Search Cottages in Anna Maria Island

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Great Location, steps to beach, 2 bd home w/ private pool

9.8 out of 10, Exceptional, (23)
"Excellent location, close to the beach, stores, and restaurants. Wasn't as clean as it should be. There were spots around beds, that looked like they hadn't been cleaned in a long time. House was as advertised. Very nice for 2 couples and a small baby as we had. Pool was nice, although it needed some cleaning too. Overall, a very nice stay."
Great Location, steps to beach, 2 bd home w/ private pool

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.

Shell Cottage - sleeps 2

9.8 out of 10, Exceptional, (33)
"We could not ask for any better of a vacation"
Shell Cottage - sleeps 2

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

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

10.0 out of 10, Exceptional, (18)
"Clean, well equipped condo with the beach for the back yard. Great location, close to Publix and local shops, restaurants and beaches, Tammy was welcoming and responsive."
Sailfish Gulf Suites #3, Modern Amenities, Steps to 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...

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...

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!"
The price is HK$2,796
HK$5,643 total
includes taxes & fees
21 Feb - 22 Feb
Newly Renovated Sea Breeze Cottage with Private Dock, Easy Access to Bimini Bay

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

Conveniently located Bungalow with private pool and tropical landscaping

9.4 out of 10, Exceptional, (23)
"We loved staying at this property! The pool and patio were perfect and location close to everything we needed. The walk to the beach was short for us- about 1.5 blocks, less than 5 minutes. Kitchen was stocked with pots, pans, baking dishes, sheet pans, etc. Having a washer and dryer on site was so convenient! I would definitely stay at this property again!"
Conveniently located Bungalow with private pool and tropical landscaping

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

Adorable and Updated 2 BR/2BA Villa with a private heated pool.

9.2 out of 10, Wonderful, (24)
"Great location as advertised a short 2-3 block walk to the beach doable with younger kids and a wagon(you have to go one block north or south on beach front road as no direct access on the street of the condo). Nice area of Holmes beach walkable to shops and restaurants but still not on a major thoroughfare. Condo itself was nice enough with decently comfortable beds and plenty of space for family of 4. As others have reviewed, would be nice if management supplied a few more items for the...
Adorable and Updated 2 BR/2BA Villa with a private 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

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

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

Beach Dream Cottage: Steps from the Beach with Private Pool and Spa!

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. "
Beach Dream Cottage: Steps from the Beach with Private Pool and Spa!

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!

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

8.8 out of 10, Excellent, (71)
"This house on Anna Maria Island was a perfect vacation. The island is obviously still recovering from hurricane damage, but in a way that probably made this stay better. It was super quiet - even with construction going on - which was expected. This house has an awesome backyard with the privacy fence and pool. The pool was heated, and although cold first couple days because I'm sure they had just finished filling it for us, the last several days with it were really nice! The beach is literally...
Old Florida-style cottage w/ private heated pool - walk to the beach - dogs OK

Bradenton Beach Home w/ Outdoor Bar & Heated Pool!

3.0 star property
2.0 out of 10, (1)
Bradenton Beach Home w/ Outdoor Bar & Heated 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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Other property types in Anna Maria Island

Anna Maria Beach Resort

3.5 star property
9.4 out of 10, Exceptional, (182)
"Enjoyed most everything about this property. Amazing views from the room, clean property and free bikes. Unfortunately the heater in the pool and hot tub wasn't working properly, and the tv in the living area of my room wasn't functioning, and there was a lot of construction going on on the first floor of the building (from the hurricanes). But will most definitely be back in the future!"
The price is HK$3,143
HK$3,978 total
includes taxes & fees
26 Jan - 27 Jan
Anna Maria Beach Resort

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!

Anna Maria Sunsets - studio

9.2 out of 10, Wonderful, (194)
"The property was lovely - everything the listing said it would be. The location was perfect, right across the road from the beach with every place I wanted to go within walking distance. Highly recommend. "
The price is HK$1,246
HK$2,394 total
includes taxes & fees
1 Feb - 2 Feb
Anna Maria Sunsets - studio
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 9.2, so you’re sure to snag the ideal place. Headed to Bradenton Beach? Queen’s Gate Resort is one property loved by travellers. 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 holidaying 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 holiday 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.