Upper Keys Vacation Rentals
Upper Florida Keys vacation rentals offer a relaxed, tropical escape with a collection of waterfront homes, island-style condos, and private retreats designed for comfort and connection. Choose from vacation homes featuring multiple bedrooms, full kitchens, outdoor living spaces, and private docks, ideal for families, couples, and group getaways. Many Upper Keys rentals include sought-after amenities such as water access, boat docks, private pools, and scenic sunset views.
Located at the gateway to the Florida Keys, the Upper Keys provide a more laid-back alternative to busier destinations further south, while still offering easy access to world-class fishing, boating, snorkeling, and diving. With a mix of oceanfront and bayfront properties, quiet neighborhoods, and a strong connection to the water, Upper Florida Keys rentals deliver an easygoing island experience with the space and privacy of a home.
Key Largo vacation rentals are known for their natural beauty and direct access to some of the best diving and snorkeling in the Florida Keys. As the northernmost island, Key Largo offers a blend of waterfront homes, canal-front properties, and condo communities—many with private docks or marina access.
Guests staying in Key Largo rentals can enjoy nearby parks, clear waters, and a slower pace, making it an ideal choice for outdoor enthusiasts and families looking to unwind. Whether you're planning a boating trip or simply want to relax by the water, Key Largo offers a peaceful and accessible island setting.
Islamorada vacation rentals provide a balance of coastal charm and upscale island living. Often referred to as the “Sportfishing Capital of the World,” Islamorada is a favorite for anglers, boaters, and guests looking for a refined yet relaxed getaway.
Vacation homes in Islamorada range from elegant waterfront estates to comfortable canal-front retreats, many featuring private pools, outdoor entertaining areas, and easy access to the water. With a variety of dining, boutique shopping, and water-based activities nearby, Islamorada rentals offer a vibrant yet laid-back atmosphere in the heart of the Upper Keys.
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119 properties available
*IMPORTANT NOTICE - New dock construction is scheduled to begin October 1st and is expected to last approximately 5–6 weeks. During this time, the dock will not be available for use. *Two floors of wraparound balconies means two floors of stunning views from this peaceful condo. And that's just the beginning - guests can enjoy access to a
License number: 25,230-1322,99. Welcome to Paradise in Key Largo – your private waterfront oasis just one mile from the breathtaking John Pennekamp Coral Reef State Park! Whether you're looking for outdoor adventures, a family retreat, or simply peace and quiet in the Florida Keys, this spacious and beautifully appointed home offers the p
Say hello to pure coastal bliss right on the harbor at this fabulous Duck Key escape. Sea and Sky will have you slipping into vacation mode in no time, as you can wake up, brew a fresh pot of coffee, and step out to your furnished deck to watch the sunrise over calm waters, mere steps away. The private dock will also be just the place to launch the
Located in Marathon, FL, this charming condo is just a stone's throw away from the renowned Sombrero Beach, one of the top-rated beaches in the state. With grocery stores, restaurants, and various retail shops within a two-mile radius, convenience is at your fingertips. Whether you're into fishing, diving, snorkeling, or simply soaking up t
Experience the laid-back charm of the Florida Keys from this beautiful waterfront condo, built in 2022 and designed for the perfect island getaway.Whether you're seeking adventure on the water or a relaxing escape in the sunshine, this bright and beautifully appointed coastal retreat offers everything you need to make unforgettable memories.Sta
Located in Marathon, FL, this spacious house is the perfect retreat for families or groups looking to enjoy the beauty of the Florida Keys. With a private pool, patio furniture, and a gas grill, the outdoor space is ideal for soaking up the sun and enjoying al fresco dining. The house features multiple levels, providing plenty of space for everyone
Welcome to Gray Pelican House, your perfect canal-front escape in the heart of Key Colony Beach, one of the Florida Keys’ most peaceful and walkable communities. Whether you're visiting to relax, explore, or fish the open waters, this home puts island living right at your fingertips. Nestled on a deep-water canal with a 37-foot dock, the
Feel the stress melt away as you step into this coastal Key Largo condo, where breezy tropical charm and peaceful surroundings set the tone for your stay. Wake up to lush greenery and the unique island landscape from your private balcony, coffee in hand, as the day begins at your own relaxed pace.Inside, the open, light‑filled layout features coast
*IMPORTANT NOTICE - New dock construction is scheduled to begin October 1st and is expected to last approximately 5–6 weeks. During this time, the dock will not be available for use.*This gorgeous townhouse in the Florida Keys is the perfect paradise vacation for those wanting to experience true serenity. With unbeatable views, beach/dock acc
Boasting some of the great fishing in the world, beautiful and sparkling beaches, and warm weather, Marathon is widely considered the best destination in Florida! This captivating, snowbird-friendly home is located near plenty of dining options and less than two miles from the Florida Keys/Marathon International Airport. This relaxing neighborhood
Nestled in the heart of Marathon, FL, this charming house offers a serene retreat with stunning water views and a private dock along the canal. The abundance of natural light throughout the home creates a warm and inviting atmosphere, perfect for unwinding and enjoying the picturesque surroundings. With a double driveway, there's ample parking
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