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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32 properties available
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
Book your next vacation hideaway at this pool-view townhome, located at the amazing Kawama Yacht Club. You’ll love the community amenities, which include an outdoor pool, an outdoor kitchen, tennis courts, and a playground. Head down to the private beach with one of the community kayaks. An on-site marina offers services for additional usage
The Keys are calling, so spoil yourself with an unforgettable stay in this fantastic canal-front home! You won't have to leave home base to soak up some of the best views, as the calm canal waters await right outside, as well as a 122-foot private dock to tie up any kayaks and toys. The exterior is a fun, bright green color, just adding to the
Whether you spend your next Florida vacation playing in the cool surf or hanging out with good friends on the private patio, you will love staying in this gorgeous retreat. Guests will be delighted by the fantastic location of this condo, offering a large pool, 2 tennis courts, a furnished clubhouse, first-come-first-served dockage, and a bayfront
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 •
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
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
Welcome to your Key Largo tropical escape — where island breezes, crystalline waters, and the classic Florida Keys lifestyle set the tone for an unforgettable stay. This dog-friendly home is perfect for families, couples, and adventure lovers looking to slow down, unwind, and live the Keys life to the fullest. Step outside to your spacious de
Escape the hustle and bustle of everyday life in the tropical Florida Keys, where tranquility and fun await. This condo is steps away from the water, with all you ever need for entertainment in a 10-mile radius. Tour the area and check out Rain Barrell Village, Theater of the Sea, the History of Diving Museum, or the Laura Quinn Wild Bird Sanctuary
Welcome to your perfect vacation retreat in Key Largo, FL! This modern and spacious townhouse is ideally located in the Kawama Oceanside community, offering the closest proximity to the marina and beach area. With 3 bedrooms and 3 baths, there's plenty of room for the entire family to relax and unwind. Inside the townhouse, you'll find a li
*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
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
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