Stunning Fully-Staffed 5 Bedroom Villa – Tryall Jamaica's Best Villa Winner!
For those who are not prepared to compromise, Villa Lolita is a striking example of 21st century architecture and with an interior that marries glamour with sophisticated style. With a breathtaking setting, Villa Lolita is an elegant sanctuary and one of the finest villas in Jamaica.
The villa features exceptional suites that offer optimum privacy with sensational views and meticulous attention to detail. It will appeal to those who are not willing to compromise and seek the best in Caribbean living.
Located on the brow of Ocean View Drive and constructed in 2008, Villa Lolita comprises 15,000 square feet of free-flowing living space where the emphasis is on stylish comfort and detailing that pays tribute to the flora and fauna of Jamaica. Built on three levels the villa is surrounded by four acres of gardens that have been painstakingly landscaped to offer a subtle medley of varying tones of green.
The main floor contains the first master suite and a guest suite; the immediate lower floor has two guest bedrooms and the second master suite occupies its own private lower floor. All suites include flat screen televisions, iPod docking stations, double sinks in the en-suite bathrooms and open showers with dual shower heads.
The magnificent Michigan Master Suite located on the main floor has large secluded terraces with views of the mountains and the ocean and feature a heated infinity plunge pool/Jacuzzi with outdoor shower, lavish extra-large indoor shower, and features a private living room in the bedroom. The indoor travertine and glass tiled shower accommodates two or more persons and overlooks both the mountains and the ocean. The Ohio Suite is located on the first level and is handicap accessible with comfort height safety bars throughout. The Washington Master Suite features a connecting living room with a queen size sofa bed, full wet bar with microwave and a garden-level extra-large private patio, with capacity for 4 (perfect for families). The Tennessee Suite features a king size bed with a large wrap-around patio, and the Illinois Suite includes two queen size beds. The property features a full gym with steam room, shower, and bath, and also features a billiard room.
Villa Lolita is located within the Tryall Golf community, which boasts 18 holes of the finest golf Jamaica has to offer. This villa has won the coveted “Best Villa” award within Tryall several times over, and is consistently considered one of the finest villas in all of Jamaica.
Relax with your favorite person or your favorite drink, as you contemplate the mesmerizing views from the living and dining pavilions that open to the ocean on one side and to a lush garden of tropical plants on the other.
The wraparound terrace has four distinct levels. One level is dedicated to sun worshippers; the second area features a two foot deep children’s pool and the main entertainment terrace which covers 2500 square feet surrounds the infinity lap pool and includes an outdoor dining gazebo, wet bar and several relaxing seating areas. The sumptuous outdoor furnishings and the fabulous views make it a perfect venue for private parties.
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Events allowed: family gatherings, birthday parties, weddings
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Pets
No pets allowed
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Smoking
Smoking is not permitted
Important information
You need to know
Property # 3697089vb
Extra-person charges may apply and vary depending on property policy
Government-issued photo identification and a credit card, debit card or cash deposit may be required at check-in for incidental charges
Special requests are subject to availability upon check-in and may incur additional charges; special requests cannot be guaranteed
Parties and events (including family gatherings, birthday parties and weddings) are allowed on site. Maximum attendees: 50
Host has not indicated whether there is a carbon monoxide detector on the property; consider bringing a portable detector with you on the trip
Host has not indicated whether there is a smoke detector on the property
About the area
Montego Bay
Montego Bay is home to this villa. Widowmaker's Cave and Montego Bay Cruise Ship Terminal are worth checking out if an activity is on the agenda, while those wishing to experience the area's natural beauty can explore Doctor's Cave Beach and Montego Bay Marine Park. Montego Bay Cultural Centre and Ahhh...Ras Natango Gallery & Garden are also worth visiting.
Montego Bay Cultural Centre - 3 min drive - 1.9 km
Harmony Beach Park - 3 min drive - 2.2 km
Getting around
Montego Bay (MBJ-Sir Donald Sangster Intl.) - 14 min drive
Restaurants
The Pork Pit - 4 min drive
Juici Patties - 3 min drive
KFC - 4 min drive
Peppa's Cool Spot - 5 min drive
A Vegan's Utopia - 4 min drive
Frequently asked questions
Is Stunning Fully-Staffed 5 Bedroom Villa – Tryall Jamaica's Best Villa Winner! pet-friendly?
No, pets are not allowed at this property.
How much does it cost to stay at Stunning Fully-Staffed 5 Bedroom Villa – Tryall Jamaica's Best Villa Winner! ?
As of 10 May 2026, prices found for a 1-night stay for 2 adults at Stunning Fully-Staffed 5 Bedroom Villa – Tryall Jamaica's Best Villa Winner! on 11 May 2026 start from AU$6,900, including taxes and fees. This price is based on the lowest nightly price found in the last 24 hours for stays in the next 30 days. Prices are subject to change. Choose your dates for more accurate prices.
What time is check-in at Stunning Fully-Staffed 5 Bedroom Villa – Tryall Jamaica's Best Villa Winner! ?
Check-in begins at 3:00 PM.
What time is check-out at Stunning Fully-Staffed 5 Bedroom Villa – Tryall Jamaica's Best Villa Winner! ?
Checkout is at 12:00 PM.
Where is Stunning Fully-Staffed 5 Bedroom Villa – Tryall Jamaica's Best Villa Winner! located?
Situated in Montego Bay, this villa is within 1 mile (2 km) of Church Street, Creek Dome and Burchell Memorial Baptist Church. Montego Bay Cultural Centre and Civic Centre are also within 2 miles (3 km).