Cliffside Cottage
Overview
Specials
Amenities
Reviews
Location

Cliffside Cottage

·
10   5
·
5
·
Estate
10 Guests
5 Bedrooms
5 Beds
Also available as
6 Guests, 3 Bedrooms
5 Bathrooms
5000 sq ft. on 2 floors
Montego Bay, Jamaica, Caribbean
Estate
Ocean View
Event Allowed
Pool

Special Offers

One Love Lives
The spirit of Jamaica endures and welcomes you back. Book this home and enjoy $250 in savings on stays through the end of October. Beautiful surroundings, warm hospitality, and the rhythms of the island await your return.
Offer applicable:
Stay: Feb 7 — Oct 31, 2026

About This Property

Panoramic Hillside Retreat at Cliffside Cottage

Welcome to Cliffside Cottage, a charming five-bedroom hillside villa perched dramatically above the Caribbean Sea with sweeping views across Montego Bay. Set on four acres of lush tropical grounds, this private retreat captures spectacular sunrises, glowing sunsets, and sparkling evening lights that shimmer across the bay.

With approximately 5,000 square feet of indoor and outdoor living space, Cliffside Cottage offers a relaxed yet elegant Caribbean escape complemented by attentive staff and access to the renowned Tryall Club.


Living Spaces

Cliffside Cottage blends traditional Caribbean charm with spacious open living areas designed to embrace its remarkable setting. The main living room features soaring rafter-and-beam ceilings and opens wide onto a wraparound verandah, allowing refreshing trade winds and breathtaking ocean views to flow naturally through the home.

Comfortable seating areas invite guests to relax while enjoying the panoramic scenery, and the home’s media setup includes cable television, a large plasma screen, DVD library, and a sound system with CD collection and wireless speaker capability.

The villa’s wraparound verandah serves as the heart of the home — a breezy gathering space perfect for morning coffee, afternoon relaxation, or sunset cocktails overlooking the sea.


Outdoor Living

Outdoor living at Cliffside Cottage centers around its expansive pool terrace and elevated vantage point overlooking Montego Bay.

• 20’ x 40’ private swimming pool
• Large cut-stone pool terrace with lounge seating
• Covered verandah with outdoor bar
• Outdoor dining area overlooking the sea
• Panoramic sunrise and sunset views
• Four acres of landscaped tropical grounds

The terrace provides a stunning setting for poolside relaxation or evening gatherings under the stars, where the lights of Montego Bay shimmer across the water.


Sleeping Accommodations | Sleeps 10

Cliffside Cottage offers five air-conditioned bedrooms, each designed for comfort and privacy.

Master Bedroom
Located in the private east wing. King-size mahogany canopy bed with French doors opening to a private ocean-view balcony and walkway to the pool terrace. En-suite bathroom with large walk-in shower.

Bedroom 2
Queen-size mahogany bed with French doors opening to an ocean-view terrace. En-suite bathroom with walk-in shower and access to an interior garden. Adjoining passageway connects to Bedroom 3.

Bedroom 3
King or twin beds at guest’s option. French doors open to a terrace with ocean and pool views. En-suite bathroom with double vanity and tub-shower combination.

Bedroom 4
King or twin beds with an additional daybed and garden views. Hall bathroom with walk-in shower.

Bedroom 5
King or twin beds with garden views. En-suite bathroom with tub-shower combination.


Dining & Entertaining

Meals at Cliffside Cottage are prepared by your private chef and can be enjoyed in a variety of scenic settings throughout the villa.

Dining options include:

• Breezy covered verandah overlooking the sea
• Cozy indoor dining room
• Romantic poolside dinners arranged by the staff

Your full staff includes:

• Chef
• Butler
• Housekeeper
• Laundress
• Gardener / night watchman

The team ensures guests enjoy both exceptional service and authentic Jamaican hospitality throughout their stay.


Location

Cliffside Cottage is located just outside the gates of the prestigious The Tryall Club on Jamaica’s scenic north coast.

Guests may access Tryall’s extensive resort amenities by paying the Temporary Membership Fee directly at the resort. Membership includes access to:

• Private beach and beach club
• Non-motorized water sports
• Tennis courts
• Fitness center
• Hummingbird Kids Club
• Great House afternoon tea and weekly events

Golf, spa services, dining, and additional resort activities are available for additional fees.


With its breathtaking hillside views, expansive verandah, private pool terrace, and access to the legendary Tryall Club, Cliffside Cottage offers a peaceful and elegant Caribbean retreat where unforgettable sunsets and relaxed island living take center stage.

Staff Insight
Cliffside Cottage gives guests the ideal vantage point to take in the breathtaking beauty of Montego Bay and Jamaica. Fully staffed for your total relaxation and peace of mind!
John Di Rienzo
Exotic Estates Staff

Bedrooms and Amenities

Flexible Layouts

The property is available to rent in the following bedroom configurations.

5 Bedrooms
10 Guests
5 Bedrooms
5 Beds
5 Bathrooms
5000 sq ft. on 2 floors
3 Bedrooms
6 Guests
3 Bedrooms

Bedrooms

Primary Bedroom — East Wing
Bed: King Bed·En-Suite Bath with Shower·Air Conditioning·Safe·Ceiling Fan·Private Balcony
Bedroom Two
Bed: Queen Bed·En-Suite Bath with Shower·Air Conditioning·Safe·Ceiling Fan·Direct Access to Terrace and Courtyard·Connects w/ Nearest Bedroom
Bedroom Three
Bed: King Bed w/Option as 2 Twin Beds·En-Suite Bath with Shower and Bathtub·Air Conditioning·Safe·Ceiling Fan·Direct Access to Terrace·Connects w/ Nearest Bedroom
Bedroom Four
Bed: King Bed w/Option as 2 Twin Beds·Bed: Twin Day Bed·Separate Bathroom·Air Conditioning·Ceiling Fan·Safe
Bedroom Five
Bed: King Bed w/Option as 2 Twin Beds·En-Suite Bath with Shower and Bathtub·Air Conditioning·Ceiling Fan·Safe

Amenities

Living Room
2 Sofas·Additional Seating·High Ceilings·Direct Access to Veranda
Outdoor Living
Pool·Bar·Dining Table - Seats 6·Dining Table - Seats 4·Lush Landscaping
Home Amenities
Access to Resort Amenities (Additional Fee), Tennis Court and Gym/Fitness Center·Complimentary Kids Club·DVD Player·Sound Dock·Sound System·IP Telephone (free to US numbers)
Services Included
Butler Service·Chef Service·Gardener·Housekeeper·Night Security

Reviews

Karlecka Party
Staff & Service: Excellent Accommodations: Excellent Overall Expectation: Exceeded Will you return: Yes Additional Comments: The Cliffside staff was amazing. from the time we entered the home until we left, it was an unforgettable experience. Everyone was attentive, dependable, accommodating, and hospitable. We were always served and waited on with the best service We loved how everything was smooth and seamless. They took great care of my grandmother, as she is visually impaired. I was blown away by the extra care and the over and beyond effort we witnessed. We truly felt like we were staying with family. Thank you to our Cliffside family! See you next time!
Crispin C.
Staff and service was great. Great food, lots of variety. We loved our stay would love to return.
Terri B.
Everything with respect to the staff & service was outstanding! Exceeded expectations. Thank you! Meals were delicious, perfect. Accommodations overall excellent, we felt very much at home. Thanks for a wonderful stay!
Ken T.
The staff is very warm, friendly. Everything is perfect. Excellent meals.

Location

Attractions

Sangster Int'l Airport: Montego Bay
12 Kilometers
Nearest Airport, Airport
Aquasol Theme Park
5.5 Kilometers
Amusement Park, Ocean Gear Rentals, Go-Kart Racing, Water Sports
Jungle Zip Lining
16 Kilometers
Zip Line
Dunn's River Falls
97 Kilometers
Activities
Montego Bay
12 Kilometers
Shopping & Restaurants
Tryall Club
9 Kilometers
Beach, Restaurants, Golf Course, Kids Club
$1,142 — $2,275 / night
Cliffside Cottage
Montego Bay, Jamaica, Caribbean
·
10   5
$1,142 — $2,275 / night
Check in | Check out
Guest
5 Bedrooms
Enter your Promo Code

This property requires our Villa Specialists to confirm availability for you. Please inquire below.

For assistance call us at 888.628.4896

Rates

  • Holiday Reservations: Please note that the holiday (higher) nightly rate will be applicable to the full duration of any reservation that includes said holiday date, regardless of rate period listed.

  • Damage Deposits: A damage deposit of 10% of the villa rental is due to secure this reservation. A mandatory damage insurance waiver covers the first $2,000 in damages. If the rental requires more than a $2,000 deposit, guest will be required to pay any damage deposit amount that exceeds the $2,000 damage waiver, which is refundable provided no damage occurs.
  • Tryall Club Reservations: The Accidental Damage Waiver policy and/or security deposit are not due for reservations occurring at the Tryall Club, as a credit card will be collected upon check-in for the security deposit and released after check-out as long as there are no incidents or damages found.
Home > All Destinations > Caribbean > Jamaica > Cliffside Cottage