While I can't speak for your friends, I (and many of us who are Inspirato members on FT) have given very specific examples of the quality and value of Inspirato. Ray1022 has provided numerous phenomenal trip reports. There are close to 400 residences (Inspirato member access only) and over 900 total vacation options. Additionally, there are world class experiences, such as Inspirato member-only cruises aboard SilverSea (last year's was a custom Rome to Monte Carlo...Inspirato members only on the entire ship), or trips to the Masters, Kentucky Derby, Super Bowl, NCAA Final Four, and on and on. With Inspriato, I can stay in one of the Fairmont Kea Lani's 2 or 3 bedroom beachfront villas for $1,000-$2,000/night versus over $3,000-$4,000/night with the resort directly. We've also experienced incredible savings at residences at the Ritz Carlton in Grand Cayman and the Terranea in Rancho Palos Verdes.

The Jaunt/Jaunt52 program is fantastic. With Jaunt, I can take a last-minute trip to Vail (or anywhere) for as little as $195 per night for a 2,800 sqft 4BR residence that typically goes for more than quadruple that. So, the value proposition is excellent. Also, Inspirato standardizes the residences and invests an average of $50k per residence to bring everything up to the quality Inspirato members expect. So, there is certainty that you don't get with a random VRBO residence. All Inspirato residences have high-end linens, daily housekeeping, stocked kitchens, pre-arrival grocery service, etc. You mentioned the service...yes, there's a dedicated vacation planning team, as well as on-site concierge at each destination. Everything is personalized and they know us and our preferences well (Pack N Plays, High Chairs, games for kids, our favorite wines)

Inspirato truly is a club. There's a phenomenal Inspirato Member Lounge at Solaris in Vail, as Inspirato has 34 properties in Vail alone. Members in large cities (Denver, LA, NY, and others) have access to FREE suite tickets to professional sporting events, concerts, etc. There are also members-only events throughout the year.

Can you find similar properties for less on VRBO? Sure. In fact, peak weeks like Christmas and New Year's can be very expensive. But that's not a fair comparison. If you're simply looking for the best price, Inspirato probably isn't for you. Inspirato blends high end residences with impeccable service and the certainty that you know what you're going to get every time regardless of the destination...similar to a Four Seasons. But, they also happen to have some really great deals. So, I'm willing to pay more for that, especially when combined with all the other benefits of being part of a club. And the most amazing part...Inspirato has a 90% retention rate. That speaks volumes of how we as members view the club. I was truly a skeptic before joining in 2014, and actually declined the first time around. After 15 Inspirato trips in 3 nearly years as members (Maui, Grand Cayman, Rancho Palos Verdes, Chicago, Las Vegas, 10 trips to Vail plus an upcoming trip to Punta de Mita), my wife and I can easily say joining was one of our best decisions.