Search Anna Maria Island Cottage Rentals from CA $252

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Browse Select Anna Maria Island Cottages

Beach nearby, sun loungers, beach towels
Charming cottage in quiet area, close to beach & bay.
10.0 out of 10, Exceptional, (232)
"This adorable little cottage is perfectly located! We could walk to restaurants, the beach and the free trolley. It was quiet and serene! The house was so clean, beautifully decorated and fully stocked! Cindy was a fantastic host! Thank you for helping make our reunion for our 35th anniversary as friends such a special experience. We will definitely be back!"
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."
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, (11)
"My husband and I thoroughly enjoyed our stay at this rental. We were in a garden view room. Bed was comfortable, kitchen stocked and steps from the beach. Would love to visit again!"
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
Property grounds
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
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)
"My wife and I stayed the week prior to Easter here at Snail’s Pace, and it really was a perfect getaway. The location is phenomenal. We spent our mornings paddle boarding in the lagoon behind the house, which is brimming with wildlife, and even saw a couple manatees hanging out. We’d then spend the rest of the day lounging by the beach, which is just a short walk. The scenery was beautiful, and it’s much quieter on the north end of the island. Plenty of good food within walking distance as well....
Snail's Pace: North End on Canal, Kayaks & Dog Friendly by Anna Maria Life Vacation Rentals
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)
"Great location, clean, comfortable and close to everything!, Captain Anthony and Joann were great to get to know, we loved it there. Highly recommend"
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
On the beach
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
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

A heated pool
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, (153)
"Beautiful and peaceful setting"
The price is CA $782
CA $981 total
includes taxes & fees
May 19 - May 20
Anna Maria Beach Resort
Garden
Pelican Post at Anna Maria Island Inn
3.0 star property
9.0 out of 10, Wonderful, (184)
"Very nice rooms. Lots of space. Newly renovated. Walking distance to everything and great pool. "
The price is CA $472
CA $592 total
includes taxes & fees
May 19 - May 20
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
1,153
Accommodation
57 Cottages
Lowest Price
CA $252
Highest Price
CA $252

Recent Reviews in Anna Maria Island
Expedia verified reviews