Let's be clear: housesitting in retirement can be wonderful. You've worked for decades. The kids are grown. You have flexibility that employed sitters don't. Homeowners actively seek retired couples because you're reliable, experienced, and available for longer sits.
But the lifestyle articles skip the hard parts. And if you're considering making housesitting a significant part of your retirement, you need the full picture.
The Health Emergency Nobody Plans For
“My husband had a heart episode during a sit in rural France. We were 40 minutes from the nearest hospital. Our travel insurance covered the medical bills, but nobody covers the homeowner who had to cut their trip short, or the guilt of leaving their animals with a stranger.”
— Forum post, experienced sitter, 68
When you're 35 and housesitting, health emergencies feel abstract. When you're 65, they're statistics. The older we get, the more likely something will happen — and it will happen far from home, far from your GP, potentially somewhere that doesn't speak your language.
What experienced retired sitters actually do:
The hard truth:
If you have a serious health condition, full-time international housesitting may not be realistic. Not because you can't manage your condition — but because you've taken responsibility for someone's home and pets. That obligation doesn't pause for emergencies.
“You Don't Have a Home Anymore”
This hits retired housesitters differently than younger nomads. You've spent 40 years building a life somewhere. You know your neighbours. Your GP knows your history. Your grandchildren know where Grandma lives.
“We sold our house and went full-time. Eighteen months in, I had a moment in yet another stranger's kitchen where I thought: I don't know where I live anymore. Not in a romantic way. In a genuinely unsettling way.”
— Retired couple, former full-time sitters
Some people thrive without a fixed address. Others discover they needed roots more than they realised. The problem is you often don't know which you are until you've already sold the house.
Questions to ask before going full-time:
Family Who Don't Understand
Your adult children expected you'd be around for grandchildren. Your siblings thought you'd finally have time for family gatherings. Instead, you're in Portugal caring for someone else's dogs.
“My daughter said 'you're choosing strangers' cats over your own grandchildren.' It wasn't fair, but I understood why she felt that way. We'd missed two birthdays and a school play.”
— Forum discussion on family relationships
The expectation that grandparents will be available — for childcare, for holidays, for emergencies — is deeply ingrained. Housesitting challenges that assumption, and not everyone in your family will adjust gracefully.
What helps:
- Block out family time in advance — no sits during key dates
- Invite family to visit during sits (if homeowner allows)
- Have the conversation early — not after you've already committed
What doesn't:
- Assuming they'll understand because you “deserve” this
- Guilt trips in either direction
- Expecting video calls to replace being there in person
The Sits That Work vs. The Ones That Don't
Not all sits are equal, and what works for a 30-year-old backpacker won't necessarily work for you.
Sits that tend to work well:
- Longer sits (2-4 weeks minimum) — less packing/unpacking
- Single-storey homes or good accessibility
- Older, calmer pets (not puppies requiring 5am walks)
- Good medical facilities nearby
- Walkable location or car provided
Sits to approach carefully:
- High-energy dogs requiring long daily walks
- Remote locations with no nearby services
- Large properties with extensive maintenance
- Multiple young pets
- Back-to-back sits with no recovery time
“We learned to say no. That beautiful farmhouse with the three border collies? Not for us anymore. Now we look for calm cats, comfortable beds, and a pharmacy within 20 minutes. Less Instagram-worthy, but sustainable.”
— Retired couple, housesitting for 4 years
The Real Financial Picture
“Free accommodation” sounds wonderful until you do the maths properly.
What “free” still costs:
Platform fees
THS: ~$200/year + new per-sit fees
Travel insurance
$1,500-3,000/year for comprehensive senior cover
Travel between sits
Flights, trains, rental cars add up fast
Gap accommodation
Hotels/Airbnb between sits
Storage
If you've given up your home: $100-300/month
The stuff you keep paying
Phone, subscriptions, health insurance
One retired couple tracked their expenses carefully for a year of full-time housesitting across Europe. Their conclusion: “We spent about the same as we would have at home, just differently. The savings were real, but not as dramatic as we expected.”
Paid housesitting changes the equation:
At $400-600/week for paid sits, you're not just saving on accommodation — you're earning. For many retired sitters, this is the sustainable model: supplement your pension with paid work rather than trying to survive on “free” sits that aren't really free.
The maths: 30 weeks of paid sits at $450/week = $13,500/year. Not a fortune, but meaningful supplementary income, doing something you actually enjoy.
Who This Actually Works For
Housesitting in retirement works well if you:
- Are genuinely healthy and mobile (not theoretically)
- Have family buy-in, or limited family obligations
- Can handle uncertainty and last-minute changes
- Have enough financial cushion for emergencies
- Find purpose in caring for animals (not just free rent)
- Travel as a couple, or are comfortable being alone
It may not work if you:
- Have health conditions requiring regular specialist care
- Have grandchildren you want to see grow up
- Need routine and predictability to feel secure
- Are doing this primarily to escape something
- Haven't tested it with shorter sits first
- Partner isn't equally enthusiastic
A More Sustainable Approach
The retirees who make housesitting work long-term usually don't go “all in” immediately. They build up gradually.
Start local
A few sits within driving distance. Test whether you actually enjoy living in someone else's space.
Try one extended trip
Three months of consecutive sits abroad. Long enough to feel the downsides, short enough to come home.
Keep your home base (at first)
Rent it out if needed, but have somewhere to return to. Only consider selling after at least a year of testing.
Build repeat relationships
Find 3-4 homeowners you genuinely click with. Returning to familiar places reduces the exhaustion of constant newness.
Consider going paid
Once you have experience and reviews, paid sits provide income rather than just “free” accommodation. More sustainable long-term.
The bottom line
Housesitting in retirement can be genuinely wonderful. But it's not an escape from the realities of ageing, and it's not a magic solution to fixed-income worries.
The retirees who thrive at this went in with eyes open, maintained strong family connections, chose their sits carefully, and knew when to stop. They didn't treat it as an identity — they treated it as one part of a rich retirement.
Getting Started
New to housesitting? Start building experience on TrustedHousesitters, HouseSitMatch, or Nomador. Local sits first, then gradually expand your range.
Already experienced? If you've got 20+ reviews and you're ready to transition to paid work, consider building a profile that showcases your experience.