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Check prices for these dates

Next weekend
15 Aug - 17 Aug
In two weeks
22 Aug - 24 Aug
In one month
5 Sept - 7 Sept
In two months
3 Oct - 5 Oct

Featured Cottages in Joe Island

Castaway Cottage + Beach + Heated Private Pool & Spa + GOLF CART INCLUDED!
Guests can enjoy a wide, sandy beach with ocean views and a scenic backdrop of trees and shrubs.

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

10.0 out of 10, Exceptional, (274)
"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!
Rustic & Cozy Island Original Cottage on the Beach- Bamboo Apts. C2
Relax in the shaded outdoor seating area, complete with barbecue grills and a scenic view.

Rustic & Cozy Island Original Cottage on the Beach- Bamboo Apts. C2

9.8 out of 10, Exceptional, (94)
"Great place. Easy access to beach and surrounding amenities. Would recommend. "
Rustic & Cozy Island Original Cottage on the Beach- Bamboo Apts. C2
Anna Maria Cottage with Golf Cart
Relax in a serene patio area with a light-colored sofa, small table, and lush greenery.

Anna Maria Cottage with Golf Cart

10.0 out of 10, Exceptional, (11)
"This cottage was the perfect anniversary getaway. Centrally located and easy to visit the beaches and explore the island on the provided golfcart"
Anna Maria Cottage with Golf Cart
Big Roomy Beach Cottage: 4 bd/3 ba -2,000 sq ft; 100 ft to beach path; priv pool
Guests can enjoy a serene beach scene with ocean views and a clear horizon.

Big Roomy Beach Cottage: 4 bd/3 ba -2,000 sq ft; 100 ft to beach path; priv pool

10.0 out of 10, Exceptional, (125)
"We had an awesome vacation! The house beach and pool were outstanding. Hope to return next year!!"
Big Roomy Beach Cottage: 4 bd/3 ba -2,000 sq ft; 100 ft to beach path; priv pool
The Cottage by Anna Maria Island
Enjoy a leisurely stroll along the beach, with easy access to the ocean and surrounding community.

The Cottage by Anna Maria Island

9.8 out of 10, Exceptional, (12)
"Great host ,nice property. We had a problem with the shower, but the host had it fixed almost immediately. Would definitely stay here again."
The Cottage by Anna Maria Island
Perfect Cottage In Art District of Gulfport
Enjoy cooking in this well-equipped kitchen with a central island, oven, microwave, and refrigerator.

Perfect Cottage In Art District of Gulfport

9.6 out of 10, Exceptional, (94)
"Very Clean and plenty of room for 2."
Perfect Cottage In Art District of Gulfport
Charming cottage in quiet area, close to beach & bay.
Guests can enjoy access to the beach via a staircase, surrounded by lush trees.

Charming cottage in quiet area, close to beach & bay.

9.8 out of 10, Exceptional, (280)
"Beautiful home and great location. Close to the beach, food and ice cream. Will definitely stay here again. Host was really responsive. "
Charming cottage in quiet area, close to beach & bay.
Pirate's Pointe Resort
Relax by the serene lake with a bench and table on the dock, surrounded by lush greenery.

Pirate's Pointe Resort

3.0 star property
9.4 out of 10, Exceptional, (215)
"Beautiful, peaceful place located on the river. Cottages are clean and spacey. Very relaxing and serene place. High recommended . "
Pirate's Pointe Resort
Cozy Holmes Beach Cottage - 3/2 - 1 block from beach!
Enjoy a serene coastal setting with ocean views and lush greenery surrounding single-family homes.

Cozy Holmes Beach Cottage - 3/2 - 1 block from beach!

9.6 out of 10, Exceptional, (23)
"Great location nicely decorated and clean"
Cozy Holmes Beach Cottage - 3/2 - 1 block from beach!
2Bd+2 Ba beach cottage w/private front/back yard, screened porch, firepit, grill
Guests can enjoy a lively beach scene with ocean views and access to various activities.

2Bd+2 Ba beach cottage w/private front/back yard, screened porch, firepit, grill

10.0 out of 10, Exceptional, (71)
"Wonderful quiet neighborhood property with very attentive property owners. Flamingo Cottage is ideally located for easy access to the beach as well as Shopping within walking distance. We look forward to our return next year!"
2Bd+2 Ba beach cottage w/private front/back yard, screened porch, firepit, grill
Starfish Cottage - sleeps 4 guests in 2 bedrooms
Enjoy stunning ocean views and lush surroundings from this coastal resort.

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
1-bedroom cottage just 10 minutes from Siesta Key Beach
Relax in a serene outdoor space surrounded by lush greenery and a canopy.

1-bedroom cottage just 10 minutes from Siesta Key Beach

9.0 out of 10, Wonderful, (36)
"We greatly enjoyed our stay. The yard is very secluded and quite large, which was ideal for us. The house was exceptionally clean, and is well laid out. Powerful a/c system, super welcome for hot florida days. It also has a very large screened in lanai, which is perfect for relaxing. "
1-bedroom cottage just 10 minutes from Siesta Key Beach
Beautiful, well-maintained home w/ heated private pool - walk to beach & dining
Relax by the serene pool surrounded by lush greenery and a shaded pergola.

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
Cozy Cottage Retreat at Tradewind Resort #32 in Bradenton Beach
Relax on a wide, sandy beach with comfortable sun loungers and beach umbrellas.

Cozy Cottage Retreat at Tradewind Resort #32 in Bradenton Beach

9.0 out of 10, Wonderful, (8)
"Great location. Very clean and well maintained. I would come back "
Cozy Cottage Retreat at Tradewind Resort #32 in Bradenton Beach
12 Mi to Beach: Home w/ Patio & Yard in Bradenton
House (3 Bedrooms) | Interior

12 Mi to Beach: Home w/ Patio & Yard in Bradenton

3.0 star property
10.0 out of 10, Exceptional, (1)
"Clean & close to the convention center"
12 Mi to Beach: Home w/ Patio & Yard in Bradenton
Blue Isle Oasis: Adorable, updated 2 bedroom cottage
Relax in a serene outdoor space with a table for two, a wicker sofa, and a comfortable chair.

Blue Isle Oasis: Adorable, updated 2 bedroom cottage

9.0 out of 10, Wonderful, (2)
"Nicely renovated interior and exterior. "
Blue Isle Oasis: Adorable, updated 2 bedroom cottage
Country Cottage Home
Relax in a serene outdoor space surrounded by a tropical mural and lush greenery.

Country Cottage Home

9.4 out of 10, Exceptional, (140)
"Perfect place for short stay. Great little cottage in a private quiet setting. Nothing super fancy but everything you need and exceptionally clean. "
Country Cottage Home
Charming 2br / 1ba Cottage < 2 Min Walk From Beach on Anna Maria Island Florida
Enjoy cooking in this well-equipped kitchen with a refrigerator, stove, and sink.

Charming 2br / 1ba Cottage < 2 Min Walk From Beach on Anna Maria Island Florida

9.8 out of 10, Exceptional, (76)
"My granddaughters thought the cottage was charming, and enjoyed staying there."
Charming 2br / 1ba Cottage < 2 Min Walk From Beach on Anna Maria Island Florida
Tropical Paradise On The Beach Permit VRC17-000168
Effortlessly prepare meals in this well-equipped kitchen featuring a coffee maker, oven, and microwave.

Tropical Paradise On The Beach Permit VRC17-000168

9.4 out of 10, Exceptional, (135)
"Quaint beach cottage tucked away from the hustle an bustle of the island. The upper unit had a spectacular view of the beach and sunsets.Communication with the property managers was great!We have already booked again for next year!Thank you for a wonderful stay!"
Tropical Paradise On The Beach Permit VRC17-000168
The Ballyhoo on Bean Point, 200 feet to a beautiful bayside beach and views!
Enjoy a tranquil beach experience with stunning ocean views and a picturesque pier.

The Ballyhoo on Bean Point, 200 feet to a beautiful bayside beach and views!

9.8 out of 10, Exceptional, (196)
"We had stayed here for a month last year and once again this year and are looking forward to the same nextcyear. I cannot say enough wonderful things about the extraordinary efforts by Ed and Audrey to make our stay possible this year after the devastating hurricanes! We are eternally grateful "
The Ballyhoo on Bean Point, 200 feet to a beautiful bayside beach and views!
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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