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Check prices for these dates

In two weeks
5 Sept - 7 Sept
In two months
17 Oct - 19 Oct
In three months
14 Nov - 16 Nov
In four months
12 Dec - 14 Dec

Featured Cottages in Anna Maria and around

Our top choices for Anna Maria 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, (276)
"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!
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, (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.
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!"
The price is €400
includes taxes & fees
25 Aug - 26 Aug
Beautiful Condo on Pine Ave, 2 Blocks to Beach
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, (119)
"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
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)
"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
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
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
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)
"The space directly above the local taco and donut shops was exactly as advertised! Clean, quaint, and perfect for our family of 5 that took full advantage of the private pool and 1 block walk to the beach. Can't wait to come back!!"
Beautiful Guest House Near the Beach with Private Pool!
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, (197)
"The location was good on the island, and just a short walk to multiple beaches. Check in was easy, and communication with the host was good. We enjoyed our stay!"
The Ballyhoo on Bean Point, 200 feet to a beautiful bayside beach and views!
Shell Cottage - sleeps 2
Beach nearby

Shell Cottage - sleeps 2

9.6 out of 10, Exceptional, (38)
"We could not ask for any better of a vacation"
Shell Cottage - sleeps 2
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, (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
Historical AMI 2 Bedroom, pet friendly beach cottage, sleeps 6
Beach nearby

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

8.6 out of 10, Excellent, (9)
"Rating Details: The property manager was very helpful. The vacation rental was very clean. I was very happy with the location. I was very satisfied with the condition of the vacation rental. Overall, I recommend this vacation rental. Reviewer Comments: The cottage is cozy and the location is everything. Walk to beach, walk to coffe, dinner, shops, and ice cream. Loved the back patio with lots of beach gear and easy place to park out bikes. Great value!"
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, (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
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, (75)
"this cottage was just amazing . location to beach and restaurants was exceptional. we had such an amazing time. quiet area . pool was great . walk to the Beach short . we really did not want to leave.. I could live there. thank you so much for an amazing vacation. hope to return again to same cottage."
Old Florida-style cottage w/ private heated pool - walk to the beach - dogs OK
Cozy Pine Ave Cottage Near Beach and Pier
Fridge, microwave, oven, stovetop

Cozy Pine Ave Cottage Near Beach and Pier

9.4 out of 10, Exceptional, (22)
"Great Location, very nice place, well stocked with supplies/etc. Will be going back and would highly recommend."
Cozy Pine Ave Cottage Near Beach and Pier
Canal-front Gem w/ Pool & Hot Tub in Anna Maria
House (2 Bedrooms) | Interior

Canal-front Gem w/ Pool & Hot Tub in Anna Maria

3.0 star property
Canal-front Gem w/ Pool & Hot Tub in Anna Maria
Serenity Cottage
Pool

Serenity Cottage

2.0 star property
Serenity Cottage
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
Sunrise Shore
Outdoor pool

Sunrise Shore

3.5 star property
Sunrise Shore
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 Hotel Reviews

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

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

10/10 Excellent
"Really great hosts and lovely cottage. As a family of four we could not have asked for more. Thank you"
Nick J. 3-night trip
Posted 3 days ago
Castaway Cottage + Beach + Heated Private Pool & Spa + GOLF CART INCLUDED!

Frequently asked questions

How much do cottages in Anna Maria cost?
Cottages in Anna Maria range between €400 and €400 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?
There are multiple cottages in Anna Maria with a total average guest review rating of 9.4. Queen's Gate Resort is a superb place to rest and unwind between adventures. This 2.5-star cottage also features a garden and pool sun loungers. 105b 12th Street South Front 2 Bedroom Apts By Redawning is another popular pick with travellers in this area. It has a 3-star rating and amenities including a barbecue grill and a swimming pool.
How many cottages are there in Anna Maria?
You can choose from 23 cottages in Anna Maria. No matter if you're travelling with the family or planning a retreat with close friends, Expedia will help you find the perfect property to enjoy nature's beauty.