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.