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
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
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
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,
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
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
Book this newly renovated home that sits on a major canal, where guests can tie off a boat, in the Indian Waterways neighborhood. The nautical-themed decoration throughout the house will truly help you leave all of your worries behind and focus on having a great time! The family dog is also welcome to join in the fun here. The home features a 60-fo
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
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
*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
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
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