Safely Winter In Key West

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Safely Winter in Key West with these five luxury boutique vacation rentals. Our Historic Key West Vacation Rentals are being sanitized in accordance with CDC guidelines and regulations put forth by the state of Florida and Monroe County, to ensure your health and safety. We are allowing adequate time between check out of the previous guest and check-in of the next guest for appropriate cleaning and sanitation. All surfaces in the property are cleaned and disinfected between each guest stay. All linens, dishware, and other service items available for use by guests have been washed and sanitized between each guest stay. Extra linens including throw blankets and decorative pillows have been removed and stored until further notice. Our enhanced cleaning protocols shine bright as the winter Key West sun. One thing that never changes is our commitment to our guests and to this wonderful Caribbean paradise we love to share with you.  

Southard Comfort - Nightly Rental 3 Bedrooms 2.5 Bath Sleeps 6

As you look around, you’ll be struck by the fact that this is a home designed for comfort and relaxation. One space flows right into the other, from the inside to the outside, from the living room to the kitchen.
You have 3 dining options, dine al fresco by the pool just through the French doors of the kitchen, dine at the granite center island, or in the formal dining room for family meals. The pool with a beautiful waterfall feature right off the living room for easy entertaining. Drive into your private rocked driveway and find parking for two vehicles.

Cloud 9 - Nightly Rental 3 Bedrooms 3 Bath Sleeps 7

From the cool gray tile, which mimics slats of hardwood, to the crisp white decor throughout, you’ll find Cloud 9 is the epitome of relaxation and comfort. A large and thoughtfully appointed gourmet kitchen with stainless steel appliances inspires creative meals and lively entertaining. The beautiful black bottom pool has plenty of loungers and outdoor spaces with seating to lure you into its magical spell. Park your car in the off-street parking spot provided, and you’ll never need to drive it at all during your stay.

Chavez House - Nightly Rental 3 Bedrooms 2 Bath Sleeps 6

Rock the morning away in the rocking chairs on the front porch as you watch the locals and tourists pass by. The covered lanai in the back of the home is perfect for reading a book, blogging about your Key West vacation, or enjoying cocktails as you make your plans for the evening. It's winter in Key West and poolside is the ideal place to be. There's an amazing pool with gorgeous, mature foliage and landscaping. Chavez House is dog-friendly. One (1) dog allowed, up to 25 lbs. Must be 1 year of age or older. Must be spayed/neutered. All vaccinations up-to-date. Please be advised some breeds are not permitted.

Villa Josine - Nightly Rental 4 Bedrooms 4.5 Bath Sleeps 8

Villa Josine boasts an incredibly private and spacious outdoor area - exactly the tropical environment you are looking for during your winter vacation in Key West. Relax by the sparkling, seasonally-heated pool with friends and family with a drink in your hand. Soak up the beautiful Florida sunshine poolside or dine outdoors under the shade on the back deck with seating for eight. A large gas grill allows you to host dinner parties and cook up the day's catch for all to enjoy. Enjoy off-street parking for one vehicle, an absolute "must-have" for guests who plan on driving down to Key West or plan on renting bikes, or a golf cart!

Potter's Cottage - Nightly Rental 2 Bedrooms 2 Bath Sleeps 5

This super cute home boasts all the amenities you would expect from a luxury hotel including a concierge and high-speed Wi-Fi. At the same time, you can live like a local by taking advantage of the fully equipped kitchen. Enjoy the privacy our tucked-away location affords smack dab in the middle of Key West’s oldest neighborhood. The first-floor French doors open to the private heated dip pool, covered lanai dining area, and ultra-comfy shaded outdoor lounge area.

Safely winter in Key West with any one of these five luxury boutique vacation rentals. Contact our team at Historic Key West Vacation Rentals. Our sunny and warm Vacation Planners are happy to help you plan your winter stay in our Caribbean paradise. Call or text us at 305.619.4880. You can also contact us via email at bookings@historickw.com.