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 30 - Nov 1
In two months
Dec 11 - Dec 13
In three months
Jan 8 - Jan 10
In four months
Feb 5 - Feb 7

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)
"Place is great and clean. Love how smooth everything was. Jenny is easy to communicate as well"
United States
Natalia D.
The price is ￥39,347
￥92,176 total
includes taxes & fees
Oct 19 - Oct 20
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, (76 reviews)
"We enjoyed our stay, close to shops and beach!"
United States
Savannah S.
The price is ￥15,644
￥33,654 total
includes taxes & fees
Oct 19 - Oct 20
The "Grouper"
A small, single-story house with a white exterior, a brick planter with palm trees, and a white picket fence.

3. 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
The price is ￥12,657
￥41,426 total
includes taxes & fees
Oct 19 - Oct 20
Cozy Private Cottage, Minutes to Anna Maria Island
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

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 ￥27,654
￥53,092 total
includes taxes & fees
Oct 19 - Oct 20
Pet-friendly Bradenton Home 1.5 Mi to Cortez Beach
A balcony with two wooden chairs and a small round table, surrounded by white railings and palm trees.

5. 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 ￥19,515
￥50,797 total
includes taxes & fees
Nov 1 - Nov 2
Sunny PaG Island rental w/bikes-just steps2beach
A pool area with a blue deck, lounge chairs, a barbecue, and a view of buildings in the background.

6. The Inn On Siesta Key

The Inn On Siesta Key
3.5 star property
Siesta Key
10.0 out of 10, Exceptional, (212 reviews)
"The property was perfect. Walk to down town and the beach. Loved the provisions for the beach which made it so convenient. Room was super clean and overall the property was well maintained."
United States
Stephen
The price is ￥38,691
￥52,470 total
includes taxes & fees
Oct 19 - Oct 20
The Inn On Siesta Key
A white house with a covered porch, surrounded by a gravel driveway and various tropical plants.

7. 3716 7th Ave W

3716 7th Ave W
3.0 star property
Bradenton
The price is ￥361,739
￥474,946 total
includes taxes & fees
Oct 28 - Oct 29
3716 7th Ave W
A patio area with a grill, potted plants, and a building with a teal door.

8. Beach Tree Cottage,Walk To Beach& Siesta

Beach Tree Cottage,Walk To Beach& Siesta
2.0 star property
Siesta Key Village
The price is ￥21,048
￥55,390 total
includes taxes & fees
Oct 19 - Oct 20
Beach Tree Cottage,Walk To Beach& Siesta
A yellow house with a blue door and the number 2202.

9. Steps 2 Beach- Cottage w/king bd +2bikes +parking

Steps 2 Beach- Cottage w/king bd +2bikes +parking
Pass-a-Grille
9.6 out of 10, Exceptional, (52 reviews)
"Clean, quiet and an easy walk to the beach."
United States
Marion W.
The price is ￥35,950
￥75,379 total
includes taxes & fees
Oct 19 - Oct 20
Steps 2 Beach- Cottage w/king bd +2bikes +parking
A yellow house with a porch, a mailbox, and a number 5306 on the door.

10. Yellow Palm Cottage, Heart of Siesta Key

Yellow Palm Cottage, Heart of Siesta Key
2.0 star property
Siesta Key Village
The price is ￥23,324
￥57,961 total
includes taxes & fees
Oct 19 - Oct 20
Yellow Palm Cottage, Heart of Siesta Key
A kitchen with a sink, stove, microwave, and refrigerator.

11. BlueDolphin Cottage Walk To Siesta Beach

BlueDolphin Cottage Walk To Siesta Beach
2.5 star property
Siesta Key Village
The price is ￥23,750
￥58,443 total
includes taxes & fees
Oct 20 - Oct 21
BlueDolphin Cottage Walk To Siesta Beach
A bedroom with a bed, a ceiling fan, a window with curtains, a wooden wardrobe, and a framed picture on the wall.

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

Cozy Lido Studio by Beach & St Armand's
Lido Key
The price is ￥26,595
￥69,044 total
includes taxes & fees
Oct 31 - Nov 1
Cozy Lido Studio by Beach & St Armand's
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 ￥14,222
￥39,031 total
includes taxes & fees
Oct 19 - Oct 20
Coastal Breeze Cottage in Sunny Sarasota. Pet friendly. King size bed.
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 Casita w Pool Steps to the Beach
Lido Key
10.0 out of 10, Exceptional, (1 review)
The price is ￥23,466
￥65,035 total
includes taxes & fees
Nov 4 - Nov 5
Lido Key Casita w Pool Steps to the Beach
A small, light blue single-story house with a front door, a garage door, and a small porch area.

15. 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 ￥22,613
￥58,659 total
includes taxes & fees
Oct 23 - Oct 24
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.

16. 🐾 1 BR Beach Cottage | Pet Friendly I Unit 8

🐾 1 BR Beach Cottage | Pet Friendly I Unit 8
Sunset Beach
The price is ￥28,041
￥81,605 total
includes taxes & fees
Oct 19 - Oct 20
🐾 1 BR Beach Cottage | Pet Friendly I Unit 8
A residential house with a white fence, a palm tree, and a parked car.

17. 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 ￥15,644
￥47,891 total
includes taxes & fees
Oct 25 - Oct 26
Drift Inn A, Heated Pool, Beach and Amenities, 2-3 min walk.
A two-story building with a blue exterior and white railings.

18. 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 ￥30,838
￥63,227 total
includes taxes & fees
Oct 19 - Oct 20
Siesta Key Beachside Getaway Cottage Walking Distance to Beach and Village
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)
"The house was truly lovely, and the hosts were exceptionally caring, kind, and attentive in their communication. It was wonderful to be so close to the beach, with stores conveniently nearby, making the stay feel comfortable and welcoming."
United States
Kandra R.
The price is ￥26,863
￥59,312 total
includes taxes & fees
Oct 25 - Oct 26
Escape near Siesta Key with Hot Tub, BBQ, and Fire pit
Shared sunbathing deck by the pool, at the resort.

20. 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 ￥17,382
￥52,115 total
includes taxes & fees
Oct 20 - Oct 21
Siesta Key Sanctuary -Pool-Kayaks-TikiHut-King bed
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

Seaside at Anna Maria Island Inn

Seaside at Anna Maria Island Inn

10/10 Excellent
"Absolutely phenomenal"
Ben 1-night trip
Posted 2 hours ago
Seaside at Anna Maria Island Inn

Find out more about Anna Maria Island

Anna Maria Island Cottages information

Number of reviews
592
Accommodation
54 Cottages
Lowest Price
￥33,654
Highest Price
￥474,946

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 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 ￥33,654 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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