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Featured Cottages in Stock Island and around

Enjoy a serene outdoor space surrounded by lush plants and a charming seating area.

"The Osprey Unit was terrific! Great location, clean, and most of all- the staff was incredibly kind and helpful."

includes taxes & fees

27 Aug - 28 Aug

Enjoy a serene canal view from this balcony with seating for two.

"Great price great location "

"Easy walk to everything! Comfortable stay. "

includes taxes & fees

14 Aug - 15 Aug

Enjoy a waterfront retreat with a balcony overlooking the water, a covered outdoor area, and access to the dock.

"The place was everything as described. Close enough to Key West and beaches that we did not stay home much during the day but nice to have a peaceful place to land in the evenings. Bedrooms and bathrooms were right but served its purpose. Jennifer and Susan were very helpful with check in. Thanks for letting my parents relive their glory days in the Keys. I would stay again if we come back!"

Relax in a serene oasis with a hot tub surrounded by lush tropical plants and a wooden fence.

"Will stay here again "

includes taxes & fees

26 Aug - 27 Aug

Surrounded by lush greenery, this charming house features a white picket fence and a welcoming front door.

"Cute, charming, clean and quiet. Great location. "

Guests can enjoy a peaceful stay in this charming single-story building surrounded by a beautifully maintained garden.

"We had a wonderful stay here with our kids. Can’t beat the location."

includes taxes & fees

12 Aug - 13 Aug

Relax in a secluded outdoor space with a hot tub surrounded by lush tropical plants and trees.

"Loved listening to live music right across the street. Very convenient location. Booze, food, coffee and beach within blocks. "

includes taxes & fees

31 Aug - 1 Sept

Cozy home with a front porch and garden, perfect for relaxation.

"We very much enjoyed our stay at the cottage. Everything you need for a comfortable stay and a location that can't be beat. Also, the off-street parking was a time, money, and sanity saver. Thanks to Marcela and family!"

Enjoy the serene marina view from the comfort of your room, featuring a spacious seating area and large windows.

"This place is exactly as described. The quirkiness was perfect for my husband and I to spend our anniversary. We had a day of rain and it was perfect!and"

Stroll through the serene garden, surrounded by lush palm trees and vibrant greenery, leading to a charming porch.

"Really nice property just as the photos had everything we needed, great surroundings with character the pool area was perfect and well kept a very relaxing and friendly environment . The attached history to the Conch Republic was very interesting and maintained. Communications with Roberta were again very easy and in a timely & friendly manner Easy walk to Duval st and other attractions. All in all a great place to stay and would highly recommend "

Enjoy a romantic meal with a serene view of the marina and calm waters.

"Property was very clean and well stocked. Perfect location on the water. Would definitely rent again "

Cozy home with a gabled roof and inviting front porch, perfect for relaxing.

Residential homes with unique architectural styles surround a large pool and well-manicured lawn.

"Good Fishing, Good local eateries. "

includes taxes & fees

5 Aug - 6 Aug

Detached houses with individual driveways and yards surround a swimming pool area adjacent to the beach.

"We enjoyed our stay. Place is exactly as described. We really enjoyed the lanai. Wanted somewhere close to Key West and this turned out perfect. Would definitely stay here again. Thanks!"

Stroll through the charming front porch, surrounded by lush tropical plants and a picket fence, to the inviting entrance with a glass door.

"Had another wonderful week at Sea Breeze Cottage. Perfect home, location, amenities, and host. Love going there. "

Charming cottage with a front porch and lush green surroundings.

"The property and location is great! The private deck was awesome. "

Relax on the beach with lounge chairs and a tranquil sea view.

"Very nice quiet place for your lower key vacation. Nice accommodations and easy drive to Key West and Islamorada and several state parks. "

Enjoy scenic views of the ocean and surrounding landscape from this coastal property featuring a pool, residential buildings, and a lush garden with palm trees.

"My husband and I stayed with our son in the cottage and it was everything we needed. Great location, beautiful pool on the water, and just enough space. "

includes taxes & fees

2 Aug - 3 Aug