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Our top choices for Anna Maria Island cottages

9.6 out of 10, Exceptional, (123 reviews)
"Great place and great location........"
United States
chris w.
The price is ¥56,460
¥113,489 total
includes taxes & fees
Mar 12 - Mar 13
Newly Renovated Sea Breeze Cottage with Private Dock, Easy Access to Bimini Bay
8.8 out of 10, Excellent, (3 reviews)
"It was great! Check in was super easy and anything you would need is nearby. "
United States
Thomas N.
The price is ¥39,632
¥108,244 total
includes taxes & fees
Mar 13 - Mar 14
Romantic Island Getaway! Just Steps from the Beach
8.8 out of 10, Excellent, (25 reviews)
"Great location, clean, and spacious. Pool didn’t work fir a couple of days but they got it fixed the day before we left "
United States
Paris K.
The price is ¥108,611
¥230,144 total
includes taxes & fees
Mar 21 - Mar 22
Beautiful Condo on Pine Ave, 2 Blocks to Beach
9.6 out of 10, Exceptional, (42 reviews)
"The house was fantastic, clean and a great location. It had Everything and more than you needed. Will definitely return for a longer trip x"
United Kingdom
Danielle E.
The price is ¥68,662
¥182,926 total
includes taxes & fees
Mar 5 - Mar 6
Adorable Cottage with Covered Balconies and Private Pool
8.8 out of 10, Excellent, (34 reviews)
"Beautiful home perfectly located near the beach, bars and restaurants. "
United States
Bibiana G.
The price is ¥71,627
¥178,609 total
includes taxes & fees
Mar 10 - Mar 11
Beautiful Guest House Near the Beach with Private Pool!
10.0 out of 10, Exceptional, (1 review)
"Absolutely lovely place to stay. The four of us were SO comfortable. The place was clean and beautiful. Very well maintained. You can tell by the high quality finishes that this is someone’s home and they maintain it as such. There was an unforeseen circumstance that popped up with the island doing some work that affected the house while we were there. I messaged the owner and within minutes he had replied and had all the necessary people on the way to fix it. They fixed it all while we were at...
United States
Devon F.
SunSalt Cottage~5 min to Beach, Shops & Restaurants~PrivatePool

Cottage in Sunny Shores

The "Grouper"
9.4 out of 10, Exceptional, (48 reviews)
"We really enjoyed our stay here. So close to AMI "
United States
Taylor B.
The price is ¥15,570
¥33,180 total
includes taxes & fees
Mar 4 - Mar 5
The "Grouper"
10.0 out of 10, Exceptional, (4 reviews)
"I stayed for 9 days. It was in a great location in Bradenton...just minutes from the beach, shopping and dining. It was clean and quiet. I would stay there again."
United States
MO L.
The price is ¥20,287
¥50,380 total
includes taxes & fees
Mar 31 - Apr 1
7mi to Anna Maria Newly Renovated Private Cottage
3.0 star property
The price is ¥31,611
¥105,268 total
includes taxes & fees
Mar 24 - Mar 25
Outdoor Kitchen & Gaming Garage: Bradenton Retreat
3.0 star property
Stylish Retro Vibes Private BBQ & Beach Access
9.2 out of 10, Wonderful, (178 reviews)
"Wonderful property with an excellent location! Beach access was across the street and the trolley pick-up was at the end of the block. The village was within walking distance as well. The property was very clean and the beds were comfortable. The washer and dryer is located right outside of the unit and beach chairs and a cooler were provided. We look forward to booking this property again in the future! "
United States
Alison B.
The price is ¥58,819
¥95,969 total
includes taxes & fees
Mar 4 - Mar 5
Siesta Key Beachside Getaway Cottage Walking Distance to Beach and Village
10.0 out of 10, Exceptional, (1 review)
"Perfect vacation get away. Host are very good to work with. Everything was exactly as we wanted it! "
United States
Kara F.
The price is ¥24,062
¥54,594 total
includes taxes & fees
Mar 11 - Mar 12
Escape near Siesta Key with Hot Tub, BBQ, and Fire pit

Cottage in Siesta Key

The Inn On Siesta Key
3.5 star property
10.0 out of 10, Exceptional, (194 reviews)
"Great place to stay! "
United States
Carlos
The price is ¥54,311
¥71,146 total
includes taxes & fees
Mar 5 - Mar 6
The Inn On Siesta Key

Cottage in Siesta Key Village

Blue Dolphin Cottage steps from the beach
Blue Dolphin Cottage steps from the beach
9.6 out of 10, Exceptional, (85 reviews)
"Great stay - flexible early check-in!"
United States
Jill P.
The price is ¥15,449
¥47,294 total
includes taxes & fees
Mar 26 - Mar 27
Drift Inn A, Heated Pool, Beach and Amenities, 2-3 min walk.

Cottage in Siesta Key Village

Yellow Palm Cottage steps from the beach
10.0 out of 10, Exceptional, (1 review)
"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.
Yellow Palm Cottage steps from the beach
10.0 out of 10, Exceptional, (3 reviews)
"The house was decorated nicely, it was clean, and inside/outside was well kept. The hosts were lovely and responded quickly to questions with precise information. If I need a place to stay in Gulfport again, I would not hesitate to stay!"
United States
Karen J.
The price is ¥22,505
¥62,508 total
includes taxes & fees
Mar 8 - Mar 9
St Pete/gulfport Tiny little small home
9.8 out of 10, Exceptional, (45 reviews)
"Quiet neighborhood away from the tourist areas. 50 steps to a beautiful white sandy beach:) charming little place, very clean and comfortable. sunsets were beautiful and almost no rain all week:)"
United States
James C.
The price is ¥71,767
¥116,457 total
includes taxes & fees
Mar 9 - Mar 10
Steps 2 Beach- Cottage w/king bd +2bikes +parking
3.0 star property
The price is ¥28,466
¥89,323 total
includes taxes & fees
Mar 30 - Mar 31
Steps to Riverwalk! Dtwn Bradenton Snowbird Haven
3.0 star property
The price is ¥41,815
¥112,320 total
includes taxes & fees
Mar 15 - Mar 16
Family Fun: Ping Pong, Bbq, Walk to Park Nearby
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

Find out more about Anna Maria Island

Anna Maria Island Cottages information

Number of reviews
568
Accommodation
61 Cottages
Lowest Price
¥33,180
Highest Price
¥230,144

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 ¥33,180 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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