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 ￥39,163
￥87,184 total
includes taxes & fees
Sep 27 - Sep 28
Newly Renovated Sea Breeze Cottage with Private Dock, Easy Access to Bimini Bay
A coastal residential area with houses, a river, and a beach.

2. Adorable Cottage with Covered Balconies and Private Pool

Adorable Cottage with Covered Balconies and Private Pool
Anna Maria
9.8 out of 10, Exceptional, (51 reviews)
"Pleasantly surprised how great this place was - awesome backyard setup and incredible location "
United States
Cyrus M.
The price is ￥39,918
￥136,809 total
includes taxes & fees
Oct 25 - Oct 26
Adorable Cottage with Covered Balconies and Private Pool
A small, single-story mobile home with a front porch, a small attached garage, and a clock tower.

3. Bridge Street Beach House | Wi-Fi | Center of All

Bridge Street Beach House | Wi-Fi | Center of All
Bridge Street
10.0 out of 10, Exceptional, (5 reviews)
"Great location, clean accommodations, good communication with host. ..."
United States
leslie m.
The price is ￥29,726
￥59,266 total
includes taxes & fees
Oct 5 - Oct 6
Bridge Street Beach House | Wi-Fi | Center of All
A covered outdoor area with wicker furniture, a glass table, and a view of a residential street.

4. Beautiful Condo on Pine Ave, 2 Blocks to Beach

Beautiful Condo on Pine Ave, 2 Blocks to Beach
Anna Maria
8.8 out of 10, Excellent, (29 reviews)
"Nice place, a little noisy in the morning but a good convenient location for a girls trip. It was clean and beds were decent. The water pressure was not great but that being said, I would stay here again!"
United States
Amy H.
The price is ￥48,004
￥138,076 total
includes taxes & fees
Oct 24 - Oct 25
Beautiful Condo on Pine Ave, 2 Blocks to Beach
A two-story house with a green exterior, a blue door, and orange trim.

5. 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 ￥15,571
￥33,182 total
includes taxes & fees
Sep 30 - Oct 1
The "Grouper"
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 ￥27,524
￥52,843 total
includes taxes & fees
Sep 28 - Sep 29
Pet-friendly Bradenton Home 1.5 Mi to Cortez Beach
A small, single-story house with a white exterior, a brick planter with palm trees, and a white picket fence.

7. 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)
"Clean and nice place"
United States
Ismael
The price is ￥9,767
￥36,932 total
includes taxes & fees
Sep 28 - Sep 29
Cozy Private Cottage, Minutes to Anna Maria Island
A balcony with two wooden chairs and a small round table, surrounded by white railings and palm trees.

8. 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, (28 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 ￥17,930
￥44,734 total
includes taxes & fees
Sep 27 - Sep 28
Sunny PaG Island rental w/bikes-just steps2beach
A white house with a covered porch, surrounded by a gravel driveway and various tropical plants.

9. 3716 7th Ave W

3716 7th Ave W
3.0 star property
Bradenton
The price is ￥308,080
￥414,003 total
includes taxes & fees
Oct 27 - Oct 28
3716 7th Ave W
A single-story house with a blue exterior, a front door, and a small porch area.

10. 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 ￥14,155
￥36,913 total
includes taxes & fees
Oct 12 - Oct 13
Coastal Breeze Cottage in Sunny Sarasota. Pet friendly. King size bed.
A hammock tied between two palm trees, a pink building with a red roof, and a bush with red flowers.

11. 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 ￥14,289
￥83,876 total
includes taxes & fees
Sep 30 - Oct 1
Pink Mango Cottage steps from the beach
A rectangular pool with white lounge chairs and a white fence, surrounded by palm trees and a building with balconies.

12. Lido Key Casita w Pool Steps to the Beach

Lido Key Casita w Pool Steps to the Beach
Lido Key
The price is ￥14,706
￥50,866 total
includes taxes & fees
Sep 28 - Sep 29
Lido Key Casita w Pool Steps to the Beach
A patio with a table set for two, a blue umbrella, and a white fence.

13. Studio by Lido Beach w heated pool

Studio by Lido Beach w heated pool
Lido Key
The price is ￥14,706
￥50,866 total
includes taxes & fees
Oct 1 - Oct 2
Studio by Lido Beach w heated pool
A small, light blue single-story house with a front door, a garage door, and a small porch area.

14. 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 ￥22,507
￥55,239 total
includes taxes & fees
Oct 8 - Oct 9
St Pete/gulfport Tiny little small home
A building with a tiled roof, a door, and two windows with shutters. There are two white chairs outside.

15. 🐾 1 BR Beach Cottage | Pet Friendly I Unit 8

🐾 1 BR Beach Cottage | Pet Friendly I Unit 8
Sunset Beach
The price is ￥29,726
￥79,186 total
includes taxes & fees
Sep 27 - Sep 28
🐾 1 BR Beach Cottage | Pet Friendly I Unit 8
A residential house with a white fence, a palm tree, and a parked car.

16. 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 ￥15,571
￥45,622 total
includes taxes & fees
Sep 28 - Sep 29
Drift Inn A, Heated Pool, Beach and Amenities, 2-3 min walk.
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 ￥18,685
￥55,520 total
includes taxes & fees
Oct 17 - Oct 18
Cozy Lido Studio by Beach & St Armand's

18. 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.
The price is ￥15,728
￥47,577 total
includes taxes & fees
Sep 30 - Oct 1
Siesta Key Sanctuary -Pool-Kayaks-TikiHut-King bed
A bathroom with a toilet, a glass-enclosed shower, and a framed picture on the wall.

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

Coastal Studio, Walk to St Armand's or Lido Beach
Lido Key
The price is ￥16,782
￥53,211 total
includes taxes & fees
Oct 4 - Oct 5
Coastal Studio, Walk to St Armand's or Lido Beach
A two-story building with a blue exterior and white railings.

20. 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)
"Loved the location of this property! The property manager was easy to contact and the property was exactly as shown in the pictures. Would stay here again!"
United States
Tracie B.
The price is ￥38,603
￥68,566 total
includes taxes & fees
Oct 2 - Oct 3
Siesta Key Beachside Getaway Cottage Walking Distance to Beach and Village
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

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

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

10/10 Excellent
"Loved this place- would stay again. Really made it a great trip!"
Gavin H. 4-night trip
Posted 13 hours ago
Naut 2 Shabby Bungalow - A sweet and cozy getaway on Pine Avenue!

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 9.6, 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 ￥33,182 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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