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
31 Jul - 2 Aug
In two months
11 Sep - 13 Sep
In three months
9 Oct - 11 Oct
In four months
6 Nov - 8 Nov

Our top choices for Anna Maria Island cottages

Balcony view

The Inn On Siesta Key

The Inn On Siesta Key
3.5 star property
Siesta Key
10.0 out of 10, Exceptional, (199 reviews)
"The room was clean and spacious with all the amenities. The location was perfect. I would highly recommend!"
United States
Amanda
The Inn On Siesta Key
House (4 Bedrooms) | Interior

4 Mi to Dtwn St Pete! Pet-friendly Home w/ Yard

4 Mi to Dtwn St Pete! Pet-friendly Home w/ Yard
3.0 star property
St. Petersburg
The price is AED 657
AED 2,241 total
includes taxes & fees
19 Jul - 20 Jul
4 Mi to Dtwn St Pete! Pet-friendly Home w/ Yard
Interior

Siesta Heron 6 / Sunset

Siesta Heron 6 / Sunset
3.0 star property
Siesta Key
The price is AED 1,807
AED 3,011 total
includes taxes & fees
11 Aug - 12 Aug
Siesta Heron 6 / Sunset
House (2 Bedrooms) | Interior

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 AED 643
AED 1,234 total
includes taxes & fees
19 Jul - 20 Jul
Pet-friendly Bradenton Home 1.5 Mi to Cortez Beach
House (3 Bedrooms) | Interior

Unwind Poolside + Walk to Beach! Sarasota Retreat

Unwind Poolside + Walk to Beach! Sarasota Retreat
3.0 star property
South Village
8.0 out of 10, Very Good, (1 review)
"The location of the property was excellent. The home was clean and had everything we needed to prepare breakfast in the morning. The 3 bedrooms and 3 bathrooms made it easy for the six of us wash up and get ready for dinner after a fun fill day at the walkable beach. Beach was great. Having a pool at the property was great for the 2 youngsters. We also made use of the wagon that was available to carry items to the beach., The property is nothing fancy but a great value for the money. "
United States
Eleuterio
The price is AED 1,223
AED 2,499 total
includes taxes & fees
5 Aug - 6 Aug
Unwind Poolside + Walk to Beach! Sarasota Retreat
Interior

Beach Road

Beach Road
2.0 star property
Siesta Key
The price is AED 2,736
AED 3,707 total
includes taxes & fees
15 Aug - 16 Aug
Beach Road
Property grounds

3716 7th Ave W

3716 7th Ave W
3.0 star property
Bradenton
The price is AED 8,538
AED 11,187 total
includes taxes & fees
24 Jul - 25 Jul
3716 7th Ave W
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

Driftwood at Anna Maria Island Inn

Driftwood at Anna Maria Island Inn

10/10 Excellent
"The property was newer, very clean except the couch was white and looked like it had some sand covering it and some spots. The beds and pillows were very comfortable. We had everything we needed even beach towels. The pool was 5 steps from the door which was so convenient as well as the parking. It was decorated with a bright fun beach vibe. My daughter and I were more than happy that the pics and reviews on the site matched what we had hoped for. We will plan to come again in six months. Thank you for a beautiful stay."
Constance Depowski 1-night trip
Posted 9 hours ago
Driftwood 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 9.3, 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.