Search Anna Maria Island Cottages

    Plan, book, stay with confidence
    bex rewards loyalty icon
    Be picky
    Search almost a million properties worldwide
    one key icon
    Treat yourself
    Save instantly and earn perks with One Key
    today icon
    Change your mind
    Book hotels with free cancellation

Compare 54 Cottages in Anna Maria Island with updated reviews, rates, and availability.

Queen's Gate Resort
2.5 star property
9.0 out of 10, Wonderful, (406)
"Quaint small complex. Was given a tour at check in, Only 13 units, all ground level. Across the street from the beach. Pool and laundry tucked in behind the units. Perfect set up! Our King room was clean and the bed was super comfortable. They provided a lot of extras, utensils, plates, beach towels, chairs and umbrella. There were extra items made available to use…coolers, extra chairs, etc. Location is great, Perfect home base to go check out more things to do in the area. Convenient beach...
Queen's Gate Resort
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.
Relaxing 1-bedroom cottage with shared pool
10.0 out of 10, Exceptional, (40)
"The place is big enough "
Relaxing 1-bedroom cottage with shared pool
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
9.6 out of 10, Exceptional, (75)
"Love this rental! Interior was clean and ready to go when we arrived. Plenty of space for 6 of us. Super close to the beach. Had beach chairs and umbrellas available. Had an amazing trip. Will definitely stay there again. "
Beautiful, well-maintained home w/ heated private pool - walk to beach & dining
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
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
Pool Side Island Cottage
9.4 out of 10, Exceptional, (19)
"Excellent location. Close to beach. Very clean. Quiet neighborhood. The kitchen did not have a dish towel or dish soap. This made if difficult to wash dishes. I had to buy them at a store. There was no beach umbrella or beach chairs. This would have been helpful. Otherwise my family had a great time. We will be back."
Pool Side Island Cottage
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...
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!
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!
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!
Adorable Cottage with Covered Balconies and Private Pool
9.6 out of 10, Exceptional, (32)
"Great property in such a cute area and just a short walk to the beach. Love the pool area and all the rooms were perfect for my friends and family."
Adorable Cottage with Covered Balconies and Private 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
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.
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
Cheerful 1-bedroom Island Cottage with shared pool
9.4 out of 10, Exceptional, (35)
"We booked a Friday through Monday stay at this cottage. Due to a canceled ball tournament, we were able to leave Thursday. The property manager accommodated us for an early arrival. She also made special accommodations while we were there to make our stay the best it could be. The location is perfect. We easily walked to the beach each day several times. Beautiful island! And the cottage accommodated our family of 4 perfectly."
Cheerful 1-bedroom Island Cottage with shared pool
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
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.
Don't see what you're looking for?
See all available properties in Anna Maria Island
Save an average of 15% on thousands of hotels when you're signed in

Other property types in Anna Maria Island

Anna Maria Beach Resort
3.5 star property
9.4 out of 10, Exceptional, (177)
"I enjoyed my stay at the resort. I was there for 4 nights and it was great! The room spacious and the bed was very comfortable, "
The price is $574
includes taxes & fees
$512 per night
Dec 1 - Dec 2
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
9.4 out of 10, Exceptional, (203)
"Perfect stay for couples. Small but beautiful. It was super easy to talk with owner. Just across from beach. "
The price is $113
includes taxes & fees
$103 per night
Nov 17 - Nov 18
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?
Anna Maria Island has multiple cottages with a total average guest review rating of 9.5. Organizing a trip to Anna Maria? Travelers recommend Queens Gate Resort, a 2.5-star option with pool sun loungers and a garden. Another top pick where you can escape life’s hustle and bustle is 105b 12th Street South Front 2 Bedroom Apts By Redawning. It has a 3-star rating and conveniences such as a swimming pool and a barbecue grill.
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.