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Housesitting: A Fun Way to Travel the World on a Dime

Here's how it works and what to watch out for


When boomers want to escape the 9-to-5 workplace grind and the demands of caregiving for parents and/or kids wane, many dream of traveling. A recent survey found that 59 percent of retirees look forward to exploring new places during the second part of their lives.
 
But people soon realize the cost of traveling for extended periods can be daunting, especially when living on a reduced income. That's why housesitting has become an increasingly popular way to live away from home without the steep pricetag.

(MORE: Boomer Travel Trend: Couchsurfing for Grown-Ups)
 
What is Housesitting?
 
Housesitting entails taking care of someone else’s property (and possibly their pets) in exchange for your stay.
 
In the past, it typically took the form of informal arrangements between people who knew each other. Less commonly, individuals or couples were hired by professional agencies that employ housesitters at a salary, usually for long periods of time.
 
Over the past decade, though, technology has spawned a new model of unpaid housesitting, with websites connecting homeowners and potential sitters for jobs lasting weeks or months at a time.

(MORE: Home-Swapping: Slash Your Travel Costs and Live Like a Local)
 
This peer-to-peer model is part of the same “sharing economy” that laid the foundation for successful businesses such as Uber and Airbnb.
 
Retirees are leading the pack among housesitting-site users. The sites are also popular with people who are semi-retired or have location-independent (portable) careers. “Without a doubt, other housesitting networks would agree that ‘silver surfers’ are a trusted mainstay of our customer base,” says Lamia Walker, founder of HouseSitMatch.com.
 
Why Housesitting Isn't Entirely Free
 
Housesitting isn’t a totally free ride. While it can offer substantial savings on accommodations, housesitters still must pay for their food, airfare and transportation costs. Since it can be difficult to coordinate sequential jobs and there may be gaps between them, some housesitters maintain a home base, incurring additional expenses such as mortgage payments, rent and utility bills.

(MORE: 8 Ways to Combat Outrageous Hidden Travel Fees)
 
The benefit to homeowners is that when they're visiting relatives for long stays, residing at their second homes or vacationing elsewhere, they can feel secure that their home is taken care of and less vulnerable to burglaries thanks to the housesitter. (Homeowner insurance policies vary but some don’t extend coverage to homes unoccupied for 30 days or more.)
 
As a condition of many jobs, housesitters are expected not only to take care of the routine maintenance of the house and property but also watch over any pets or handle other responsibilities requested by the homeowner.
 
In fact, devotion to pets is a major factor propelling the growth of housesitting. Many pet owners see it as a way to avoid long kennel stays for their animals, says Andy Peck, director of TrustedHousesitters.com, one of the largest sites with over 500,000 visitors and close to 1,500 housesitting listings each month.
 
“Many people housesit, too, out of sheer love for pets, especially single travelers or those who don’t have a pet because of personal circumstances,” says Peck.
 
The Intangible Rewards of Housesitting
 
In anticipation of their first foray into housesitting, retirees Colleen and Rick Ray (now 56 and 67, respectively) put their house up for rent in California and placed all their belongings in storage. In May 2012, they flew to the historic city of Merida, Mexico and spent two months caring for two dogs and four cats in a lovingly restored colonial home. During their stay, they visited Mayan ruins and old haciendas and got a taste of local food and culture.
 
“It was a cost effective way to stretch our travel budget and allowed us to spend a longer period of time in a place that interested us,” says Rick.
 
After that rewarding experience, they watched over nine other houses for periods ranging from three weeks to more than two months — in places as diverse as Seattle, Wash. to Edinburgh, Scoland to Kauai, Hawaii.
 
The couple especially enjoyed the relationships they developed with homeowners and their friends and neighbors. “We’ve been invited to neighborhood parties and dinners, and even went Christmas caroling with neighbors in Kauai last year,” Rick says.
 
During their 10 years of housesitting, a couple from the UK, Angela and John Laws, now 68 and 70, have traveled to over five continents.
 
“We live like locals, not vacationers,” says Angela. “The lifestyle allows us to indulge our passion for travel, pets and having new adventures in a way we could not otherwise afford.”
 
Landing a Housesitting Gig
 
Each housesitting site operates slightly differently (see a list of some popular sites below) with membership or registration fees ranging from $10 to $90 per year (listings placed by homeowners are typically free). The sites also differ in terms of the regions covered and types of properties listed.
 
Once enrolled, housesitters submit online profiles describing themselves and their experiences. They're also advised to provide a criminal records check and references.
 
Then they evaluate what’s available from, and required by, homeowners.
 
The sites typically let registered users sign up for daily email alerts announcing new opportunities. “We would encourage people to use these alerts because good opportunities require a quick response,” says Rick Ray, noting that competition can be keen.
 
After an online match is made, the parties often use Skype or Google Hangouts to communicate (by phone or video conference), exchange photos, get to know each other and ask questions before hammering out a written agreement outlining roles and responsibilities.
 
Australian Ian White was one of the first to set up a housesitting matching service almost 14 years ago. Like some others, his HouseCarers.com site offers users templates for preparing written agreements.
 
Look Before You Leap
 
Peck, of TrustedHousesitters, calls these arrangements a “win-win dynamic,” benefiting both parties. “They are also perfect for housesitters hoping to avoid cold winters, check out potential retirement options or take a ‘gray year’ before retirement,” he says.
 
While the idea of housesitting is alluring, it isn’t suitable for everyone.
 
“Housesitting requires someone who is flexible and able to adapt to new circumstances, places and people with a sense of ease,” says Colleen Ray. “People want you to temporarily step into their shoes and take care of their homes and pets in the same manner they do, and that may be different from the way you would do it.”
 
Because there are no regulations governing this relatively new “cottage industry” that crosses international borders, even with due diligence, housesitters (and homeowners) must be willing to take some degree of risk. As with other sectors of the sharing economy, the strengths and pitfalls of housesitting are built on a foundation of trust among strangers.
 
Matching Services:

Housesitting Blogs for Inspiration:

Irene S. Levine is a psychologist, lifestyle and travel journalist, and member of the Society of American Travel Writers who produces MoreTimeToTravel.com, a blog offering advice and inspiration for travelers over 50.

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