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Key West Time
May 22nd
11:59am •

Key West Vacation Rentals Blog

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Give the Gift of Sunshine this Holiday Season


What nicer way to warm the hearts of your loved ones for the holidays, than to give them a Key West winter vacation in the sunshine. The winter and early spring months in sub-tropical Key West remind many of the best summer days in the northern climates. Pull out that bathing suit, shorts, linen shirt and flip flops, and wrap them up with a reservation for a Key West vacation rental. Vacation Homes of Key West is here to help you find the perfect place to stay … see you in the sunshine!





Thanksgiving in a Key West, FL Vacation Rental

In honor of the Thanksgiving holiday, Vacation Homes of Key West (VHKW) is showcasing a few of our favorite kitchens and dining rooms from homes in our exclusive vacation rental inventory. If you love to cook, imagine the fun you can have preparing Thanksgiving dinner with your family and friends in the privacy of ‘your own home’ while on vacation. Our vacation rentals offer guests a chance to feel at home, while away from home, and preparing meals and eating together while on holiday is one of the nicest ways to make memories for a lifetime.

This illustrates one of many benefits that comes with staying at one of our Key West vacation rentals vs. a hotel room. This glimpse of gourmet kitchens and wonderful dining areas is just a taste of the many special features offered in homes available for rent by VHKW. Most of these homes are reserved 6 months or more in advance of upcoming holidays, so it’s not too early to make plans soon for next holiday season. Cheers!

Tropical ~ Tranquility



Key West Wabi Sabi ~ Weekly Rental


Seaport Treasure Estate ~ Monthly Rental



The Caroline House Estate ~ Weekly Rental

Offering Two Full Kitchens & Large Formal Dining Room



Key West Film Festival 2014

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Tonight Nov. 12th @ 6:00 p.m. the Key West Film Festival kicks off with a celebration at the Southernmost house. This is fallowed with a screening of Dumb & Dumber @ 8:00 P.M. on the beach behind the Southernmost cafe. Sound like a good time? Thats only the start, with the event running through the weekend. This Key West cultural happening is a must for visitors and locals alike.

Described As:
“Creativity, Diversity, Sustainability, and Beauty.
The Key West Film Festival is an annual celebration of film and filmmakers, set to take place November 12-16, 2014

Showcased films will represent a broad cross-section of categories that offer a broad set of opportunities for filmmakers, both aspiring and established, to show off what they’ve got.

By combining the best of the world of film with the best location in the tropics, we feel confident that this will be an event that you won’t want to miss. Whether you join us as a showcasing filmmaker, an audience member, a volunteer, or a partner, there’s a special place for you at KWFF 2014 and we look forward to seeing you here!”

You can buy tickets in advance HERE. Most of the films will also be shown individually at Tropic Cinema. See the complete schedule by clicking the link below.


Our Newest Monthly Rental

Little Digs Key West

Meet ‘Little Digs Key West,’ our newest monthly vacation rental. Diminutive in size but huge in style, ‘Little Digs Key West,’ authenticates how ‘big things’ really do happen in small spaces. Key West was centuries ahead of its time in the modern day ‘tiny house movement.’ Long before small living spaces became a fashionable ecological trend, living on a little 2 x 4 mile island, ipso facto, spawned some beautiful and luxurious little dwellings.

Painted periwinkle blue with white trim, the curbside presence is a delightful ‘Old-West-Meets-Caribbean.’ In aesthetic contrast to the gingerbread cottage next door, this studio property sits in colorful harmony with other nearby dwellings. In our slide show, ‘Little Digs Key West’ is the pint-size house to the right as you face the property, displaying the popular 1900’s western-style false-front extension at the roof-line.Little Digs Monthly Vacation Rental