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
32 properties available
The Tree Lane Fish Camp: Updated, Cozy home in TavernierBed Sizes: 2 Queen, 1 Double Trundle Bed, 2 Double Sleep SofasWelcome to your laid-back diving retreat in Tavernier, where life moves with the tides and every day ends with a sunset over the water. Nestled in the heart of the Florida Keys, this home is built for anglers, boaters, and anyone wh
*Please note that this home only allows minimum night stays of 28 nights or longer. This is enforced by the HOA, and we cannot make any exceptions. This home is perfect for anyone coming to the Keys to spend time on the water. The two-story home sits on the widest canal in Hammer Point that leads to Florida Bay and has its own private dock capable
Experience Key Largo at its finest when you book a stay at Afternoon Delight! Nestled alongside the water and equipped with a spectacular list of private amenities, your vacation will be shrouded in sunshine, lined by palms, and hugged by the sea breeze. Spend your days splashing in the heated pool, throwing cookouts for your family (thanks to the
Dolphin Paradise: Dog-Friendly home in Key Largo with a private heated pool that sits on a waterfront lot with a private dock and amazing views!Dolphin Paradise is your perfect escape in the heart of Key Largo, where laid-back island living meets comfort and style. This spacious 5-bedroom, dog-friendly home sits on a beautiful waterfront lot, offer
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
Prepare for true canal-front living at this home! Casual in nature and comfortable in every room, this home is ready with central air conditioning and enough seating for everyone. Cards and chips for late-night poker games are included for impromptu games, as well as a telescope for looking out at the sky over the ocean. Store the boat at the dock
Marvelous views will fill your vision when you call this sun-soaked home your next vacation destination! When you can peel yourself away from the tantalizing turquoise views, check out the area's many amusements. All less than eleven miles away, you will discover the Laura Quinn Wild Bird Sanctuary, Theater of the Sea, the History of Diving Mus
Just a short walk from a lovely community park, this friendly home has plenty of room for guests to come in and relax. Unwind in central air conditioning inside or enjoy a beverage out on the private, furnished patio. If you're coming back from the ocean, the private washer/dryer will take care of the swimsuits and towels while you relax. The s
Step into your own slice of paradise at this sunlit, open-concept home overlooking the turquoise waters of the Florida Keys. With enchanting views from nearly every room, Tollgate Tides is the perfect retreat for a surf trip with friends, a romantic couples’ getaway, or a family vacation by the shore. ⭐ Location Highlights • Robbie&rsquo
*Please note that this home only allows minimum night stays of 28 nights or longer. This is enforced by the HOA, and we cannot make any exceptions. Enjoy incredible beach and ocean views from this family-friendly, waterfront retreat. This home features a beautiful, sandy backyard that leads directly to the ocean, a private boat dock, four beach cru
Welcome to Ohana Keys, your island getaway where stress drifts away on the breeze and paradise greets you at every turn. Nestled in the sought-after Kawama Yacht Club, this vibrant townhome offers not only comfort and style but also access to world-class amenities: a private beach with firepits and tiki bars, sparkling pools, a swimmable lagoon, gr
This splendid paradise of a home will be just the perfect place to bring the whole family for an unforgettable vacation! Enjoy an unbeatable canal-front location within a short drive of Lake Surprise. The canal seamlessly opens to the bay side and is just minutes away by boat from Adam's Cut for those wanting ocean access. The home boasts a pri
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