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
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 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)
"Very nice property! Clean and lovely water view!"
United States
Sadie E.
The price is ￥39,170
￥91,762 total
includes taxes & fees
Sep 27 - Sep 28
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.
The price is ￥15,574
￥33,503 total
includes taxes & fees
Sep 26 - Sep 27
The "Grouper"
A patio with two blue lounge chairs, a potted plant, and a gravel area.

3. 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 ￥27,529
￥52,853 total
includes taxes & fees
Sep 24 - Sep 25
Pet-friendly Bradenton Home 1.5 Mi to Cortez Beach
A keyless entry system with a red pathway leading to a gated entrance.

4. 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.
The price is ￥9,911
￥38,200 total
includes taxes & fees
Sep 27 - Sep 28
Cozy Private Cottage, Minutes to Anna Maria Island
A white house with a covered porch, surrounded by a gravel driveway and various tropical plants.

5. 3716 7th Ave W

3716 7th Ave W
3.0 star property
Bradenton
The price is ￥352,689
￥464,422 total
includes taxes & fees
Oct 6 - Oct 7
3716 7th Ave W
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.
The price is ￥17,933
￥44,899 total
includes taxes & fees
Sep 27 - Sep 28
Sunny PaG Island rental w/bikes-just steps2beach
A yellow building with a blue door and a white staircase.

7. 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.
Pass-a-Grille Beach Getaway| Walkable| Bikes +Gear
A small, light blue single-story house with a front door, a garage door, and a small porch area.

8. 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 ￥22,511
￥58,080 total
includes taxes & fees
Sep 24 - Sep 25
St Pete/gulfport Tiny little small home
A two-story building with a blue exterior and white railings.

9. 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)
"Right across the beach Less then 5 minutes Good space - rooms nice ad clean "
United States
ASHISH
The price is ￥38,610
￥70,467 total
includes taxes & fees
Oct 2 - Oct 3
Siesta Key Beachside Getaway Cottage Walking Distance to Beach and Village
A house with a red door, a blue chair, and palm trees in the yard.

10. 🌊 Family Beach Retreat | Sleeps Up to 12

🌊 Family Beach Retreat | Sleeps Up to 12
Sunset Beach
The price is ￥106,538
￥224,505 total
includes taxes & fees
Sep 29 - Sep 30
🌊 Family Beach Retreat | Sleeps Up to 12
A yellow house with a white door and number 5306.

11. Yellow Palm Cottage steps from the beach

Yellow Palm Cottage steps from the beach
Siesta Key Village
10.0 out of 10, Exceptional, (2 reviews)
"This place was so cute and quaint! It was just a short walk to the village and to the beach. The grounds were beautiful! A little oasis in the backyard. . Would stay here again!!!"
United States
Tami B.
The price is ￥15,051
￥89,512 total
includes taxes & fees
Sep 24 - Sep 25
Yellow Palm Cottage steps from the beach
A hammock tied between two palm trees, a pink building with a red roof, and a bush with red flowers.

12. Pink Mango Cottage steps from the beach

Pink Mango Cottage steps from the beach
Siesta Key Village
10.0 out of 10, Exceptional, (1 review)
The price is ￥15,667
￥87,570 total
includes taxes & fees
Sep 30 - Oct 1
Pink Mango Cottage steps from the beach
A single-story house with a blue exterior, a front door, and a small porch area.

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

Coastal Breeze Cottage in Sunny Sarasota. Pet friendly. King size bed.
Desoto Lakes
The price is ￥14,158
￥37,707 total
includes taxes & fees
Sep 25 - Sep 26
Coastal Breeze Cottage in Sunny Sarasota. Pet friendly. King size bed.
A two-story building with a blue and white exterior, a balcony, and a sign that reads "Gidget's Coastal Preserve."

14. Beach Road

Beach Road
2.0 star property
Siesta Key
The price is ￥108,701
￥149,185 total
includes taxes & fees
Oct 2 - Oct 3
Beach Road
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
The price is ￥14,708
￥53,235 total
includes taxes & fees
Sep 24 - Sep 25
Lido Key Casita w Pool Steps to the Beach
A small, single-story building with a blue roof and yellow walls, surrounded by a white picket fence and palm trees.

16. Blue Dolphin Cottage steps from the beach

Blue Dolphin Cottage steps from the beach
Siesta Key Village
Blue Dolphin Cottage steps from the beach
A bedroom with a bed, a ceiling fan, a window with curtains, a wooden wardrobe, and a framed picture on the wall.

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

Cozy Lido Studio by Beach & St Armand's
Lido Key
The price is ￥14,708
￥53,864 total
includes taxes & fees
Sep 24 - Sep 25
Cozy Lido Studio by Beach & St Armand's
A well-maintained garden with artificial grass, palm trees, and a pathway leading to a building with a light-colored facade.

18. 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.
Downtown Cottage | Walk Everywhere, Park once
A residential house with a white fence, a palm tree, and a parked car.

19. 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
9.6 out of 10, Exceptional, (90 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 ￥15,574
￥47,362 total
includes taxes & fees
Sep 24 - Sep 25
Drift Inn A, Heated Pool, Beach and Amenities, 2-3 min walk.
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

The Retreat at Anna Maria Island Inn

The Retreat at Anna Maria Island Inn

10/10 Excellent
"clean room, friendly staff, great ac, personal parking"
Alejandro H 2-night trip
Posted 1 hour ago
The Retreat at Anna Maria Island Inn

Find out more about Anna Maria Island

Anna Maria Island Cottages information

Number of reviews
444
Accommodation
59 Cottages
Lowest Price
￥38,200
Highest Price
￥464,422

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 9.8, 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.
What are the best cheap cottages in Anna Maria Island?
With cottages starting at only ￥38,200 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 cozy charm of a cottage is perfect for vacationing 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 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.

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