When I was a kid, Labor Day signaled the end of summer. The end of freedom. The end of vacation season.

As an adult, Labor Day feels much different to me. The kids in our neighborhood attending year-round school have been in class for nearly a month, and families are looking forward to the three-week break that begins in mid-October. Some are planning time with their Grandparents at Walt Disney World, while others are perusing guidebooks for things to do in the mountains of Colorado.

In more and more parts of the country–from Wake County, North Carolina to Phoenix, Arizona–schools are moving to a mandatory year-round calendar. Year-round and home schooling mean a growing number of families with school-aged children can now enjoy vacations throughout the year without missing class.

While that may be bad news for individual travelers, honeymooners and couples who have always had more flexibility with their dates, it’s great news for vacation rental property managers and homeowners.

Property managers and owners likely keep records of the families that have rented their vacation homes. As a renter, I’m surprised that the property management companies that I use over and over again have never once pro-actively reached out to me.

Maybe they assume I’ll come back year after year or maybe they don’t need my business. I’m not sure, but what I am sure of is that if they reached out to me and asked, I’d tell them: “Yes, we vacation with small children during times of the year when other families might not.” Then, when they did have last-minute availability in what they considered their shoulder- and off-seasons, they might be able to entice me back with little effort.

Repeat business is all about connecting with customers and providing the best experience every time. If you have an unusual way of staying in touch with your customers so that you’re top of mind when they think of vacation rentals (especially during non-peak travel seasons), tell us about it in the comments below or email me.

In the meantime, welcome Labor Day! I look forward to planning our upcoming vacation, which we can sometimes take at half the price and definitely with half the crowds!

Posted: August 30th, 2007 under Vacation Rentals.
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Fun

A few years ago, my wife and I joined the growing number of people looking for vacation lodging alternatives to the typical hotel room. Frequent family visits to both New York and Europe sent us in search of better value and amenities (kitchen, bedrooms, fireplace, private hot tub, etc.) than hotels provided. More importantly it meant we could stay in neighborhoods away from the typical tourist areas. This led us through a series of vacation rentals including:

• A two-bedroom beachfront condo in Maui that provided a full kitchen and balcony;
• An awesome one-bedroom apartment in New York City with hardwood floors in the heart of Greenwich Village (a great neighborhood with no hotels);
• A long-term stay in a one-bedroom apartment in Paris’ Marais district (another great “local” neighborhood with no hotels)
• A beachside apartment in Dubrovnik, Croatia.

Profit

While planning for an extended trip to Europe, we were concerned about leaving our own house unoccupied for an extended period of time. Faced with two unappealing options; paying a house-sitter or asking friends to “look in” on our house, it finally dawned on us that we could rent out our house which would keep it “lived in” while we were gone, and, as a bonus, help to finance our vacation.

Without knowing what to expect, we wrote a full description of our house, photographed it, and began interviewing prospective renters. Everything turned out great with that initial rental, and our experiences so far, as both renters and “property managers”, have been overwhelmingly positive.

Challenges

Though positive, our experiences have not been without challenges. The primary challenges, both as renters and owners, are not what we initially feared; poor accommodations, nightmare renters, and the like. Instead, the problems encountered on both sides of renting vacation properties are around the process of renting a vacation home:

• Financial transactions: As both owners and renters, the financial transaction was awkward. Neither party was 100% sure of the other party, and fairly large sums of money were involved.
• Legitimacy: We were always a little nervous that perhaps there wouldn’t be an apartment, condo, or house there at all when we arrived!
• Locating the “right” rental: It was really hard to find the right place to stay due to the sheer number and disparity of vacation rental sites, many with extremely hard to use search capabilities.
• Availability: Even when we did find good rental prospects, the online availability data was frequently incorrect or altogether non-existent.
• Listing our property affordably: Listing our property on various vacation rental sites cost a flat $100-$300 per year, no matter how often it was rented, which adds up quickly when listing on multiple sites. Even worse, there didn’t seem to be any incentive for those sites to feature our property after we had paid our yearly fee. Finally, we had to pay the same flat fee for the two weeks per year that our house was available that others paid to rent their properties every day of the year.
• Targeting our listing’s visibility (and cost) to particular travel seasons: It was easy to rent out our house during high season, but that didn’t always coincide with when we were away. The sites we listed on offered no way for us to indicate that the focus of our $300 yearly fee should be on a certain period (or even a certain weekend) of the year. Our property received the same treatment on those sites regardless of whether it was our high or low season.

Overcoming these challenges provided the motivation for starting PickPackGo, with the aim of enabling more people to enjoy the benefits of renting vacation homes with fewer hassles. I’d love to hear other people’s comments on their experiences as both renters and owners/managers, as well as suggestions for improving the vacation rental marketplace.

Posted: August 23rd, 2007 under Technology, Travel, Vacation Rentals.
Comments: none

What would the first blog entry be without a big “Welcome to PickPackGo!”

Down the road, the PickPackGo team will be commenting here about travel and technology, the vacation rental industry, traveling with friends and taking multi-generational family vacations. We’ll also fill you in on new additions to our site and controversial (at least internally) features being developed.

By better connecting renters, property managers and owners in this forum and on our site, we believe renting a vacation property can become as mainstream as renting a hotel room.

Our founding team has worked together for the past 15 years on a wide variety of software products and services for Silicon Valley companies. We love building products that we can actually use ourselves and along the way, we’ve managed to find millions of others in the same boat.

We started PickPackGo because as renters and owners, we had similar experiences with vacation homes. Without a recommendation, it wasn’t easy to find a place or qualify a renter, and often we were amazed at just how long the rental process took. There had to be an easier way to do it, but we couldn’t find one, so we decided to build one ourselves.

We’ve pulled together a team of people and some great ideas to solve this problem. We want to make PickPackGo the best place to find, compare and rent a vacation property online. At the same time, PickPackGo will be the best place for property managers and owners to advertise and market vacation rentals. If you haven’t seen the site, here’s a quick look:

PickPackGo differs from other vacation rental listing sites in some immediately apparent ways (like our new website design and free listings). As we get going, we think you’ll discover many more reasons property managers and owners will benefit and renters will keep coming back. In the meantime, we invite you to take a look around and let us know what you think!

Posted: August 16th, 2007 under Family Vacation, Technology, Travel, Vacation Rentals.
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