This Is My New Golden Rule for Renting Vacation Homes (I Was Doing It All Wrong)
My friends and I are big on annual group trips, and to pull it off we love renting unique vacation homes where we can make lasting memories together. Over the years we’ve tried everything from renting a cliffside villa in Mexico to a cozy winter cabin nestled in the Pocono mountains. And while those trips have been unforgettable, every time we try to plan a new vacation, it’s tougher and tougher to find a home to rent that will make everyone happy.
Because we’re a large group that has already agreed on a specific set of dates and location, when we do find a rental listing we all love, the property is either booked solid or completely out of our price range. As it turns out, I’ve just been going about the search the wrong way. I’ve recently cracked the code, and I’m going to share it with you.
The secret to finding an incredible home to rent for your vacation is actually a simple one — start with the “what,” not the “where.” Look for great entertainment first and a destination second. For more stress-free travel planning, follow this golden rule when renting a vacation home. You’ll have more unique options to choose from and won’t feel like you have to settle or book super early to snag a great vacation home.
Looking through homes in one place, with specific features available on certain dates, is like trying to complete a puzzle with pieces that just don’t fit. But if you focus on the fun stuff you need in the perfect rental first — like pickleball, a pool, or a great grill and patio combo — and broaden your search to look for homes that offer everything on your list, despite the location, you could discover that your dream vacation rental isn’t where you expected it to be. You’re still getting all of that great downtime with friends and family, just maybe two towns or one island over.
I had this epiphany at a press preview with Vrbo to celebrate the brand’s list of Vacation Rentals of the Year 2024. Each year Vrbo recognizes a curated list of private home rentals that meet a specific criteria: They must be top rated (and raved about) by past guests, offer unique spaces and amenities that promote prime togetherness, and be rented by what’s called a “Premier Host” who values offering an overall quality guest experience.
The homes on this year’s list ranged from affordable cottage getaways in Big Sky, Montana, and Winchendon, Massachusetts, to luxe hideaways in Cabo San Lucas and Austin, Texas.
I spent three nights at a cliffside escape in St. John, U.S. Virgin Islands, called Villa Cin Cin. The home was breathtaking, with panoramic views of the island, oversized suites for guests, and cozy indoor and outdoor dining and entertainment areas for yoga and swimming.
Christine, the home’s owner and host, told me it’s often booked by big families looking for a place where they can have à la carte fun for all. Her villa is popular because it checks that box, thanks to its private beach access and spacious suites large enough for entire families to visit together, she says.
Going forward I’ll start group vacation planning with a list of “musts,” like a secluded location where we won’t disturb anyone laughing loudly all night or a heated pool for a night swim. I’ll worry less about the destination and more about giving everyone on the trip the amenities they need to piece together their perfect stay, especially on trips where we rarely ever leave the rental.
Now I search an entire region, like “Caribbean,” or a state, like “Utah,” and select the home features that will make us the happiest. Doing this shows more incredible (and available) options than I have available days off. It also shows more options at every budget and better availability too. No matter where you’re looking, consider expanding your view of family (or friend) time, and your search will widen with it.
Happy vacation home hunting!
Do you have a secret or tip for booking great vacation homes? Tell us about it in the comments below.
