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.
Not sure what you're looking for? Keep Searching: Islamorada Vacation Rentals, Key Largo Vacation Rentals, Middle Keys Vacation Rentals, Lower Keys Vacation Rentals, Key West Vacation Rentals
123 properties available
Welcome to your tropical escape in Marathon, FL! This bright and spacious condo combines comfort with adventure, making it the perfect retreat for families, couples, or solo travelers. With a king bed and a double bed, the home easily accommodates your group, while modern amenities—like a fully equipped kitchen (fridge, stove, oven, and dishw
Create unforgettable memories in the heart of the Florida Keys with a stay at this delightful waterfront townhouse on picturesque Duck Key. Set along a serene canal with easy proximity to nearby restaurants, spas, and excursions, this home offers everything you need for a relaxing and adventure-filled getaway. Step inside to find a bright, coastal-
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 shared pool (visible from the balconies!) and the use of a shared dock all throughout their stay. Inside the condo, guests will unwind in a stylish space cooled by central air conditioning.
Located on the upscale Duck Key in a quiet neighborhood known as the Village in Hawks Cay, this waterfront townhouse offers the ideal restful retreat. Take in breathtaking views of the Duck Key Marina, Toms Harbor, and the Seven Mile Bridge in the distance! Spend leisurely afternoons fishing from the shoreline, right outside your door. You'll 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
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
With a wonderful location and a private sandy beach just steps away, this family-friendly townhouse is all set up for your beach getaway. Step inside and you'll be greeted by the charming full kitchen, remodeled as of spring 2021 and featuring granite countertops and full-size appliances for your cooking projects. Central air-conditioning will
Nestled in the picturesque Key Colony Beach, Florida, this exquisite home is the perfect destination for your dream coastal getaway! With its spacious layout and comfortable accommodations, it promises to provide you and your loved ones with a truly memorable vacation experience. Plus, your furry companions are welcome to join in on the fun! As soo
This lovely waterfront duplex hosting lush interiors and incredible water views will surely be the highlight of your next Key Colony Beach escape! Ideally located for fun and recreation, you’ll find Key Colony Beach Golf, Sunset Park, and Florida Keys Aquarium Encounters all within a two-mile radius. Spend a day playing a leisurely round of g
Gorgeously situated at the edge of an ocean canal, this Duck Key townhome is a place for azure water views, fragrant sea breezes, and basking in the blissfully slower pace of the Florida Keys. Spend your days fishing, getting out on the water, and unwinding in peace and scenery on your two-story waterfront porch. You'll also have access to a bo
Completely remodeled by HGTV, this home boasts beautiful furnishings, perfect interior design, and timeless decor that will have you feeling right at home the moment you step through the door! The full kitchen is complete with stainless steel appliances, marble countertops, and a massive island, so cook up your favorite recipes with ease. Though th
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