Overlook
Overview
Specials
Amenities
Location

Overlook

·
10   5
·
Villa
10 Guests
5 Bedrooms
7 Beds
Also available as
8 Guests, 4 Bedrooms
5 Bathrooms
1 floor
Tryall Club, Montego Bay, Jamaica, Caribbean
Villa
Ocean View
Mobility Friendly
Pool with heating
Hot Tub

Special Offers

One Love Lives
The spirit of Jamaica endures and welcomes you back. Book this home and enjoy $750 in savings on stays through the end of April. Beautiful surroundings, warm hospitality, and the rhythms of the island await your return.

Offer applicable:
Stay: Feb 7 — Oct 31, 2026
Jamaica Escape - Stay 4 Nights for the Price of 3

Trade the everyday for turquoise waters, warm island breezes, and unforgettable sunsets. For a limited time, enjoy one complimentary night in your fully staffed villa when you book a four-night stay in beautiful Jamaica.

*Full non-refundable payment required at time of booking. No Tryall Temporary Membership Dues will be applied to the free night in this promotion.
Offer applicable:
Stay: Jun 6 — Oct 31, 2026 · Book: Feb 14 — May 31, 2026
Jamaica Escape - Stay 7 Nights for the Price of 5

Trade the everyday for turquoise waters, warm island breezes, and unforgettable sunsets. For a limited time, enjoy two complimentary nights in your fully staffed villa when you book a seven-night stay in beautiful Jamaica.

*Full non-refundable payment required at time of booking. No Tryall Temporary Membership Dues will be applied to the free night in this promotion.
Offer applicable:
Stay: Jun 6 — Oct 31, 2026 · Book: Feb 14 — May 31, 2026

About This Property

The Overlook Villa is idyllically nestled in the Jamaican hillside and features sweeping views of the cobalt Caribbean Sea while surrounded by lush greenery, majestic palms, and tropical blooms. Its location offers guests easy walking or golf cart access to all that The Tryall Club has to offer. Breezy, wide-open spaces, together with nostalgic Caribbean décor provide an authentic Jamaican experience.

Overlook’s heated swimming pool, with jacuzzi platforms at each side, features a refreshing outdoor shower and is fed by a quiet babbling fountain. Surrounded by royal palm trees, planters abundant with colorful bougainvillea, and spectacular sunshine, this is the ultimate spot for relaxation.

Overlook’s experienced and professional Villa staff, including a Butler, Chef, Housekeeper, Laundress, and Gardner, are dedicated to ensuring all your vacation needs are met. Work in consultation to design menus to your exact taste with your talented Chef. Have your Butler arrange all the details of your day whether you golf, play tennis, or explore far or nearby. Dinner can be under the stars or in the Villa’s air-conditioned dining room and throughout the Villa, you will enjoy Wi-Fi and surround sound audio. As well, all televisions are SMART and connected through Starlink, offering North American coverage.

Overlook sits on the upper elevation of Copperwood Ridge and is within easy walking distance of the Great House, gym and tennis courts, spa and a short ride by the villa’s complimentary golf carts to the legendary Tryall Golf course and the beach.

For your family or friends, Overlook Villa combines elevated service with laid-back Jamaican style. Wake up to cooling trade winds, move through a day filled with activities, or adventure, or simply lounge the day away. Then meet back for views of a glorious sunset and a delicious signature dinner.

The Tryall Club Experience
Guests of this villa enjoy access to the prestigious Tryall Club, set across 2,200 acres of beautifully landscaped hillside and beachfront. Amenities include the renowned 18-hole championship golf course, tennis courts (day and night play), private beach club, fitness center, jogging trails, Kids Club, and complimentary non-motorized watersports such as snorkeling, kayaking, and sailing. Guests also enjoy afternoon tea at the Great House and weekly social events including the Manager’s Cocktail Party.
*While many facilities are included, additional fees apply for golf, spa services, dining and bar charges, motorized watersports, and select special events.

Temporary Tryall Membership Dues

All villa guests are required to register for a Temporary Membership during their stay. Current rates are US$170 per person (16+) per week, or US$34 per person per day for stays under 7 days (plus 15% service charge). Children 13–15 receive a 50% discount; children 12 and under are complimentary. Fees are payable directly to the Club upon arrival.
*Please note that certain facilities may occasionally close for private events, and membership offerings and fees can be subject to change at any time without notice.

Bedrooms and Amenities

Flexible Layouts

The property is available to rent in the following bedroom configurations.

Default
10 Guests
5 Bedrooms
7 Beds
5 Bathrooms
1 floor
4 Bedroom
8 Guests
4 Bedrooms

Bedrooms

Bedroom One
Bed: King Bed·En-Suite Bath·Flat-Screen, Smart TV·Safe·Ocean View
Bedroom Two
Bed: King Bed·En-Suite Bath·Flat-Screen, Smart TV·Safe·Ocean View
Bedroom Three
Bed: King Bed·En-Suite Bath·Flat-Screen, Smart TV·Safe·Ocean View
Bedroom Four
Bed: 2 Twin Beds w/Option as King Bed·En-Suite Bath·Flat-Screen, Smart TV·Safe·Ocean View
Bedroom Five
Bed: 2 Twin Beds w/Option as King Bed·En-Suite Bath·Flat-Screen, Smart TV·Safe·Ocean View

Amenities

Living Area
Sofas·Multiple Seating Areas·Flat-Screen, Smart TV
Kitchen
Fully Equipped Kitchen
Dining Area
Dining Table - Seats 10
Outdoor Living
Heated Pool·Hot Tub·Outdoor Shower·Organic Vegetable Garden·Fountains
Laundry Area
Washer & Dryer
Home Amenities
Air Conditioning·Ceiling Fan·Wireless/WiFi Internet Access·Sound System·CD Player·DVD Player·Books·Hair Dryer·Wet Bar
Services Available
Butler Service·Chef Service·Gardener·Housekeeper·Private Laundry Service
Transportation
2 Golf Carts

Location

Attractions

Sangster International Airport
14.7 Miles
Nearest Airport
Tryall Club
0.5 Mile
Beach, Restaurants, Golf Course, Kids Club
Round Hill Resort
4.6 Miles
Golf Course, Tennis Court, Spa, Gym, Trails, Beach Access, Kids Club
Aquasol Theme Park
13.0 Miles
Amusement Park, Ocean Gear Rentals, Go-Kart Racing, Water Sports
Hip Strip
13.0 Miles
Shopping & Restaurants, Sightseeing, Adventure & Exploring
Doctor's Cave Beach
13.6 Miles
Beach, Beach Club, Beach Access
Ahhh...Ras Natango Gallery and Garden
15.8 Miles
Nature Preserve, Galleries, Lookout
Cinnamon Hill
22.5 Miles
Golf Course
Kool Runnings Waterpark
31.7 Miles
Amusement Park, Water Park
Royal Palm Reserve
34.8 Miles
Botanical Garden
$1,913 — $3,993 / night
Overlook
Tryall Club, Montego Bay, Jamaica, Caribbean
·
10   5
$1,913 — $3,993 / night
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This property requires our Villa Specialists to confirm availability for you. Please inquire below.

For assistance call us at 888.628.4896

Rates

Please note, quote is not inclusive of Temporary Tryall Membership Fees due at the property upon check-in. Please inquire with your Villa Specialist for current rates.