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.
SUMMER SALE! Sunrise Condo at Seaside – Lower Rates & 2-Night Minimum! Your perfect Key West getaway starts here! Sunrise Condo is a comfortable two-bedroom, two-bath retreat designed for up to six guests to relax, recharge, and soak up everything the island has to offer. After a day of exploring, cool off in the sparkling community pool or soak your cares away in the hot tub. Inside, kick back in the cozy living room with free WiFi and a flatscreen TV, or whip up a delicious meal in the fully equipped kitchen. A private, covered parking spot adds extra ease to your stay. Family- and dog-friendly! A Graco Pack 'n' Play with sheets is provided free of charge, and additional baby gear is available for rent. Bring along your furry friend too—one well-behaved dog (up to 25 lbs) is welcome with a pet fee. Special Summer Offer: Enjoy reduced rates and a flexible 2-night minimum now through the end of September! Book your stay today and get ready for your unforgettable Key West escape!
Welcome to Key Haven Coastal Retreat! Escape to your private waterfront oasis just minutes from Old Town Key West! This beautifully maintained 3-bedroom, 2-bath home features an open-concept living space, gourmet kitchen, sparkling pool, canal access, and modern amenities like dual-zone AC and in-unit laundry. Family-friendly touches include a complimentary Pack 'n Play and available baby gear rentals. Whether you're lounging by the pool, boating from your backyard, or exploring Duval Street, Key Haven Coastal Retreat offers the perfect blend of luxury, comfort, and tropical relaxation.
Pure Bliss Villa is one of Key West’s premier private vacation homes, thoughtfully designed for ultimate comfort and relaxation. The spacious open-plan living area flows effortlessly into a lush outdoor oasis, complete with a private pool, tropical landscaping, and comfortable lounge seating. Inside, the chef’s kitchen features top-of-the-line appliances and all the essentials for preparing gourmet meals. Step outside to the fully equipped outdoor kitchen and dining area—perfect for alfresco meals under the palms. Each bedroom is tastefully appointed with plush bedding, generous storage, and charming island-inspired decor. Whether you’re sunbathing by the pool, grilling in the garden, or strolling the vibrant streets of Old Town just minutes away, Pure Bliss Villa offers a luxurious and convenient retreat in the heart of Key West.
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!”