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Compare 24 Cottages in Anna Maria with updated reviews, rates, and availability.

We will be accepting new reservations from January 2025 going forward only.

9.8 out of 10, Exceptional, (187)
"We enjoyed our stay. The rental is close to beaches and trolley takes you anywhere on the island. Rental is clean and owner checks in with you often. "
We will be accepting new reservations from January 2025 going forward only.

Castaway Cottage + Beach + Heated Private Pool & Spa = R & R! Near Bean Point!

10.0 out of 10, Exceptional, (261)
"Family of 4 stayed here comfortably for 3 nights in April. Had an excellent time on the island. And we were really impressed with the property and its location. Cool little trail, steps from the door take you straight to Bean Point."
Castaway Cottage + Beach + Heated Private Pool & Spa = R & R! Near Bean Point!

Charming cottage in quiet area, close to beach & bay.

9.8 out of 10, Exceptional, (268)
"We really enjoyed our weekend stay!! The cottage is super clean and cute! Backyard sitting in the evenings is the best. The cottage has everything you need, just bring a bathing suit!! Beds are comfortable, we slept very well. Close to the beach, restaurants and shops. This was my first trip to AMI but it wonā€™t be my last and Iā€™d definitely stay here again."
Charming cottage in quiet area, close to beach & bay.

Shell Cottage - sleeps 2

9.8 out of 10, Exceptional, (34)
"Shell Cottage was cute as can be . It was very clean , beautifully decorated and well equipped. However; there is an alarm on the entry door that is ear shattering. The check-in information states it is part of the rental license rules which I understand. There was no grey box on the outside of the door which can be pressed to allow entry within 45 seconds before the alarm goes off. There was a button on the inside that allowed us to leave the cottage.. Iā€™m not sure I would stay here again...
Shell Cottage - sleeps 2

Beautiful Condo on Pine Ave, 2 Blocks to Beach

8.8 out of 10, Excellent, (23)
"Great location, very comfortable property! We loved the 2 covered porch areas at the front and back of the unit. We had a little trouble with the AC but the owner was very responsive. We would certainly rent this unit again!"
The price is AEDĀ 1,190
AEDĀ 3,447 total
includes taxes & fees
13 Apr - 14 Apr
Beautiful Condo on Pine Ave, 2 Blocks to Beach

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

8.8 out of 10, Excellent, (72)
"It was myself, husband and 2.5 year old son who stayed at the property. The pool, proximity to the beach and walking distance to restaurants and ice cream shops couldn't have been any better. The house itself has some serious wear and tear though. Although I believe the cleaners did a great job, the condition/cleanliness of the furniture, and wear and tear on the house made it feel a little uncomfortable and dirty. We ate in for every meal and felt the kitchen was sparsely stocked, but we made...
Old Florida-style cottage w/ private heated pool - walk to the beach - dogs OK

Historical AMI 2 Bedroom, pet friendly beach cottage, sleeps 6

8.0 out of 10, Very Good, (3)
"We rented the SeaShell Cottage for the weekend of our daughter's wedding for our son, daughter - in - law and their daughter. It was only 2 blocks from the Venue - The Sandbar which was very convenient for them with an infant. The cottage was super clean and just down right adorable! We would definitely recommend and would love to return soon. "
Historical AMI 2 Bedroom, pet friendly beach cottage, sleeps 6

Adorable Cottage with Covered Balconies and Private Pool

9.6 out of 10, Exceptional, (35)
"We vacation multiple times at AMI. Our group loved the location right on Pine Avenue. Amenities were all top-notch everything you need. It was there."
Adorable Cottage with Covered Balconies and Private Pool

Seahorse Cottage - sleeps 2 guests in 1 bedroom

9.8 out of 10, Exceptional, (48)
"Seahorse Cottage was perfect and fit all our needs. Close to the beach, great pool, and the accommodations were very nice. We both would have preferred a firmer mattress on the bed but that would not stop us from visiting again. Idyllic Holiday Properties was very easy to deal with and Liane had excellent communication skills in planning for our trip. Debbie, the Property Manager in Anna Maria, was also very quick to respond to texts while we were there. All around, a great experience and a...
Seahorse Cottage - sleeps 2 guests in 1 bedroom

Beautiful, well-maintained home w/ heated private pool - walk to beach & dining

9.6 out of 10, Exceptional, (77)
"We were in town for a lacrosse tournament and this house was so perfect, clean and relaxing."
Beautiful, well-maintained home w/ heated private pool - walk to beach & dining

Newly Renovated Sea Breeze Cottage with Private Dock, Easy Access to Bimini Bay

9.6 out of 10, Exceptional, (112)
"Located fairly close to City Pier area. View of inlet. There are 15 wooden steps up into the house. Quiet neighborhood. "
The price is AEDĀ 1,319
AEDĀ 2,651 total
includes taxes & fees
14 Apr - 15 Apr
Newly Renovated Sea Breeze Cottage with Private Dock, Easy Access to Bimini Bay

Charming 2br / 1ba Cottage < 2 Min Walk From Beach on Anna Maria Island Florida

9.8 out of 10, Exceptional, (71)
"The location of this property was unbeatable. Steps to the beach and restaurants but still peaceful and quiet. Anthony and Joann were more than gracious hosts and made me, my husband and my kids feel very welcome."
Charming 2br / 1ba Cottage < 2 Min Walk From Beach on Anna Maria Island Florida

Barefoot Gypsy = Steps to beach | Near Bayfront Park | Bean Point | Rod & Reel

10.0 out of 10, Exceptional, (35)
"Great house, great location, great weather!"
Barefoot Gypsy = Steps to beach | Near Bayfront Park | Bean Point | Rod & Reel

Starfish Cottage - sleeps 4 guests in 2 bedrooms

9.8 out of 10, Exceptional, (42)
"Every thing was just as described on the listing. Cute cottage super close to the beach with a cute pool in the backyard. We had a great vacation! "
Starfish Cottage - sleeps 4 guests in 2 bedrooms

Beautiful Guest House Near the Beach with Private Pool!

8.4 out of 10, Very Good, (26)
"Great place, super clean, convenient location, awesome pool!"
Beautiful Guest House Near the Beach with Private Pool!

Guest House in the Business District with Private Pool

9.4 out of 10, Exceptional, (22)
"Location was amazing! Walking distance to all shops, restaurants and beach. Property had everything we needed even beach chairs which was so great since we flew. It was clean and comfortable. "
Guest House in the Business District with Private Pool

Canalfront Anna Maria Cottage w/ Pool & Hot Tub!

3.0 star property
Canalfront Anna Maria Cottage w/ Pool & Hot Tub!

Serenity Cottage

2.0 star property
Serenity Cottage

Sunrise Shore

3.5 star property
Sunrise Shore

Going Coastal by SeaBreeze

3.0 star property
Going Coastal by SeaBreeze
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

Sandy Cheeks: Ground-level home with plunge pool. Close to pier, park, & Bay!

9.6 out of 10, Exceptional, (11)
"The interior was all new. Furnishings, decor, kitchen supplies, and everything fresh and tastefully done. Quiet neighborhood just a couple blocks from beach. Exterior privacy will improve as landscape recovers. Parking and access easy. "
Sandy Cheeks: Ground-level home with plunge pool. Close to pier, park, & Bay!

Adorable Beach cottage just steps Bean Point beach!

9.8 out of 10, Exceptional, (51)
"This house was perfect for our family of 4. Loved the open concept. The small pool was refreshing and the location was amazing - so close to the most beautiful section of the beach. We will be back! "
Adorable Beach cottage just steps Bean Point beach!

Anna Maria Home with Saltwater Pool Near Beaches & Shopping - Sunrise Shore

9.4 out of 10, Exceptional, (46)
"This was a great stay, the only reason I didn't give a 5 star on everything was because we were missing a bedroom door on the main level. "
Anna Maria Home with Saltwater Pool Near Beaches & Shopping - Sunrise Shore
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

How much do cottages in Anna Maria cost?
Cottages in Anna Maria range between and per night. These stays offer a chance to reconnect with nature ā€” at a price you can afford. These prices were available on Expedia within the past 7 days, for a hotel booking with a check-in date within the next year. Prices reflect current offers and availability is subject to change. Additional terms may apply.
What are the best cottages in Anna Maria?
A traveler favorite is Queenā€™s Gate Resort. Make yourself comfortable at this 2.5-star stay which offers a garden and a swimming pool. 105b 12th Street South Front 2 Bedroom Apts By Redawning is another popular option to check out. Book into this 3-star cottage and make the most of amenities like a swimming pool and a barbecue grill. You can pick from multiple cottages in Anna Maria with a total average guest review rating of 9.3.
How many cottages are there in Anna Maria?
You can choose from 24 cottages in Anna Maria. No matter if youā€™re traveling with the family or planning a retreat with close friends, Expedia will help you find the perfect property to enjoy natureā€™s beauty.
Why book your cottage in Anna Maria with Expedia?
Expedia has some great cottages in Anna Maria, so get ready for a memorable stay close to nature. If youā€™re sticking to a budget, select how much youā€™d like to spend and the star rating of your property. Or, try out our filters to search for cottages with a kitchen or a pool. Weā€™ll help you find the right place whatever your trip looks like.
How can I find cheap cottages in Anna Maria?
With Expediaā€™s helpful filter tool, getting your hands on cheap cottages in Anna Maria has never been simpler. To discover accommodations thatā€™ll make your wallet smile, narrow your search by star rating, amenities and budget.