Luxury travel without the luxury price tag: That’s the dream of many travel optimizers, myself included. It’s why I got into points and miles in the first place, and one of the reasons why I was interested in Inspirato Pass, a luxury travel subscription service.

Here’s the idea behind Inspirato Pass: For a flat monthly fee (currently $2,500 per month), you can book luxury accommodation throughout Inspirato’s global portfolio. You don’t get charged extra fees, taxes or anything else — no matter what property you book.

What’s alluring about this proposition is the quality of some offerings within the portfolio, which includes seaside villas, condos in Hawaii, five-star hotels around the world and hundreds of other properties that would qualify as once-in-a-lifetime travel experiences.

(Note: Inspirato also offers an unrelated “Club” option that allows a la carte reservations of these properties. This review covers Inspirato Pass, not Inspirato Club.)

Obviously, $2,500 a month isn’t cheap, especially for those who only travel once or twice per year. But as a digital nomad, I was interested in optimizing Inspirato Pass by jumping from luxury property to luxury property while not being tied to home or rent payments. I was also interested in renting large houses for group trips, splitting the effective cost to make it more manageable on my finances.

Unfortunately, Inspirato Pass is very difficult to use in this way.

Jump to:

Built-in limitations.

Search and availability.

Missing inventory.

The properties.

The bottom line.

Built-in limitations

Inspirato is a company trying to make money, so it's not going to let someone bleed it dry by booking back-to-back reservations at five-star hotels. The company deals with this by limiting how and when you can book travel with a Pass membership.

At the time I tested the program, Inspirato Pass only allowed me to book one trip at a time, and it didn’t let me book my next trip until my current one was completed. It also didn’t offer any bookings that were less than a week out. For example, if my first trip was from Sep. 1 through Sep. 5, then I wouldn’t be able to book a new trip until Sept. 5, and the earliest booking options at that point would be Sept. 12 (a week later).

It takes a while to wrap your head around these rules, but the upshot is that you’re only going to be able to make a few reservations per month, at the absolute maximum, with long spaces of a week or more between reservations. When I spoke to the sales rep at Inspirato, he was very up front about this limitation.

Yet for someone like me — with unlimited flexibility — the program could still be very valuable (in theory).

Note: Inspirato Pass has slightly changed its rules and now technically allows more than one reservation at a time; however, the same logic still applies for those trying to maximize reservation value.

Search and availability

Before signing up for Inspirato Pass, I spent several weeks browsing the program’s public search tool to check availability. I wanted to understand whether I could maximize the service by booking as many trips as possible within as short a time period as possible.

On its surface, Inspirato’s search tool is one of its best features. It offers powerful filters, intuitive date selection and quick load times. Want to get a ski chalet with three rooms in March? You can narrow the available trips down within seconds.

Without applying any filters and sorting by “best value,” you can see some top properties in the portfolio with the longest periods of availability. These are pretty enticing, since booking one of these luxury homes for even a week would cost much more than $2,500 through a normal vacation rental service.

However, this is where I encountered some of the hidden limitations of Inspirato Pass. When I filtered for availability within the same month, the options thinned dramatically.

Almost all the houses fell off the calendar for short-term bookings, leaving only hotels. And, importantly, many of these trips were only two or three days long, and often only available mid-week. This meant that I could end up spending $2,500 to book a hotel room for a few days — hardly a great deal.

But I did notice diamonds in the rough. Some large houses were available within two months or so, and some very high-end (as in penthouse) hotel rooms would pop up from time to time. Because of the flexible cancellation policy, I figured I could book longer-term trips and then nab these gems when they appeared on the search tool. As a veteran travel rewards maximizer, I was used to booking premium cabin award flights in the same way.

Yet I found that, unlike airline award search tools that show real-time availability for flights that can be booked immediately, Inspirato Pass’s search tool was not displaying actual inventory.

Missing inventory

When you sign up for Inspirato Pass, you'll be assigned a dedicated customer service team that you can contact directly at any time. To book a trip, you can either click “book” through the search tool or email your customer service team directly.

But here’s the thing: Clicking “book” doesn’t actually book the room. It basically sends an email to your customer service team, requesting that they book it. Why does this matter? Because often the search tool shows availability that doesn’t actually exist.

I learned this the hard way shortly after my subscription started, when I tried to book a three-night stay at one of my favorite hotels in the world: The Andaz Maui. This booking was a good example of a “diamond in the rough,” since rooms at the Andaz can easily cost more than $1,000 per night the winter I was traveling.

However, I received an email back from my care team, apologizing that the Andaz room was no longer available, and offering alternatives at the much less appealing Hyatt Regency Maui. This was annoying, given that I was looking forward to the Andaz, but I chalked it up to a system glitch. Yet, one month later, I encountered exactly the same issue when I tried to book the Penthouse Suite at the Andaz Los Angeles, which was available in the search tool at the time.

Here’s what my rep said via email:

“I’m so sorry but the hotel has sold out of that room type. The Pass list does not always show availability in real-time, so the Penthouse Suite should not appear as available on the website.”

So basically, my strategy of grabbing last-minute, high-value bookings wasn’t going to work because these bookings weren’t actually available. This same issue occurred repeatedly throughout my seven months with Inspirato Pass, to the point where I wondered whether the search tool was actually representative of anything real on the backend and not just a marketing tool to lure potential subscribers.

To its credit, Inspirato representatives repeatedly apologized for the problems. I spoke to a manager about my issues; the manager issued me a refund for one month of my subscription, which was somewhat of a balm. But I canceled my subscription after seven months because the service was proving to be far more of a hassle than it was worth.

The properties

All of these serious technical and logistical problems aside, when I was actually able to book an Inspirato property, I had a blast. My friends and I booked several long stays at villas at the Terranea Resort in Rancho Palos Verdes, California, which offered a level of luxury and service well beyond our usual price range.

I stayed at the exquisite Chileno Bay Resort in Cabo San Lucas, Mexico, booked a luxurious hotel room in London for a week (no mean feat under my usual travel budget), and generally lived like a part-time king for those seven months. What’s fun about Inspirato Pass is that it incentivizes you to seek out the most absurdly expensive options. This does away with the usual trade-off between comfort and cost when booking accommodation.

By far the best value comes from the houses rather than the hotel rooms, though these were rarely available less than two months out. Eating through two months of Pass availability was the equivalent of $5,000, so I was generally reluctant to go this route. That said, if I had it to do over again I would have targeted long stays at houses with friends and family rather than shorter and more frequent stays at hotels and resorts. If nothing else, I could split the cost with friends.

The bottom line

In this review, I focused on the mechanisms of Inspirato Pass and its drawbacks, rather than the properties and experiences themselves, because this was the weak link that broke the chain for me. I signed up for the service because of the availability displayed on the search tool, and when that availability was not, well, available, Inspirato Pass was rendered far less valuable.

If you’re someone with an annual travel budget north of $30,000 ($2,500 x 12) and only take a few trips every year, then Inspirato Pass might be worth it. The best thing it offers is simplicity: You don’t have to worry about how much a particular booking costs, or whether taxes and fees are included. You just pay a flat monthly fee and get to book world-class travel (when it’s available).

But if you’re a travel-maximizing cheapskate like me, or someone looking to book trips with friends and split the cost, you should probably pass on Inspirato Pass. The properties are great, as advertised, but the hassle of booking stays, coupled with the misleading faux-availability shown on the search tool, totally cripples its value.

Do I regret my seven months with Inspirato Pass? Not at all. I got a free month at sign-up and a free month for my repeated reservation problems, so the cost proved manageable. But would I recommend it to a friend who wasn’t a bajillionaire? Not a chance.