Key West Winter Rentals

Choose from these five Key West vacation rentals for your 2021 winter getaways. Who wants to shovel snow when you can open up windows, doors and sometimes entire walls to let the sunshine in.  Should you spend winter inside or outside? Winter in Key West and you can do both. Historic Key West Vacation Rentals will show you how to enjoy a Caribbean winter getaway.

Steamplant 208 is a two level, 5 Star luxury residence with breathtaking panoramic views of Key West. Luxury amenities include a private rooftop twrrace with an elevated pool, a parking garage, a private elevator, and it's pet-friendly! There's a Viking Chef’s Kitchen for the culinary enthusiast of the family or for those traveling with a personal chef. Use the free high speed WiFi to stream your favorite music on your BOSE Soundtouch Wireless Music. Traveling by yacht? The residences at the Steamplant offer boat slips that can accommodate vessels from 19 feet to 195 feet. Available for January and March 2021.

Cayo Limon features all the outdoor amenities you could ask for during your pet-friendly Key West vacation: a private, seasonally heated pool, a covered outdoor eating area, a large gas grill, an outdoor shower and plenty of poolside seating. The home also features a front porch and a balcony off the spare bedroom. There is designated parking for two cars! Available for January 2021.

The Historic Chavez House on Margaret Street is a pet-friendly, two story eyebrow house that was built in 1870 and is on the National Register of Historic Places. Newly renovated and very well appointed, it provides fine linens, gorgeous furniture, ultra comfortable mattresses, and a cool and calming color palette. At 1415 sq ft this home comfortably sleeps 6. Enjoy a dip in the new private pool and work on your tan on the large exterior deck. Individual weeks are available during January and February 2021 and the entire month of March is open!

Inn Cogneato is a newly renovated beautiful pet-friendly home located in one of the oldest parts of Historic Key West. The brand new saline pool measures 14 x 8 feet, is 5 feet deep, has an in pool bench for sitting. This pool is heated in season and has a beautiful custom waterfall. There is a patio and propane grill for grilling your Key West catch of the day. Available for February and March 2021.

The Bohemian House is a restored historic home full of delightful surprises! This home is placed on the National Registry of Historic Places and proudly bears the star of the Historic Florida Keys Foundation, and the Old Island Restoration Foundation Key West House Tour plaque. it has a private salt water poolwith plenty of outdoor shaded seating for lunches on the lanai, Adirondack chairs for soaking up the sun and even a hammock are a pure delight! There is even a propane grill for your grilling your catch of the day. It comes with covered parking for one car and it's pet-friendly, too! Available February 2021.

A winter getaway to Key West is the perfect way to stay and play, remote work and learn, and to let the sunshine into your life. Our homes 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.

How do you get started? Reserve your favorite right on our website or ask our sunny and warm Vacation Planners for recommendations. Enjoy these five Key West vacation rentals for your 2021 winter getaways!