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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31 properties available
Welcome to Your Waterfront Escape in Key Largo! Tucked along a peaceful canal with stunning water views, this tropical retreat is your gateway to both relaxation and adventure in the Florida Keys. Perfectly positioned between the Atlantic Ocean and Florida Bay, you’re just minutes from world-class boating, fishing, snorkeling, and sunsets you
Your Waterfront Escape in the Heart of Islamorada Awaits! Welcome to your dream getaway in the Florida Keys—where turquoise waters, tropical breezes, and that unmistakable “island time” feeling set the tone for an unforgettable stay. Nestled right on the water in beautiful Islamorada, this spacious 3-bedroom home offers the perfec
Feel the stress melt away as you step through the front door of this tropical Key Largo condo, boasting serene oceanfront views from two private balconies. The top-floor location immerses you in beautiful water views and gentle breezes on your private Tavernier Escape. Enjoy on-site amenities like the community pool and gazebo, a waterfront caf&eac
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
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
Sun-soaked days and cool ocean breezes await you when you book your next retreat to this oceanfront Key Largo getaway. Featuring sweeping ocean views and shared amenities like a pool, on-site tennis, and beach access, fun will always be easy to find! Steps from the gently rolling waves, and just over seven miles from the heart of the island, you
Get the whole group together for a sun-soaked getaway at this canal-front home in Key Largo! Boasting views of the water, easy access to a dock and the nearby beach, and room for up to nine guests, this family-friendly retreat will give you a well-deserved tropical getaway. After a day spent relaxing on the beach or boating in the surrounding area,
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
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
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
This canal-front home has a nice upper-level balcony overlooking the water, which is excellent for morning coffee or evening cocktails. The spacious living area invites everyone to kick back, relax, and enjoy watching TV or planning their next adventure. Take advantage of the well-equipped kitchen and treat your group to a tasty homemade meal. WHAT
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
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