TOP 30 Upscale vacation rentals in Key Largo, Florida

Baker's Cay Resort Key Largo, Curio Collection by Hilton is a luxurious lodging destination located at 97000 Overseas Highway in Key Largo, Florida, United States. Nestled amidst the stunning natural beauty of the Florida Keys, this resort offers a perfect blend of tropical paradise and upscale amenities. Guests can enjoy spacious rooms and suites, a private beach, multiple swimming pools, on-site dining options, a fitness center, and a variety of recreational activities. Whether you're looking for a relaxing getaway or an adventurous vacation, Baker's Cay Resort Key Largo has something for everyone.

Bungalows Key Largo is a luxurious, all-inclusive, adults-only resort located at 99010 Overseas Highway in Key Largo, Florida. Nestled within a botanical garden with 1000 feet of ocean shoreline, this intimate resort offers a peaceful oasis for guests to unwind and disconnect. With a focus on relaxation and indulgence, Bungalows Key Largo provides a unique blend of upscale accommodations and top-notch amenities. Guests can enjoy organic textures, soothing tropical hues, and all-natural materials in the resort's luxurious bungalows, each featuring a private veranda for outdoor living. The on-site restaurant, Bogie & Bacall's, offers a culinary experience showcasing local seafood and bold Mexican flavors with stunning views of the surrounding landscape.

Luxury Rental IN is a luxurious lodging option located at 10 Exuma Road in Key Largo, Florida, United States. Situated in the heart of Ocean Reef®, this institution offers a perfect retreat for families looking to enjoy the amenities of the area. The property features a stunning Great Room with a soaring 22-foot ceiling and a flatscreen TV, an upstairs Den with a pull-out sofa and wet bar area, and a covered patio with retractable screens and a large outdoor TV. Guests can also enjoy a large heated swimming pool with ledge loungers and a built-in landing, ideal for keeping an eye on small children. The second upstairs deck overlooks Villa Cay Park, providing a wonderful spot for star-gazing and watching holiday fireworks. Daily rates are available, with negotiable options for longer stays. Please note that cleaning fees are not included.

Florida Luxury Rentals is a premier vacation rental agency located at 2501 East Commercial Boulevard in Fort Lauderdale, Florida. Offering a wide selection of luxurious properties, from beachfront villas to upscale condos, our rentals provide the perfect accommodation for your next getaway to the Sunshine State. With top-notch amenities, stunning views, and personalized concierge services, Florida Luxury Rentals ensures a truly unforgettable stay for every guest. Experience the ultimate in comfort and relaxation with our exclusive properties in one of the most desirable destinations in the United States. Book your dream vacation with us today!

Key Largo Ocean Resorts Co-Op is a stunning waterfront community located at 94825 Overseas Highway in Key Largo, Florida. This exclusive co-op offers luxurious accommodations and a range of amenities for residents and guests to enjoy. With breathtaking views of the ocean and easy access to water activities, Key Largo Ocean Resorts Co-Op is the perfect destination for those seeking a relaxing and upscale retreat in the Florida Keys. Whether you are looking to unwind by the pool, explore the nearby coral reefs, or simply soak in the sun on the private beach, this resort has something for everyone. Experience the ultimate in luxury living at Key Largo Ocean Resorts Co-Op.

KeysCaribbean Resorts is a premier lodging institution located at 97501 Overseas Highway in Key Largo, Florida, United States. Our team of professional agents is available 24 hours a day to ensure a stress-free and exceptional vacation experience for our guests. Choose from our select rentals at premier Upper & Middle Keys resort communities, where you'll have exclusive access to top-notch amenities such as private swimming pools, boat dockage, Jacuzzi tubs, and more. Whether you're planning a family reunion or a getaway with friends, we can accommodate your needs with our range of rental options.

The Inn at Ocean Reef is a luxurious lodging facility located in North Key Largo, Florida, United States. Situated in a picturesque coastal setting, this institution offers guests a tranquil and upscale retreat. With elegant accommodations, top-notch amenities, and personalized service, The Inn at Ocean Reef provides a truly unforgettable experience for visitors looking to relax and unwind in style. Whether you're seeking a romantic getaway, a family vacation, or a business trip, this charming inn is the perfect choice for your stay in the Florida Keys.

Tamarind Bay Club is a luxurious waterfront resort located at 104500 Overseas Highway in Key Largo, Florida, United States. This exclusive club offers stunning views of the bay and provides guests with a tranquil and upscale retreat. With spacious accommodations, top-notch amenities, and impeccable service, Tamarind Bay Club is the perfect destination for those seeking a relaxing and memorable vacation experience. Whether you're looking to unwind by the pool, enjoy water sports, or explore the nearby attractions, Tamarind Bay Club has something for everyone. Come and experience the beauty and serenity of this hidden gem in the heart of Key Largo.

Watson Luxury Properties at Ocean Reef is a prestigious real estate agency located at 9 Barracuda Lane in Key Largo, Florida. Specializing in luxury properties in the Ocean Reef community, our experienced team of professionals is dedicated to providing top-notch service to our clients. Whether you are looking to buy, sell, or rent a high-end property, we are here to assist you every step of the way. With a focus on quality, integrity, and personalized attention, Watson Luxury Properties at Ocean Reef is the go-to agency for those seeking the finest real estate opportunities in the area.

Fairway Lakes 9a at Ocean Reef Club is a luxurious lodging option located at 13 Lakeside Lane in Key Largo, Florida. Situated within the prestigious Ocean Reef Club, this institution offers upscale accommodations with stunning views of the surrounding fairways and lakes. Guests can enjoy access to top-notch amenities such as a golf course, tennis courts, swimming pools, and fine dining options. Whether you're looking for a relaxing getaway or an active vacation, Fairway Lakes 9a at Ocean Reef Club is the perfect destination for a memorable stay in the beautiful Florida Keys.

Bennett’s Beach Estate, Joyce Bennett, LLC, is a charming lodging institution located at 95490 Overseas Highway in Key Largo, Florida. Situated on a private, two-acre estate overlooking the Florida Bay, this vacation getaway is centrally located in south Key Largo, close to Sunset Pointe. The estate features six vacation rentals, ranging from the spacious three-bedroom Coral House to the cozy camping bungalow. Perfect for small to medium-sized events, Bennett’s Beach Estate offers a picturesque waterfront location for weddings, reunions, and birthday celebrations. Guests can enjoy amenities such as fast Wi-Fi, waterfront activities, and a full electric barbecue grill. Off-site activities, including parasailing, jetskiing, and swimming with dolphins, are just a short drive away. Local eateries, from casual to upscale, are highly rated and offer a variety of dining options.