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Our top choices for Anna Maria Island cottages

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, (37 reviews)
"Everything was fantastic!"
United States
Kevin O.
The price is AU$1,201
includes taxes & fees
14 May - 15 May
Beautiful Guest House Near the Beach with Private Pool!

Newly Renovated Sea Breeze Cottage with Private Dock, Easy Access to Bimini Bay

Newly Renovated Sea Breeze Cottage with Private Dock, Easy Access to Bimini Bay
Anna Maria
9.6 out of 10, Exceptional, (125 reviews)
"Was very enjoyable! Great place for our family to stay and visit!"
United States
john V.
The price is AU$910
includes taxes & fees
3 May - 4 May
Newly Renovated Sea Breeze Cottage with Private Dock, Easy Access to Bimini Bay

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, (26 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$1,399
includes taxes & fees
16 May - 17 May
Beautiful Condo on Pine Ave, 2 Blocks to 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, (45 reviews)
"Everything was wonderful. We would love to stay there again. Great location, lots of room, and very comfy beds. "
United States
Jennifer B.
The price is AU$1,388
includes taxes & fees
1 May - 2 May
Adorable Cottage with Covered Balconies and Private Pool

Coastal Luxury 7mi to Anna Maria Private Cottage

Coastal Luxury 7mi to Anna Maria Private Cottage
Bradenton
10.0 out of 10, Exceptional, (7 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$395
includes taxes & fees
4 May - 5 May
Coastal Luxury 7mi to Anna Maria Private Cottage

The "Grouper"

The "Grouper"
Sunny Shores
9.4 out of 10, Exceptional, (65 reviews)
"I would recommend this place to anyone! It was extremely clean and neat, and we had a lovely time here! The host was very responsive and kind too. Overall, this place was above my expectations and a great place to stay."
United States
Lana
The price is AU$297
includes taxes & fees
19 May - 20 May
The "Grouper"

Florida Charm Minifarm🐓 HotTub-POOL-Chickens! Near I75, I275. Pets, trailers OK

Florida Charm Minifarm🐓 HotTub-POOL-Chickens! Near I75, I275. Pets, trailers OK
Palmetto
10.0 out of 10, Exceptional, (2 reviews)
"The accommodations were very comfortable and clean. Quiet neighborhood. Host was extremely helpful and pleasant. The screened porch off of the kitchen was a great place to relax with the dogs. We didn't get an opportunity to enjoy the pool and hot tub because of our other obligations but definitely will plan on staying again the next time I need to visit the area. It was like a home away from home."
United States
Douglas T.
The price is AU$342
includes taxes & fees
19 May - 20 May
Florida Charm Minifarm🐓 HotTub-POOL-Chickens! Near I75, I275. Pets, trailers OK

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

Escape near Siesta Key with Hot Tub, BBQ, and Fire pit
Sarasota
7.8 out of 10, Good, (7 reviews)
"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$481
includes taxes & fees
23 May - 24 May
Escape near Siesta Key with Hot Tub, BBQ, and Fire pit

Private historical completely renovated cottage with 60 ft dock on Sarasota Bay

Private historical completely renovated cottage with 60 ft dock on Sarasota Bay
cortez
10.0 out of 10, Exceptional, (104 reviews)
"The host was always available! The cottage is adorable and homey. Wonderful location and had everything you need for a fun experience."
United States
Janice C.
The price is AU$434
includes taxes & fees
18 May - 19 May
Private historical completely renovated cottage with 60 ft dock on Sarasota Bay

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

Tropical Treehouse · Siesta Key Sanctuary -Pool-Kayaks-TikiHut-King bed
Siesta Key
9.6 out of 10, Exceptional, (8 reviews)
"The most well maintained property I've ever stayed."
United States
Russ H.
The price is AU$512
includes taxes & fees
19 May - 20 May
Tropical Treehouse · Siesta Key Sanctuary -Pool-Kayaks-TikiHut-King bed

4 Mi to Dtwn St Pete! Pet-friendly Home w/ Yard

4 Mi to Dtwn St Pete! Pet-friendly Home w/ Yard
3.0 star property
St. Petersburg
The price is AU$762
includes taxes & fees
3 May - 4 May
4 Mi to Dtwn St Pete! Pet-friendly Home w/ Yard

St Pete/gulfport Tiny little small home

St Pete/gulfport Tiny little small home
St. Petersburg
10.0 out of 10, Exceptional, (4 reviews)
"Really nice place to stay and host communication was excellent "
United States
Susan D.
The price is AU$507
includes taxes & fees
13 May - 14 May
St Pete/gulfport Tiny little small home

Pass-a-Grille Beach Getaway| Walkable| Bikes +Gear

Pass-a-Grille Beach Getaway| Walkable| Bikes +Gear
Pass-a-Grille
10.0 out of 10, Exceptional, (23 reviews)
"Super cute location and unit! Close parking and within walking distance to restaurants (dinner, lunch, breakfast) and soooo close to the beach! "
United States
Shaunte W.
The price is AU$508
includes taxes & fees
4 May - 5 May
Pass-a-Grille Beach Getaway| Walkable| Bikes +Gear

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, (182 reviews)
"Right across the beach Less then 5 minutes Good space - rooms nice ad clean "
United States
ASHISH
Siesta Key Beachside Getaway Cottage Walking Distance to Beach and Village

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, (87 reviews)
"Great stay - flexible early check-in!"
United States
Jill P.
The price is AU$426
includes taxes & fees
20 May - 21 May
Drift Inn A, Heated Pool, Beach and Amenities, 2-3 min walk.

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, (20 reviews)
"Short walk to the beach and well-kept property. Very neat area."
United States
Emily M.
The price is AU$469
includes taxes & fees
1 May - 2 May
Sunny PaG Island rental w/bikes-just steps2beach

Downtown Cottage | Walk Everywhere, Park once

Downtown Cottage | Walk Everywhere, Park once
Historic Old Northeast
10.0 out of 10, Exceptional, (8 reviews)
"Host was wonderful and very communicative. Location of property was great."
United States
David B.
The price is AU$576
includes taxes & fees
5 May - 6 May
Downtown Cottage | Walk Everywhere, Park once

New Listing Sunset Tropical Beach Bungallow

New Listing Sunset Tropical Beach Bungallow
Sunset Beach
9.8 out of 10, Exceptional, (38 reviews)
"Great location! We'll definitely book again!"
United States
Carolyn J.
The price is AU$551
includes taxes & fees
28 May - 29 May
New Listing Sunset Tropical Beach Bungallow

Lido Key Getaway - Bikes & Beach Gear

Lido Key Getaway - Bikes & Beach Gear
Lido Key
The price is AU$601
includes taxes & fees
20 May - 21 May
Lido Key Getaway - Bikes & Beach Gear

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$1,212
includes taxes & fees
11 May - 12 May
Nook Cottage Across street from beach and Heated Pool
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
754
Accommodation
59 Cottages
Lowest Price
AU$297
Highest Price
AU$1,388

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