Lolita at Tryall, Jamaica
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$1,299.00 / Nt
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Lolita at Tryall

Montego Bay, Jamaica
‎(7 reviews)
4 King
2 Queen
5 En-suite
Children Welcome

Villa Lolita at the Tryall Club on Jamaica is a stunning 14,500 square foot contemporary villa designed by a noted Chicago architect. Set on four acres in Montego Bay with breathtaking panoramic views of the Caribbean Sea, the villa offers beautiful living areas both indoors and out. Touches of rich mahogany and Italian travertine add elegance to the decor.

The covered entry leads to a dramatic great room opening to the marble pool terrace outside. Discover comfortable white sofas and a long dining room table situated near open walls with sea views. A 45-inch plasma TV and a library filled with movies and books grace the air-conditioned study.

Enjoy memorable meals prepared by your personal chef in the granite and stainless steel kitchen, served indoors or al fresco under a protected portico. A second outdoor living room and the bar on the terrace are ideal for friends and family gathering after spending the day on the beach or on the golf course. The five Villa Lolita bedrooms offer king beds, private en-suite baths, flat screen satellite TVs and WiFi Internet access.

As a guest of the Tryall Club, you will enjoy all the amenities of a premiere private club for an exceptional island getaway. Take advantage of the onsite private beach, tennis, water sports and events including exciting beach parties and cocktail parties. Use the complimentary golf cart to explore the grounds and book a tee time at the spectacular Tryall Club Golf Course that features manicured fairways along the water. Families with children will find a 24-inch section of the heated pool, as well as a second heated kiddie pool across the terrace. The Hummingbird Kids Club provides toys, games, videos and activities like jungle treks, arts and crafts and talent shows.

The Tryall Club supplies guests at Villa Lolita with the services of a professional staff, including a cook, a laundress and a butler for a carefree tropical vacation.

Villa Lolita at the Tryall Club Staff includes:
Cost of food and gratuities not included

Villa Lolita at the Tryall Club additional amenities:
The Trayll Club Temporary Membership
The Tryall Club Resort Fee: US$130 +15% per week for each guest 16 or older, or US$26+15% per day per person for stays of less than 7 days.​
Tryall Club private beach
Tennis court access nearby
Golf course preferred fees at the Tryall Club
Complimentary facilities of the resort
Location: Tryall Club, Montego Bay

Note: Please note special Holiday weeks (e.g. Thanksgiving) may be charged at Premium rate.

Featured in Isle Blue Magazine: Experience the Tryall Club in Jamaica.

Lot Size: 4 acres Interior Area Size: 14500 ft²

Shawn Jun, 2019

We just got back from our annual adult trip with our group of five couples and we stayed at Villa Lolita at Tryall. I cannot express enough how incredible this house is along with the service. The staff starting with Martin, Chef Marlon, Inez, Carlton and the rest were amazing. They took such good care of us. Our group was amazed at the service excellence our staff displayed. If you have never stayed somewhere where you have a full-time staff at your beckoning call then you need to stay at Villa Lolita. Truly a pampered experience where you do nothing. All meals were prepared daily by Chef Marlon and he is truly exceptional. Martin served us drinks wherever and whenever we wanted as well as meals. He was remarkable. Clothes were washed daily and rooms cleaned. This house was immaculate. Great layout. Staff truly makes this experience one of the best our group has ever had. Thank you for your hospitality. This is a vacation our group will never forget. We plan on returning soon.

Source: TripAdvisor/FlipKey

Maya H. Mar, 2019

Inez, Conley, Chef Marlon, Loraine, Kamara, Samntha, Carlton, Damian, Robert (driver). These are all the staff that are at this villa. I mentioned all the staffs names, but I just want to say that truly everyone is incredible! Inez is amazing, she's like the den mother of the house and all that I was staying with are all girls so she made sure that we had everything we needed and a comfortable stay. Conley is a fantastic butler, he will make sure that you have a lot of fun on your trip and he will get your right. Chef Marlon is a fantastic Chef, he makes sure that you are eating whatever it is that you like and whatever you request he will have it for you. The rest of the staff is incredibly friendly, they will give you tours, change your linens, do your laundry, set up whatever you need, gt your groceries, and etc. This trip was one of my favorite trips just because the staff was amazing! I hope everyone stays here and gets the experience I felt!

Antony D. Oct, 2018

We recently spent a fantastic week with friends at Villa Lolita and could not have a more fantastic experience. When you turn the corner to enter the driveway, you realize you have made the right choice. The villa is your own mini resort and spa, with all en-suite bedrooms, awesome views, world-class furnishings and a staff that catered to our every need. The private chef made it difficult to fit into our bathing suits, but we could not say no! He began every meal by announcing, "and the flavor continues!" The beach is a short golf cart ride, but you will not want to stay long, because you want to get back the villa. Don't miss an opportunity to stay at Villa Lolita. It is a very special place!

Source: TripAdvisor/FlipKey

Deidra G. May, 2018

A group of us stayed a Villa Lolita for a birthday celebration. We didn't have to draw straws for rooms because there was not a room that you wouldn't want to stay in. The property was amazing but the service was most memorable! Inez, Connley, Samantha, Chef Marlon, Jermaine, and all the other staff were very attentive and made sure we were comfortable and happy.

Source: TripAdvisor/FlipKey

Jerome W. Jun, 2017

This is probably the coolest, most contemporary Villa at Tryall. The staff, specifically Chef Scott, Butler Adrian, and head housekeeper Inez are the strongest, friendliest, and most accommodating team ever!! Villa Lolita is a "don't miss" experience.

Source: TripAdvisor/FlipKey

Ronald May, 2017

Had a GREAT stay at Villa Lolita. The facility is outstanding with great views of the ocean. Love being with the staff. They were excellent,. This is my second time staying on this property. I recommended my friends to join us on the trip. We all had fun relaxing and enjoy the service. They made you feel right at home during our stay. The Villa was voted as the top property with in the Tryall Club.

Source: TripAdvisor/FlipKey

Jasmine K. Apr, 2017

What an amazing experience my 5 friends & I had visiting Tryall Club. We stayed in the absolutely amazing Villa Lolita. The staff was amazing . Adrian, Inez & Chef Scott too incredible care of our ever need. The other staff was great as well. This was not our first time visiting Jamaica, however it was our first time visiting Tryall. We will definitely be back.

Source: TripAdvisor/FlipKey

All bedrooms are air conditioned, equipped with flat screen TV with satellite, WiFi, safe, and have a walk-in closet and an en-suite bathroom.

Main Level

Bedroom 1: Master bedroom suite with a king-size bed, sound system, sitting room, large east and north facing balconies with views, outdoor shower, heated swimming pool, and en-suite bathroom with a his and hers open shower with 4 shower-heads, vanity, WC. 2 guests maximum.

Bedroom 2: Bedroom with a king-size bed, private balcony with access to the pool and en-suite bathroom with two shower-heads (rain forest + handheld). 2 guests maximum.

Middle Level

Bedroom 3: Bedroom with a king-size bed, sitting area, direct access to the gardens and terraces, great views and en-suite bathroom with shower, double vanity, WC. 2 guests maximum.

Bedroom 4: Bedroom with two queen-size beds, sitting area, direct access to the gardens and terraces, great views and en-suite bathroom with shower, double vanity, WC. 2 guests maximum.

Lower Level

Bedroom 5: Bedroom with a king-size bed, direct access to a large stone terrace and en-suite bathroom with walk-in shower, double vanity and WC. 2 guests maximum.

  • Air Conditioning - Bedrooms
  • Alfresco Dining Area
  • Beach Towels
  • Bed and Bath Linens
  • Cable TV
  • CD Player
  • Ceiling Fans
  • Chef Service
  • Children Welcome
  • Coffee Maker
  • Computer
  • Connected Bedrooms
  • Daily Turndown Service
  • Dishwasher
  • Dryer
  • DVD Player
  • Film Library
  • Fitness Room - Private
  • Games Library
  • Golf (Nearby)
  • Golf Cart
  • Gourmet Kitchen
  • Hair Dryer
  • Hammam
  • Internet
  • iPod Dock
  • Iron
  • Jacuzzi/Whirlpool
  • Kayak
  • Kettle
  • Library
  • Media Room
  • Office
  • On-Site Heliport
  • Outdoor Bar
  • Outdoor Grill
  • Outdoor Shower
  • Outdoor Speakers
  • Patio/Terrace
  • Phone
  • Playground
  • Pool Table
  • Resort Privileges
  • Safe
  • Secured Parking
  • Steam Room
  • Sunbed
  • Surround Sound
  • Treadmill
  • Tub
  • View - Ocean/Sea
  • Voltage - 110
  • Washer
  • Wheelchair Accessible
  • WiFi
  • Butler/Host
  • Chef/cook
  • Gardener
  • Housekeeper(s)
  • Laundress
  • Property Manager on Call
Housekeeping: Maid service 7 days a week
* Unless stated otherwise, the expenses for food and beverages are excluded and will be invoiced separately by the property.
  • Heated
  • Outdoor
  • Private

Rates based on 10 guests.

Note: The rates above are subject to 15% Tax/Service Charge.
Payments accepted in US Dollars, Canadian Dollars, Euros, British Pound, Swiss Franc, Australian Dollars, New Zealand Dollars.
Major credit cards accepted in US Dollars.
Rates are subject to change without prior notice.

  • Reservation deposit is 30%. Full balance is due 90 days prior to arrival.
  • Cancellation Policy: General Conditions: For cancellations greater than 61 days prior to arrival, 25% of the deposit paid is forfeited. Cancellations within 60 days, 100% of gross rental is forfeited. Thanksgiving Conditions: For cancellations greater than 91 days prior to arrival, 25% of the deposit paid is forfeited. Cancellations within 90 days, 100% of gross rental is forfeited. Please note for Thanksgiving week all payment are non refundable for the following villas: Rio Chico, Lime-Acre, and Sundown. Holidays/Festive Conditions: For cancellations greater than 121 days prior to arrival, 25% of the deposit paid is forfeited. Cancellations within 120 days, 100% of gross rental is forfeited. Please note for Festive season all payment are non refundable for the following villas: Rio Chico, Lime-Acre, Sundown, Whispering Waters, Keela Wee, Happy Hour, and Sea Grapes.
  • Check In / Check Out: 3pm / 11am
  • Damage Deposit: Mandatory US$149.00 fee covering up to US$2,500 worth of damage
  • Children Welcome (all ages)
  • No Pets Allowed
  • No Smoking
  • Baggage service handling
  • Club Membership
  • Full capacity rate required during Thanksgiving week.
  • Holiday/Festive Booking Condition: 50% deposit required. Balance due by September 1st.
  • Kids Club
  • Provisions and groceries are not included
  • Rates are set in US Dollars. Prices in other currencies may fluctuate.
  • Staff gratuity is 10% of the gross rental rate in High Season, 15% in Low Season, divided among the staff members. Amount to be paid in cash at the villa.
  • Thanksgiving Booking Condition: 50% deposit required.
  • Utilities included
  • VAT taxes included in rates.
  • Villa orientation
  • Tryall Club Temporary Membership Fee for 7+ night stays - $160 + tax
  • Tryall Club Temporary Membership Fee for stays of less than 7 days - $32 + tax per guest per day
  • Jamaica fee - US$ 50
  • Mandatory US$149.00 fee covering up to US$2,500 worth of damage

Once a vacation home is selected, the pampered adventure begins. Our concierge team will assist with creating a magical and immersive vacation experience. Our services include

* at select destinations

While available for advanced requests, the concierge team connects with guests 30 days prior to arrival to coordinate arrivals and to reserve desired services and experiences. Guests with scheduled Christmas/New Year stays will be contacted 90 days prior to arrival.

Advice, Answers and Tips
Explore our support articles for answers to your questions
Common Questions
Do we share the villa? click to close
No. You will not share the villa with another party. The villa is exclusively yours. If a larger villa offers a lower bedroom rate category, the villa will remain exclusively yours but the unrented bedrooms will be locked off.
For example, a 5 bedroom villa that offers a 3 bedroom rate will be the exclusive use of the guest but two bedrooms and their en-suite bathrooms will be locked off. Capacity is capped at 2 guests per bedroom.
Are we protected from fraud? click to open
Yes. Isle Blue stands behind you throughout your entire vacation. Unlike other companies, each property we offer has been hand picked to ensure that our standards are met. All property managers are vetted and payments are required to be held in escrow. Our primary obligation is to ensure your satisfaction and to have an exceptionally memorable vacation.
Can you explain the reservation process? click to open
Once a reservation request is received, Isle Blue will request a contract from the property manager for your dates of interest. Once the dates are confirmed and contract is received from the property manager, a payment will be required to confirm your reservation.
Once a reservation is confirmed, a concierge will welcome you to the planning stages of your vacation to assist with arrival logistics, rental cars, transfers, and a host of concierge services.
Can we arrange an early check in? click to open
Early check in may be possible but is at the sole discretion of the property manager. Early check in permission may not be granted until 24 hours prior to arrival.
Can we arrange a late check out? click to open
A late check out is rarely granted due to the turnover needs of a villa. A late check out may only be granted 24 hours prior to your departure from the property and only when there is no check in scheduled on the day of your check out. If a late check out is urgently needed please contact us.
Are transfers to the property included? click to open
Select villas may include a one way or roundtrip airport transfer while others may provide an escort or meeting point. Arrival logistics will be handled by your dedicated concierge as well as other concierge needs. The property's transfer policy will be listed under the Policies section.
What to expect upon arrival? click to open
In general, a villa orientation will be provided along with a key turnover. During the orientation, information and instructions for the property will be provided. Emergency contact information will be provided. We are available 7 days a week to assist with any urgent needs.
The arrival procedures vary from villa to villa, select villas may include welcome provisioning while other properties will provide basic arrival information.
What is the cancellation policy? click to open
Since these vacation homes are one of a kind properties, the cancellation policy is strict. We highly recommend considering trip/travel insurance to protect against any unexpected cancellations or issues that may arise.
For more details, please visit Travel Protection
What happens if the property becomes unavailable after I reserve? click to open
In the unlikely event, the rented property becomes unavailable due to a major issue that may affect a guest's experience or a transfer of ownership, Isle Blue will coordinate with the property manager to find an alternate property of equal or superior standard that is subject to the guest's approval. If an alternate property is not acceptable to the guest, the guest will receive a full refund.
Do you accept credit cards (American Express, Mastercard, or Visa)? click to open
Yes, we accept all major credit cards. American Express, Visa, Mastercard and Discover are accepted. Please note that credit card charges may be subject to additional fees. There are no fees with payment by wire transfer or check.
In the near future, we expect to accept a greater variety of payment methods and currencies via Stripe.
Is housekeeping included? click to open
Housekeeping tends to be a standard among vacation homes but the frequency may vary greatly depending on the property manager’s standards. Most properties will offer daily housekeeping (except Sunday and holidays) while other villas may only provide a mid-week cleaning. Please refer to the Staff section to learn about the housekeeping frequency of the property.
Are towels and linens provided? click to open
Yes. The property will provide bath and pool towels along with linens. Towels and linens will be refreshed as needed.
Are toiletries and tissues provided? click to open
A property may supply an initial supply of soap, shampoo, toilet paper and paper towels but replenishment of supplies once exhausted may be the responsibility of the guest. Each property varies in their handling of toiletries and paper products.
Is a hair dryer available? click to open
A hair dryer should be available at the property. Upon arrival, please check the bathrooms or closet. Typically, a hair dryer is included in each bathroom.
Is an iron included? click to open
Typically yes, irons tend to be standard equipment for vacation homes. Please ask the property representative upon orientation for the location of the iron.

  • Escape to Paradise with Our Villa Promotion!

    Book a 5-night stay or longer with a minimum of US$5000 rental rate, and we'll pamper you with a US$200 Concierge Credit that can be used towards a range of exclusive services to make your stay truly unforgettable.

    Use Your US$200 Concierge Credit for:

    Spa Services: Relax and rejuvenate with a wide range of spa treatments right in the comfort of your villa. Indulge in massages, facials, and more.
    Charters: Set sail on a private yacht or boat charter and explore the pristine waters of your destination. Discover hidden coves, snorkel in crystal-clear waters, and soak up the sun in style.
    Tours: Explore the local culture and attractions with our curated tours. From historical sites to culinary adventures, we've got you covered.
    Excursions: Dive into thrilling adventures with our exciting excursions. 

    Don't miss out on this incredible opportunity to elevate your villa experience! Book your 5-night stay or longer and take advantage of our US$200 Concierge Credit.

    Terms and Conditions:
    - Promotion valid for new bookings made between April 1, 2024 and June 30, 2024.
    - Concierge Credit is non-transferable and has no cash value.
    - Concierge Credit does not apply to car rental or chef service.
    - Services are subject to availability and must be booked in advance.
    - Other terms and conditions may apply.


    Offer ends: June 30, 2024

    Offer cannot be combined with other offers | Offer based on availability | Minimum night stay required | Non-transferrable | No cash value | Promotion is only valid on new reservations | Black-out dates may apply | Rates subject to tax and service charge
(Updated Intermittently)
Date Unavailable Availability calendar may not reflect up to date reservation information.
Availability subject to change.

Location, Directions & Nearby Villas

* Due to villa's privacy policy, the nearest town is presented on the map
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"Isle Blue is everything they say they are. They were a pleasure to deal with and were very responsive and informative. The pictures on their website are exactly what you end up getting and they provide full concierge service throughout your stay. My family and I had an amazing time and before we even returned home, we went to the Isle Blue website to check out their inventory for our next vacation. They really are just that good!"
Marc W.
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