beach house! It's so close to the beach.And such a nice quiet location!"
United States
Cathy P.
The price is €294
includes taxes & fees
1 Dec - 2 Dec
Rays Baseball close! Beach Getaway| Bikes +Gear
A white house with a covered porch, surrounded by a gravel driveway and various tropical plants.

14. 3716 7th Ave W

3716 7th Ave W
3.0 star property
Bradenton
The price is €2,757
includes taxes & fees
6 Nov - 7 Nov
3716 7th Ave W
Shared sunbathing deck by the pool, at the resort.

15. Siesta Key Sanctuary -Pool-Kayaks-TikiHut-King bed

Siesta Key Sanctuary -Pool-Kayaks-TikiHut-King bed
Siesta Key
9.6 out of 10, Exceptional, (8 reviews)
"The most well maintained property I've ever stayed."
United States
Russ H.
Siesta Key Sanctuary -Pool-Kayaks-TikiHut-King bed
A backyard with a tree, a wooden fence, a blue shed, and a house with a door.

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

Coastal Breeze Cottage in Sunny Sarasota. Pet friendly. King size bed.
Desoto Lakes
Coastal Breeze Cottage in Sunny Sarasota. Pet friendly. King size bed.
A two-story building with a blue exterior and white railings.

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

Siesta Key Beachside Getaway Cottage Walking Distance to Beach and Village
Sarasota
9.2 out of 10, Wonderful, (192 reviews)
"The property was perfect for our time in Siesta Key. Being right across the road from beach access and having the free trolly pick up/drop off right at the corner of the street was great! Only a quick few minute trolly ride to Siesta Key Village. We would definately stay here again!"
United States
Jacci W.
Siesta Key Beachside Getaway Cottage Walking Distance to Beach and Village
A residential house with a white fence, a palm tree, and a parked car.

18. Drift Inn A, Heated Pool, Beach and Amenities, 2-3 min walk.

Drift Inn A, Heated Pool, Beach and Amenities, 2-3 min walk.
South Village
9.8 out of 10, Exceptional, (91 reviews)
"Would definitely stay here again. Great location and great house! Owner was quick and helpful with communication."
United States
Clarissa S.
The price is €275
includes taxes & fees
10 Nov - 11 Nov
Drift Inn A, Heated Pool, Beach and Amenities, 2-3 min walk.
A modern house with a driveway, a tree with purple lighting, and a white car parked in front.

19. Escape near Siesta Key with Hot Tub, BBQ, and Fire pit

Escape near Siesta Key with Hot Tub, BBQ, and Fire pit
Sarasota
8.4 out of 10, Very good, (10 reviews)
"Very close drive to the beach! Nice place to stay!"
United States
Rocio S.
The price is €322
includes taxes & fees
8 Nov - 9 Nov
Escape near Siesta Key with Hot Tub, BBQ, and Fire pit
A small, light blue single-story house with a front door, a garage door, and a small porch area.

20. 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 €323
includes taxes & fees
5 Nov - 6 Nov
St Pete/gulfport Tiny little small home
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 Island Hotel Reviews

Pelican Post at Anna Maria Island Inn

Pelican Post at Anna Maria Island Inn

10/10 Excellent
"Very pleasant experience overall"
Jeff 1-night trip
Posted 3 hours ago
Pelican Post at Anna Maria Island Inn

Find out more about Anna Maria Island

Anna Maria Island Cottages information

Number of reviews
656
Accommodation
54 Cottages
Lowest Price
€275
Highest Price
€2,757

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 9.5, 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 favoured by travellers. 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.
What are the best cheap cottages in Anna Maria Island?
With cottages starting at only €275 per night, you can afford an extra couple of nights in Anna Maria Island for outdoor fun. If Bradenton Beach is on your travel radar, book a room at Queen's Gate Resort. A garden and a swimming pool help make this option an excellent choice. You'll also find inexpensive cottages in Holmes Beach. Take deep, calming breaths in nature during your stay at Queen's Gate Resort and take advantage of conveniences like pool sun loungers and a garden. If you're exploring Anna Maria Island and want to save money, there are many fabulous free attractions to put on your itinerary. Anna Maria Beach and Coquina Beach are always popular with visitors. 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 Island?
There are indeed. Whether it's in one of Anna Maria Island's busy cities or way out in nature, the cosy charm of a cottage is perfect for holidaying families. If Bradenton Beach is on your radar, book a stay at Queen's Gate Resort. This 2.5-star option offers a nearby beach and a barbecue grill. Another superb choice is 105b 12th Street South Front 2 Bedroom Apts By Redawning. Also in Bradenton Beach, this family-friendly cottage has a 3-star rating and includes WiFi and a barbecue grill. You'll find plenty of awesome things to do with the family in Bradenton Beach. Anna Maria Beach and Coquina Beach promise a fantastic day out.
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 traveller 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 accommodation that'll make your hip pocket happy, tailor your search results by budget, amenities and star rating.

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