Book your Key West winter escape now and work from paradise for a month
Each year when the snow begins to fall and daylight disappears before dinner, there are those who wistfully dream of warm ocean breezes, sunshine and sand between their toes.
But by then it’s really too late to do anything meaningful to change those circumstances.
That’s why it’s important to stay ahead of Old Man Winter. Yes, summer is the perfect time to begin planning a work-from-paradise escape to Key West. Whether you’re a remote professional wanting to escape the rat race, a couple seeking a break from the cold, or a snowbird craving a change of scenery, December through April is prime time to experience the charm and warmth of the island.
With strong Wi-Fi, comfortable workspaces, and inspirational locations near beaches, culture and cafés, our historic homes offer everything you need to make a month in Key West feel like home. This is the ultimate work-from-paradise destination—and Historic Key West Vacation Rentals has the perfect home for your extended stay.
But you must act soon. Planning a winter month in a tropical wonderland is not a new idea, and competition is fierce for a place in the sun.
‘Key’ reasons why winter rules
- Unbeatable weather: Say goodbye to icy commutes and hello to sunny days, balmy breezes, and comfortable temps perfect for bike rides, beach days, and outdoor dining.
- Peak island life: From art festivals to open-air concerts, the island is buzzing this time of year—but never overwhelming. You’ll find the perfect balance of energy and relaxation.
- Extended stay perks: When you stay for a month, you truly get to experience the island’s rhythm. Shop local markets, attend community events, and explore every hidden corner of Old Town.
- Remote-work ready: Our properties offer Wi-Fi and serene surroundings that help you stay productive while enjoying island life on your breaks.
- More than just a vacation: With longer stays, you’ll have time to truly settle in. Explore historic neighborhoods, get to know your favorite bartenders, and wake up each day with no rush, no snow, and no stress.
- The island lifestyle: Take a conference call from the porch. End the day with a paddleboard session. Grab lunch at a Cuban café. Living like a local in Key West is not just fun—it’s good for the soul.
Featured vacation homes for winter stays
Here are four hand-picked homes that are ideal for extended getaways—and perfectly suited for working remotely in comfort and style:
- Palm Hideaway: A true hidden gem tucked away in a lush tropical setting, this tranquil 3B/2BA home offers peace and privacy with a layout that’s ideal for remote work and relaxation. Offering a pool and parking, it’s perfect for families and friends seeking fun in the sun with room to relax. Located in a walkable neighborhood, you’re never far from Old Town’s best restaurants and shops.
- Sunset Cove: Trade your winter blues for ocean views! This 2BR/3BA waterfront rental features a modern kitchen, comfortable living spaces, and high-speed internet to support all your work needs. After hours, unwind on your private balcony, enjoy unbeatable sunsets, watch boats drift by, or take a dip in either the pool or the refreshing gulf waters. A serene retreat with easy access to everything Key West has to offer.
- Sunny Daze Cottage: This newly constructed, 2BR/2BA, Conch style home is ideal for exploring the island with friends or family. Filled with natural light, colorful accents, and Key West charm, the cottage is just steps from Duval Street but offers a peaceful hideaway when you want to focus. With a full kitchen, open-concept layout, and private outdoor seating, it’s a comfortable and stylish place to stay for a month—or longer.
- Sanctuary on South: If you’re looking for a quiet, luxurious escape right in the heart of Old Town, this 4BR/3.5BA private oasis with pool and patio lives up to its name. This elegant two-story home boasts a private pool, secluded outdoor space, and high-end finishes throughout. The Casa Marina district is synonymous with luxury and provides a tranquil respite not too far from the attractions on Duval Street.
Browse other monthly rentals.
Month long winter rentals book quickly
Winter is our most sought-after season—and for good reason. The weather is perfect, the calendar is full of cultural events, and our vacation homes fill quickly. Booking early ensures you get the home that fits your lifestyle, your work routine, and your dream of a warm-weather escape.
Let us help you settle in
Historic Key West Vacation Rentals offers more than just great homes—we offer personalized concierge services. Our team includes experienced, friendly and super knowledgeable specialists with a flair for elevating your Key West experiences. They’ll provide just the right personal touch to your experiences and assist you with your individual needs. Whether you need to arrange fishing charters, snorkel trips, kayaking and paddleboarding, ghost tours and more, our team makes it easy and can even arrange delivery of some transportation options to your vacation rental.
Concierge Services are available via phone at 305.296.1010, Option 5 or via email at [email protected].
Published on Sunday, June 22, 2025