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Featured 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!"
The price is AU$702
includes taxes & fees
19 Oct - 20 Oct
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 AU$782
includes taxes & fees
16 Oct - 17 Oct
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 AU$579
includes taxes & fees
15 Oct - 16 Oct
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 AU$710
includes taxes & fees
15 Oct - 16 Oct
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 AU$408
includes taxes & fees
16 Oct - 17 Oct
The Inn On Siesta Key
The "Grouper"
9.2 out of 10, Wonderful, (40)
"Great location."
The price is AU$330
includes taxes & fees
26 Oct - 27 Oct
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 AU$379
includes taxes & fees
15 Oct - 16 Oct
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 AU$484
includes taxes & fees
19 Oct - 20 Oct
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 AU$414
includes taxes & fees
12 Nov - 13 Nov
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 AU$642
includes taxes & fees
15 Oct - 16 Oct
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 AU$467
includes taxes & fees
27 Oct - 28 Oct
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 AU$341
includes taxes & fees
19 Oct - 20 Oct
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 AU$469
includes taxes & fees
20 Oct - 21 Oct
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 AU$567
includes taxes & fees
15 Oct - 16 Oct
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!"
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 AU$572
includes taxes & fees
16 Oct - 17 Oct
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 AU$634
includes taxes & fees
21 Oct - 22 Oct
Steps 2 Beach-Island Cottage w/king bd+2bike+parking
5 star Guest House heated pool on the water!
The price is AU$790
includes taxes & fees
15 Oct - 16 Oct
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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