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.
Sunrise Condo at Seaside in Key West – Reduced Prices & 2-Night Minimum! Plan your unforgettable Key West getaway at Sunrise Condo! This comfortable two-bedroom, two-bath home is the perfect home base for up to six guests to relax, recharge, and explore all the vibrant sights and sounds of the island. After a day of adventure, cool off in the shared pool or unwind in the hot tub. Inside, kick back in the cozy living area with free WiFi and a flatscreen TV, or whip up your favorite meals in the fully equipped kitchen. The condo also includes a private, covered parking spot for added convenience. Traveling with your furry friend? This dog-friendly unit welcomes one well-behaved pup up to 25 lbs (pet fee applies). We’d love to host you! Enjoy reduced nightly rates now through the end of September and take advantage of our flexible 2-night minimum stay. Reserve your dates today and start planning your Key West escape!
Welcome to Key Haven Retreat, a luxurious waterfront sanctuary nestled in the exclusive Key Haven community, just minutes from the vibrant heart of Old Town Key West and the renowned Duval Street. This meticulously maintained island home offers an unparalleled blend of modern elegance and tropical tranquility, making it the perfect getaway for those seeking both relaxation and adventure.
Welcome to your dream vacation in the Florida Keys! This newly built two-bedroom, two-bathroom home in the gated Venture Out Resort on Cudjoe Key offers the perfect blend of modern comfort and island charm. Whether you're here to fish, boat, snorkel, or simply unwind, you'll love the convenience of resort-style amenities and a prime location just 30 minutes from Key West. Guests have access to Venture Out’s heated pool, marina, boat ramp, tennis courts, and more, making it easy to enjoy the best of the Florida Keys lifestyle. Whether you're planning a romantic getaway, a fishing trip, or a fun-filled family vacation, this brand-new rental is the perfect place to call home. ???????Located inside Venture Out on Cudjoe Key. A Registration/Check-In Fee of $125 (subject to change) will be charged by Venture Out at time of arrival. Parking for 1 vehicle per Unit. Extra parking permit may be available at the Guard Station for an additional nightly fee for a maximum of 14 days depending on availability. Must follow all the Rules and Regulations during your stay.
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.
“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!”