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Check prices for these dates

In two weeks
12 Sept - 14 Sept
In two months
24 Oct - 26 Oct
In three months
21 Nov - 23 Nov
In four months
19 Dec - 21 Dec

Featured Cottages in Anna Maria Island

Our top choices for Anna Maria Island cottages

Castaway Cottage + Beach + Heated Private Pool & Spa + GOLF CART INCLUDED!
Beach nearby, sun-loungers, beach towels

Castaway Cottage + Beach + Heated Private Pool & Spa + GOLF CART INCLUDED!

10.0 out of 10, Exceptional, (277)
"So many great features at this house in Bean Point including great access to the beach, Pine Street and a pool area that has it all. Thank you Dan and Lori for a wonderful stay!"
Castaway Cottage + Beach + Heated Private Pool & Spa + GOLF CART INCLUDED!
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, (94)
"Great place. Easy access to beach and surrounding amenities. Would recommend. "
Rustic & Cozy Island Original Cottage on the Beach- Bamboo Apts. C2
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, (47)
"Perfect beach cottage for a family! Steps form amazing beaches!! House was clean and super cozy, and had everything you need "
Beach Basket Cottage: Cute Old Florida Style Beach Cottage just steps to the Beach!
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, (283)
"Excellent location. House looks exactly like pics. Very clean and decorated beautifully. Short walk to beach. Restaurants within walking distance overall great location. Quiet area, easy checkin. Everything we needed was supplied in house. Would definitely stay again for a longer trip. "
Charming cottage in quiet area, close to beach & bay.
Romantic, Cute Cottage on Anna Maria Island. Close To Everything. Pet Friendly!
Sun-loungers, beach towels

Romantic, Cute Cottage on Anna Maria Island. Close To Everything. Pet Friendly!

10.0 out of 10, Exceptional, (19)
"We had such a great stay at the Seabreeze Cottage. The space is so nice with everything you need to stay in and cook and feel comfortable. Such an easy walk to the beach, bay and tons of restaurants. We will definitely be coming back! "
Romantic, Cute Cottage on Anna Maria Island. Close To Everything. Pet Friendly!
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 had a good time and enjoyed to live near the beach. Just a few steps in the morning and we could dive into the sea. The apartment was a good size for the four of us. Everything we needed was there or could be found in the stores right around the corner. We also enjoyed the outdoor barbecue place and to sit outside for breakfast and dinner. Just a nice place to recommend."
Charming Ground Level Resort Style 3 unit Condo - unit C
Beautiful Condo on Pine Ave, 2 Blocks to Beach
A heated pool

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!"
Beautiful Condo on Pine Ave, 2 Blocks to Beach
Historic beach cottage with private pool - walk 1 block to beach & free trolley
Beach

Historic beach cottage with private pool - walk 1 block to beach & free trolley

9.0 out of 10, Wonderful, (48)
"Great location next to the beach. Pool area is fantastic."
Historic beach cottage with private pool - walk 1 block to beach & free trolley
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, (136)
"We loved our stay! The location was perfect and made it so easy to enjoy the beautiful beach. The house had everything we needed and the property manager was quick to resolve the minor issue we had. We would be happy to return!"
Tropical Paradise On The Beach Permit VRC17-000168
Anna Maria Cottage with Golf Cart
Terrace/patio

Anna Maria Cottage with Golf Cart

10.0 out of 10, Exceptional, (12)
"This cottage was the perfect anniversary getaway. Centrally located and easy to visit the beaches and explore the island on the provided golfcart"
Anna Maria Cottage with Golf Cart
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, (120)
"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
Cozy Cottage Retreat at Tradewind Resort #32 in Bradenton Beach
Sun-loungers, beach towels

Cozy Cottage Retreat at Tradewind Resort #32 in Bradenton Beach

9.0 out of 10, Wonderful, (9)
"Great location. Very clean and well maintained. I would come back "
Cozy Cottage Retreat at Tradewind Resort #32 in Bradenton Beach
Blue Isle Oasis: Adorable, updated 2 bedroom cottage
Outdoor dining

Blue Isle Oasis: Adorable, updated 2 bedroom cottage

9.0 out of 10, Wonderful, (2)
"Nicely renovated interior and exterior. "
Blue Isle Oasis: Adorable, updated 2 bedroom cottage
Seahorse Cottage - sleeps 2 guests in 1 bedroom
Beach nearby

Seahorse Cottage - sleeps 2 guests in 1 bedroom

9.8 out of 10, Exceptional, (51)
"Enjoyed our time and will be back!"
Seahorse Cottage - sleeps 2 guests in 1 bedroom
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, (76)
"Great Location, super clean, great pricing, and Owners were always available.Great time!!"
Charming 2br / 1ba Cottage < 2 Min Walk From Beach on Anna Maria Island Florida
Romantic Island Getaway Just Steps from the Beach
TV

Romantic Island Getaway Just Steps from the Beach

2.0 star property
8.8 out of 10, Excellent, (3)
"It was great! Check in was super easy and anything you would need is nearby. "
Romantic Island Getaway Just Steps from the Beach
Starfish Cottage - sleeps 4 guests in 2 bedrooms
Beach nearby

Starfish Cottage - sleeps 4 guests in 2 bedrooms

9.8 out of 10, Exceptional, (45)
"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
Ocean72, 2-bedroom cottage in Holmes Beach with Pool and Spa
Microwave, oven, stovetop, dishwasher

Ocean72, 2-bedroom cottage in Holmes Beach with Pool and Spa

10.0 out of 10, Exceptional, (1)
"This place was really good. The unit was clean and perfect for a family of four. The pool was in need of cleaning, but Jennifer was on it and had it cleaned and shocked the next morning. The jacuzzi was a smash hit. The home has all you need to be comfortable. Beds were on point and linens and towels were fresh. The TV (Roku live) was a little difficult to find stations, but we figured it out quickly. It was nice to find other guests leave behind some kitchen and cooking supplies for the next...
Ocean72, 2-bedroom cottage in Holmes Beach with Pool and Spa
Quiet Nights of Quiet Stars on Anna Maria Island
On the beach, sun-loungers, beach umbrellas, beach towels

Quiet Nights of Quiet Stars on Anna Maria Island

10.0 out of 10, Exceptional, (68)
"Our family of 4 absolutely loved our stay! The house is as described and has everything you need. Kitchen is well stocked, and the beds were very comfortable. No beach chairs since Helene, but we honestly didn't need them because we spent all of our time in the beautiful water! Beach access was very easy and we never had trouble finding somewhere to park. PSA : Rent a golf cart! We had a wonderful week at Quiet Nights of Quiet Stars and are already planning our next visit. Hopefully sooner...
Quiet Nights of Quiet Stars on Anna Maria Island
Beach Cottage! Beautiful Pool/Spa, Steps to sand, Fun Golf Cart.
A heated pool

Beach Cottage! Beautiful Pool/Spa, Steps to sand, Fun Golf Cart.

10.0 out of 10, Exceptional, (7)
"Wonderful property. Easy check in and out. Pool and location are perfect. Highly recommend!! "
Beach Cottage! Beautiful Pool/Spa, Steps to sand, Fun Golf Cart.
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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Top Anna Maria Island Hotel Reviews

Find out more about Anna Maria Island

Find out more about Anna Maria Island

Anna Maria Island Cottages information

Number of reviews
449
Accommodation
65 Cottages
Lowest Price
Highest Price

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