Discover the vibrant charm and tropical allure of the Florida Keys with our carefully selected vacation rentals. Whether you’re seeking a peaceful retreat in a quiet corner of the islands, a stay near the lively energy of Key West, or a secluded hideaway immersed in nature, we have the perfect property for your dream vacation.
At Southernmost Stays, we specialize in offering unique homes that combine luxury, comfort, and an authentic island experience. From world-class fishing and pristine coral reefs to local culture and adventure, the best of the Keys is at your doorstep. Our dedicated team is here to ensure your stay is seamless and unforgettable, offering personalized service and expert local knowledge to help you create lasting memories.
Start planning your perfect escape today – your island adventure is waiting!
Discover extraordinary featured rentals that offer exceptional hospitality, comfort, and unforgettable experiences.
Ocean-view 2BR/2BA condo just steps from Smathers Beach and a quick bike ride to Duval Street. King primary suite, flexible second bedroom, private balcony, and brand new kitchen appliances.
Welcome to Sunrise Condo, where comfort and affordability meet in a peaceful Key West setting. This updated two-bedroom, two-bath retreat sleeps up to six guests with a king bed, queen bed, and queen sleeper sofa. Recent upgrades include new kitchen countertops, faster WiFi, new TVs, and a plush mattress for added comfort. Perfect for families or couples, Sunrise Condo is both dog- and family-friendly, offering a Pack ’n’ Play at no charge and welcoming one small dog (up to 25 lbs) with a pet fee.
Enjoy the best of Key West living in this spacious three-bedroom, two-and-a-half-bath home that comfortably sleeps up to six guests. The property features two bedrooms in the main house and a separate cabana bedroom for added privacy. Relax in your outdoor oasis with a dedicated swimming pool, patio seating, and outdoor shower, perfect after a day at the beach. The home also offers off-street parking with additional free street parking nearby and is located in a quiet residential neighborhood just minutes from Key West’s beaches, dining, and attractions. Dogs may be considered with owner approval and a pet fee.
New Property!!! Discover your own slice of paradise at this contemporary Key West retreat just steps from Duval Street and Fort Zachary Taylor Beach. Built in 2019, this elegant home blends modern design with tropical charm, featuring an open floor plan, high-end kitchen, and seamless indoor–outdoor living. Lounge by the private heated pool and waterfall, soak up the sun on the patio, or enjoy evening breezes from one of the covered porches. With stylish furnishings, private parking, and an unbeatable Old Town location, this home is the perfect setting for your next island getaway.
This newly built 2-bedroom, 2-bath home in the gated Venture Out community on Cudjoe Key offers modern comfort with island charm—just 30 minutes from Key West. Perfect for fishing, boating, snorkeling, or relaxing, you'll enjoy resort-style amenities including a heated pool, marina, boat ramp, tennis courts, and more. Ideal for couples, families, or anglers, this stylish retreat is your home base for Keys adventure. (Trailer parking at Venture Out is on a first-come first-served basis. However, this home has worked out an agreement with a lot owner just 10 minutes away to accommodate your trailer for your stay at a modest cost.)
Waterfront 3BR/2BA with Private Dock & Outdoor Living Calle Uno Waterfront Retreat offers relaxed island living with direct canal access, a private dock, and spacious outdoor areas. Inside, you’ll find a bright, open layout with a full kitchen and comfortable living spaces. Ideal for boating, unwinding, and enjoying the Keys lifestyle. Available for monthly stays and long-term rentals (6 months + 1 day). Pets considered with approval; pet rent applies.
“This property and experience exceeded all expectations. I would recommend for all groups or couples looking for their own piece of paradise on the island.”
“Elizabeth's Secret is a magical little place very close to the action on Duval. Everything else is pretty walkable from here as well. Stayed with my husband and adult children and we had plenty of space. The magic really happens at the pool! Great outdoor space and pool was clean and the perfect temp. Loved everything about this little gem!”