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Browse Select Anna Maria Island Cottages

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

10.0 out of 10, Exceptional, (275)
"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

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

Anna Maria Cottage with Golf Cart

10.0 out of 10, Exceptional, (11)
"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

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

9.8 out of 10, Exceptional, (282)
"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.

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

9.6 out of 10, Exceptional, (23)
"Great location nicely decorated and clean"
Cozy Holmes Beach Cottage - 3/2 - 1 block from beach!

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

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

9.8 out of 10, Exceptional, (30)
"My husband and I loved this place. It was private and we had a blast. It was close to the beach. "
Perfect location, cute cottage, 2 min walk to beach, 2bd/2ba home w/private pool

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

10.0 out of 10, Exceptional, (88)
"Enjoyed our stay"
Vintage Island Cottage on the Beach- Sunset Views - Bamboo Apts. C1

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

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!"
The price is £523
includes taxes & fees
25 Aug - 26 Aug
Beautiful Condo on Pine Ave, 2 Blocks to 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

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

9.6 out of 10, Exceptional, (80)
"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

Cozy Cottage Retreat at Tradewind Resort #32 in Bradenton Beach

9.0 out of 10, Wonderful, (8)
"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

9.0 out of 10, Wonderful, (2)
"Nicely renovated interior and exterior. "
Blue Isle Oasis: Adorable, updated 2 bedroom cottage

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

9.8 out of 10, Exceptional, (76)
"My granddaughters thought the cottage was charming, and enjoyed staying there."
Charming 2br / 1ba Cottage < 2 Min Walk From Beach on Anna Maria Island Florida

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

Adorable Cottage with Covered Balconies and Private Pool

9.6 out of 10, Exceptional, (39)
"This property definitely did not disappoint! Fantastic location that’s close to both the beach and the pier. Shops and food are all within walking distance. The backyard was a hit. The pool and putting green were a fun addition to the large backyard space. Great communication from the hosts who made sure our check in process went well and called to make sure everything was going well and to let them know if we needed anything. Would definitely stay at this space again. "
Adorable Cottage with Covered Balconies and Private Pool

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!

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

Charming Ground Level Resort Style 3unit condo unit B a few steps from the beach

10.0 out of 10, Exceptional, (16)
"Very pleased with remodel and condition of the property. Love coming down to Anna Maria Island and staying here"
Charming Ground Level Resort Style 3unit condo unit B a few steps from the beach
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