The Tryall Club is one of Jamaica's premier country clubs and home to some of Montego Bay's best golf, dining, and club settings. Tryall Club villa rentals are among the finest in Montego Bay thanks to their impressive size, attention to detail, and the care and service provided by their professional staff.
Renting a Tryall Club villa is easy with Rental Escapes. First, your Villa Specialist finds the best villas available for your dates and preferences. From there, your Concierge personalizes your villa experience through extras like villa pre-stocking, setting up meal plans for your private chef, planning excursions, and handling any special requests you may have.
Located on a private 2,200-acre estate on Jamaica's north coast, approximately 25-35 minutes from Sangster International Airport (MBJ), the Tryall Club has welcomed discerning travelers since 1958. This exclusive gated community is celebrated for its championship golf course, pristine private beach club, and collection of architecturally distinct luxury Tryall Club villas.
Want a deeper look at the club experience? Explore our Tryall Club Jamaica guide, including golf, beach club access, dining, villa accommodations, gratuities, and what to know before booking.
Each Tryall Club villa is privately owned, architecturally distinct, and often home to antiques, artwork, and other thoughtful touches that give these properties their unique personality. Immaculate landscaping ensures lush and welcoming surroundings, while the indoor-outdoor Caribbean design, with expansive verandas, open-air lounges, and private infinity pools, creates natural gathering spaces where ocean breezes and tropical gardens become part of your daily rhythm.
Choosing a luxury Tryall Club villa for rent over a traditional hotel offers an entirely different vacation experience. Instead of a standard room, you gain an entire private estate with multiple bedrooms, expansive living areas, private pools, lush gardens, and sweeping terraces. Picture starting your day with breakfast on your oceanview veranda, spending afternoons between your private pool and the beach club, and enjoying sundowners on your own terrace as the Caribbean sun sets over the sea.
For groups and families, Tryall Club villas offer exceptional value compared to booking multiple luxury hotel suites. You gain shared living spaces, private pools, dedicated staff, and the kind of privacy that makes celebrations and gatherings truly special. Plus, your temporary club membership (required for all villa guests aged 16 and older) unlocks access to world-class amenities including the championship golf course, tennis center, beach club, fitness facilities, swimming pools, and supervised kids' activities.
At the Tryall Club, the best stays are shaped before you arrive. Your Concierge can help coordinate temporary membership details, airport transfers, golf carts, villa pre-stocking, chef preferences, tee times, tennis lessons, spa treatments, and off-property excursions throughout Montego Bay.
For golfers, that might mean early tee times, caddies, club rentals, and lunch waiting back at the villa after a morning on the course. For families, it might mean nanny service, kids' activities, beach club days, and private dinners timed around younger guests.
Back at the villa, your Concierge works with the house staff to make the stay feel personal, from favorite breakfast orders and dietary needs to celebration dinners, rum tastings, beach picnics, and relaxed evenings on the veranda.
The Tryall Club's beach club anchors the waterfront experience with two beautiful stretches of soft white sand meeting calm Caribbean waters. Guests enjoy cushioned loungers, attentive bar and restaurant service, and water sports including kayaking, paddleboarding, and Hobie Cat sailing. The beauty of staying in a Tryall villa is the effortless flow between your private pool and the communal beach club, so you can enjoy both worlds throughout your stay.
When selecting your villa, it's important to understand the different waterfront settings available. Beachfront luxury Tryall Club villas are located on or immediately adjacent to sandy beaches, offering the easiest access for families and beach lovers who want to step directly from their terrace onto the sand. Oceanfront Tryall Club villas in Jamaica are positioned along rocky shoreline or elevated platforms, featuring dramatic wave sounds, sea ladders, viewing decks, and some of the most spectacular sunset views on the property.
Hillside villas, while set back from the water, offer their own advantages: elevated ocean and golf course views, cooling breezes, enhanced privacy, and larger pool areas. Golf carts (typically included with your villa rental) make accessing the beach club quick and easy.
Discover our selection of oceanfront and beachfront Tryall Club villas
With a secure gated estate, Penn State-certified nannies, supervised kids' programs, calm beach areas, and activities that appeal to all ages, the Tryall Club is one of the premier spots for a family vacation in the Caribbean.
Tryall Club villas for families are thoughtfully designed with multigenerational groups in mind. You'll find a variety of bedroom configurations—king suites, queen rooms, twin bedrooms, bunk rooms, and connecting rooms—that accommodate different family structures and ages. Many villas feature single-level or accessible layouts ideal for older guests or those with mobility considerations, plus family-friendly amenities like media rooms, games rooms, expansive lawns, and pools with graduated depths.
The private chef service is particularly valuable for families, as chefs can customize kids' menus around picky eaters, allergies, and preferred meal times. Whether it's early dinners for young children, poolside lunches, or special birthday celebrations, your villa chef adapts to your family's rhythm.
Some of the best family-friendly luxury Tryall Club villas 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, quaint 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.
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 villas Jamaica are spread throughout this expansive 2,200-acre estate, with each area offering a distinct setting while sharing access to all club amenities. Understanding these different locations helps you choose the villa that best matches your priorities.
Hillside & Garden Villas occupy elevated positions with sweeping views of both the Caribbean Sea and the championship golf course. These properties benefit from cooling breezes, lush tropical gardens, typically larger pool areas, and enhanced privacy given their secluded settings. They're ideal for groups seeking tranquility and dramatic vistas.
Fairway & Golf-View Villas are positioned along or near the championship course, making them perfect for golf groups who want to maximize their time on the links. These golf villas offer easy access to the clubhouse, practice facilities, and pro shop, with many featuring direct fairway views from their terraces.
Beachfront & Oceanfront Villas occupy the most coveted waterfront positions, offering the closest proximity to sand and sea. These are the first-choice properties for families with young children, beach lovers, and anyone who prioritizes waking up to ocean views and the sound of waves.
Great House Villas & Apartments are smaller units clustered around the historic Great House, the estate's original 19th-century manor. These properties share a communal pool and offer the quickest access to core club facilities, making them good choices for couples or small families seeking a more intimate Tryall experience.
Many of the most coveted Tryall Club villas are positioned along the waterfront, offering stunning views and direct access to the Caribbean Sea. Due to limited inventory, beachfront and oceanfront villas book early, especially for Christmas, New Year's, and school holiday periods.
Some of the most popular beachfront and oceanfront Tryall Club villas 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 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.
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 complementing 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.
One of the defining features of Tryall Club luxury villas is the exceptional staff service that comes standard with most properties. In fact, the staff is consistently listed as one of the highlights of staying in a Tryall Club villa in our guest reviews. Your villa team typically includes a private chef or cook, butler, housekeeper, laundress, and gardener, all working together to deliver resort-level service in the privacy of your own estate. This means daily housekeeping, laundry service, table service, and personalized meal preparation, allowing you to simply relax and enjoy your fully-staffed Jamaican escape.
Before you even arrive, your Rental Escapes Concierge works with you to organize meal planning and villa pre-stocking, ensuring your favorite foods, beverages, and specialty items are waiting when you walk through the door. Your private chef then handles everything from early breakfasts and poolside lunches to elaborate dinner parties and special-occasion celebrations, with flexible timing that adapts to your schedule rather than forcing you into rigid meal times.
Culinary offerings blend authentic Jamaican favorites like jerk chicken, fresh-caught fish, festival, and callaloo with international cuisine tailored to your preferences. Chefs excel at accommodating diverse dietary needs, including vegan, vegetarian, gluten-free, dairy-free, and allergy-sensitive menus. With advance notice, they can also focus on specific wellness goals, whether that's clean eating, Mediterranean-style dishes, or family-friendly nutrition. The use of fresh, locally-sourced seafood and produce ensures every meal celebrates Jamaica's incredible culinary bounty.
Want to learn more about what to expect from chef service, butlers, housekeeping, and villa staff? Read our guide to luxury Jamaica villas with staff.
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 teams that elevate group bookings into experiences that are not soon forgotten.
For the largest gatherings, groups can choose between booking one expansive estate or clustering multiple nearby villas, allowing different family units or friend groups their own space while staying close together.
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 Hanover 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.
Many Tryall Club villas can accommodate weddings and special events, subject to villa owner and club approval. Your Rental Escapes Concierge can help coordinate event planning, from arranging additional catering and florals to organizing photography and entertainment.
Golf: 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, whether you're an experienced golfer or a beginner. Professional instruction, club rentals, and experienced caddies are all available.
Tennis & Racquet Sports: 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 pros ready to help you elevate your game through clinics and private lessons, no matter your starting level.
Beach & Water Sports: 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, Hobie Cat sailing, and snorkeling in calm Caribbean waters.
Wellness & Fitness: Many villas include private gyms, but the club also offers a full fitness center. In-villa massage and spa services can be arranged through your Concierge, and the expansive villa terraces provide perfect settings for sunrise yoga or meditation overlooking the sea.
Off-Property Excursions: Your Concierge can arrange private drivers for exploring Montego Bay's attractions, including river rafting on the Martha Brae, visiting Dunn's River Falls, touring historic Rose Hall Great House, or experiencing Jamaica's vibrant culture and cuisine at local markets and restaurants. All transportation is arranged with vetted private drivers.
The Tryall Club is located on Jamaica's north coast in Montego Bay, approximately 25-35 minutes west of Sangster International Airport (MBJ) on a private 2,200-acre gated estate.
The drive from Sangster International Airport to the Tryall Club takes approximately 25-35 minutes depending on traffic. Airport transfers can be arranged by your Rental Escapes Concierge.
The C5 Electronic Passenger Declaration is mandatory for all visitors entering Jamaica, including guests traveling to Tryall Club. This online form consolidates Immigration and Customs documentation and must be completed before your arrival. Visit enterjamaica.gov.jm to submit your declaration.
Yes, most luxury Tryall Club villas include full staff service with a private chef or cook, butler, housekeeper, laundress, and gardener, delivering resort-level hospitality in your private villa. Your Concierge can also arrange any additional staff you may need.
Yes, all villa guests must purchase a temporary membership. The fee applies to guests aged 16 and older, with children under 16 exempt. This membership grants access to all club amenities including golf, tennis, beach club, pools, and fitness facilities.
Absolutely. The Tryall Club is one of the Caribbean's premier family destinations, featuring a secure gated estate, Penn State-certified nannies, kids' programs, calm beach areas, and family-friendly Tryall Club villas with varied bedroom configurations.
Many Tryall Club villas for rent can accommodate weddings and special events, subject to villa owner and club approval. Your Rental Escapes Concierge can help coordinate all event planning and vendor arrangements.
Peak season runs December to March with the mildest weather and lowest precipitation. Shoulder season (April to June) offers better deals and smaller crowds with only occasional afternoon showers. Summer and early fall (July to November) provide the best value but correspond to hurricane season with higher precipitation.
Tryall Club villa rentals typically include a golf cart for navigating the expansive estate. For off-property excursions, private driver service can be arranged through your Concierge.
The Tryall Club offers a private estate setting with golf, staffed villas, and a quiet feel, which sets it apart from many other areas on Jamaica’s north coast. It’s one of the most exclusive spots in Montego Bay, known for wide grounds, full-service villas, and a strong sense of space and privacy.
Montego Bay: Compared to beachfront areas closer to town, Tryall is more peaceful and self-contained. You get a country-club style layout with golf, tennis, a beach club, and low-density surroundings. If you prefer being closer to restaurants and nightlife, you may like areas such as Ironshore or Reading instead, but they won’t offer the same level of estate-style living.
Ocho Rios: In Ocho Rios, the appeal is direct access to waterfalls, adventure parks, and natural sights. Villas there often sit closer to major attractions, so it’s great for activity-focused trips. Tryall, by contrast, is better for guests who want relaxation, golf, and full villa service on a private estate.
Discovery Bay & Runaway Bay: Both Discovery Bay and Runaway Bay offer some of the best beachfront villas in Jamaica, with calm water and wide bays. These areas are ideal if beach access is your top priority. Tryall offers a beach as well, but the draw here is the estate lifestyle, golf course, and large, private homes rather than a long bay beach environment.
In short, Tryall is perfect if you want golf, service, and a private club feel; Ocho Rios is best for attractions and adventure; and Discovery Bay and Runaway Bay are ideal for pure beachfront stays.
Yes, the private chefs at Tryall Club villas excel at accommodating all dietary needs including vegan, vegetarian, gluten-free, dairy-free, and allergy-sensitive menus with advance notice provided to your Concierge.
The mandatory temporary membership fee applies to all guests aged 16 and older. Children under 16 are exempt, making the club attractive for family bookings.
Gratuities are a key part of the Tryall Club experience. It is customary to leave a cash gratuity for the entire villa staff upon departure. The recommended rate is 10% to 15% of the gross villa rental cost (excluding the temporary membership fee), which is then divided among the staff team.
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. Your villa's private chef prepares all meals using the freshest ingredients and can accommodate your dietary needs and preferences.
The Tryall Club sees temperate and balmy weather year-round, with average temperatures of 88°F (31°C). April is the sunniest month overall, with 253 hours of sunshine. 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).
The Tryall Club stands as the ultimate luxury villa community in Jamaica: a prestigious estate where privately owned villas, full-service staff, championship golf, exclusive beach club access, and tailored experiences come together to create an unparalleled Caribbean escape.
Rental Escapes offers a carefully curated collection of the finest beachfront, oceanfront, golf-view, family, and large Tryall Club villas. Our Villa Specialists bring intimate knowledge of each property and work closely with you to understand your group's unique needs, matching you with the perfect villa for your occasion. From there, our dedicated Concierge team takes over, handling everything from temporary membership coordination to custom itineraries, villa pre-stocking, chef menu planning, tee time reservations, and off-property excursions.
Contact our Villa Specialists today to reserve your Tryall Club luxury villa and let our Concierge team design a bespoke Jamaican escape tailored to your group.
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