Search Cottages in Anna Maria Island

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Check prices for these dates

Next weekend
27 Jun - 29 Jun
In two weeks
4 Jul - 6 Jul
In one month
18 Jul - 20 Jul
In two months
15 Aug - 17 Aug

Cottages in Anna Maria Island

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, (272)
"Beautiful home and great location. Close to the beach, food and ice cream. Will definitely stay here again. Host was really responsive. "
Charming cottage in quiet area, close to beach & bay.
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, (78)
"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
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!
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, (192)
"Great place to stay."
The Ballyhoo on Bean Point, 200 feet to a beautiful bayside beach and views!
Perfect location, cute cottage, 2 min walk to beach, 2bd/2ba home w/private pool
A heated pool

Perfect location, cute cottage, 2 min walk to beach, 2bd/2ba home w/private pool

9.8 out of 10, Exceptional, (30)
"We were very pleased with this rental, particularly the private pool and 3 minute walk to a pristine beach."
Perfect location, cute cottage, 2 min walk to beach, 2bd/2ba home w/private pool
Anna Maria Cottage with Golf Cart
Terrace/patio

Anna Maria Cottage with Golf Cart

9.8 out of 10, Exceptional, (9)
"Very comfortable property. Shower wall was loose and water pressure was low, but overall a nice property and would stay there again "
Anna Maria Cottage with Golf Cart
Historical AMI 2 Bedroom, pet friendly beach cottage, sleeps 6
Beach nearby

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

9.0 out of 10, Wonderful, (8)
"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
Charming Ground Level Resort Style 3 unit Condo - unit C
Outdoor pool, a heated pool

Charming Ground Level Resort Style 3 unit Condo - unit C

9.6 out of 10, Exceptional, (14)
"we will be back!"
Charming Ground Level Resort Style 3 unit Condo - unit C
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
Tropical Paradise On The Beach Permit VRC17-000168
Fridge, microwave, oven, stovetop

Tropical Paradise On The Beach Permit VRC17-000168

9.4 out of 10, Exceptional, (132)
"Quaint beach cottage tucked away from the hustle an bustle of the island. The upper unit had a spectacular view of the beach and sunsets.Communication with the property managers was great!We have already booked again for next year!Thank you for a wonderful stay!"
Tropical Paradise On The Beach Permit VRC17-000168
Sailfish Gulf Suites #3, Modern Amenities, Steps to the Beach
Outdoor dining

Sailfish Gulf Suites #3, Modern Amenities, Steps to the Beach

10.0 out of 10, Exceptional, (19)
"Clean, well equipped condo with the beach for the back yard. Great location, close to Publix and local shops, restaurants and beaches, Tammy was welcoming and responsive."
Sailfish Gulf Suites #3, Modern Amenities, Steps to the Beach
Rustic & Cozy Island Original Cottage on the Beach- Bamboo Apts. C2
Outdoor dining

Rustic & Cozy Island Original Cottage on the Beach- Bamboo Apts. C2

9.8 out of 10, Exceptional, (88)
"Great place. Easy access to beach and surrounding amenities. Would recommend. "
Rustic & Cozy Island Original Cottage on the Beach- Bamboo Apts. C2
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, (116)
"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
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, (38)
"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
Charming, fully remodeled cottage steps from beach with WiFi & central AC
Beach nearby

Charming, fully remodeled cottage steps from beach with WiFi & central AC

8.2 out of 10, Very Good, (22)
"Very clean, comfortable, easy to reach the beach, and located in good neighbor "
Charming, fully remodeled cottage steps from beach with WiFi & central AC
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
Cozy Holmes Beach Cottage - 3/2 - 1 block from beach!
Sun loungers, beach towels

Cozy Holmes Beach Cottage - 3/2 - 1 block from beach!

9.4 out of 10, Exceptional, (19)
"Great location nicely decorated and clean"
Cozy Holmes Beach Cottage - 3/2 - 1 block from beach!
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
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
Vintage Island Cottage on the Beach- Sunset Views - Bamboo Apts. C1
On the beach

Vintage Island Cottage on the Beach- Sunset Views - Bamboo Apts. C1

10.0 out of 10, Exceptional, (85)
"Enjoyed our stay"
Vintage Island Cottage on the Beach- Sunset Views - Bamboo Apts. C1
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

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