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 Keys escape in Tavernier, Florida! This oceanfront condo puts you right at the water’s edge, where endless blue horizons and island breezes set the tone for your stay. Blending comfort with the laid-back charm of the Keys, it’s the perfect retreat for couples, families, or friends ready to soak up paradise. Start your mo
TROPICAL ESCAPE Welcome to your private slice of paradise in Key Largo, FL! This stunning waterfront retreat offers breathtaking views, direct access to adventure, and all the comforts of home. WHY YOU’LL LOVE IT • Relax in the private hot tub while watching gorgeous sunsets • Launch kayak from the private dock right outside •
Make this canal side Key Colony Beach rental your home away from home on your next vacation to the Florida Keys. Enjoy deluxe amenities throughout your rental and beach access through your Cabana Club membership, as well as access to a pool and bar area. Drop a kayak or canoe off the 35-foot dock behind your rental and paddle around your neighborho
Escape to the sunny Florida Keys with this nautically-themed Marathon vacation rental! Complete with a private deck and free Wi-Fi, this charming duplex is the perfect antidote to beat those winter blues. If you prefer to travel by land, you're only five miles from the mangrove swamps of Curry Hammock State Park, where you can rent kayaks, watc
This charming oceanfront two story townhouse offers uninterrupted water views and the laid-back luxury that Duck Key is known for. Perfect for families seeking a peaceful retreat with easy access to world-class boating, fishing, and waterfront relaxation. Step inside to a bright, coastal-inspired living space with comfortable seating and large wind
Anglers take note - you’ve found the perfect getaway at this charming, lime-green Marathon home, offering a canal-front location and easy access to the Atlantic. With an ice maker, fish fryer, and bait freezer on the ground level, you’ll be even more prepared when it comes to landing the big one. And those who prefer to stay land bound
Welcome to 107 Coastal Vibes, a beautifully updated and fully furnished corner residence offering a bright, breezy coastal atmosphere with peek-a-boo views of the Atlantic Ocean. This charming condo features a spacious primary suite with king bed accommodations and a newly updated bathroom, while the light-filled living area flows seamlessly to a p
Feel the stress melt away as you step through the front door of this tropical Key Largo condo, where serene oceanfront views greet you from two private balconies. Perched on the top floor, your Tavernier Escape offers sweeping water views and gentle breezes that set the tone for a peaceful getaway.Enjoy on‑site amenities including the community poo
Welcome to your own private slice of the Florida Keys.Perfectly positioned on a quiet waterfront point in Tavernier, this stunning oceanfront retreat offers panoramic turquoise water views, a private dock, resort-style pool, and multiple expansive balconies designed to capture some of the most breathtaking sunrises and sunsets in the Keys.Located b
If you're looking for a family vacation in paradise, look no further than this three-bedroom, single-level home in Marathon. The private, outdoor pool is the perfect place to cool off, and the screened patio is ideal for enjoying the great outdoors during the day and retiring to at night for dinner, drinks, and conversation. The central air-con
☀️ Bright, Modern & Designed for RelaxationFull of natural sunlight and modern coastal furnishings, this spacious home is ideal for families or groups seeking a peaceful extended getaway. Whether you’re unwinding indoors or enjoying the fresh air outside, every space is crafted for comfort.🌴 Indoor Comfort & Coastal StyleRecline in t
This gorgeous canal-front home boasts views of the water, a dock that can accommodate a 25-foot boat, and two private pools - one with a swim-up bar. The elegant decor and grand kitchen will make you never want to leave! The outdoor area of this home is large and great for gatherings, featuring a hammock, a firepit, a very large ice machine for fis
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