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Compare 59 Cottages in Anna Maria Island with updated reviews, rates, and availability.

Terrace/patio
Charming cottage in quiet area, close to beach & bay.
10.0 out of 10, Exceptional, (233)
"This charming 2 bed, 1 bath cottage is in the perfect location. It is in walking distance to coffee shops, breakfast spots and dinner restaurants. Close to the beach one direction and city pier the other. It is well stocked with all you would need and exceptionally clean. The screened porch in back with solar lighting in the back yard is ideal for your evening glass of wine! Definitely recommend!"
Charming cottage in quiet area, close to beach & bay.
A heated pool
Great location, cute cottage, short walk to beach, 2 bd home w/private pool
10.0 out of 10, Exceptional, (23)
"We came to the area for the first time for a short spring break trip. This property was awesome. It had everything we needed down to a cooler to take to the beach . The location was wonderful and the beach was a very short walk. The property was very clean and we thoroughly enjoyed the private backyard and pool area. Nearly Salt Bar and Table was fabulous."
Great location, cute cottage, short walk to beach, 2 bd home w/private pool
Property grounds
Sunny 1-bedroom island cottage with shared pool
10.0 out of 10, Exceptional, (17)
"This was a perfect little spot...super clean, super cute, super easy walk to the beach."
The price is $300
$490 total
includes taxes & fees
May 28 - May 29
Sunny 1-bedroom island cottage with shared pool
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Beach nearby
COZY APT IN QUADRAPLEX HOME. 1BR/1BA Sleeps up to 4. 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 4. POOLSIDE. STEPS TO BEACH!
On the beach
Sailfish Gulf Suites #3, Modern Amenities, Steps to the Beach
10.0 out of 10, Exceptional, (12)
"We stayed here for our honeymoon, and had the BEST time. It was so conveniently located, and we had everything we needed. My only complaint was the furniture was a tad uncomfortable, but we definitely plan to stay here again so it wasn’t that bad. It was nice that we had nice beach chairs and umbrellas, and we didn’t have to buy or rent anything. Definitely one of my favorite VRBO’s."
Sailfish Gulf Suites #3, Modern Amenities, Steps to the Beach
Sun loungers, beach towels
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!
Beach nearby
A lovely 2 bed and 2 bath property just moments from the beach
10.0 out of 10, Exceptional, (18)
"Perfect location, calm, relax, peaceful"
A lovely 2 bed and 2 bath property just moments from the 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!
On the beach
Vintage Island Cottage on the Beach- Sunset Views - Bamboo Apts. C1
10.0 out of 10, Exceptional, (81)
"This was a perfect location for us......see the ocean, walk to the beach, and enjoy ourselves. The gift basket was a special treat.....we will be back!!"
Vintage Island Cottage on the Beach- Sunset Views - Bamboo Apts. C1
Exterior
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."
The price is $270
$452 total
includes taxes & fees
May 28 - May 29
Relaxing 1-bedroom cottage with shared pool
Terrace/patio
Summer Breeze: North End, Dog Friendly, Kayaks, on Canal by Anna Maria Life Vacation Rentals
10.0 out of 10, Exceptional, (45)
"Excellent!"
Summer Breeze: North End, Dog Friendly, Kayaks, on Canal by Anna Maria Life Vacation Rentals
Terrace/patio
Snail's Pace: North End on Canal, Kayaks & Dog Friendly by Anna Maria Life Vacation Rentals
10.0 out of 10, Exceptional, (56)
"Thank you for the time in Anna Marie, look forward to coming back"
Snail's Pace: North End on Canal, Kayaks & Dog Friendly by Anna Maria Life Vacation Rentals
Pool | A heated pool
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
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
On the beach
Sailfish Gulf Suites #2, Beachfront, Steps to the Sand
9.8 out of 10, Exceptional, (8)
"Great host, very responsive. Excellent location - on the beach and close to Manatee Beach and amenities including the trolley stop. We loved our stay and hope to return."
Sailfish Gulf Suites #2, Beachfront, Steps to the Sand
Property grounds
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
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
Property grounds
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
Beach towels
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...
A heated pool
Beautiful, well-maintained home w/ heated private pool - walk to beach & dining
9.6 out of 10, Exceptional, (72)
"We loved our stay. Everything was perfect. We have 3 kids ages 3-7 and the layout and location was excellent. I also appreciate how clean it was when we arrived. Kitchen is very well stocked and we did most meals at the home. The walk to beach is just across the street. Highly recommend!"
Beautiful, well-maintained home w/ heated private pool - walk to beach & dining
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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

Exterior
Perfectly Located Home with Pool and Spa
9.6 out of 10, Exceptional, (20)
"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
On the beach, white sand, beach towels
Anna Maria Beach Resort
3.5 star property
9.4 out of 10, Exceptional, (155)
"Had an amazing stay. Will definitely be back!"
The price is $683
$857 total
includes taxes & fees
May 23 - May 24
Anna Maria Beach Resort
Garden
Pelican Post at Anna Maria Island Inn
3.0 star property
9.0 out of 10, Wonderful, (186)
"Very nice rooms. Lots of space. Newly renovated. Walking distance to everything and great pool. "
The price is $347
$435 total
includes taxes & fees
May 23 - May 24
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
1,157
Accommodation
59 Cottages
Lowest Price
$185
Highest Price
$300

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 9.5. 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
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