Tryall Club Villas & Luxury Vacation Rentals

Luxury Villa Rentals for 2+ people


Tryall Club





7 14 8 + 1 half
$3,240 - $7,174 /night
6 12 5 + 1 half
$2,530 - $5,343 /night
10 20 10
$2,282 - $8,185 /night

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Your Guide to Tryall Club Villa Rentals

The Tryall Club is one of Jamaica's premiere country clubs and is home to some of Montego Bay's best golf, dining, and landscaping. Tryall Club villa rentals further this pedigree and are among the best in Montego Bay thanks to their impressive size, attention to detail, and the care and service provided by their professional staff.

Choosing the right villa, then, depends first on identifying your party size. Tryall Club villas include several different bedroom configurations, so having an approximation of how many people will be traveling, their ages, and if they have any special needs will go a long way in narrowing down your choices.

From there, it's just a question of choosing which of these gorgeous Tryall villas are right for you. Your Rental Escapes reservations specialist can find the best villas available for your dates and preferences, which should make the task easier. After, your concierge can personalize your villa experience through extras like villa pre-stocking (for food and beverage), setting up meal plans for your private chef, planning excursions, and so much more, including any special requests you may have.


Luxury Tryall Club Villas

For many seasoned travelers to Montego Bay, a luxury Tryall Club villa is their first choice for accommodation, especially when traveling with a group. Each of the villas are privately owned, with the owner overseeing both their construction and their décor. That means that they are all architecturally distinct, and often home to antiques, artwork, and other little touches that give Tryall villas their unique personality.

The standard of quality and service seen across the resort is evident throughout the Tryall Club's villas as well. Immaculate landscaping ensures a lush and welcoming surrounding; food is sourced from the highest quality ingredients; and, perhaps most of all, villa staff demonstrate the professional and welcoming attitude that has made the Tryall Club such an institution since its founding in 1958.

Oceanfront Tryall Club Villas

Many of the top Tryall Club villas are perched atop a hill overlooking the shimmering Caribbean Sea. These oceanfront villas tend to book quick, especially for peak season, and are always a favorite choice of our guests.

Some of the most popular choices include:

Karma Bay: Located directly in front of the water and just a short walk to the Tryall beach club, Karma Bay is an impressive 6-bedroom villa that melds Asian and Caribbean influences to create a uniquely scenic ode to island living. The sound of the waves is sure to soothe you, while all the little details, like the waterfall showers, sprawling lawn and pool area, and creative chef, are sure to delight you even more. 

Sunset: One of the very few Tryall villas with its own strip of private beach, and located near the championship golf course, the 5-bedroom Sunset benefits from one of the most privileged locations in the Tryall Club. All the extra little details, like four out of the five bedrooms having outdoor showers, make for an even more luxurious experience. An excellent choice for a family that wants to enjoy their own private beach – provided you book early enough to snag it.

Aqua Bay: Located on the Tryall Club's western edge, Aqua Bay is a 4-bedroom villa that is blessed with direct sea access, as well as an elevated, white-sand beach. The villa itself is also stunning, with rainwater waterfalls, an open design, and vaulted ceilings with cedar shingles all complimenting its oceanfront location. It also has two seawater-fed swimming holes, an infinity pool with an exercise lap lane, a private gym, a fire pit, and a professional staff ready to take your vacation to the next level.

Tryall Club Villas for Large Groups

From family gatherings to special events (including destination weddings!), the Tryall Club is an ideal spot for large groups thanks to its amenities, activities, and service. Tryall Club villas further facilitate large groups thanks to their spacious, open floor plans and their professional staff.

From chefs, cooks, housekeepers, waiters, butlers, and more, the staff at Tryall Club villas elevate group bookings into experiences that are not soon forgotten.

Some of the most popular Tryall Club villas for groups include:

Hanover Grange: When a villa has had as much love and attention poured into it as Hannover Grange, then it becomes something very special indeed. This 9-bedroom manor has been meticulously designed and decorated by its owners. It features a minimalist design, marble and mahogany flooring, a gallery showcasing artwork from some of Jamaica's best artists, and a plethora of luxurious details which accent everything from the bedrooms to the bathrooms. A true testament to the art and beauty of Jamaica.

Haystack: The long-celebrated Haystack is a 10-bedroom villa set over three levels that offers some of the best views of the Tryall Club that you'll find anywhere. From the moment you drive in and see the waterfall at the entrance, you know you're in for something special. From discerning choices of furnishings to its contemporary art collection, Haystack is a testament to fine living. For an added bit of fun, though, there's also a full entertainment room, a private gym, and a large pool deck.

Dragonfly: A more recent construction, Dragonfly has quickly become a favorite Tryall Club villa for larger groups thanks to its uncompromising design. Featuring unobstructed ocean views, vaulted ceilings, and deep verandas, the villa itself is truly an architectural sight to behold. It also includes lots of fun additions like a basketball court, home theatre, full gym, and a games room, as well as a professional and charismatic staff. A great choice for family gatherings, special events, and business retreats.

Tryall Club Villas for Families

With so many activities that appeal to both adults and kids alike, as well as a team of nannies on hand that have all been certified in childcare by Penn State, the Tryall Club is one of the premiere spots for a family vacation in the Caribbean.

Tryall Club villas for families further this pedigree by ensuring a variety of bedroom configurations, accessibility options, and child-friendly touches.

They include:

Sugar Hill: Sugar Hill is an ideal choice for multigenerational families thanks to its expansive one-floor (and wheelchair accessible) layout, its accessibility options for media, and its variety of bedroom combinations that include king, queen, and two single bed configurations. The villa itself is also stunning, with one of the best gardens in all the Tryall Club, as well as handcrafted furniture, sprawling veranda, private gym, quant library, outdoor pizza oven, and more. 

Infinity – Named after its large, heated infinity pool, Infinity is a 5-bedroom villa that's at once sophisticated and child-friendly. Its meticulous design revolves around ocean views and easy living, and the sunken bar connecting the family room to the outdoor living room is a testament to how this craftsmanship results in an amazing vacation experience for all as a result.

Bumper's Nest: A perennial favorite, Bumper's Nest exudes that distinct sense of Caribbean style and sophistication. Designed to maximize airflow and natural light, the villa makes exquisite use of its location overlooking both the Caribbean Sea and the Tryall Club's lush landscaping and famous golf course. The 50-foot infinity pool, 100-foot pool deck and 12-person Jacuzzi are recent additions that make this villa even more special.

Tryall Club FAQ


What Should I Know Before Traveling to the Tryall Club?

If you're renting a villa at the Tryall Club, you will have to become a temporary member. The cost is $130/week/guest, plus a 15% service charge for guests 16 and older (or $26/day for stays less than one week).

How to Travel to the Tryall Club?

Most Tryall Club guests will be arriving to Jamaica via the Sangster International Airport in Montego Bay. From there it's about a 30-minute drive to the Tryall Club.

Airport transfers can be arranged by your concierge, and so can a personal driver for the duration of your stay. Because the roads can be tricky, renting a car in Jamaica is generally not recommended.

How do I get Around the Tryall Club?

Tryall Club villa rentals usually include a golf cart, which will be able to take you around the resort. If you need to leave the resort, then a driver service can be arranged by your concierge.

Best Time of Year to Visit the Tryall Club?

Peak season at the Tryall Club runs from December to March. This time of year sees the lowest overall precipitation and the mildest weather, making it a favorite for many.

That said, if you want to take advantage of smaller crowds and better deals on Tryall Club villa rentals, then booking during shoulder season from April to June is recommended. While there is a higher chance of precipitation at this time, it's mostly relegated to quick showers in the afternoon.

The absolute best deals can be found in the summer and early autumn months from July to November, though do be aware that this corresponds to hurricane season. While your actual chances of encountering a hurricane are quite low, this time of year also sees the most precipitation.

Best Things to do in the Tryall Club?


Go Golfing: Since its inception in 1958, the Tryall Club's 18-hole, Ralph Plummer-designed championship golf course has been celebrated by pros and amateurs alike. Staying in the Tryall Club gives you unique access to one of the best maintained and well-loved courses in the Caribbean – take advantage, even if you're a beginner.

Play Tennis: Tennis is almost as much a part of the Tryall Club as golf, with the Tennis Club being introduced in 1959. Today it features nine courts – four Agile Turf and five Nova Cushion – as well as 24 pros ready to help you elevate your game, no matter where you're starting from.

Visit the Beach Club: The Tryall Club's beach club includes not one but two beaches, including a more secluded option for those seeking a little more refuge. Regardless of which you choose, expect to find the elevated service that the Tryall Club is known for, as well as fun options like kayaking, paddleboarding, and Hobbie Cat sailing.

How is the Food at the Tryall Club?

The Tryall Club has a very high standard for food and dining. Fresh seafood and produce are the order of the day, whether you're having lunch at the beach bar or the organic garden, or if you're enjoying private dining at your villa or even in the 19th century Great House. 

On that note, our Tryall Club villa rentals include chef service, so you can be sure that all your meals are being prepared using the freshest ingredients and meet your dietary needs and preferences. Your concierge can arrange a meal plan with you before you arrive, or you can just let the chef surprise and delight you based on your feedback.

Your concierge can also arrange villa pre-stocking, so you can be sure that your favorite foods and drinks will be waiting for you as soon as you enter the villa.

What is the Weather Like at the Tryall Club?

The Tryall Club sees temperate and balmy weather year-round, with average temperatures of 88°F (31°C). April is the sunniest months overall, with 253 hours of sunshine.

And while the chance of rain is very low during peak season, it increases somewhat in the afternoons during shoulder season from April to June.

The wettest months are September to December, when temperatures also dip to 85°F (29°C).

Book a Tryall Club Villa with Rental Escapes

To enjoy the best of this island paradise, book with Rental Escapes and elevate your Tryall Club villa rental into a true luxury experience.

Our portfolio includes the finest properties in Montego Bay, including oceanfront, family, and large Tryall Club villas. Your Rental Escapes reservation expert can find the best villa for your group, and from there your concierge personalizes the trip to create the ultimate Tryall Club villa experience.

Contact us today to book your next dream holiday!

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