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 59 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, (381)
"The Location 100 steps to the beach ! Property manager Kathy and assistant manager Pete were amazing they attended to every need we had , gave us a tour of the property and followed up every day on how our stay was ."
Queen's Gate Resort
Charming cottage in quiet area, close to beach & bay.
9.8 out of 10, Exceptional, (236)
"The best location with all the beach supplies you could need. There’s a washer and dryer and a dishwasher! A nice screened in porch and pretty big backyard. You are SO close to the beach and sandbar restaurant. Would highly recommend this place. Great communication and flexibility. If I could give 10 stars I would. Thank you!! "
Charming cottage in quiet area, close to beach & bay.
Sunny 1-bedroom island cottage with shared pool
10.0 out of 10, Exceptional, (18)
"This was a perfect little spot...super clean, super cute, super easy walk to the beach."
Sunny 1-bedroom island cottage with shared pool
Save an average of 15% on thousands of hotels when you're signed in
Charming 2br / 1ba Cottage < 2 Min Walk From Beach on Anna Maria Island Florida
9.8 out of 10, Exceptional, (67)
"My friend and I, to celebrate Mother's Day without kids, spend 4 days at this delightful cottage on Anna Maria Island. I have only glowing reports regarding the location and the hosts. This cute and old-fashioned cottage sits in a great location and is in walking distance to shops, the Anna Maria Pier, restaurants and especially, the beach! It sits next to Capt Anthony's fish market which would have been interesting to watch; however, the owners were on vacation so we missed the action. Joanne...
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, (13)
"There are not enough words to convey how perfect our trip was. The property was even more beautiful than the photos online. The amenities included made it so easy to simply relax and enjoy the beach that was only steps from our door. Our unit was absolutely immaculate, and we cannot wait to go back!"
Sailfish Gulf Suites #3, Modern Amenities, Steps to the Beach
Great location, cute cottage, 2 min walk to beach, 2 bd home w/private pool
10.0 out of 10, Exceptional, (24)
"We were very pleased with this rental, particularly the private pool and 3 minute walk to a pristine beach."
Great location, cute cottage, 2 min walk to beach, 2 bd home w/private pool
Experience the passion of hospitality, cleaning, and good location!
9.6 out of 10, Exceptional, (125)
"The place was quaint and was the perfect location to the beach and downtown area."
The price is $220
$380 total
includes taxes & fees
Jun 9 - Jun 10
Experience the passion of hospitality, cleaning, and good location!
COZY APT IN QUADRAPLEX HOME. 1BR/1BA Sleeps up to 3. POOLSIDE. STEPS TO BEACH!
10.0 out of 10, Exceptional, (147)
"Family beaxh vacation mom, dad and 2 children"
COZY APT IN QUADRAPLEX HOME. 1BR/1BA Sleeps up to 3. POOLSIDE. STEPS TO BEACH!
Historical Anna Maria Island 2 Bedroom, pet friendly beach cottage, sleeps 6
Historical Anna Maria Island 2 Bedroom, pet friendly beach cottage, sleeps 6
Relaxing 1-bedroom cottage with shared pool
10.0 out of 10, Exceptional, (35)
"We enjoyed our long weekend in Anna Marie Island! The apartment was all around great. Would highly recommend to anyone. It was a great location with walking less the 5 mins to the beach. The apartment was very clean and well maintained."
Relaxing 1-bedroom cottage with shared pool
Charming & Vintage Anna Maria Cottage. Easy Walk to Beaches, Stroll Pine Avenue!
8.8 out of 10, Excellent, (5)
"Best location on the island. Cottage is exactly what you want to find at the beach. This is my second of many more to come."
Charming & Vintage Anna Maria Cottage. Easy Walk to Beaches, Stroll Pine Avenue!
Cheerful 1-bedroom Island Cottage with shared pool
9.6 out of 10, Exceptional, (32)
"My husband and I rented this unit for our 30th wedding anniversary and we cannot be happier with our decision! The location is perfect, just a short walk to the beach, or to the free trolley bus stop…no need to move the car if you don’t want to. The apartment was perfectly clean and beautifully decorated. My only recommendation is that the mattress needs to be changed and the coffee maker requires Keurig coffee cups and the ones left at the apartment, were from a different brand so we couldn’t...
Cheerful 1-bedroom Island Cottage with shared pool
Rustic & Cozy Island Original Cottage on the Beach- Bamboo Apts. C2
9.8 out of 10, Exceptional, (83)
"Thanks to all of the prior raters who gave this property such a good reputation. It’s very clean, is well maintained, has beautiful grounds, is only steps to the beach, is centrally located, has a grocery within walking distance…. Too many good things to list. We were fortunate enough to meet our host and she’s just the most pleasant and likable person. Great stay all around!!"
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, (34)
"Stayed for 9 nights and had a wonderful time. Twin dolphin is a clean, cute, and cozy place to stay. Very convenient area for walking. I highly recommend staying here. You won’t regret it."
Charming Cottage, FREE Wi-Fi & Trolley, Close to Gulf & Bay Beach, Stroll the...
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
Romantic, Cute Cottage on Anna Maria Island. Close To Everything. Pet Friendly!
10.0 out of 10, Exceptional, (9)
"Amazing stay for Spring break 2024. Your cottage was absolutely perfect and we had an amazing time exploring all of beautiful AMI. Loved watching the sunset from the rooftop and having our morning coffee on the back deck. Boys loved the outdoor shower and everything about your cottage was perfect! We can’t wait to come back! Perfect location in all the action. Loved the bike path over to Longboat key and Beer Can Island was such a gem. Thank you for an amazing time. Cheers!!!"
Romantic, Cute Cottage on Anna Maria Island. Close To Everything. Pet Friendly!
Newly Renovated Sea Breeze Cottage with Private Dock, Easy Access to Bimini Bay
9.6 out of 10, Exceptional, (106)
"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
Starfish Cottage the largest of a cluster of 3 properties sharing a free form pool
9.8 out of 10, Exceptional, (37)
"Love everything about this place! Great location! Close to beach, close to shopping, close to restaurants!! What more could we ask for! Will be back!!"
Starfish Cottage the largest of a cluster of 3 properties sharing a free form pool
Experience the passion of hospitality, cleaning, and good location!
9.2 out of 10, Wonderful, (102)
"The property was clean, basic furnishings, too close to the road."
The price is $220
$368 total
includes taxes & fees
Jun 9 - Jun 10
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!
Don't see what you're looking for?
See all available properties in Anna Maria Island
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.

Other property types in Anna Maria Island

Anna Maria Beach Resort
3.5 star property
9.4 out of 10, Exceptional, (157)
"the location was just perfect - beach, pool were wonderful "
The price is $689
$865 total
includes taxes & fees
Jun 26 - Jun 27
Anna Maria Beach Resort
Perfectly Located Home with Pool and Spa
9.8 out of 10, Exceptional, (21)
"The house is great, with the ease of having a pool and the beach being only 2 blocks away. This was our first time visiting Anna Maria. We have been finding other options the last couple years since we used to go to Captiva and that was destroyed in the hurricane almost 2 years ago. The island is pretty small but has different sections to explore. We enjoyed Coquina beach for a coupem hours one day, the restaurants were good very vactiony normal island grub type places. We did enjoy a great meal...
Perfectly Located Home with Pool and Spa
Pelican Post at Anna Maria Island Inn
3.0 star property
9.2 out of 10, Wonderful, (190)
"This place is so beautiful I do not want to leave. The only improvement I would suggest would be a USB port for charging devices. Other than that the place is clean,comfortable and about perfect. "
The price is $229
$288 total
includes taxes & fees
Jun 13 - Jun 14
Pelican Post at Anna Maria Island Inn
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.

Anna Maria Island Cottages information

Number of reviews
1,405
Accommodation
59 Cottages
Lowest Price
$220
Highest Price
$220

Frequently asked questions

What are the best cottages in Anna Maria Island?
Anna Maria Island offers multiple cottages with a total average guest review rating of 9.6. Planning to visit Bradenton Beach? Travelers recommend Queens Gate Resort, a 2.5-star property with pool sun loungers and a swimming pool. Another top pick where you can get away from the routine is 105b 12th Street South Front 2 Bedroom Apts By Redawning. It has a 3-star rating and conveniences that include 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 for an unforgettable vacay on nature’s doorstep. If you have a certain budget, click on how much you want to spend and the star rating of your property. Or, use our handy filters to search for cottages with a hot tub or free WiFi. We’ll help you find the perfect fit whatever your getaway looks like.
How can I find cheap cottages in Anna Maria Island?
Expedia is here to help you look for cheap cottages in Anna Maria Island. To discover the perfect stay in a matter of clicks, use our convenient filter tool to refine your search by amenities, star rating and budget.

Recent reviews of Anna Maria Island hotels
Expedia verified reviews