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Check prices for these dates

Next weekend
13 Jun - 15 Jun
In two weeks
20 Jun - 22 Jun
In one month
4 Jul - 6 Jul
In two months
1 Aug - 3 Aug

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

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

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

9.8 out of 10, Exceptional, (271)
"A lovely last minute find that got us out of the cold north for a little sunshine. Great location and helpful host. We so enjoyed our stay! "
Charming cottage in quiet area, close to beach & bay.
Castaway Cottage + Beach + Heated Private Pool & Spa = R & R! Near Bean Point!
Beach nearby, sun loungers, beach towels

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

10.0 out of 10, Exceptional, (266)
"Castaway Cottage exceeded our expectations! The location is an easy 2 minute walk to the beach and dining is an easy 3 minute golf cart ride. The owners outfitted the home to perfection. We loved our stay and look forward to another visit soon."
Castaway Cottage + Beach + Heated Private Pool & Spa = R & R! Near Bean Point!
Newly Renovated Sea Breeze Cottage with Private Dock, Easy Access to Bimini Bay
Beach towels

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

9.6 out of 10, Exceptional, (115)
"Beautiful quiet stay on the water. I would definitely stay here again!"
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
Fridge, microwave, oven, stovetop

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

9.8 out of 10, Exceptional, (74)
"Steps from the beach as well as great restaurants and shops, with great hosts."
Charming 2br / 1ba Cottage < 2 Min Walk From Beach on Anna Maria Island Florida
The Ballyhoo on Bean Point, 200 feet to a beautiful bayside beach and views!
Beach nearby, sun loungers, beach towels

The Ballyhoo on Bean Point, 200 feet to a beautiful bayside beach and views!

9.8 out of 10, Exceptional, (190)
"Great place to stay."
The Ballyhoo on Bean Point, 200 feet to a beautiful bayside beach and views!
Seahorse Cottage - sleeps 2 guests in 1 bedroom
Beach nearby

Seahorse Cottage - sleeps 2 guests in 1 bedroom

9.8 out of 10, Exceptional, (50)
"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
Historical AMI 2 Bedroom, pet friendly beach cottage, sleeps 6
Beach nearby

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

8.8 out of 10, Excellent, (5)
"Rating Details: The property manager was very helpful. The vacation rental was spotless. I was very happy with the location. I was more than satisfied with the condition of the vacation rental. Overall, I recommend this vacation rental. Reviewer Comments: Lots of beach time"
Historical AMI 2 Bedroom, pet friendly beach cottage, sleeps 6
Beautiful Condo on Pine Ave, 2 Blocks to Beach
Terrace/patio

Beautiful Condo on Pine Ave, 2 Blocks to Beach

8.8 out of 10, Excellent, (23)
"Me and my family loved our stay. We loved being right in the middle of all the Anna Maria action! Thank you!"
Beautiful Condo on Pine Ave, 2 Blocks to Beach
Beautiful, well-maintained home w/ heated private pool - walk to beach & dining
A heated pool

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
Adorable Cottage with Covered Balconies and Private Pool
A heated pool

Adorable Cottage with Covered Balconies and Private Pool

9.6 out of 10, Exceptional, (37)
"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
Beach Basket Cottage: Cute Old Florida Style Beach Cottage just steps to the Beach!
Beach nearby

Beach Basket Cottage: Cute Old Florida Style Beach Cottage just steps to the Beach!

10.0 out of 10, Exceptional, (46)
"Wonderful location, place, pool. We hope to be back."
Beach Basket Cottage: Cute Old Florida Style Beach Cottage just steps to the Beach!
Shell Cottage - sleeps 2
Beach nearby

Shell Cottage - sleeps 2

9.8 out of 10, Exceptional, (35)
"We could not ask for any better of a vacation"
Shell Cottage - sleeps 2
Old Florida-style cottage w/ private heated pool - walk to the beach - dogs OK
Beach

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

8.8 out of 10, Excellent, (73)
"Property is one house away from beach access on a very quiet street. Walking distance to great spots. Pool and screened in patio were our favorite spots. They also had beach chairs and sand toys which was an added bonus."
Old Florida-style cottage w/ private heated pool - walk to the beach - dogs OK
Starfish Cottage - sleeps 4 guests in 2 bedrooms
Beach nearby

Starfish Cottage - sleeps 4 guests in 2 bedrooms

9.8 out of 10, Exceptional, (43)
"We loved everything about starfish cottage. The backyard pool, proximity to the beach, shopping, and restaurants. Clean and quiet with everything we needed for a relaxing vacation. Master bed was a little outdated. Other than that, everything was wonderful. "
Starfish Cottage - sleeps 4 guests in 2 bedrooms
Barefoot Gypsy = Steps to beach | Near Bayfront Park | Bean Point | Rod & Reel
Property grounds

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

10.0 out of 10, Exceptional, (35)
"Great cottage with all the amenities. Loved that is was close to the beach and kept very clean. Also had beach supplies available. Loved our stay."
Barefoot Gypsy = Steps to beach | Near Bayfront Park | Bean Point | Rod & Reel
Beautiful Guest House Near the Beach with Private Pool!
A heated pool

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!
Canal-front Gem w/ Pool & Hot Tub in Anna Maria
House (2 Bedrooms) | Interior

Canal-front Gem w/ Pool & Hot Tub in Anna Maria

3.0 star property
Canal-front Gem w/ Pool & Hot Tub in Anna Maria
Guest House in the Business District with Private Pool
Fridge, microwave, oven, stovetop

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
Serenity Cottage
Pool

Serenity Cottage

2.0 star property
Serenity Cottage
Going Coastal by SeaBreeze
Cottage, 2 Bedrooms, Private Pool, Canal View | Terrace/patio

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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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 — 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?
Pick from multiple cottages in Anna Maria that have a total average guest review rating of 9.7. Queen’s Gate Resort is a terrific place to rest and put your feet up between adventures. This 2.5-star cottage also has a barbecue grill and a swimming pool. 105b 12th Street South Front 2 Bedroom Apts By Redawning is another top option with travelers to this area. It has a 3-star rating and amenities including a barbecue grill and a swimming pool.
How many cottages are there in Anna Maria?
You can choose from 24 cottages in Anna Maria. No matter if you’re traveling with the family or planning a retreat with close friends, Expedia will help you find the perfect property to enjoy nature’s beauty.