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This waterfront apartment is located in Lower Matecumbe, Islamorada, at mile marker 76.5, just a short distance from Robbie's Marina, Bud & Mary's Marina, and World Wide Sportsman. The property enjoys an excellent user rating, indicating a high level of satisfaction among previous guests.
This three-bedroom, three-bathroom vacation rental spans 1400 square feet and comfortably accommodates up to six guests. The apartment features a fully equipped kitchen, a private terrace or balcony, a garden, a spa, and a large dock with plenty of space for boat owners.

This studio apartment is located in Islamorada, Village of Islands, offering ocean views and proximity to downtown restaurants accessible via a complimentary resort transportation app.
This accommodation sleeps up to three guests and features a kitchen with a fridge and microwave, air conditioning, a swimming pool, a garden, complimentary Wi-Fi, and access to Founders Park and Caloosa Cove Resort and Marina amenities.

This charming cottage is located at mile marker 76.7 in Islamorada, just a short drive from Caloosa Cove Marina and Robbie's Marina, offering a peaceful retreat away from the hustle and bustle of the main tourist areas. The cottage has consistently received excellent ratings from previous guests for its cleanliness, location, and overall experience.
The cottage has two bedrooms and comfortably accommodates four guests. Enjoy a refreshing dip in the heated swimming pool, shared exclusively with a select few cottages at Shady Palms, and take advantage of the starter pack with essential supplies, convenient parking, and family-friendly features.

This Islamorada houseboat offers a unique floating home experience in the Village of Islands, conveniently located near local attractions (specific distances require knowing the barge's precise location).
The two-bedroom, one-bathroom vessel sleeps seven guests and features a full kitchen, air conditioning, and a deck perfect for sunset viewing; all essential amenities are included for a comfortable stay.

This smoke-free vacation home is located in Matecumbe, a district of Islamorada, within walking distance of Matecumbe United Methodist Church, Florida Keys Brewing Co., and the Hurricane Monument. The "New Caribbean Home. Resort Access To Pool" offer comes with excellent user ratings.
This two-bedroom, two-bathroom home is perfect for families or groups of friends. Amenities include a fully equipped kitchen, a TV, and internet access, as well as parking.

This unique houseboat accommodation is located in the Matecumbe neighborhood of Islamorada, offering proximity to the Keys History & Discovery Center and the History of Diving Museum.
This 1-bedroom houseboat accommodates up to 2 guests and features air conditioning, internet, and a living area with a futon.

This beachfront villa in Matecumbe, Islamorada, offers direct ocean access and is a short 15-minute walk from Indian Key Historic State Park and Bud n' Mary's Dive Center.
This 540-square-foot, one-bedroom, one-bathroom property sleeps six and includes a pool, terrace, concierge service, and amenities such as a refrigerator, microwave, and TV, all within easy reach of Hurricane Monument and Florida Keys Brewing Co.

Marlin House, a four-bedroom, four-bathroom vacation home, is located in the exclusive Tarpon Point community in Islamorada, offering direct oceanfront access and proximity to Islamorada's cultural district and various restaurants and shops.
This oceanfront property boasts a private waterfront pool, a chef's kitchen, smart TVs in every bedroom and living room, and accommodates up to eight guests, with access to a community fishing pier and beach area.

This Islamorada condo, near Caloosa Cove Marina, offers easy access to the ocean and boasts excellent pool views.
The one-bedroom, two-bathroom unit sleeps six with two queen beds, a queen pull-out sofa, two balconies, a full kitchen, and access to a resort pool and beach area.

This Islamorada waterfront apartment, a former courthouse uniquely renovated, offers direct access to boating and fishing, and is centrally located, a 30-minute drive from Key Largo and Marathon, and 1 hour 45 minutes from Key West.
The three-bedroom, two-bathroom rental boasts a private boat dock (up to 30 feet), a tiki hut with outdoor TV and refrigerator, screened porch, and accommodates up to six guests, including all kitchen appliances and air conditioning.

This Islamorada townhouse rental, located at mile marker 87 in the Executive Bay Club, offers easy access to Founders Park and its beach, plus proximity to John Pennekamp Coral Reef State Park and Indian Key Historic State Park.
This 1,370-square-foot, three-bedroom, two-bathroom vacation home sleeps six and features a fully equipped kitchen, in-unit laundry, a private terrace, access to a community pool, tennis/pickleball courts, and a private beach.

This 2-bedroom, 3-bathroom boat is docked in Anglers Reef, an exclusive gated community in Islamorada, Village of Islands. The boat has an excellent user rating and is located within walking distance of shops and restaurants.
It features a private dock, access to complimentary paddle boards and kayaks, a temperature-controlled pool with ocean views, and modern amenities such as granite countertops, stainless steel appliances, and a gas BBQ. The boat can accommodate up to 6 guests and is pet-friendly.