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Cottages in Anna Maria Island

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
Adorable Cottage with Covered Balconies and Private Pool
9.6 out of 10, Exceptional, (39)
"Amazing cottage with plenty of amenities and a fantastic location. Just a few minutes walk to the beach, shopping and restaurants. Check-in and check-out were a breeze. The only hiccup was issues with parking. Often the single reserved space below was taken by restaurant clients."
The price is ¥32,203
¥75,756 total
includes taxes & fees
Oct 16 - Oct 17
Adorable Cottage with Covered Balconies and Private Pool
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. "
The price is ¥24,493
¥56,449 total
includes taxes & fees
Oct 14 - Oct 15
Romantic Island Getaway! Just Steps from the Beach
Beautiful Guest House Near the Beach with Private Pool!
8.6 out of 10, Excellent, (29)
"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!!"
The price is ¥29,228
¥68,814 total
includes taxes & fees
Oct 15 - Oct 16
Beautiful Guest House Near the Beach with Private Pool!
The Inn On Siesta Key
3.5 star property
10.0 out of 10, Exceptional, (184)
"clean and close proximity to beach and restaurants"
The price is ¥23,113
¥34,489 total
includes taxes & fees
Oct 14 - Oct 15
The Inn On Siesta Key
The "Grouper"
9.2 out of 10, Wonderful, (40)
"Great location."
The price is ¥14,968
¥32,048 total
includes taxes & fees
Oct 14 - Oct 15
The "Grouper"
7mi to Anna Maria Newly Renovated Private Cottage
10.0 out of 10, Exceptional, (2)
"I stayed for 9 days. It was in a great location in Bradenton...just minutes from the beach, shopping and dining. It was clean and quiet. I would stay there again."
The price is ¥9,525
¥36,260 total
includes taxes & fees
Oct 14 - Oct 15
7mi to Anna Maria Newly Renovated Private Cottage
Siesta Key Sanctuary -Pool-Kayaks-TikiHut-King bed
9.2 out of 10, Wonderful, (5)
"We really enjoyed the cleanliness and location. Pool was great. Having our own deck was nice. Great views. Highly recommend. "
The price is ¥18,899
¥46,869 total
includes taxes & fees
Oct 19 - Oct 20
Siesta Key Sanctuary -Pool-Kayaks-TikiHut-King bed
Steps to Beach+bikes VaCay getaway on PaG island
10.0 out of 10, Exceptional, (15)
"cute little home in a darling old style florida village. a block from the beach and great sunsets. Lisa was a good communicator and everything went smoothly."
The price is ¥19,957
¥40,997 total
includes taxes & fees
Oct 22 - Oct 23
Steps to Beach+bikes VaCay getaway on PaG island
Siesta Key Beachside Getaway Cottage Walking Distance to Beach and Village
9.2 out of 10, Wonderful, (175)
"my friends and I traveled from across the country to meet for our annual “girls” trip. Location is amazing. You can walk to the beach, you can rent cabanas and there are lounge chairs for your use. The pool is sparkling and the trolley stop is right outside the property entrance. I just love Siesta key and this is a wonderful place to get away from it all, but have easy access to all of the fun and shopping. "
The price is ¥25,249
¥62,216 total
includes taxes & fees
Oct 15 - Oct 16
Siesta Key Beachside Getaway Cottage Walking Distance to Beach and Village
Drift Inn A, Heated Pool, Beach and Amenities, 2-3 min walk.
9.6 out of 10, Exceptional, (78)
"Its right next to everything we needed"
The price is ¥14,968
¥45,519 total
includes taxes & fees
Oct 23 - Oct 24
Drift Inn A, Heated Pool, Beach and Amenities, 2-3 min walk.
Florida Charm Minifarm🐓 HotTub-POOL-Chickens! Near I75, I275. Pets, trailers OK
The price is ¥12,095
¥33,375 total
includes taxes & fees
Oct 22 - Oct 23
Florida Charm Minifarm🐓 HotTub-POOL-Chickens! Near I75, I275. Pets, trailers OK
Sunny PaG Island rental w/bikes-just steps2beach
9.0 out of 10, Wonderful, (18)
"Short walk to the beach and well-kept property. Very neat area."
The price is ¥19,050
¥39,669 total
includes taxes & fees
Oct 20 - Oct 21
Sunny PaG Island rental w/bikes-just steps2beach
Cozy 2BR Cottage Steps2 Pier, Vinoy, Beach Dr+Bikes
10.0 out of 10, Exceptional, (4)
"The location is great. in a few minutes you are in North Shore Park walking along Tampa Bay. The cottage was clean and cozy. We just might rent it again next time we visit family in the area."
The price is ¥22,679
¥54,807 total
includes taxes & fees
Oct 14 - Oct 15
Cozy 2BR Cottage Steps2 Pier, Vinoy, Beach Dr+Bikes
Nook Cottage Across street from beach and Heated Pool
10.0 out of 10, Exceptional, (4)
"They have really thought of everything and gone above and beyond to make our stay as comfortable as possible. Everything was very clean! Paige was a wonderful guide and host for the local area!"
The price is ¥36,449
¥71,713 total
includes taxes & fees
Oct 16 - Oct 17
Nook Cottage Across street from beach and Heated Pool
Cabana Cottage Across street from Beach and Heated Pool
10.0 out of 10, Exceptional, (5)
"This was our first time in Siesta Key. We found the location of the Inn to be perfect. Within walking distance to the Village with all the shops and restaurants plus right across the street from the beach access. Plus the free trolley stop is right across the street. The staff was super friendly and very accommodating. They really go above and beyond to make you feel welcome. The cottage was very clean and had everything we needed for our stay and more! The decor and feel of the cottage was the...
The price is ¥43,670
¥63,287 total
includes taxes & fees
Oct 16 - Oct 17
Cabana Cottage Across street from Beach and Heated Pool
Steps 2 Beach-Island Cottage w/king bd+2bike+parking
9.8 out of 10, Exceptional, (40)
"Quiet neighborhood away from the tourist areas. 50 steps to a beautiful white sandy beach:) charming little place, very clean and comfortable. sunsets were beautiful and almost no rain all week:)"
The price is ¥25,763
¥52,697 total
includes taxes & fees
Oct 21 - Oct 22
Steps 2 Beach-Island Cottage w/king bd+2bike+parking
5 star Guest House heated pool on the water!
The price is ¥37,798
¥76,956 total
includes taxes & fees
Oct 14 - Oct 15
5 star Guest House heated pool on the water!
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

What are the best cottages in Anna Maria Island?
There are multiple cottages in Anna Maria Island with a total average guest review rating of , so you're sure to snag a place that suits your style. Planning to stay in Bradenton Beach? Queen's Gate Resort is one property favored by travelers. This 2.5-star cottage includes amenities such as a swimming pool and a garden. 105b 12th Street South Front 2 Bedroom Apts By Redawning is another highly rated escape where you'll be close to nature. A barbecue grill and a swimming pool are two of the conveniences waiting for you at this 3-star pick in Bradenton Beach.
What are the best cheap cottages in Anna Maria Island?
With cottages starting at only per night, you can afford an extra couple of nights in Anna Maria Island for outdoor fun. If Bradenton Beach is on your travel radar, book a room at Queen's Gate Resort. A garden and a swimming pool help make this option an excellent choice. You'll also find inexpensive cottages in Holmes Beach. Take deep, calming breaths in nature during your stay at Queen's Gate Resort and take advantage of conveniences like pool sun loungers and a garden. If you're exploring Anna Maria Island and want to save money, there are many fabulous free attractions to put on your itinerary. Anna Maria Beach and Coquina Beach are always popular with visitors. This price was 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.
Are there any family-friendly cottages in Anna Maria Island?
There are indeed. Whether it's in one of Anna Maria Island's busy cities or way out in nature, the cozy charm of a cottage is perfect for vacationing families. If Bradenton Beach is on your radar, book a stay at Queen's Gate Resort. This 2.5-star option offers a nearby beach and a barbecue grill. Another superb choice is 105b 12th Street South Front 2 Bedroom Apts By Redawning. Also in Bradenton Beach, this family-friendly cottage has a 3-star rating and includes WiFi and a barbecue grill. You'll find plenty of awesome things to do with the family in Bradenton Beach. Anna Maria Beach and Coquina Beach promise a fantastic day out.
Why book your cottage in Anna Maria Island with Expedia?
Reserving a cottage in Anna Maria Island is as simple as entering your travel dates and choosing an ideal place for a getaway in nature. From ritzy retreats to affordable properties and cottages that feature amenities like a kitchenette, Expedia has something for all traveler styles. As for the best offers around? We've got them as well!
How can I find cheap cottages in Anna Maria Island?
With Expedia's helpful filter tool, sourcing cheap cottages in Anna Maria Island has never been simpler. To discover accommodations that'll make your hip pocket happy, tailor your search results by budget, amenities and star rating.

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