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Key West Time
April 19th
3:52am •

Key West Vacation Rentals Blog

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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


Trip Insurance

Although this Hurricane Season has been quite mild for the region, it is always a good idea to be prepared. People booking for next years season might consider the insurance. Here is a great write up from a previous article.

When I got the official “City of Key West Hurricane Guide” this week, I tried to embrace it as a ‘friendly reminder.’  I appreciate the notation from Mayor Cates that says, “This time of year we must face the fact that although we live in paradise, there’s a price we pay for that luxury, and it’s called Hurricane Season.” This gentle warning brings back vivid memories of recent hurricanes that have come through Key West starting with ‘Hurricane Georges’ in 1998. Thoughts flood through my mind of boarding up houses, staring at the weather channel to see if we’re ‘in the cone,’ deciding when and if to evacuate. Then the aftermath of long power outages, large fallen ficus trees, flooded out rooms, and the labor of ‘neighbor to neighbor’ clean-up.

Key West has always managed to get things cleaned up in a very short order.  And a ‘silver lining in the storm events’ in Key West is they awaken a deep sense of community spirit and everyone seems to pitch in and help one another. But, regardless of our hometown compassion, for those of us who have been through enough hurricanes, we know how big the price can be in terms of stress as well as dollars.

So June is here and now it begins again. We all hope and many pray that we don’t have any storms this year, and that if we do they are ‘mild.’ But we also know that we can’t just ‘wish the storms away.’  We must get our act together, get our hurricane preparedness checklists together, and each of us needs to begin thinking about making our own individual and business plans.

Being in the vacation rental business brings on it’s own unique challenges during hurricane season. Summer vacation brings many families, couples, and friends together in vacation rental properties where they can relax and enjoy private down time. The beaches are beautiful in the summer, the water is perfect for swimming, the fishing is outstanding, almost all Key West restaurants, activities, and attractions are open for business … plus the summer time brings discounted off-season rates!  So what happens with vacation rental guests on a Key West vacation, and a hurricane starts pointing our way?  They’ve paid their money to be here, and some just don’t want to leave and lose their vacation investment.  So now what?

The hard reality is that in the event of an impending storm, we must do our best to protect our guests and our properties, and follow the official edicts for evacuation. When a ‘hurricane watch’ is declared, properties need to be secured with storm shutters or plywood and outdoor furniture needs to be stored. And when a tourist evacuation is officially ordered, our guests must pack up and leave just like all the other tourists.

In all my years of being in this business, I have had a handful of guests insist that they want to “stay and experience a hurricane.” To which I reply, “you’d be boarded up in the house, there won’t be any air conditioning during and after the storm, there won’t be any ice, businesses will be closed, and there may be a huge mess to clean up afterwards.” For most people, once they think about actually being uncomfortable and inconvenienced, they pack up and leave. So how do we address the loss of their vacation rental investment and offer some peace of mind?  There is actually a simple and affordable solution – Travel Insurance.  Specifically, ‘Trip Cancellation and Interruption Insurance.’


In the vacation rental business,  most guests rent vacation properties well in advance of the trip, and most rental companies have no cancellation and no refund policies. While at first thought, a no refund policy may seem tough, it’s important to recognize the fact that property owners and vacation rental agencies that provide and maintain vacation rentals, depend on this business income to pay for property mortgages and expenses for their livelihoods.  The good news is that travel insurance, specifically “trip cancellation and interruption insurance” guarantees guests a refund, while at the same time guarantees property and business agencies their expected income.  Of course this win-win benefit trickles down to mean that Monroe County will collect expected bed taxes and the State of Florida will receive expected sales tax.

Some people are still not aware that they can purchase travel insurance to cover a lost or interrupted stay in a vacation rental house that has been prepaid and is non-refundable. By purchasing travel insurance, tourists can recover their loss through their travel insurance policy. Purchasing ‘trip cancellation and interruption insurance’ is especially important for travelers planning summer vacations anywhere on the Eastern seaboard and the Caribbean during hurricane season.  And please note …  travel insurance must be purchased in advance and cannot be purchased when there is already an impending storm.

Over a decade ago, I had a few people publicly argue with me for ‘sticking to my guns’ about our no-refund policy for lost vacation rentals due to impending storms. With the onslaught of hurricanes  since 1998, most folks have come to understand how important the expected income from vacation rentals is to our tourist industry.  Now the possibility of our valued tourists losing their investment can be protected with travel insurance.

Vacation Homes of Key West is affiliated with ‘Travel Guard International,’ a large reputable travel insurance company. Our website provides a link to the Travel Guard website to ease the process of purchasing insurance.  During our affiliation we have been impressed with the ease and expediency in which our vacation rental guests have been able to recover financial losses.  Why risk losing your vacation investment when you can easily and affordably protect it?

More Trip Insurance Information Here

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Quantum Key West International Yacht Race Week 2015

KWR0057 Vacation Homes of Key West is getting excited for the 2015 international Key West Yacht Race Week. This annual event takes place January 18-23. The events will kick off with sailing vessels ranging in size from 23 to 72 feet. The boats will compete in the waters off Key West for their chance at the win. Last year provided some blustery racing conditions  with seas and wind making it an incredible show for spectators. VHKW looks forward to seeing the yachtsmen in town. Below is a list of the available rental properties for the event.