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 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.
Now through September: Reduced Rates + 2-Night Minimum! The owners of Sunrise Condo have made thoughtful upgrades based on guest feedback, including brand-new TVs, faster WiFi, and a new mattress to make your stay even more comfortable. This two-bedroom, two-bath condo is the perfect retreat for up to six guests looking to relax, recharge, and enjoy everything Key West has to offer. The primary bedroom features a king bed, the second bedroom has a queen, and there's a queen-size pullout couch in the living room—plenty of space for everyone to sleep comfortably. After a day of exploring, cool off in the sparkling community pool or unwind in the hot tub. Inside, the cozy living room invites you to kick back with free WiFi and a flatscreen TV, and the fully equipped kitchen has everything you need to prepare a delicious meal at home. A private covered parking spot makes your stay even more convenient. Sunrise Condo is both family- and dog-friendly. A Graco Pack 'n' Play with sheet is provided at no charge, and additional baby gear is available for rent. One well-behaved dog (up to 25 lbs) is welcome with a pet fee. Take advantage of our special summer offer—reduced rates and a flexible two-night minimum stay now through the end of September. Book your Key West escape today!
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.
Island Time Casa – Relaxed Family Living in Casa Marina Welcome to Island Time Casa, a sun-soaked, family-friendly getaway in Key West’s peaceful Casa Marina neighborhood. Thoughtfully designed for comfort, connection, and coastal living, this charming retreat offers everything you need to settle into "island time." Perfect for families, this spacious multi-level home features a third-floor sleeping loft kids will love, cozy bedrooms for grown-ups, and plenty of shared space to relax. Start your day with coffee on the front porch or private balcony, then head just a few blocks to Higgs Beach — where you’ll find calm waters, a playground, beach café, and plenty of sun and sand. Cool off in the shared backyard pool, challenge the crew to a game of pickleball or tennis nearby, or rent bikes to explore Old Town’s tropical charm. With porches for lounging, a fully equipped kitchen, WiFi, and cozy living areas, Island Time Casa blends comfort and character in one of Key West’s most beloved neighborhoods. Whether you're watching the sunset from the porch, grilling by the pool, or making beach memories with the kids, this is where your family’s island story begins.
“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!”