Every time you book a vacation rental, you’re really booking a story. For a period of time, you’re able to step into someone else’s home and ask yourself: What if I was this person? What if I had a multi-use barn/wedding venue that overlooked the Hudson River? What kind of person would I be if I came to this mid-century bungalow every weekend and not just begrudgingly for one overpriced bachelor party?
The annual Vrbo Vacation Rentals of the Year are a showcase of the best of the best of these alternate realities. The selection process for the 2025 winners, officially announced today, began back in July when the company sifted through rentals by a number of strict criteria: 1. The properties had to have over a 9.8 rating. 2. The properties had to have “Premier Host” status. 3. They needed at least three-bedrooms and 4. They had to have standout amenities. Every 2025 honoree has a pool or a hot tub (obviously) but extra weight was given to above-and-beyond perks like an on-site mini golf course.
Thrillingly, I was able to visit one of this year’s winners in-person to see what it was like to stay at one of the best vacation rentals in the country. “Under the Tram” is a literally-named, ski-in/ski-out luxury lodge located directly under the world-famous Jackson Hole aerial tram. Along with a private sauna and hot tub, the four-bedroom mountain house has a full locker room for ski gear, a tub that allows you to take a bubble bath while watching skiers zip by outside, an outdoor BBQ area, a gym, a full bar and many decorative antlers. It was the perfect blend of secluded snowy cabin and activity-filled paradise, with direct access to one of Jackson Hole Mountain Resort’s runs. (One of the best ski resorts in the America!)
What was it like to stay at one of Vrbo's vacation rentals of the year?
Walking through the foyer into the grand main living room, I considered a fact my Uber driver from the airport had shared: most millionaires were now getting priced out of Jackson Hole with only billionaires remaining. The house was far and away more luxe than any rental I’ve stayed in before with soaring windows, multiple fireplaces and a sweeping central staircase. Interestingly enough, it also felt even larger in person than the photos portrayed it in the listing.
The house is located within walking distance of Teton Village, and at the foot of the jaw-dropping Teton Mountain Range, but there’s also a feeling of seclusion thanks to being tucked away in the forest. That dual quality is another factor that helped the property earn a spot on this year’s list thanks to a travel trend that Vrbo is calling JOMO (the joy of missing out). In 2025, the company says, more travelers are placing an emphasis on quiet and secluded spots where they can easily reconnect with family and loved ones. My weekend stay was exceptionally quiet, but not quite so secluded—thanks to the welcome, and frequent, intrusion of the neighbors' delightfully friendly dogs.
What are the best things to do in Teton Village?
The main reasons that Under the Tram made it on this year’s list are the standout amenities it offers and the wealth of activities in the surrounding Jackson Hole area. In order to get the fullest picture of what a stay would be like there, I set out for a day of skiing on Saturday—pushing off from just outside the patio and joining a run to reach the Bridger Gondola in mere minutes. After a day of skiing alone across some very, very steep mountains (which provided both a sense of meditative calm and general existential unease), I skied directly back to the rear entrance of the house, an amenity you’ll only find in a handful of places and more than enough, in my opinion, to bump this into the top tier of rentals.
Non-skiers will find plenty to do both in the nearby Teton Village and a short drive away in the town of Jackson. The next day, I left our world-class digs and headed down into town for a day of dog sledding at Call of Wyld, which gives one-hour private dogsled tours at the base of the Teton Mountains. A large portion of their clientele, I’m told, are overconfident skiers who take one look at Jackson Hole’s ultra-steep terrain and decide they’ll be having less of a ski trip and more of a general mountain vacation. I get it!
It was heartwarming to meet all of the dogs that work at the company and hear a little bit more about how they’re lovingly cared for and where they came from. The actual sledding was a bit slower than I was expecting but it was fun to hear about the history of dog sledding during the tour. (Turns out, Balto wasn’t the standout star he’s made out to be.) I even got to try my hand at driving the sled myself. If you get the chance, I'd recommend it! It wasn't as hard as you might think.
What else is there to do in Jackson Hole?
Later, we took a 20-minute cab ride into the town of Jackson for an afternoon of hat-making at Encounter Hat Co. Seeing the artistry of this craft in person was eye-opening—especially the delicate precision in which the artists construct each hat from the sizing and the molding to the brim trimming and accessories. After a blast of a two-hour private session, I left with a beautiful hat that, nevertheless, made me look like the man from Curious George. That, however, was my fault and not the hat. The evening was rounded out by happy hour at the one-of-a-kind, historic Million Dollar Cowboy Bar and a fantastic steak dinner at Local. After a short Uber ride, we were back at our luxurious digs.
While it was hard to leave my own Million Dollar Cowboy experience at Under the Tram, my trip back to the airport the next morning was bittersweet thanks to my knowledge that anyone (or at least anyone who has $5,000/night to spare) could book the house for their own yee-haw getaway. Want a once-in-a-lifetime story of your own? Check out the full list of this year’s 2025 Vacation Rentals of the Year below and book one for yourself. But be sure to do it quickly! They’re among the fastest-booked rental properties in the US.
This classic A-Frame cabin is surrounded by pristine Maine wilderness.
An hour from Austin, this massive complex boasts an insane entertainment room.
3. Folly Beach, South Carolina
A retro, waterfront home that overlooks the Folly River.
This Smoky Mountains cabin has the most 10-star reviews on the list.
You just read 1,000 words on this one.
A quaint upstate cabin that’s the most affordable rental on the list.
A family-friendly, Scottsdale area home with its own pickleball court.
This waterfront Lake Michigan home is the biggest property on this year’s list.
A pristine beachfront home in Florida with two private pools.
This property has a huge outdoor space with pizza ovens and a mini-golf course.