Search Cottages in Anna Maria Island

Start date: Check-in selected.
To Date
End date: Check-out
    calendar shield illustration

    Change your mind

    Book hotels with free cancellation
    deals illustration

    Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in
    bed illustration

    Be picky

    Search almost a million properties worldwide

Check prices for these dates

Next weekend
10 Oct - 12 Oct
In two weeks
17 Oct - 19 Oct
In one month
31 Oct - 2 Nov
In two months
28 Nov - 30 Nov

Cottages in Anna Maria Island

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)
"Castaway Cottage is paradise! The charm, the amenities, and the little extra touches made for the most relaxing vacation. Dan and Goose are the best!"
Castaway Cottage + Beach + Heated Private Pool & Spa + GOLF CART INCLUDED!
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, (289)
"Clean and quiet and the best location for a weekend getaway! "
Charming cottage in quiet area, close to beach & bay.
Tropical Paradise On The Beach Permit VRC17-000168
Property grounds

Tropical Paradise On The Beach Permit VRC17-000168

9.2 out of 10, Wonderful, (140)
"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
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
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!
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
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
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, (90)
"easy to beach great views"
Vintage Island Cottage on the Beach- Sunset Views - Bamboo Apts. C1
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)
"The house was perfectly clean when we arrived!! The pool was so relaxing and enjoyable after a long day on the beach. Highly recommend renting this home!"
Historic beach cottage with private pool - walk 1 block to beach & free trolley
Tropical Paradise Cottage on the Beach VRC17-000167
Exterior

Tropical Paradise Cottage on the Beach VRC17-000167

9.2 out of 10, Wonderful, (107)
"Very hidden, very private Great family place Cant wait to go back"
Tropical Paradise Cottage on the Beach VRC17-000167
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
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
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)
"Nicely renovated interior and exterior. "
Blue Isle Oasis: Adorable, updated 2 bedroom cottage
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
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. "
The price is AED 655
AED 1,444 total
includes taxes & fees
1 Oct - 2 Oct
Romantic Island Getaway! Just Steps from the Beach
Quiet Nights of Quiet Stars on Anna Maria Island
Exterior

Quiet Nights of Quiet Stars on Anna Maria Island

10.0 out of 10, Exceptional, (69)
"Our family of 4 absolutely loved our stay! The house is as described and has everything you need. Kitchen is well stocked, and the beds were very comfortable. No beach chairs since Helene, but we honestly didn't need them because we spent all of our time in the beautiful water! Beach access was very easy and we never had trouble finding somewhere to park. PSA : Rent a golf cart! We had a wonderful week at Quiet Nights of Quiet Stars and are already planning our next visit. Hopefully sooner...
Quiet Nights of Quiet Stars on Anna Maria Island
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
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.
Adorable Cottage with Covered Balconies and Private Pool
Terrace/patio

Adorable Cottage with Covered Balconies and Private Pool

9.6 out of 10, Exceptional, (39)
"Amazing cottage with plenty of amenities and a fantastic location. Just a few minutes walk to the beach, shopping and restaurants. Check-in and check-out were a breeze. The only hiccup was issues with parking. Often the single reserved space below was taken by restaurant clients."
The price is AED 1,098
AED 2,275 total
includes taxes & fees
6 Oct - 7 Oct
Adorable Cottage with Covered Balconies and 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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Anna Maria Island Hotel Reviews

Pelican Post at Anna Maria Island Inn

Pelican Post at Anna Maria Island Inn

10/10 Excellent
"We loved the property, room, amenities, and close proximity to Bradenton Beach, as well as our favorite shops and restaurants! Our rental car easily got us around to the other beaches, nature preserves, and outskirts! There is a free island trolley as well!"
Lisa Ann 4-night trip
Posted 4 days ago
Pelican Post at Anna Maria Island Inn

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