Search Cottages in Anna Maria Island

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3 Oct - 5 Oct
In one month
17 Oct - 19 Oct
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In three months
12 Dec - 14 Dec

Cottages in Anna Maria Island

Our top choices for Anna Maria Island cottages

Castaway Cottage + Beach + Heated Private Pool & Spa + GOLF CART INCLUDED!
Property grounds

Castaway Cottage + Beach + Heated Private Pool & Spa + GOLF CART INCLUDED!

10.0 out of 10, Exceptional, (279)
"Everything was amazing; no detail was missed. Castaway Cottage is the perfect spot. Our group could not stop talking about all the things we loved, especially the pool and outdoor shower! "
Castaway Cottage + Beach + Heated Private Pool & Spa + GOLF CART INCLUDED!
Tropical Paradise On The Beach Permit VRC17-000168
Property grounds

Tropical Paradise On The Beach Permit VRC17-000168

9.2 out of 10, Wonderful, (139)
"My family and I thoroughly enjoyed our stay! We will definitely rent again in the future. It’s in a great location and just steps away from the beautiful ocean! "
Tropical Paradise On The Beach Permit VRC17-000168
Charming cottage in quiet area, close to beach & bay.
Exterior

Charming cottage in quiet area, close to beach & bay.

9.8 out of 10, Exceptional, (287)
"Clean and quiet and the best location for a weekend getaway! "
Charming cottage in quiet area, close to beach & bay.
Shell Cottage - sleeps 2
Exterior

Shell Cottage - sleeps 2

9.6 out of 10, Exceptional, (38)
"There were a few quirky things. Could not put the AC higher than 75 or it would freeze up the AC.We were only allowed 1 roll of TP we had to buy our own. And it said cookware is provided…1 small 6-8 inch skillet was supplied. And 1 small sauce pan. Everything else was fine."
Shell Cottage - sleeps 2
Rustic & Cozy Island Original Cottage on the Beach- Bamboo Apts. C2
Exterior

Rustic & Cozy Island Original Cottage on the Beach- Bamboo Apts. C2

9.8 out of 10, Exceptional, (94)
"Great place. Easy access to beach and surrounding amenities. Would recommend. "
Rustic & Cozy Island Original Cottage on the Beach- Bamboo Apts. C2
Seahorse Cottage - sleeps 2 guests in 1 bedroom
Exterior

Seahorse Cottage - sleeps 2 guests in 1 bedroom

9.8 out of 10, Exceptional, (52)
"Enjoyed our time and will be back!"
Seahorse Cottage - sleeps 2 guests in 1 bedroom
Coastal Home with Heated Pool, Close to Beach!
Property grounds

Coastal Home with Heated Pool, Close to Beach!

10.0 out of 10, Exceptional, (31)
"Great place with a nice pool."
Coastal Home with Heated Pool, Close to Beach!
Vintage Island Cottage on the Beach- Sunset Views - Bamboo Apts. C1
Exterior

Vintage Island Cottage on the Beach- Sunset Views - Bamboo Apts. C1

10.0 out of 10, Exceptional, (89)
"Enjoyed our stay"
Vintage Island Cottage on the Beach- Sunset Views - Bamboo Apts. C1
Charming Ground Level Resort Style 3 unit Condo - unit C
Exterior

Charming Ground Level Resort Style 3 unit Condo - unit C

9.6 out of 10, Exceptional, (14)
"We had a good time and enjoyed to live near the beach. Just a few steps in the morning and we could dive into the sea. The apartment was a good size for the four of us. Everything we needed was there or could be found in the stores right around the corner. We also enjoyed the outdoor barbecue place and to sit outside for breakfast and dinner. Just a nice place to recommend."
Charming Ground Level Resort Style 3 unit Condo - unit C
Historic beach cottage with private pool - walk 1 block to beach & free trolley
Exterior

Historic beach cottage with private pool - walk 1 block to beach & free trolley

9.0 out of 10, Wonderful, (48)
"Great location next to the beach. Pool area is fantastic."
Historic beach cottage with private pool - walk 1 block to beach & free trolley
Anna Maria Cottage with Golf Cart
Exterior

Anna Maria Cottage with Golf Cart

10.0 out of 10, Exceptional, (13)
"We had a family of four stay here. Perfect size for what we needed and close to everything. It was our 2nd time on the Island and this place was perfect. "
Anna Maria Cottage with Golf Cart
Newly Renovated Sea Breeze Cottage with Private Dock, Easy Access to Bimini Bay
Property grounds

Newly Renovated Sea Breeze Cottage with Private Dock, Easy Access to Bimini Bay

9.6 out of 10, Exceptional, (120)
"Beautiful quiet stay on the water. I would definitely stay here again!"
Newly Renovated Sea Breeze Cottage with Private Dock, Easy Access to Bimini Bay
Beautiful, well-maintained home w/ heated private pool - walk to beach & dining
Outdoor dining

Beautiful, well-maintained home w/ heated private pool - walk to beach & dining

9.6 out of 10, Exceptional, (80)
"We were in town for a lacrosse tournament and this house was so perfect, clean and relaxing."
Beautiful, well-maintained home w/ heated private pool - walk to beach & dining
Cozy Cottage Retreat at Tradewind Resort #32 in Bradenton Beach
Exterior

Cozy Cottage Retreat at Tradewind Resort #32 in Bradenton Beach

9.0 out of 10, Wonderful, (9)
"Great location. Very clean and well maintained. I would come back "
Cozy Cottage Retreat at Tradewind Resort #32 in Bradenton Beach
Blue Isle Oasis: Adorable, updated 2 bedroom cottage
Outdoor dining

Blue Isle Oasis: Adorable, updated 2 bedroom cottage

9.4 out of 10, Exceptional, (3)
"Lovely renovation! Great access to restaurants, beach, and dog park!!"
Blue Isle Oasis: Adorable, updated 2 bedroom cottage
Charming 2br / 1ba Cottage < 2 Min Walk From Beach on Anna Maria Island Florida
Fridge, microwave, oven, stovetop

Charming 2br / 1ba Cottage < 2 Min Walk From Beach on Anna Maria Island Florida

9.8 out of 10, Exceptional, (76)
"Great Location, super clean, great pricing, and Owners were always available.Great time!!"
Charming 2br / 1ba Cottage < 2 Min Walk From Beach on Anna Maria Island Florida
Romantic Island Getaway! Just Steps from the Beach
Exterior

Romantic Island Getaway! Just Steps from the Beach

2.0 star property
8.8 out of 10, Excellent, (3)
"It was great! Check in was super easy and anything you would need is nearby. "
Romantic Island Getaway! Just Steps from the Beach
Charming, fully remodeled cottage steps from beach with WiFi & central AC
Exterior

Charming, fully remodeled cottage steps from beach with WiFi & central AC

8.2 out of 10, Very Good, (23)
"Very clean, comfortable, easy to reach the beach, and located in good neighbor "
Charming, fully remodeled cottage steps from beach with WiFi & central AC
Beach Cottage! Beautiful Pool/Spa, Steps to sand, Fun Golf Cart.
Exterior

Beach Cottage! Beautiful Pool/Spa, Steps to sand, Fun Golf Cart.

10.0 out of 10, Exceptional, (7)
"Wonderful property. Easy check in and out. Pool and location are perfect. Highly recommend!! "
Beach Cottage! Beautiful Pool/Spa, Steps to sand, Fun Golf Cart.
Beautiful Guest House Near the Beach with Private Pool!
Outdoor dining

Beautiful Guest House Near the Beach with Private Pool!

8.6 out of 10, Excellent, (28)
"The space directly above the local taco and donut shops was exactly as advertised! Clean, quaint, and perfect for our family of 5 that took full advantage of the private pool and 1 block walk to the beach. Can't wait to come back!!"
Beautiful Guest House Near the Beach with Private Pool!
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

Bridgewalk Resort

Bridgewalk Resort

10/10 Excellent
"Angie at the front desk was super friendly. Jamal. the parking attendant graciously helped us with an issue entering our room. The room was large, clean and well appointed. We loved the spacious lanai, as well. We will definitely be regulars in the future!"
Debra 2-night trip
Posted 1 day ago
Bridgewalk Resort

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.
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.

Explore a world of travel with Expedia

Explore a world of travel with Expedia