Show All Photos
Villa Lolita , Montego Bay , Tryall  1 / 10
Villa Lolita , Montego Bay , Tryall  2 / 10
Villa Lolita , Montego Bay , Tryall  3 / 10
Villa Lolita , Montego Bay , Tryall  4 / 10
Villa Lolita , Montego Bay , Tryall  5 / 10
Villa Lolita , Montego Bay , Tryall  6 / 10
Villa Lolita , Montego Bay , Tryall  7 / 10
Villa Lolita , Montego Bay , Tryall  8 / 10
Villa Lolita , Montego Bay , Tryall  9 / 10
Villa Lolita , Montego Bay , Tryall  10 / 10
Add to Favourites
Villa Lolita
Villa Lolita
Villa Lolita
Villa Lolita
Villa Lolita
Villa Lolita
Villa Lolita
Villa Lolita
Villa Lolita
Villa Lolita
From $1,571 USD - $5,566 USD / nt

Villa Lolita

Montego Bay , Tryall  Jamaica
5
5
From $1,571 USD - $5,566 USD / nt
From $1,571 USD - $5,566 USD / nt
We love this villa because...
it perfectly blends modern design with Caribbean luxury, offering spacious suites, stunning ocean views, private pools, and dedicated staff for a truly unforgettable villa experience.

Villa Lolita – Luxury Caribbean Villa Rental

Villa Lolita is an extraordinary private retreat offering contemporary architecture, generous living spaces and elevated ocean views. Designed for guests seeking luxury villas in Jamaica and premium Caribbean villa rentals, this impressive residence delivers privacy, comfort and first-class amenities in a spectacular island setting.

Set high above the coastline on Ocean View Drive, the villa is surrounded by four acres of manicured tropical gardens, creating a peaceful escape ideal for families, friends and guests looking for exclusive villas in Jamaica.


Refined Island Living

  • Approximately 14,000 sq ft of stylish indoor and outdoor living space.

  • Elevated hillside location with panoramic sea views.

  • Lush landscaped grounds providing privacy and tranquillity.

  • Ideal for vacation villas in Jamaica and luxury villas to rent in the Caribbean.

Villa Lolita seamlessly blends modern design with relaxed Caribbean elegance, offering an exceptional setting for a memorable island holiday.


Five Spacious Suites with Premium Comfort

The villa features five beautifully appointed bedroom suites, each offering privacy and high-end finishes—perfect for Jamaica family villa rentals and private villa rentals in Jamaica.

Suite Highlights

  • En-suite bathrooms with open-plan showers and dual showerheads.

  • Flat-screen televisions and in-room entertainment systems.

  • Stunning views of the gardens or Caribbean Sea.

Bedroom Configuration

  • Michigan Master Suite

    • Private terraces.

    • Heated infinity plunge pool.

    • Outdoor shower.

  • Washington Master Suite

    • Separate sitting area.

    • Queen sofa bed.

    • Wet bar.

  • Tennessee Suite – King bed.

  • Illinois Suite – Two queen beds.

  • Ohio Suite – Fully wheelchair accessible with comfort-height features.


Exceptional Outdoor Spaces

Villa Lolita is designed for outdoor living, making it one of the most appealing villas in Jamaica with pool and luxury entertainment areas.

  • Multi-level terraces ideal for relaxation and socialising.

  • Expansive main terrace with infinity lap pool.

  • Shallow children’s pool for younger guests.

  • Sun loungers, shaded dining gazebo and outdoor wet bar.

These amenities make Villa Lolita an excellent choice for guests searching for Jamaica vacation villas, private villas in Jamaica, and luxury Caribbean villas.


Personalised Service & Staff

  • Dedicated team of 8 household staff.

  • Attentive yet discreet service throughout your stay.

  • Ideal for guests seeking Jamaica villas with staff and seamless holiday living.


Rental Information

  • Offered as a 4-bedroom rental option.

  • Rates from US$4,000 per night.

  • Total bedrooms: 5.

  • Sleeps up to 10 guests.


An Exceptional Caribbean Villa Experience

Villa Lolita is perfectly suited for travellers looking for:

  • Luxury villas in Jamaica.

  • Jamaica villas to rent with space and privacy.

  • Holiday villas to rent in Jamaica for families or groups.

  • High-end Caribbean villas with panoramic ocean views.

For guests seeking refined comfort, personalised service and an elevated island escape, Villa Lolita stands out as one of the most desirable luxury villa rentals in the Caribbean.

Plan Your Luxury Caribbean Escape

Discover the ultimate in privacy, comfort and elevated island living at Villa Lolita.

Enquire today with CaribbeanDreamVillas.com to check availability, receive personalised rates and start planning an unforgettable luxury villa holiday in Jamaica.

Contact Caribbean Dream Villas today:

Explore More Villas in Jamaica

USA/ Canada:  +1 347 707 1195

UK / International : +44 1978 368531

Email: [email protected]

For luxury villas to rent in other areas of the Caribbean  visit: www.worldwidedreamvillas.com

See more details...

Looking for Jamaica Villas to Rent?

Looking for Jamaica Villas to Rent?Caribbean Dream Villas, a trusted Caribbean villa specialist and part of Worldwide Dream Villas, offers a handpicked selection of luxury villas to rent in Jamaica. Whether you’re seeking a beachfront villa, a private pool retreat, or a family-friendly holiday home near Jamaica’s top attractions, we provide some of the finest Jamaica villa rentals available. Explore villas to rent in popular areas like Montego Bay, Negril, and Ocho Rios. With stunning ocean views, professional concierge services, and easy access to Jamaica’s best beaches, dining, and golf courses, our villas for rent in Jamaica are ideal for couples, families, and groups looking for a memorable Caribbean vacation. Book your perfect Jamaica villa getaway with Caribbean Dream Villas today!

Rates

From To Min Stay Nightly Rate Weekly Rate
25-Jul-2026 30-Oct-2026 7 $1,571 USD $11,000 USD
From To Min Stay Nightly Rate Weekly Rate
20-Dec-2025 02-Jan-2026 7 $4,841 USD $33,888 USD
04-Jan-2026 06-Mar-2026 7 $3,458 USD $24,206 USD
07-Mar-2026 27-Mar-2026 7 $3,803 USD $26,627 USD
28-Mar-2026 24-Apr-2026 7 $3,458 USD $24,206 USD
25-Apr-2026 24-Jul-2026 7 $2,074 USD $14,523 USD
25-Jul-2026 30-Oct-2026 7 $1,900 USD $13,302 USD
31-Oct-2026 20-Nov-2026 7 $2,074 USD $14,523 USD
21-Nov-2026 28-Nov-2026 7 $3,803 USD $26,627 USD
29-Nov-2026 11-Dec-2026 7 $2,074 USD $14,523 USD
12-Dec-2026 18-Dec-2026 7 $3,458 USD $24,206 USD
19-Dec-2026 02-Jan-2027 7 $4,841 USD $33,888 USD
From To Min Stay Nightly Rate Weekly Rate
20-Dec-2025 02-Jan-2026 7 $5,566 USD $38,966 USD
04-Jan-2026 06-Mar-2026 7 $3,976 USD $27,833 USD
07-Mar-2026 27-Mar-2026 7 $4,373 USD $30,616 USD
28-Mar-2026 24-Apr-2026 7 $3,976 USD $27,833 USD
25-Apr-2026 24-Jul-2026 4 $2,546 USD $17,826 USD
25-Jul-2026 30-Oct-2026 7 $2,357 USD $16,505 USD
31-Oct-2026 20-Nov-2026 7 $2,546 USD $17,826 USD
21-Nov-2026 28-Nov-2026 7 $4,373 USD $30,616 USD
28-Nov-2026 11-Dec-2026 7 $2,546 USD $17,826 USD
12-Dec-2026 18-Dec-2026 7 $3,976 USD $27,833 USD
19-Dec-2026 02-Jan-2027 7 $5,566 USD $38,966 USD

Plan Your Trip

Amenities

  • Air Conditioned bedrooms
  • Air Conditioning
  • Car Parking on site
  • Childrens Activities
  • Communal Facilities
  • Gazebo
  • Golf Resort
  • Gym/Fitness Room
  • On site security
  • Private Garden
  • Private Pool
  • Restaurant
  • Sea view
  • Shop
  • Spa
  • Staffed Villa
  • Sunbeds
  • Tennis Court
  • TV
  • WaterSports
  • Well Equipped Kitchen
Bedroom : 5
Bathroom : 5

Staff

  • Butler
  • Chef
  • Gardener
  • House keeper
  • House Manager
  • Laundress

Location

Have a Question?

USA/CANADA: +1 347 707 1195
BARBADOS: +246-432-6307
UK / INTERNATIONAL: +44 1978 368531

Other Properties you may like

Get In Touch

CONTACT US

USA/CANADA: +1 347 707 1195
UK /International : +44 1978 368531
Barbados: +1 246-432-6307

Email : [email protected]

 

UK: 40 Knutsford Road, Alderley Edge, Cheshire SK9 7SF

Barbados: Indigo Courtyard, Holetown, Barbados Bb24917

Live Chat


A great way to communicate as we can answer your questions in real time. We are usually available 6 days a week between 9am and 8pm.

FOLLOW US

Subscribe to our Newsletter