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.
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.
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.)
Welcome to Elizabeth's Secret! You have found your secret! A very private and secluded tropical oasis awaits you behind the private gated entrance at Elizabeth’s Secret, but just steps to all that Key West has to offer.
Island Time Casa – Relaxed Family Living in Casa Marina Welcome to Island Time Casa, a sunny, family-friendly retreat in Key West’s peaceful Casa Marina neighborhood. This multi-level home features cozy bedrooms, a fun third-floor loft for kids, and plenty of space to unwind. Enjoy coffee on the porch or balcony before strolling to nearby Higgs Beach, where calm waters, a playground, and a beach café await. Cool off in the shared backyard pool, play pickleball or tennis nearby, or bike through Old Town. With a full kitchen, WiFi, and charming coastal details, Island Time Casa is your perfect home base for laid-back island living and unforgettable family memories.
Welcome to Key Haven Coastal Retreat – Your Private Waterfront Paradise Experience luxury island living at its finest at Key Haven Coastal Retreat, a beautifully maintained waterfront home nestled in the exclusive Key Haven neighborhood. Just minutes from the heart of Old Town Key West and iconic Duval Street, this serene escape offers the perfect balance of privacy, comfort, and convenience. With three spacious bedrooms and two modern bathrooms, including a private en-suite, the home comfortably accommodates up to six guests. The open-concept living area is filled with natural light and designed for connection—whether you're gathering around the dining table, relaxing in the inviting living room, or preparing meals in the chef’s kitchen. The kitchen features a gas range, oversized island, breakfast bar, and ample storage—ideal for everything from casual breakfasts to full family feasts. Step outside to your private outdoor oasis, where a sparkling pool, shaded patio, and lush tropical landscaping create the ultimate spot to unwind. Easy-maintenance artificial turf and an outdoor shower add thoughtful touches that make coming home from a day in the sun effortless. Enjoy peaceful canal-front living with direct waterfront access—perfect for morning coffee by the water or simply soaking in the tranquil atmosphere. Key Haven Coastal Retreat is designed with families in mind, offering a Graco Pack 'n Play at no charge and optional baby gear available (at an additional cost) for added convenience. Stay cool and connected with dual-zone air conditioning, in-unit laundry, and custom hallway storage with built-in charging stations. Whether you're lounging poolside, launching a day of adventure, or exploring the vibrant charm of Key West, this upscale retreat offers the ideal home base for your unforgettable island getaway. Please note: Boat lift is not available for guest use. Guests may tie up at the seawall.
Elizabeth’s Retreat – Poolside retreat in Old Town Key West New to Southernmost Stays, this beautifully furnished 2BR/2BA conch cottage offers the perfect blend of location and privacy. Just steps from Duval Street yet tucked away in a quiet neighborhood, you’ll enjoy a private pool, spacious deck with outdoor grill, and a well-stocked kitchen with high-end appliances. Guests rave about the comfortable furnishings, spotless interiors, and unbeatable location. Walk to restaurants, shops, and attractions, then come home to relax in your own tropical oasis.
“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!”