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Compare 58 Cottages in Anna Maria Island with updated reviews, rates, and availability.

Old Florida-style cottage w/ private heated pool - walk to the beach - dogs OK
Beach

Old Florida-style cottage w/ private heated pool - walk to the beach - dogs OK

8.8 out of 10, Excellent, (70)
"The Mangrove Cottage was perfect for my family of 4. Great location to the beach! Backyard was like our own tropical oasis! We loved the pool!! Comfortable beds! Hot water lasted a really long time with no issues of running out (4 baths/showers, dishes and laundry on same evening). I enjoyed the sitting in the screened porch in the mornings drinking my coffee. Washer and dryer worked really well. House cleaning staff could have done a better job, but it wasn't terrible. The dishes could...
Old Florida-style cottage w/ private heated pool - walk to the beach - dogs OK
Beautiful, well-maintained home w/ heated private pool - walk to beach & dining
A heated pool

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

9.6 out of 10, Exceptional, (76)
"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
Experience the passion of hospitality, cleaning, and good location!
Beach nearby

Experience the passion of hospitality, cleaning, and good location!

9.6 out of 10, Exceptional, (131)
"Enjoyed staying here it’s close to the beach"
Experience the passion of hospitality, cleaning, and good location!
Vintage Island Cottage on the Beach- Sunset Views - Bamboo Apts. C1
On the beach

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

10.0 out of 10, Exceptional, (85)
"My wife and i had a great weekend in Alice's cottage..Pkace was clean and clearly well maintained. Oh and did i mention only a few steps to a white, soft sandy beach? Yes this was a great old Florida' experience. Not many of these gems left"
Vintage Island Cottage on the Beach- Sunset Views - Bamboo Apts. C1
Rustic & Cozy Island Original Cottage on the Beach- Bamboo Apts. C2
On the beach

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

9.8 out of 10, Exceptional, (88)
"We loved the historical feel of the cottage and proximity to the beach. It was a relaxing, rejuvenating visit and we appreciated the hospitality basket upon our arrival. We have found most VRBO’s do not offer this simple but much appreciated touch. On top of everything, the owner, Alice, is a delight"
Rustic & Cozy Island Original Cottage on the Beach- Bamboo Apts. C2
Charming Cottage, FREE Wi-Fi & Trolley, Close to Gulf & Bay Beach, Stroll the...
Beach towels

Charming Cottage, FREE Wi-Fi & Trolley, Close to Gulf & Bay Beach, Stroll the...

9.6 out of 10, Exceptional, (40)
"The property was as described and absolutely amazing! It was beautiful inside, beds were comfortable, living area had comfortable furniture. Amenities were excellent. Not a bad thing to say about this place. Easy check in/out. Will definitely stay there again! "
Charming Cottage, FREE Wi-Fi & Trolley, Close to Gulf & Bay Beach, Stroll the...
Romantic, Cute Cottage on Anna Maria Island. Close To Everything. Pet Friendly!
Sun loungers, beach towels

Romantic, Cute Cottage on Anna Maria Island. Close To Everything. Pet Friendly!

10.0 out of 10, Exceptional, (15)
"We had such a great stay at the Seabreeze Cottage. The space is so nice with everything you need to stay in and cook and feel comfortable. Such an easy walk to the beach, bay and tons of restaurants. We will definitely be coming back! "
Romantic, Cute Cottage on Anna Maria Island. Close To Everything. Pet Friendly!
Experience the passion of hospitality, cleaning, and good location!
Beach nearby

Experience the passion of hospitality, cleaning, and good location!

9.2 out of 10, Wonderful, (106)
"Very close to beach access point. Smaller units but a good price for the area. Parking is convenient. Only $15 for late checkout. "
Experience the passion of hospitality, cleaning, and good location!
New Retro Style Home with Large Pool Close to Downtown Holmes Beach and Walk to Beach!
Outdoor pool, a heated pool

New Retro Style Home with Large Pool Close to Downtown Holmes Beach and Walk to Beach!

10.0 out of 10, Exceptional, (6)
"Great private pool and newer duplex, everything you could want, beach walking distance 5 min, great central spot to the island, the back yard and pool was the highlight for me..to be able to spend time at beach then come back and relax in pool is the best. Thank you for a nice stay"
New Retro Style Home with Large Pool Close to Downtown Holmes Beach and Walk to Beach!
Home with Private Pool, Two Blocks from the Beach! - Queen Palms
A heated pool

Home with Private Pool, Two Blocks from the Beach! - Queen Palms

10.0 out of 10, Exceptional, (23)
"we stayed for a week and overall loved our stay. The house was clean and we were provided with basic necessities and there were plenty of towels and beach towels. They also had a wagon and beach chairs for beach trips. We loved that the Queen palm is walking distance to so many restaurants, shops and of course the beach. There is a pool on the property which is nice if you’re not up for the beach but take note that it might be just big enough for a small number of people. Overall, when we go...
Home with Private Pool, Two Blocks from the Beach! - Queen Palms
Perfect family vacation home near the beach
A heated pool

Perfect family vacation home near the beach

9.4 out of 10, Exceptional, (29)
"Had a wonderful week at this home. Large clean kitchen, good sized rooms and bathrooms. Pool was clean and larger than expected. Only issue was that the pool handle on the stairs was gone and broken off. Only covered by a pvc pipe that stuck out of the water and was a major hazard for our 2 small kids as they could have easily gotten very hurt. Not having a handle was also challenging for my older parents who stayed with us as it was hard to get in and out of the pool. I wish this would have...
Perfect family vacation home near the beach
Charming cottage in quiet area, close to beach & bay.
Beach nearby, sun loungers, beach towels

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

9.8 out of 10, Exceptional, (252)
"Stayed there again for a few days for our anniversary. Great location, nice place, wonderful host. We couldn't ask for anything better. That's why we keep going back. We left just before Hurricane Helene and are praying for Cindy and Anna Maria Island. "
Charming cottage in quiet area, close to beach & bay.
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, (69)
"This little cottage is a great location right near the beach. We enjoyed walking down to Bean Point at sunrise and seeing all the snook in the surf. The beach near the cottage is perfect for the kids since it is very shallow and gradual."
Charming 2br / 1ba Cottage < 2 Min Walk From Beach on Anna Maria Island Florida
Sailfish Gulf Suites #3, Modern Amenities, Steps to the Beach
On the beach

Sailfish Gulf Suites #3, Modern Amenities, Steps to the Beach

10.0 out of 10, Exceptional, (17)
"This is such a dreamy location and living space, worth every penny!"
Sailfish Gulf Suites #3, Modern Amenities, Steps to the Beach
Beautiful Home with Private Pool, One Block to the Beach! - Ainsley Beach House
A heated pool

Beautiful Home with Private Pool, One Block to the Beach! - Ainsley Beach House

9.6 out of 10, Exceptional, (48)
"This home was everything we were looking for. So close to the beach. The property came with a wagon for the beach chairs as also a cabana. The pool was a perfect fit for our 3 year old, and location for some fun shops for my 13 year old. We loved walking down every night to watch the sunset. The washer and dryer were an added bonus to clean towels after a day at the beach"
Beautiful Home with Private Pool, One Block to the Beach! - Ainsley Beach House
Charming Ground Level Resort Style 3 unit Condo - unit C
Outdoor pool, a heated pool

Charming Ground Level Resort Style 3 unit Condo - unit C

9.6 out of 10, Exceptional, (12)
"The rental was exactly as stated. It is small but it has everything you need for a perfect vacation. You can’t beat the location and the pool was a big bonus. We would definitely stay here again in the future."
Charming Ground Level Resort Style 3 unit Condo - unit C
Newly renovated Cozy Beach Cottage B 1/2 of a duplex, 3min walk to beach
Beach nearby, sun loungers, beach towels

Newly renovated Cozy Beach Cottage B 1/2 of a duplex, 3min walk to beach

9.8 out of 10, Exceptional, (20)
"My son and father had a great stay here. The only real down side is that there are no dresser in either bedroom. You are able to hang your items up but no where to put anything else. A dresser or closet organizer would be a great addition. They really enjoyed sitting out on the back patio, it is fully shaded and quiet. The location of the house is great- short walk to the beach and a great central location to everything else. They enjoyed their stay and would be happy to go back."
Newly renovated Cozy Beach Cottage B 1/2 of a duplex, 3min walk to beach
Cute beach cottage with pool and hot tub
A heated pool

Cute beach cottage with pool and hot tub

9.8 out of 10, Exceptional, (39)
"Great location. House was clean and pool was nice. It was a short 5 minute walk to the beach restaurants and ice cream. Nice family vacation would stay here again no concerns at all. "
Cute beach cottage with pool and hot tub
Experience the passion of hospitality, cleaning, and good location!
Beach

Experience the passion of hospitality, cleaning, and good location!

9.4 out of 10, Exceptional, (151)
"Over all great"
Experience the passion of hospitality, cleaning, and good location!
Newly Renovated Sea Breeze Cottage with Private Dock, Easy Access to Bimini Bay
Beach towels

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

9.6 out of 10, Exceptional, (109)
"Great little cottage with amazing views, warm and welcoming place to stay! Owner was responsive and wonderful to work with, super flexible letting us get a golf cart dropped off before checkin and was great to work with. Great vacation in the beautiful quiet part of AMI!"
Newly Renovated Sea Breeze Cottage with Private Dock, Easy Access to Bimini Bay
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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Other property types in Anna Maria Island

Anna Maria Beach Resort
On the beach, white sand, beach towels

Anna Maria Beach Resort

3.5 star property
9.4 out of 10, Exceptional, (178)
"Love the place, near a beautiful beach, staff friendly and accommodating, best beds and linens ever! I did not want to leave! Thank you! "
The price is ￥70,650
￥89,413 total
includes taxes & fees
Jan 2 - Jan 3, 2025
Anna Maria Beach Resort
Anna Maria Sunsets - studio
Sun loungers, beach towels

Anna Maria Sunsets - studio

9.4 out of 10, Exceptional, (204)
"Thank you, we had a great time"
The price is ￥18,601
￥39,253 total
includes taxes & fees
Jan 3 - Jan 4, 2025
Anna Maria Sunsets - studio
Luxury home with Pool, Putting Green, Beach Bikes!
A heated pool

Luxury home with Pool, Putting Green, Beach Bikes!

9.6 out of 10, Exceptional, (28)
"Absolutely stunning house! Decor is beautiful, beds are comfortable, porch is amazing, location is great and pool/spa is perfect!! Best house we have ever stayed in! Would recommend to all my family and friends. "
Luxury home with Pool, Putting Green, Beach Bikes!
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.

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 the ideal place. Headed to Bradenton Beach? Queen’s Gate Resort is one property loved by travelers. This 2.5-star cottage includes amenities like a barbecue grill and pool sun loungers. 105b 12th Street South Front 2 Bedroom Apts By Redawning is another highly rated getaway where you’ll be in touch with nature. A barbecue grill and a swimming pool are two of the conveniences waiting for you at this 3-star pick in Bradenton Beach.
Are there any family-friendly cottages in Anna Maria Island?
Yes there are. Whether it’s in one of Anna Maria Island’s busy cities or way out in the wilderness, the rustic charm of a cottage is perfect for vacationing families. If Bradenton Beach is on your travel itinerary, make a booking at Queen’s Gate Resort. This 2.5-star option features a nearby beach and laundry facilities. Another terrific 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. Bradenton Beach has plenty of family-friendly attractions when it’s time to go sightseeing. Coquina Beach and Fish Hole Adventure Golf has something for all ages.
Why book your cottage in Anna Maria Island with Expedia?
Expedia has some terrific cottages in Anna Maria Island, so start packing your bags for a memorable vacation on nature’s doorstep. If you have a budget, choose how much you’re willing to spend and the star rating of your property. Or take advantage of our filters to search for cottages with free WiFi or a pool. We’ll help you find the right digs whatever your getaway looks like.
How can I find cheap cottages in Anna Maria Island?
Expedia is here to help you easily source cheap cottages in Anna Maria Island. To discover the perfect stay in a few clicks, simply use our convenient filter tool to refine your search by star rating, budget and amenities.