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February 23rd
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Key West Vacation Rental Blog

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Vacation Homes of Key West (VHKW) News. We are on your favorite social networks. Friend Us, Like Us, & follow Us for updates on the latest additions to our vacation rental property inventory, and beautiful pictures of and information about Key West.

New Vacation Rental Properties

We are excited to introduce our newest additions to our private vacation rental inventory. At VHKW we like to offer something for everyone, and these new properties have a lot to offer. Please look over the details below and don't hesitate to contact us about availability and pricing.


Windward Park Monthly Rental - 2BR/2BA

This monthly vacation rental is located in the Windward Park development on Truman just a block off Duval Street. The grounds are private and feature a large shared pool. Call or email for more details.

Shipyard Weekly Vacation Rental - 2BR/1BA

This condo makes for an affordable home base for those looking to explore the area. This location in Truman Annex is just off Southard Street and the entrance to Truman Waterfront & Fort Zachary Taylor. Park the car in the provided space and enjoy the shared pool after a day walking Duval. For more information please call or email.

VHKW ~ Vacation Homes of Key West Celebrates 21 Years With New Logo

Over the past 21 years, we have grown and continually evolved as a premier locally owned and operated boutique company in the vacation rental industry. Our new streamlined logo was inspired by our deep roots in Key West, our long-established position on the island, and the need to differentiate our company from other Key West vacation rental businesses. Read More

Key West Lobster Fest August 9th - 12th

22 Years of celebrating the delectable lobster. This festival celebrates the islands favorite crustacean. Featuring a street festival with vendors from near & far. Read More

Hemingway Days Celebration 2018

38 Years of celebrating Ernest Hemingway by gathering in Key West for a one of the most unique look-alike contests you can imagine. Read More

10 Things To Do When It Rains In Key West

When it rains, it pours in Key West. But no worries. There are lots of fun things to do around the island that will keep you entertained inside! Read More

Lazy May Days In Key West

What to know what to do in the Off-Season in Key West? This tiny island plays host to countless festivals along with musical and cultural events that out number many more well known destinations. Rental rates are less expensive too, so it's a great time to same money too! Read this and get some ideas for a last minute trip to our tropical paradise. Read More

The 36th Annual Conch Republic Independence Celebration 2018

Long Live the Conch Republic! For 36 years we have been celebrating our unique culture that makes us different from any place on the planet. Come and experience our history with our week-long Independence Celebration, that takes place at various locations around the island, on land and sea. Read More

2019 Monthly Vacation Rental Availability

Next winter's 2019 Key West rental season may seem a long way out, but many of our monthly vacation rentals have been re-booked by this years customers. Our rental agents have spoken with current guests and have confirmed what properties are available in January, February and March of 2019. Now is the chance to reserve these properties. Read More

Key West Songwriters Festival 2018

The Key West Songwriters Festival is the largest of it's kind. The island is filled with incredibly talented musicians and songwriters. Good to book a vacation rental in advance for this popular event. Read More

Hurricane Irma Takes Some Trees but Not Key West Spirit

Mother nature is incredibly resilient, and as refreshing rains followed Hurricane Irma, green leaves began to quickly sprout from the trees. At first the skyscape seemed nearly barren with trees down and leaves blown off by the storm. But already the canopy is green and flourishing. Read More

The Holidays Come To Key West

Key West is getting into the Holiday Spirit with decorations and lights going up around the island. The Key West Historic Seaport has done a wonderful job of lighting up the Harbor Walk. There are wreaths and red ribbon string up all over the island. Strolling down Duval St. you can find the lampposts decorated with holiday spirit. Read More

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Bad Boy Burrito is a favorite locals walk-up eatery. Located on Simonton Street, not far from South Street and the Southernmost Point of the USA.
This gentle Governor's Retreat in the Key West Meadows is an immaculate luxury vacation rental cottage in an elegant and very quiet garden setting for those with discerning tastes. The property is the perfect Key West setting for rest, relaxation, and rejuvenation. It is ideal for the person of distinction who is looking for the perfect home-away-from-home to set up a mobile writing or work office for a Winter, Spring, or Summer season. Governor's Retreat | 2 Bedroom Monthly Vacation Rental
Originally built in the late 1940's, this unique home has been completely renovated to a state of understated elegance with attention to every detail. The property is situated to create a very private compound which incorporates two neighboring cottages on the opposite end of three lots. Governor's Retreat | 2 Bedroom Monthly Vacation Rental
This genuine Key West combo of our Private Pool Garden Villa plus a classy private studio cottage that adjoins the property next door, can be your very own get-away for a week or more. When rented together, we call the property the Lazy Iguana. Off-the-beaten path of most tourist homes and harkening back to the last bastion of Key West bohemia, the Lazy Iguana vacation rental is a fixture of the remaining literary old guard in Key West. With this property you will enjoy beautiful authenticity th
Located just off Duval on Catherine Street, Key West Dreamin', is an important representation of how the history of our architectural culture is tied to the boom of the cigar industry in the late 1800's. Today the neighborhood is part of Key West's historic preservation district. So the front facade of the houses look very similar to how they originally looked, giving the wonderful effect of maintaining the charm of the neighborhood. Key West Dreamin' | 2 Bedroom Nightly Vacation Rental
Key West Dreamin' vacation rental is a private historic home that is beautifully furnished and offers all the amenities of a luxury accommodation situated in a genuine Old Town Key West location.Key West Dreamin' | 2 Bedroom Nightly Vacation Rental
Entrance to the Bahama Village neighborhood in Key West on Whitehead St., is announced with this beautiful Caribbean style sign. Creative shops and wonderful restaurants (like Blue Heaven) are found down this charming road.
Key West has long been loved for its playful spirit, forever attracting all genres of fun-loving artists, musicians, and writers. In recognition for the island’s historical humor, we have fondly named this beautiful upscale home, On Hemingway’s Rounds. Paying tongue-in-cheek homage to Papa’s established daily trail from home-to-bar-and-back-again, the owner of this elegantly renovated historic house placed a discrete sign, amongst a trumpet vine, that whispers ‘Hemingway Pissed Here.’ And you kn
The story of the The QM ~ Quartermaster House Key West vacation rental, begins in 1925 during a time of historic proportions for the Keys. Imagine for a moment, it was the roaring 20’s and the first Florida land boom was in full swing. The popular Ford Model T was sparking visions of driving to Key West, making it inevitably more reachable, and the momentous Federal Wrecking Act was passed which banned foreigners from salvaging ships in the Florida Keys. The QM ~ Quartermaster House Key West | 3
Porch sitting can easily become an everyday pastime at Belle Maison Du Port | 3 Bedroom Monthly Vacation Rental