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Our top choices for Anna Maria Island cottages

Romantic Island Getaway! Just Steps from the Beach

Romantic Island Getaway! Just Steps from the Beach
2.0 star property
Bradenton Beach
8.8 out of 10, Excellent, (3 reviews)
"It was great! Check in was super easy and anything you would need is nearby. "
United States
Thomas N.
The price is AU$818
includes taxes & fees
19 Jan - 20 Jan
Romantic Island Getaway! Just Steps from the Beach

Adorable Cottage with Covered Balconies and Private Pool

Adorable Cottage with Covered Balconies and Private Pool
Anna Maria
9.6 out of 10, Exceptional, (41 reviews)
"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."
United States
C. S.
The price is AU$1,181
includes taxes & fees
22 Jan - 23 Jan
Adorable Cottage with Covered Balconies and Private Pool

Beautiful Condo on Pine Ave, 2 Blocks to Beach

Beautiful Condo on Pine Ave, 2 Blocks to Beach
Anna Maria
8.8 out of 10, Excellent, (25 reviews)
"Great location, clean, and spacious. Pool didn’t work fir a couple of days but they got it fixed the day before we left "
United States
Paris K.
The price is AU$1,109
includes taxes & fees
20 Jan - 21 Jan
Beautiful Condo on Pine Ave, 2 Blocks to Beach

Beautiful Guest House Near the Beach with Private Pool!

Beautiful Guest House Near the Beach with Private Pool!
Anna Maria
8.8 out of 10, Excellent, (32 reviews)
"Beautiful home perfectly located near the beach, bars and restaurants. "
United States
Bibiana G.
The price is AU$1,118
includes taxes & fees
20 Jan - 21 Jan
Beautiful Guest House Near the Beach with Private Pool!

SunSalt Cottage~5 min to Beach, Shops & Restaurants~PrivatePool

SunSalt Cottage~5 min to Beach, Shops & Restaurants~PrivatePool
Anna Maria
10.0 out of 10, Exceptional, (1 review)
"Absolutely lovely place to stay. The four of us were SO comfortable. The place was clean and beautiful. Very well maintained. You can tell by the high quality finishes that this is someone’s home and they maintain it as such. There was an unforeseen circumstance that popped up with the island doing some work that affected the house while we were there. I messaged the owner and within minutes he had replied and had all the necessary people on the way to fix it. They fixed it all while we were at...
United States
Devon F.
SunSalt Cottage~5 min to Beach, Shops & Restaurants~PrivatePool

The Inn On Siesta Key

The Inn On Siesta Key
3.5 star property
Siesta Key
10.0 out of 10, Exceptional, (193 reviews)
"Great place to stay! "
United States
Carlos
The price is AU$527
includes taxes & fees
21 Jan - 22 Jan
The Inn On Siesta Key

Escape near Siesta Key with Hot Tub, BBQ, and Fire pit

Escape near Siesta Key with Hot Tub, BBQ, and Fire pit
2.0 star property
Sarasota
10.0 out of 10, Exceptional, (1 review)
"Perfect vacation get away. Host are very good to work with. Everything was exactly as we wanted it! "
United States
Kara F.
The price is AU$512
includes taxes & fees
19 Jan - 20 Jan
Escape near Siesta Key with Hot Tub, BBQ, and Fire pit

The "Grouper"

The "Grouper"
Sunny Shores
9.4 out of 10, Exceptional, (45 reviews)
"We really enjoyed our stay here. So close to AMI "
United States
Taylor B.
The price is AU$322
includes taxes & fees
7 Feb - 8 Feb
The "Grouper"

3 Mi to Downtown Bradenton: Family Home w/ Yard!

3 Mi to Downtown Bradenton: Family Home w/ Yard!
3.0 star property
Bradenton
The price is AU$722
includes taxes & fees
8 Feb - 9 Feb
3 Mi to Downtown Bradenton: Family Home w/ Yard!

Tropical Treehouse · Siesta Key Sanctuary -Pool-Kayaks-TikiHut-King bed

Tropical Treehouse · Siesta Key Sanctuary -Pool-Kayaks-TikiHut-King bed
Siesta Key
9.2 out of 10, Wonderful, (5 reviews)
"We really enjoyed the cleanliness and location. Pool was great. Having our own deck was nice. Great views. Highly recommend. "
United States
Rolly N.
The price is AU$485
includes taxes & fees
19 Jan - 20 Jan
Tropical Treehouse · Siesta Key Sanctuary -Pool-Kayaks-TikiHut-King bed

7mi to Anna Maria Newly Renovated Private Cottage

7mi to Anna Maria Newly Renovated Private Cottage
Bradenton
10.0 out of 10, Exceptional, (3 reviews)
"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."
United States
MO L.
The price is AU$418
includes taxes & fees
26 Jan - 27 Jan
7mi to Anna Maria Newly Renovated Private Cottage

Drift Inn A, Heated Pool, Beach and Amenities, 2-3 min walk.

Drift Inn A, Heated Pool, Beach and Amenities, 2-3 min walk.
South Village
9.6 out of 10, Exceptional, (82 reviews)
"Great condo. The location is perfect. The pool was the best. Will stay here again."
United States
Jeanne J.
The price is AU$457
includes taxes & fees
11 Feb - 12 Feb
Drift Inn A, Heated Pool, Beach and Amenities, 2-3 min walk.

1-bedroom cottage in a park like setting! Close to Spring Training and Beaches.

1-bedroom cottage in a park like setting! Close to Spring Training and Beaches.
2.0 star property
Bayou Oaks
The price is AU$163
includes taxes & fees
1 Feb - 2 Feb
1-bedroom cottage in a park like setting! Close to Spring Training and Beaches.

St Pete/gulfport Tiny little small home

St Pete/gulfport Tiny little small home
St. Petersburg
10.0 out of 10, Exceptional, (3 reviews)
"The house was decorated nicely, it was clean, and inside/outside was well kept. The hosts were lovely and responded quickly to questions with precise information. If I need a place to stay in Gulfport again, I would not hesitate to stay!"
United States
Karen J.
The price is AU$600
includes taxes & fees
18 Jan - 19 Jan
St Pete/gulfport Tiny little small home

Siesta Key Beachside Getaway Cottage Walking Distance to Beach and Village

Siesta Key Beachside Getaway Cottage Walking Distance to Beach and Village
Sarasota
9.2 out of 10, Wonderful, (177 reviews)
"Wonderful property with an excellent location! Beach access was across the street and the trolley pick-up was at the end of the block. The village was within walking distance as well. The property was very clean and the beds were comfortable. The washer and dryer is located right outside of the unit and beach chairs and a cooler were provided. We look forward to booking this property again in the future! "
United States
Alison B.
The price is AU$671
includes taxes & fees
19 Jan - 20 Jan
Siesta Key Beachside Getaway Cottage Walking Distance to Beach and Village

Sunny PaG Island rental w/bikes-just steps2beach

Sunny PaG Island rental w/bikes-just steps2beach
Pass-a-Grille
9.0 out of 10, Wonderful, (18 reviews)
"Short walk to the beach and well-kept property. Very neat area."
United States
Emily M.
The price is AU$589
includes taxes & fees
2 Feb - 3 Feb
Sunny PaG Island rental w/bikes-just steps2beach

Nook Cottage Across street from beach and Heated Pool

Nook Cottage Across street from beach and Heated Pool
Siesta Key
10.0 out of 10, Exceptional, (4 reviews)
"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!"
United States
Derek N.
The price is AU$994
includes taxes & fees
18 Jan - 19 Jan
Nook Cottage Across street from beach and Heated Pool

Steps 2 Beach-Island Cottage w/king bd+2bike+parking

Steps 2 Beach-Island Cottage w/king bd+2bike+parking
Pass-a-Grille
9.8 out of 10, Exceptional, (42 reviews)
"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:)"
United States
James C.
Steps 2 Beach-Island Cottage w/king bd+2bike+parking

Cozy 2BR Cottage Steps2 Pier, Vinoy, Beach Dr+Bikes

Cozy 2BR Cottage Steps2 Pier, Vinoy, Beach Dr+Bikes
Historic Old Northeast
10.0 out of 10, Exceptional, (4 reviews)
"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."
United States
Cynthia S.
The price is AU$676
includes taxes & fees
19 Jan - 20 Jan
Cozy 2BR Cottage Steps2 Pier, Vinoy, Beach Dr+Bikes
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

Anna Maria Island Cottages information

Number of reviews
535
Accommodation
0 Cottages
Lowest Price
AU$322
Highest Price
AU$1,181

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