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Featured Cottages in Anna Maria

Historical Anna Maria Island 2 Bedroom, pet friendly beach cottage, sleeps 6
Beach nearby
Historical Anna Maria Island 2 Bedroom, pet friendly beach cottage, sleeps 6
Historical Anna Maria Island 2 Bedroom, pet friendly beach cottage, sleeps 6
Charming cottage in quiet area, close to beach & bay.
Beach nearby, sun-loungers, beach towels
Charming cottage in quiet area, close to beach & bay.
9.8 out of 10, Exceptional, 240 reviews
"This one of the cleanest, most homey, and reasonably priced rentals we've ever visited on Anna Maria Island--or anywhere else, for that matter. The cottage is nicely located near the beaches, the Anna Maria city pier, and a variety of top-notch restaurants. Our dog, Rosie, enjoyed the large, fenced-in backyard. A great stay all around. Thanks, Cindy!"
Charming cottage in quiet area, close to beach & bay.
Charming 2br / 1ba Cottage < 2 Min Walk From Beach on Anna Maria Island Florida
Charming 2br / 1ba Cottage < 2 Min Walk From Beach on Anna Maria Island Florida
9.8 out of 10, Exceptional, 68 reviews
"My friend and I, to celebrate Mother's Day without kids, spend 4 days at this delightful cottage on Anna Maria Island. I have only glowing reports regarding the location and the hosts. This cute and old-fashioned cottage sits in a great location and is in walking distance to shops, the Anna Maria Pier, restaurants and especially, the beach! It sits next to Capt Anthony's fish market which would have been interesting to watch; however, the owners were on vacation so we missed the action. Joanne...
Charming 2br / 1ba Cottage < 2 Min Walk From Beach on Anna Maria Island Florida
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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, 106 reviews
"Great little cottage with amazing views, warm and welcoming place to stay! Owner was responsive and wonderful to work with, super flexible letting us get a golf cart dropped off before checkin and was great to work with. Great vacation in the beautiful quiet part of AMI!"
Newly Renovated Sea Breeze Cottage with Private Dock, Easy Access to Bimini Bay
Starfish Cottage the largest of a cluster of 3 properties sharing a free form pool
Pool
Starfish Cottage the largest of a cluster of 3 properties sharing a free form pool
9.8 out of 10, Exceptional, 38 reviews
"A great vacation spot !"
Starfish Cottage the largest of a cluster of 3 properties sharing a free form pool
Charming & Vintage Anna Maria Cottage. Easy Walk to Beaches, Stroll Pine Avenue!
Beach nearby, beach towels
Charming & Vintage Anna Maria Cottage. Easy Walk to Beaches, Stroll Pine Avenue!
9.0 out of 10, Wonderful, 6 reviews
"We enjoyed our stay on the property. It was clean and cozy. My only complaint is they had two different papers displayed with the trash pickup days and they were both different days so we ended up missing the trash pickup while we were there."
Charming & Vintage Anna Maria Cottage. Easy Walk to Beaches, Stroll Pine Avenue!
Charming Cottage, FREE Wi-Fi & Trolley, Close to Gulf & Bay Beach, Stroll the...
Beach towels
Charming Cottage, FREE Wi-Fi & Trolley, Close to Gulf & Bay Beach, Stroll the...
9.6 out of 10, Exceptional, 36 reviews
"Everything was clean.and in the kitchen had everything that we need. Great."
Charming Cottage, FREE Wi-Fi & Trolley, Close to Gulf & Bay Beach, Stroll the...
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, 67 reviews
"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
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, 73 reviews
"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
Shell Cottage is a cosy 1 bed cottage sharing a free form pool
Beach nearby
Shell Cottage is a cosy 1 bed cottage sharing a free form pool
9.8 out of 10, Exceptional, 30 reviews
"Shell cottage is a small cozy cabin. My daughter and family stayed at an adjoining cabin, so it was perfect. Very close to the beach, easy to walk back and forth. Pool was very nice and we divided up our time between the beach and pool. I would stay there again."
Shell Cottage is a cosy 1 bed cottage sharing a free form pool
Seahorse Cottage is a spacious 1 bed property sharing a free form pool
A heated pool
Seahorse Cottage is a spacious 1 bed property sharing a free form pool
9.8 out of 10, Exceptional, 46 reviews
"Great location, easy walk to beaches and shops, clean and well-appointed. Would stay here again!"
Seahorse Cottage is a spacious 1 bed property sharing a free form 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!
Cute Old Florida Style Beach Cottage just steps to the Beach!
Beach
Cute Old Florida Style Beach Cottage just steps to the Beach!
10.0 out of 10, Exceptional, 43 reviews
"This was our second visit to this home. Love the old Florida feel. Kitchen fully stocked. Pool was great! Would have like pool temperature a little warmer but not a big deal. Can’t wait to stay again!"
Cute Old Florida Style Beach Cottage just steps to the Beach!
Vibrant Island Home w/ Pool, 1 Block to Beach
Interior
Vibrant Island Home w/ Pool, 1 Block to Beach
3.5 star property
8.0 out of 10, Very good, 1 review
"The perfect location !! We could walk to almost everything it was perfect. There were a few minor things around the house to mention for future use. TVs don’t work correctly although we weren’t there to watch tv. I just like to fall asleep to it at night. Some door knowere lose and the tub handles were missing. Outside of that everything was nice. I couldn’t was the remaining dishes due to no rags or sponges . Sry "
Vibrant Island Home w/ Pool, 1 Block to Beach
Coquina Cottage 2 Bedroom Cottage by RedAwning
Apartment, 2 Bedrooms | Beach
Coquina Cottage 2 Bedroom Cottage by RedAwning
3.5 star property
Coquina Cottage 2 Bedroom Cottage by RedAwning
Sunrise Shore
Cottage, Multiple Beds, Private Pool | Pool
Sunrise Shore
3.5 star property
Sunrise Shore
Going Coastal by SeaBreeze
Outdoor pool
Going Coastal by SeaBreeze
3.0 star property
Going Coastal by SeaBreeze
Don't see what you're looking for?
See all available properties in Anna Maria
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

Beachfront Paradise w/ Totally PRIVATE BEACH ON THE WATERFRONT , Bring your dog
Exterior
Beachfront Paradise w/ Totally PRIVATE BEACH ON THE WATERFRONT , Bring your dog
9.6 out of 10, Exceptional, 160 reviews
"Everything I wanted for a vacay! Nice views nice home and everything we need was there!"
The price is NZ$1,548
per night
21 Jul - 22 Jul
Beachfront Paradise w/ Totally PRIVATE BEACH ON THE WATERFRONT , Bring your dog
Updated, Charming Florida Cottage
View from property
Updated, Charming Florida Cottage
10.0 out of 10, Exceptional, 24 reviews
"It was our first time on Anna Marie Island. The location was great towards most things and the property was perfect/above expectations for us! I think we'll book again next year!!!"
Updated, Charming Florida Cottage
Beautiful Villa, Perfect Small Getaway. Close to beach, beach gear provided!
Beach nearby, sun-loungers, beach towels
Beautiful Villa, Perfect Small Getaway. Close to beach, beach gear provided!
10.0 out of 10, Exceptional, 105 reviews
"This place was great! Super clean and the most perfect location. Thank you!"
Beautiful Villa, Perfect Small Getaway. Close to beach, beach gear provided!
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 Cottages information

Number of reviews
633
Accommodation
21 Cottages
Lowest Price
Highest Price

Recent Reviews in Anna Maria
Expedia verified reviews

Surf's Up | 2 Bed, 2 Bath

Surf's Up | 2 Bed, 2 Bath

5/5 Excellent
Enjoyed every single day!
"Property was very clean, close to the beach. We enjoyed every single day, Thank you so very much… we will definitely be back soon."
A verified traveller stayed at Surf's Up | 2 Bed, 2 Bath
Posted 2 days ago
Surf's Up | 2 Bed, 2 Bath