3 reasons to make an impromptu winter escape to the Florida Keys

1. Dreaming On Duval

Escape to the heart of Key West with Dreaming On Duval, a spacious Old Town retreat that feels like your own private haven just steps from the iconic Duval Street. This 5 BR, 4.5 BA home comfortably sleeps up to 10 guests, making it ideal for family gatherings, multi-generation trips, or groups of friends looking for space, comfort, and convenience.
Why it’s amazing
● Location, location, location. Walk everywhere from your front porch, from shops and galleries to top restaurants and lively nightlife.
● Private pool and outdoor living. Sip cocktails under the stars or unwind after a day of island exploration in your own backyard oasis.
● Multiple indoor and outdoor gathering spaces. Spread out with ease whether you’re planning game nights, family dinners, or simply relaxing together.
Available dates:
●       Jan. 20-27
●       Feb. 1-9
●       Feb. 21-25
Secure this gorgeous home for your warm-weather escape and experience the best of Key West right where the action is.

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2. Cloud 9

Make your winter warm and bright at Cloud 9, a delightfully charming nightly rental nestled in historic Old Town. With 3 BR and 3 BA, this home is perfectly suited to families, groups of friends, or remote workers who want both proximity to Duval Street and the privacy of a private pool and courtyard retreat.
The highlights
● Private pool & outdoor lounging. A refreshing amenity for unwinding after beach days or sunset sails.
● Flexible indoor/outdoor spaces. Multiple seating areas, balconies, and patios mean everyone can find their perfect spot.
● Steps from local favorites. Right in Old Town, you’re close to cafes, shops, and historic charm while still feeling tucked away in your own island hideaway.
Available dates:
● Jan. 13-15
● Jan. 19-22
● Feb. 7-21
Whether you’re extending winter break or sneaking in a long overdue getaway, Cloud 9’s mix of comfort and convenience makes it a standout choice.

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3. Southard Comfort

If you crave a blend of authentic island living and welcoming comfort, Southard Comfort delivers. This 3 BR, 2.5 BA nightly rental captures the spirit of Key West with thoughtful indoor-outdoor design, a cozy patio and private cocktail pool, and an easy stroll to the historic seaport and Duval Street.
Why it stands out
● Indoor-outdoor living at its best. French doors open to patios and a refreshing pool that diners, swimmers, and sunset loungers alike will love.
● Well-appointed kitchens and gathering spaces. Cook dinner together after a day at the beach or fill the dining table with fresh local seafood prepared just the way you like.
● Quiet Old Town charm. Situated north of Truman Avenue, you’re close to key attractions while enjoying serene neighborhood vibes.
Available dates:
● Jan. 20-23
● Jan. 29-Feb 2
● Feb. 7-19
Southard Comfort is ideal for those who want a home-like experience with all the perks of island escape just a short walk or bike ride from everything Key West has to offer.

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Why book now?
Winter in Key West doesn’t just offer better weather and fewer crowds. It’s a season of experiences, from festivals to art showcases and live music under starlit skies. The longer you stay, the deeper the island becomes part of your rhythm. Historic Key West Vacation Rentals’ concierge team is available to help you plan it all. Grocery provisioning, sunset sails, golf cart or bike rentals, and curated recommendations that make every stay feel personal.

Ready to escape the cold?
Choose your winter dates, claim one of these spectacular homes, and start dreaming about sunshine, sea breezes and Key West life lived slowly. Find out more at www.historickeywestvacationrentals.com.