Tryall Club Villas & Luxury Vacation Rentals

Your Guide to Tryall Club Villa Rentals

The Tryall Club is one of Jamaica's premier country clubs and home to some of Montego Bay's best golf, dining, and landscaping. 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.

About the Tryall Club

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.

Luxury Tryall Club Villas in Jamaica

Each Tryall Club villa is privately owned, with owners overseeing both construction and décor. That means they are all 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—featuring 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.

Why Rent a Villa at the Tryall Club?

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 Jamaican villas offer exceptional value compared to booking multiple luxury hotel suites. You're not just paying for bedrooms—you're gaining 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.

Beaches & Oceanfront Experiences at the Tryall Club

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—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

Tryall Club Villas for Families

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 premiere 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.

For more great options, explore our collection of large family villas.

Where to Stay Within the Tryall Club

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.

Beachfront & Oceanfront Tryall Club Villas

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 – 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.

Fully Staffed Tryall Club Villas with Private Chefs

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—jerk chicken, fresh-caught fish, festival, 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.

Tryall Club Villas for Large Groups & Celebrations

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.

Things to Do at the Tryall Club & Around Montego Bay

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—take advantage, even if you're 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.

Frequently Asked Questions about Tryall Club Villas