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Key West Time
October 16th
10:21pm · 82°F

Key West Winter Rentals

The weather has been perfect for bike riding around Key West. The sunny skies and mild temperature make for ideal cruising conditions. Come see what winter in Key West looks like and take in the sites with VHKW. Then book your stay in a Key West vacation rental. It is sure to warm up your winter!

There are a select few monthly rentals available for the remainder of the season. These rentals are available for the dates listed below. Please contact Vacation Homes of Key West for more information and pricing. See all Vacation Rental Specials here.


Villa On The Green

Available March 2017 - 3 BR / 2 BA

Enter the Villa on the Green vacation rental, and take-in the mid-century decor of bright white tropical wicker and bamboo displayed in the sky-blue great-room. Pastel floral patterns and wispy white café curtains, create a timeless island style that is a refreshing contrast to the abundance of exotic ‘Tommy Bahama’ rattan décor found in the tropics today. See more about staying in this monthly rental here: Villa On The Green

Seaport Treasure Estate

Available April 2017 - 6 BR / 6.5 BA

The Seaport Treasure Estate is available for the month of April, 2017. An exceptional degree of creativity is displayed in this detailed renovation that artfully intertwines 3 dwellings: two unique classic 2-story 1900’s wooden houses – a main ‘family house’ and a separate ‘master house’ – plus a private guest cottage. All three are melded together with an exotic outdoor focal point, a spacious resort-style swimming pool courtyard. See more about staying in this monthly rental here: Seaport Treasure Estate

Avant Garde Luxury Home

Available May 2017 - 2 BR / 2 .5 BA

Extraordinary upscale renovation. Traditional Key West architecture is flawlessly melded with a minimalist contemporary interior. Exotic and calming, this unique home is offers all the best features of classic and modern island living. See more about staying in this monthly rental here: Avant Garde Key West Luxury Home

Latest Pins On Pinterest

Governor’s Retreat is a monthly rental home in Key West, FL. #cottage #facade #facadedesign
Our favorite beach in Key West is Fort Zachary Taylor Beach, located inside a state park that’s filled to the brim with local Civil War history. #beach #history #beachvibes
This super-fun spash park is fun for kids and adults, and cools you down on a hot day in the Florida Keys. VHKW has lots of rental homes close to the park. #florida #splash #waterpark
For fishing fans, few places match the magic of Key West. #fishing #fishingislife #keywestflorida #fishingaddict
These two kayakers enjoy a magical Key West sunset. #keywestflorida #sunset #sunsetphotography #kayaking
Rob Oneal is a brilliant local photographer who captured this rare, beautiful view of the Key West Lighhouse. #keywestflorida #lighthouse #photography #photoshoot
A gorgeous shot from above of Key West, Florida, with the White Street Pier in clear view. #keywestflorida #island #islandlife #ocean #airplane
This charming vestibule is what you see when you walk through the front door at Key West Poolside Loft. Climb the stairs to the bright and open living and dining area!
This calming space is the perfect place to recharge at the end of the day.
There's space for three to sleep in this colorful and comfortable sleeping loft.