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Check prices for these dates

Next weekend
11 Rab. II - 13 Rab. II
In two weeks
18 Rab. II - 20 Rab. II
In one month
2 Jum. I - 4 Jum. I
In two months
30 Jum. I - 1 Jum. II

Compare 26 Cottages in Anna Maria with updated reviews, rates, and availability.

We will be accepting new reservations from January 2025 going forward only.
Beach nearby, sun loungers, beach towels

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!
Beach nearby, sun loungers, beach towels

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

10.0 out of 10, Exceptional, (258)
"My sixth year returning to reset and relax… I was so relieved to see little Castaway still standing and looking fabulous after Helene and Milton- kudos to Dan and Goose for their hospitality and even welcoming a new puppy to the scene. It was wonderful to see businesses and folks coming back from the devastation and look forward to next time! "
Castaway Cottage + Beach + Heated Private Pool & Spa = R & R! Near Bean Point!
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, (263)
"This cottage is just as described. New appliances and a fully equipped kitchen. Lots of towels, two king beds with excellent mattresses, and a large back yard with lounge chairs, a grill and comfy screened porch. Contact with and instructions from the hostess were outstanding. Easy walk to the beach and several excellent restaurants. "
Charming cottage in quiet area, close to beach & bay.
Shell Cottage - sleeps 2
Beach nearby

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.. I’m not sure I would stay here again...
Shell Cottage - sleeps 2
Beautiful Condo on Pine Ave, 2 Blocks to Beach
Terrace/patio

Beautiful Condo on Pine Ave, 2 Blocks to Beach

9.0 out of 10, Wonderful, (21)
"Great location, clean, and spacious. Pool didn’t work fir a couple of days but they got it fixed the day before we left "
Beautiful Condo on Pine Ave, 2 Blocks to Beach
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, (71)
"This house on Anna Maria Island was a perfect vacation. The island is obviously still recovering from hurricane damage, but in a way that probably made this stay better. It was super quiet - even with construction going on - which was expected. This house has an awesome backyard with the privacy fence and pool. The pool was heated, and although cold first couple days because I'm sure they had just finished filling it for us, the last several days with it were really nice! The beach is literally...
Old Florida-style cottage w/ private heated pool - walk to the beach - dogs OK
Historical AMI 2 Bedroom, pet friendly beach cottage, sleeps 6
Beach nearby

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
A heated pool

Adorable Cottage with Covered Balconies and Private Pool

9.6 out of 10, Exceptional, (34)
"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
Seahorse Cottage - sleeps 2 guests in 1 bedroom
Beach nearby

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
A heated pool

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

9.6 out of 10, Exceptional, (76)
"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
Beach towels

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

9.6 out of 10, Exceptional, (111)
"Beautiful quiet stay on the water. I would definitely stay here again!"
The price is SAR 1,347
SAR 2,669 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
Fridge, microwave, oven, stovetop

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

9.8 out of 10, Exceptional, (69)
"This little cottage is a great location right near the beach. We enjoyed walking down to Bean Point at sunrise and seeing all the snook in the surf. The beach near the cottage is perfect for the kids since it is very shallow and gradual."
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
Property grounds

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

10.0 out of 10, Exceptional, (34)
"The Barefoot Gypsy is a gem. It is super cute and recently fully remodeled post hurricanes. It is totally adorable with great finishes and is also super clean. The location is excellent and the managers were very friendly and helpful. I could not recommend it more."
Barefoot Gypsy = Steps to beach | Near Bayfront Park | Bean Point | Rod & Reel
Starfish Cottage - sleeps 4 guests in 2 bedrooms
Beach nearby

Starfish Cottage - sleeps 4 guests in 2 bedrooms

9.8 out of 10, Exceptional, (41)
"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!
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!
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
Canalfront Anna Maria Cottage w/ Pool & Hot Tub!
Interior

Canalfront Anna Maria Cottage w/ Pool & Hot Tub!

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

Serenity Cottage

2.0 star property
The price is SAR 3,320
SAR 5,895 total
includes taxes & fees
21 Apr - 22 Apr
Serenity Cottage
Sunrise Shore
Outdoor pool

Sunrise Shore

3.5 star property
Sunrise Shore
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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Other property types in Anna Maria

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

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!
A heated pool

Adorable Beach cottage just steps Bean Point beach!

9.8 out of 10, Exceptional, (49)
"Enjoyed our stay very much, Cannot wait to go back!!"
The price is SAR 2,165
SAR 4,692 total
includes taxes & fees
6 Apr - 7 Apr
Adorable Beach cottage just steps Bean Point beach!
Waterfront dog-friendly home with heated private pool, dock, views, and lanai
Fridge, microwave, oven, stovetop

Waterfront dog-friendly home with heated private pool, dock, views, and lanai

8.0 out of 10, Very Good, (67)
"Overall this worked great for us. About 2 blocks from the gulf coast. Fishing access on an inlet behind the house and pool was great for us and kids. Out of the way for major island traffic but close enough to the coast to walk and enjoy it"
The price is SAR 1,594
SAR 3,187 total
includes taxes & fees
1 Apr - 2 Apr
Waterfront dog-friendly home with heated private pool, dock, views, and lanai
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 — 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 Queen’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 9.2.
How many cottages are there in Anna Maria?
You can choose from 26 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.
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 you’re sticking to a budget, select how much you’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. We’ll help you find the right place whatever your trip looks like.
How can I find cheap cottages in Anna Maria?
With Expedia’s helpful filter tool, getting your hands on cheap cottages in Anna Maria has never been simpler. To discover accommodations that’ll make your wallet smile, narrow your search by star rating, amenities and budget.