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From $928 - $2,142 / nt

Cliffside Cottage

Montego Bay  Jamaica
5
5
From $928 - $2,142 / nt
From $928 - $2,142 / nt
We love this villa because...
its breathtaking hillside views, full staff service, and exclusive Tryall Club access.

Cliffside Cottage, Tryall Club – Exclusive Jamaica Villa Rental with Ocean Views

Overview

Perched on a verdant hillside overlooking the Caribbean Sea, Cliffside Cottage is a private and peaceful escape with sweeping views across Montego Bay. From golden sunrises to sparkling evening lights along the coastline, this villa offers a truly memorable setting for your Caribbean getaway.

Blending classic island charm with modern comfort, this is one of the most desirable Jamaica villa rentals for travellers seeking space, privacy, and a relaxed luxury lifestyle.


At a Glance

  • 5-bedroom, 5-bathroom private villa.

  • Approx. 5,000 sq. ft. of living space.

  • Set on 4 acres of tropical grounds.

  • Private 20' x 40' swimming pool.

  • Outdoor bar and multiple dining areas.

  • Tryall Club membership access.

As part of an exclusive estate, Cliffside Cottage stands out among Jamaica luxury villas and premium vacation villas in the Caribbean.


Living Areas

Designed to maximise light, views, and airflow, the villa’s interiors offer a relaxed yet elegant atmosphere.

  • Spacious living room with vaulted ceilings and exposed beams.

  • Seamless access to a wrap-around verandah.

  • Indoor and outdoor dining options.

  • Comfortable lounge areas for socialising or unwinding.

This open-plan layout is ideal for guests searching for vacation villas in Jamaica with a true indoor-outdoor lifestyle.


Outdoor Lifestyle

Cliffside Cottage makes the most of its elevated setting with exceptional outdoor spaces.

  • Private swimming pool with sea views.

  • Sun terrace with loungers and shaded seating.

  • Verandah bar for sunset drinks.

  • Landscaped gardens surrounding the villa.

These features place it among the most appealing villas in Jamaica with pool and sought-after Caribbean villas.


Bedrooms & Layout

Perfect for families or groups, the villa offers flexible accommodation across five well-appointed bedrooms, making it ideal for Jamaica family villa rentals.

Master Suite

  • Private wing for added seclusion.

  • King-size canopy bed.

  • Private balconies with ocean views.

  • En-suite bathroom with walk-in shower.

  • Direct access to pool terrace.

Guest Bedrooms

  • Mix of king, queen, or twin configurations.

  • En-suite or adjacent bathrooms.

  • Ocean, pool, or garden views.

  • Interconnecting rooms suitable for families.

This versatile layout makes it one of the most comfortable Jamaica villas to rent for a variety of group sizes.


Staff & Services

A dedicated team ensures every stay is effortless and enjoyable, highlighting why this is one of the top Jamaica villas with staff.

  • Private chef preparing tailored menus.

  • Butler service.

  • Housekeeping and laundry.

  • Gardener and night security.

From casual breakfasts to elegant evening dining, guests enjoy the full experience of private villa rentals in Jamaica.


Amenities

  • Air conditioning in all bedrooms.

  • High-speed wireless internet.

  • Cable TV, DVD, and media library.

  • Sound system with wireless speakers.

  • In-room safes.

  • Complimentary international calls.

  • Laundry facilities.


Tryall Club Privileges

Guests have access to the renowned Tryall Club, adding exceptional value to this already impressive Jamaica private villa experience.

Included Access

  • Private beach.

  • Tennis courts and gym.

  • Non-motorised water sports.

  • Kids club and social events.

Additional Details

  • Daily membership fee applies.

  • Select services (golf, spa, dining) available at extra cost.

  • Access subject to resort policies.


Ideal For

Cliffside Cottage is well suited to:

  • Families looking for holiday villas to rent in Jamaica.

  • Groups seeking spacious Jamaica vacation villas.

  • Couples wanting a scenic, private escape.

  • Travellers exploring luxury villas to rent in the Caribbean.


Why Choose Cliffside Cottage

  • Elevated location with panoramic views of Montego Bay.

  • Spacious and private setting within an exclusive estate.

  • Fully staffed for a relaxed, luxury experience.

  • Access to world-class resort amenities.

  • A standout choice among villas to rent in Jamaica.


Discover More Villas

Explore a wider portfolio of Jamaica villas to rent and handpicked Caribbean villas, as well as a curated selection of Barbados villas for rent, all offering exceptional locations and high standards of comfort.


Book Your Jamaica Villa

Cliffside Cottage offers a rare combination of scenery, service, and space, making it one of the most attractive Jamaica holiday villas available.

Contact Jamaica Dream Villas today to reserve your stay and experience one of the finest luxury villas in Jamaica.

Contact Jamacian 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...

Rates

From To Min Stay Nightly Rate Weekly Rate
17-Mar-2026 03-Apr-2026 7 $1,214 USD $8,498 USD
12-Apr-2026 15-Apr-2026 7 $1,214 USD $8,498 USD
16-Apr-2026 20-Nov-2026 7 $928 USD $6,496 USD
29-Nov-2026 14-Dec-2026 5 $928 USD $6,496 USD
15-Dec-2026 18-Dec-2026 7 $1,214 USD $8,498 USD
04-Apr-2027 15-Mar-2027 7 $1,214 USD $8,498 USD
16-Apr-2027 19-Nov-2027 5 $928 USD $6,496 USD
28-Nov-2027 14-Dec-2027 5 $928 USD $6,496 USD
15-Dec-2027 18-Dec-2027 7 $1,214 USD $8,498 USD
From To Min Stay Nightly Rate Weekly Rate
17-Mar-2026 03-Apr-2026 7 $1,428 USD $9,996 USD
04-Apr-2026 11-Apr-2026 7 $1,428 USD $9,996 USD
12-Apr-2026 15-Apr-2026 7 $1,428 USD $9,996 USD
16-Apr-2026 20-Nov-2026 7 $1,142 USD $7,994 USD
21-Nov-2026 28-Nov-2026 7 $1,285 USD $8,995 USD
29-Nov-2026 14-Dec-2026 5 $1,142 USD $7,994 USD
15-Dec-2026 18-Dec-2026 7 $1,428 USD $9,996 USD
19-Dec-2026 26-Dec-2026 7 $2,000 USD $14,000 USD
27-Dec-2026 02-Jan-2027 7 $2,142 USD $14,994 USD
03-Jan-2027 26-Mar-2027 7 $1,428 USD $9,996 USD
27-Mar-2027 03-Apr-2027 7 $1,428 USD $9,996 USD
04-Apr-2027 15-Apr-2027 7 $1,428 USD $9,996 USD
16-Apr-2027 19-Nov-2027 5 $1,142 USD $7,994 USD
20-Nov-2027 27-Nov-2027 7 $1,285 USD $8,995 USD
28-Nov-2027 14-Dec-2027 5 $1,142 USD $7,994 USD
19-Dec-2027 26-Dec-2027 7 $2,000 USD $14,000 USD
27-Dec-2027 03-Jan-2028 7 $2,142 USD $14,994 USD

Plan Your Trip

Amenities

  • Air Conditioned bedrooms
  • Bar
  • Beach Club Facility
  • Car Parking on site
  • Golf Resort
  • Gym/Fitness Room
  • Private Garden
  • Private Pool
  • Restaurant
  • Sea view
  • Sound System
  • Spa Wellness Suite
  • Staffed Villa
  • Sunbeds
  • Tennis Court
  • TV
  • WaterSports
  • Well Equipped Kitchen
  • Wireless Internet
Bedroom : 5
Bathroom : 5

Staff

  • Butler
  • Chef
  • Gardener
  • House keeper
  • Laundress
  • Night Watchman

Location

Have a Question?

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

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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

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