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Key West Time
August 13th
4:26pm · 90°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

Be on the lookout for these “sea cows” and their calves. They are all over the place in springtime. #manatees #keywest #florida #island #sealife
One of our favorite neighborhoods in Key West is the Historic Seaport. ⛵️🚤🛳
Key West “sorta” has seasons. 🐣 Case in point: spring chickens! 🐣 Keep an eye out for these little balls of fluff! 🐣 #keywest
Island charm meets modern elegance at Uptown Key West Luxury Villa. #keywest #island #livingroomdecor
🌸 There’s lots of reasons to skip the hotel and rent a home in Key West instead. Perhaps one of our favorite reasons is the access to a full kitchen. 🌴 Don’t underestimate what a difference it makes to be able to wake up and brew your own coffee without having to wait for room service. Or fix a quick snack before heading to the beach. Or heat up some leftovers from your favorite Key West restaurant. 🐬 There’s no doubt about it— the kitchen is the MVP of your Key West rental home.
A fun beach sign in Key West that details the distance from other locations. #keywest #signs #beach
Equal parts crispy and juicy, the fried chicken at Dion’s Quik Mart is a Key West local fave. 🍗 Located all up and down the Keys from Florida City to Key West, Quik Chik is a perfect road trip snack too. 🍗 At first, you may think gas station fried chicken is no big deal… but trust us. You’ll want to try some when you’re here. 🍗 #keywestflorida #friedchickenrecipes #localbusiness
On April 23, 1982, frustrated by a US Border Patrol check point that was a huge inconvenience, the “Conch Republic” was formed. 🌴 They quickly declared war against the US, promptly surrendered, and then applied for $1 billion in foreign aid. 🌴 Each year, we celebrate our “sovereign state of mind” and this year marks the 40th anniversary of “seceding where others failed.” 🌴 #conchrepublic #keywest #islandlife