Cliffside Cottage
Cliffside Cottage at Tryall Club – Private Jamaica Villa Rental with Panoramic Sea Views
Overview
Set high above the Caribbean coastline, Cliffside Cottage is a beautifully positioned private retreat offering uninterrupted views across Montego Bay. Surrounded by lush tropical greenery, this charming residence captures the essence of island living, with breathtaking sunrises and glowing sunsets that define the experience.
This exceptional home is a standout among Jamaica villa rentals, offering a perfect blend of comfort, privacy, and timeless Caribbean character. Ideal for families or groups, it ranks among the most sought-after Jamaica vacation villas for a relaxing and scenic escape.
Villa Highlights
Five-bedroom private villa with five bathrooms.
Approximately 5,000 sq. ft. of indoor and outdoor living space.
Set within four acres of tropical gardens.
Private 20' x 40' swimming pool with spacious terrace.
Outdoor bar and shaded dining veranda.
Full access to Tryall Club amenities.
As one of the leading luxury villas in Jamaica, Cliffside Cottage delivers both space and style in an exclusive setting.
Living & Entertaining Spaces
The villa is designed to embrace its surroundings, with open living areas that flow effortlessly դեպի outdoor spaces.
Expansive living room with vaulted, beamed ceilings.
Wrap-around verandah with sweeping ocean views.
Indoor dining room and al fresco dining options.
Comfortable lounge areas ideal for relaxing or entertaining.
These features make it a perfect choice for travellers seeking vacation villas in Jamaica with authentic charm and modern comfort.
Outdoor Living
Outdoor spaces are central to the villa’s appeal, offering multiple areas to unwind while enjoying the Caribbean climate.
Large private pool overlooking the sea.
Sun terrace with loungers and shaded seating.
Outdoor bar for entertaining.
Lush landscaped gardens with scenic viewpoints.
This setting places Cliffside Cottage among the most desirable villas in Jamaica with pool and premium Caribbean villas.
Accommodation
With five well-appointed bedrooms, the villa is ideal for Jamaica family villa rentals and groups seeking space and flexibility.
Master Suite
Private east wing location.
King-size canopy bed.
Dual balconies with ocean views.
En-suite bathroom with walk-in shower.
Direct access to pool terrace.
Guest Bedrooms
Flexible king or twin configurations.
En-suite or nearby bathrooms.
Ocean, pool, or garden views.
Interconnecting options for families.
The thoughtful layout makes this one of the most comfortable Jamaica villas to rent for both small and larger groups.
Staff & Service
A professional in-house team ensures a seamless stay, placing the villa among the finest Jamaica villas with staff.
Private chef preparing customised meals.
Butler service.
Housekeeping and laundry.
Gardener and night security.
From relaxed breakfasts to elegant dinners under the stars, guests can enjoy the full experience of Jamaica private villas.
Amenities
Air conditioning in all bedrooms.
Wireless internet access.
Cable TV, DVD player, and media library.
Sound system with iPod dock and speakers.
In-room safes.
Complimentary international calls.
Laundry facilities.
Hair dryers in all bathrooms.
Tryall Club Access
Guests benefit from membership at the exclusive Tryall Club, enhancing their stay at one of the top Jamaica luxury villas.
Included Access
Private beach.
Non-motorised water sports.
Tennis courts.
Fitness centre.
Kids club and social events.
Additional Information
Daily membership fee applies.
Selected services such as golf, spa, and dining are extra.
Membership terms subject to change.
Perfect For
Cliffside Cottage is ideal for:
Families seeking holiday villas to rent in Jamaica.
Groups looking for spacious vacation villas in the Caribbean.
Couples wanting a peaceful and scenic retreat.
Travellers searching for private villa rentals in Jamaica.
Guests exploring luxury villas to rent in the Caribbean.
Why Book Cliffside Cottage
Elevated setting with panoramic sea views.
Spacious layout ideal for entertaining and relaxation.
Full staff for a personalised experience.
Access to one of Jamaica’s most exclusive resorts.
A standout choice among villas to rent in Jamaica.
Discover More Caribbean Villa Rentals
If you are exploring multiple destinations, consider a range of Barbados villas for rent or other handpicked vacation villas in the Caribbean, each offering a unique island lifestyle.
Book Your Stay
Cliffside Cottage offers an exceptional combination of location, service, and authentic charm, making it one of the most appealing Jamaica villas to rent today.
Contact Caribbean Dream Villas to reserve your stay at this stunning private retreat and experience the very best of Jamaica holiday villas.
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
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
Staff
- Butler
- Chef
- Gardener
- House keeper
- Laundress
- Night Watchman