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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30 properties available
Sun‑soaked days and cool ocean breezes await you at this oceanfront Key Largo retreat. With sweeping ocean views and shared amenities such as a pool, on‑site tennis, and private beach access, you'll find that fun and relaxation are always within reach.Just steps from the gently rolling waves and a little over seven miles from the heart of the i
Feel the stress melt away as you step into this coastal Key Largo condo, where breezy tropical charm and peaceful surroundings set the tone for your stay. Wake up to lush greenery and the unique island landscape from your private balcony, coffee in hand, as the day begins at your own relaxed pace.Inside, the open, light‑filled layout features coast
*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
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 Relaxation Time, your peaceful Key Largo retreat on 2nd Road. Designed for extended monthly stays, this comfortable home offers a bright, welcoming atmosphere and a convenient location close to marinas, dining, and the best outdoor experiences in the Upper Keys.Featuring an open living area filled with natural light, a fully equipped kit
This waterfront home offers multiple levels of indoor/outdoor living and entertaining space paired with a prime location mere steps from the water! Bring your own boat (up to 25 feet) or rent one -- this property features a private dock nestled along the canal with quick access to the Atlantic. Scuba diving and snorkeling are the top activities her
✨ Tollgate Tides blends comfort and adventure in one perfect waterfront escape. Whether you’re here for fishing, snorkeling, sunset cruises, or simply soaking up the tropical vibe, you’ll find everything you need to create unforgettable Florida Keys memories.⭐ Location Highlights Robbie’s of Islamorada (10 miles): Feed the famous
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
Your Oceanfront Escape Awaits in Tavernier!Imagine waking up to endless ocean views, sipping your morning coffee on a private balcony, and feeling the warm island breeze. Welcome to your Florida Keys getaway in beautiful Tavernier, where relaxation, adventure, and laid-back island living come together!This inviting oceanfront condo offers the perfe
Your Tropical Getaway Awaits at Kawama Yacht Club in Key Largo!Escape to paradise and experience the laid-back charm of the Florida Keys in this inviting, pool-view townhome located in the sought-after Kawama Yacht Club community in Key Largo! Whether you're planning a relaxing beach getaway, a fun-filled family vacation, or a peaceful escape t
Welcome to Ohana Keys, a bright and inviting townhome in the sought-after Kawama Yacht Club in Key Largo, where island adventures, resort-style amenities, and laid-back Florida Keys living come together.Whether you're here to relax by the pool, spend the day on the water, or explore the Keys, Ohana Keys gives you the perfect home base for your
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
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