Inspirato Residence

4.3 · 17 reviews

Cassia

Montego Bay, Jamaica

6.5

7,000 sqft

Hilltop villa with Jamaican-inspired architecture and contemporary floor plan
Beautiful ocean views
Short walk to Tryall Club’s world-class amenities
Swimming pool

Features & Amenities

Quick walk to Tryall Club’s world-class amenities
Three-minute golf cart ride to the championship Tryall Golf Course
Elevated ocean views
Full staff including a butler, chef, housekeepers, and more
Swimming pool
Covered outdoor veranda with two seating areas and a dining area
Game room with pool table and eight-foot HDTV projector
Formal dining room with seating for twelve
Air conditioning in bedrooms only
Two golf carts
Two-car garage
Daily laundry service
Sonos sound system

Full access to the amenities at Tryall Club, including:

Resort pool
Private beach with wide selection of non-motorized water sports equipment
18-hole championship golf course
On-site restaurant, bar, cafe, and shopping
Top-rated tennis center with four Agile Turf courts, five Nova Cushion hard courts, training facilities, and on-site professionals
Ability to book tee times and tennis lessons
Fully equipped fitness center
Basketball, football, volleyball, and croquet
Kids’ club
Complimentary daily afternoon tea
Complimentary nightly entertainment
Manager's cocktail party every Monday night

Amenities

Air Conditioning
Fitness Center
Full Service Spa
Ocean View
Pool
Resort Access

Bedding

Primary Bedroom
- One King Bed
Bedroom 2
- One King Bed
Bedroom 3
- One King Bed
Bedroom 4
- One King Bed
Bedroom 5
- Two Twin Beds
Bedroom 6
- Two Twin Beds

Know before you go

check-in time4:00 PM

check-out time11:00 AM

This home is staffed, managed, and maintained by our trusted partners at The Tryall Club.
Hurricane Melissa: Please note there may be visible impacts outside of the resort area in surrounding communities from Hurricane Melissa. The resort is fully open. There is a new check-in location for the front desk at The Tryall Club. Please contact your Care team with any questions.
Between August 1 - October 6, there may be restaurant and business closures due to hurricane season. Be sure to check availability with your Destination Concierge.
Please note that the living and dining rooms are open-air living areas that do not have AC.
Please note bedroom six encompasses two twin beds and may be most suitable for young adults or children.
For an additional fee (referred to as membership dues), members have access to the amenities of the Tryall Club. For guests ages 16 and older, dues begin at $45 per day. Dues for guests aged 13–15 are $25 per day, while children 12 and under enjoy complimentary access. All fees, along with any incidental charges incurred at the Tryall Club, are managed directly through our partner and may be applied to your Tryall Club folio.

Additional Information:

Cancellation policy: The Standard Inspirato Cancellation Policy applies for this property. Please note the Peak Reservation policy applies for Christmas and New Year’s weeks and certain other travel dates.
Maximum occupancy: Stated occupancy cannot be exceeded.
Pet policy: No pets allowed.

Members-Only Benefits:

Eliminate the hassle of procuring travel documents for this trip and trust the passport and travel visa experts at Swift Passport Services to expedite your documents.

Location

The Tryall Club is located about 35 minutes from Montego Bay's Sangster International Airport (MBJ). Numerous airlines offer service here; from the U.S. you can fly American, Delta, Frontier, JetBlue, United, or US Airways.

Renting a car isn't necessary during your stay, as Jamaica always has taxis readily available and private transportation or tour transfers can always be arranged by your concierge. Additionally, you will be provided with two golf carts for exploring the resort's more than 2,000 acres. If you do decide you want to explore the island on your own, a rental car from Club partner Avis might be ideal. Keep in mind, though, they drive on the left side of the road in Jamaica.

Need help booking flights? Our luxury airfare concierge can book your preferred seats and flight times at the best available price.

Reviews

1 - 5 of 17 reviews

Patrice G

House a 4. Staff a 5

This was a girls' trip to Cassia (Stella), completing a visit that had been interrupted by the hurricane in 2025.

The home itself is spacious, with comfortable bedrooms, a large open veranda, and beautiful, expansive views. Its elevated position offers a wide, open perspective of the sea. If you are looking for the sound of crashing waves, however, that is not part of the experience here due to the elevated position.

To reach the level of other Inspirato homes, this property would benefit from some additional refinement, to be Inspirato-fied, if you will. With a few thoughtful updates, it could feel more aligned with the rest of their portfolio. The updates and special touches that are needed are what give this a "4" rating.

What truly sets this home apart is the staff. Jackle, Nicki, Ricky, Pauline, and Derrick were exceptional. They were attentive, warm, and genuinely enjoyable to be around. Their level of care made the experience feel special. In fact, they are the reason we were motivated to return to that home to finish out our trip. They absolutely deserve a "five."

It is also worth noting that they are caring for guests while continuing to rebuild after a devastating natural disaster, which makes their effort all the more meaningful.

At the Tryall Club, we enjoyed Reggae Night on the beach and spent time at both the pool and beach areas. The staff there was consistently pleasant and helpful.

Jessica M

Not Our Best Inspirato Experience

Spent spring break 2026 at Villa Cassia and really wish I had read the member reviews before we booked! Our experience was very similar to those others have shared - the house is not at the level we have come to expect from Inspirato. Run down, outdated, sparsely furnished. The location, while providing an amazing view, is close to a very busy and very loud street (highway?) that you can hear from early in the am until the sun sets. The Tryall Club is nice enough, but nothing special given the pricing. The house staff were okay overall, but left us feeling either a bit neglected at best or at worst, like we were imposing on them. We have done many villa rentals with Inspirato in the DR and Italy and all of them were outstanding (which is why I felt confident booking this home without reading the reviews - lesson learned). I would not return to Villa Cassia or the Tryall Club again based on this experience.

Eileen O

Stellar Stay at Villa Stella - Cassia

We had such a wonderful introduction to Jamaica at Villa Stella - Cassia at the Tryall Club. We expected our January 2026 trip would be cancelled after Hurricane Melissa tore through Montego Bay in October, but we were assured the club facilities, the home, and the staff were ready for us. Upon arrival we could tell Montego Bay was still recovering, but the roads were clear, the weather was beautiful and the people were warm and welcoming. The Tryall Club property was in near perfect condition – including the golf course, tennis/pickle courts, oceanside clubhouse, and beach front facilities. Our experience with the tennis/pickle and golf were heightened by our instructors, ballboys and caddies. They made everything we did even more fun! In addition, the yoga studio at the Spa was stunning and the classes were always challenging. Cassia was the perfect home for our group of family and friends. The home is beautifully situated with gorgeous views of the club property and ocean, and it is comfortable, tastefully decorated, and spotlessly clean. We cannot say enough good things about the wonderful staff at Villa Stella that took care of us and our home throughout our weeklong stay! Jackie, Ricky, Chef Nicky, Pauline and Derek - this team not only kept us comfortable, well taken care of and well fed (delicious meals!), but they were also a lovely group of people who we were sorry to say goodbye to. When we did not eat at home being wonderfully fed by Chef Nicky, we had two incredible dinners at the Ooshan Restaurant at Tryall and at the Round Hill Resort, a short drive from Cassia. We had an all-around fabulous time at Villa Stella at Tryall, and we hope to return someday soon!

Evan L

Unless a great deal, would avoid

Below is the note I sent to Inspirato. We just checked out of Cassia and wanted to touch base to give you some constructive feedback. Unfortunately, the string of bad reviews (3,3 and I will be a 2) is going to continue and for a lot of the same reasons identified by other Inspirato members. This was not a great stay, largely due to the unfriendly staff. The house needs a big update it’s not a typical Inspirato level house but we knew that going in so no worries there. Except for Ricki the butler -who is great-so nice, friendly and laid back, the staff makes you feel as if you are an unwelcome guest in their home, and subject to an endless array of rules and judgments that stress you out (esp my wife). We are just trying to enjoy a nice, laid back vacation with our family to end the summer. It was a very uncomfortable feeling similar to the feedback from prior guests. My wife actually found it stressful interacting with house manager Jackie. Dian never responded at all, Mayra disappeared after sending an initial email. This is not what we expect from Inspirato. Even if we booked last minute, we paid full price for this season (not a jaunt) so if you can’t offer your normal services with a decent, friendly staff, just shut it down for the season imho or else if these bad reviews keep coming it maybe a property most members seek to avoid as most reviews are glowing for most properties. Now to some specifics FWIW as you evaluate member feedback: Our villa was not ready when we arrived so they dropped us at the beach club but said someone from the Villa would come to get us by 230. 230 came and went. Then 3. And 330. At around 4 we started texting and calling but no response from the numbers of the contacts listed. Finally we got someone at the beach bar to take us back to the check in/reception and they said oh yea it’s ready, but they forget to come get you. Ok, no biggie. Off we went to the villa. Upon being brought to Villa, the normal Inspirato destination welcome person was not there to greet us or show us around. We were shown around the villa by Nicki the chef and asked to let them know what rooms we would be in. We are only a family of four so not a big crowd or high maintenance guests for the size of the house. We selected our rooms and they brought our luggage, which was appreciated. Little did we know they asked that so that Jackie could literally lock us out of all the other rooms, without even telling us. I realized this the next day when I had to do a work call and did not want to wake my wife but all the other rooms were locked, ac turned off, etc. I was stuck. This is absurd, we rented the entire house NOT three rooms. When I asked for the other rooms to be opened, Jackie said “well that’s $70 a day PER PERSON”. Excuse me, what? To do a work call you are going to hold me up and demand a payment. Are you kidding me, holding me hostage to open the rooms to an Inspirato house I rented. This is beyond. I told her that’s not what we paid for and to hold me hostage to open rooms when I needed to get on an important work call is not something I am agreeing to, her approach is inappropriate (our first convo by the way) and to open the bedroom or we are leaving. This is not to even mention that prior to all this we were awaken by a 6am alarm we never set. They forget to reset the alarms from the prior guests. My wife and I could not fall back asleep and were exhausted all day. Normally, we would not care about such minor things, which we know are not intentional and happen. But when 90% of Jackie’s interactions are rude (see below) or asking for money, then how about you just focus on your job and not stressing out guests trying to enjoy a family trip. Then, that same afternoon at around 4, without asking us or even telling us, they treated the pool and Jackie told us you cant use it from 5pm until the next morning. We are only here three days then off to meet friends at Half Moon (thank god). So my kids who wanted to swim could not. At least tell us or ask us if we plan to swim. Chef Niki makes good food, we all enjoyed her cooking, but she is also extremely cold and always seems inconvenienced. Never once came out to ask us how the food was or if we needed anything else at any meal. We tried to tell her how great the food was and thank her but she always just seemed annoyed at us for no reason. Maybe she was mad we picked up the food since we had the car stop on the way from the airport versus her getting it? We don’t know. We ran out of oil which we bought and she told us “YOU” have to go to the store that morning to get more or no lunch or dinner. The house does not have cooking oil, no problem, we took the cart and we went. But again felt like we had done something wrong. So odd. The women staff also often go into the kitchen all together and actually close the kitchen door. So you have to open it and when you walk in they don’t say hi but instead send a signal that makes you feel like we need to get out of the house kitchen and are intruding on their hang out. It’s the freakin only kitchen for the house that we are renting this is insane to essentially be chased out. At bottom, Jackie may mean well but it feels like the principal is following you around the house you paid for and are trying to enjoy pointing out every little thing or reminding you about paying them. “Close the doors”. “You’re going to dinner and leaving your kids, are you sure”. Ah yes our daughter is not a baby and babysits at home so we can go out one freakin night as adults without a snide comment from you. “Inspirato takes 6months to pay us we want Zelle or cash on exit”. How about helping us with our bags that my wife actually took up. She just needs to mind her own business and actually provide a service in a somewhat friendly manner. We are very down to earth, laid back people. We are mark demanding at all or high maintenance. My wife is very non confrontational but so stressed she was about to tell her she does not want to see or talk to her anymore. Just to please leave us alone. Again, consistent with feedback from other guests. Sorry, don’t shoot the messenger, but I must confirm some of the prior reviews, unfortunately (esp the last two). If they continue you may not have any takers coming here, unless the deal is too good to pass up. Thanks. Evan

Rob D

Average

Overall a good trip. The house is great, but a little dated. The staff is sometime hard to deal with, the amount of rules is exhausting, you feel think they are looking over your shoulder to tell you that you broke a house rule. The chef did a good job but seems like a waste if you want to eat out a few times. We could have cooked ourselves. They don't arrive until after 7:00 a.m. so no early breakfasts. The Tryall Club person who came and checked us in was not the nicest. Plan on 30 minutes filling out forms where ever person staying in the house needs to be present to fill out and sign forms. For the amount they charge for food and beverages at the Tryall Club, they don't need to charge you a weekly membership fee. That fee should be included in the cost of the house for the week. The high tea was a big disappointment, not what we were expecting, it was a super small buffet line and a box to choose your tea out of. The house sleeps 12, but you only get a golf carts for 8 people, we had to order an additional golf cart for a fee. There is no other way to get around the property, big miss not having golf carts for the amount of people staying in the house. Overall I wouldn't go back, super expensive for the resort and amenities. Not up to par with other places I have stayed with Inspirato

Cassia

Features & Amenities

Amenities

Bedding

Primary Bedroom

Bedroom 2

Bedroom 3

Bedroom 4

Bedroom 5

Bedroom 6