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This Islamorada pet-friendly cottage, located in the Matecumbe district, offers easy access to Bud n' Mary's Dive Center (a 14-minute walk) and Indian Key Historic State Park (a 6-minute walk).
This one-bedroom, one-bathroom vacation home sleeps four and features a private balcony, shared pool access, kayaks, bicycles, free Wi-Fi, and a fully equipped kitchen; nearby attractions include Hurricane Monument and several state parks.

The Green Cottage is located in Turtle Cove, a private community of five vacation homes in Islamorada, Florida, offering pool and ocean views.
This 2-bedroom, 1-bathroom cottage accommodates up to 5 guests and features a queen bed in the master bedroom and a full/twin bunk bed in the second bedroom, with shared amenities including a pool, boat basin, kayaks, and paddleboards.

This Islamorada beachfront cottage in Matecumbe offers direct ocean access, a 15-minute walk from Indian Key Historic State Park and Bud n' Mary's Dive Center, and under a mile from the Hurricane Monument and Florida Keys Brewing Co.
The 450-square-foot, one-bedroom, one-bathroom vacation home sleeps four and includes a private balcony, air conditioning, Wi-Fi, a swimming pool, parking, and concierge services.

This oceanfront vacation home in Islamorada, Village of Islands, located at Mile Marker 83, offers direct access to the Atlantic Ocean with a private sandy beach and a skiff dock.
This four-bedroom, three-bathroom villa sleeps eight guests and features a heated beachside pool, a separate spa, a main house with two living spaces, and a garden cottage, making it an ideal location for fishing, water activities, and destination weddings.

Little Bay Cottage, a bayside retreat in Islamorada, Village of Islands, is located directly on Florida Bay at Mile Marker 82.2, offering protected dockage for boats up to 34 feet within a gated, one-acre tropical compound.
This 2-bedroom, 2-bathroom vacation rental accommodates up to 6 guests with a queen-size sleeper sofa, featuring panoramic Florida Bay views from a covered balcony, a full kitchen with modern appliances, and access to hammocks, a pergola, and a tiki hut, with proximity to John Pennekamp Coral Reef State Park and Robbie's Marina.

This Islamorada, Florida Keys vacation home is conveniently located within a 15-minute walk of the Islamorada Brewery & Distillery, Keys History & Discovery Center, and History of Diving Museum.
This two-bedroom, two-bathroom rental sleeps four guests and features a fully equipped kitchen, in-unit laundry, a private swimming pool, and spa, plus access to an on-site water park and barbecue grills.