Cliffside Cottage

Cliffside Cottage

Montego Bay, Jamaica, Caribbean· 5
$1,000 — $2,000 / night
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5 Bedrooms
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This property requires our Villa Specialists to confirm availability for you. Please inquire below.

For assistance call us at 888.628.4896

Special Offer
Take $250!
Book your reservation at one of these select destinations for travel through December 15, and receive $250 off.
Offer applicable to stays during May 24 → Dec 15, 2024


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.
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Cliffside Cottage is both elegant and welcoming. This Jamaican villa rests on a striking Jamaican hillside overlooking Montego Bay and the blue waters of the Caribbean Sea. The private, ocean-view villa is the ideal setting for a glamorous Caribbean vacation. 

The fully staffed, five-bedroom villa is surrounded by four acres of stunning property. Cliffside Cottage offers guests a total of 5,000 square feet of indoor and outdoor living space. From the lofty location, guests can see both the dramatic sunrise and sunset each day. 

Guests can step outside and enjoy the balmy weather on the villa's wraparound veranda. The veranda leads out to the cut stone terrace and 20-foot by 40-foot pool. Swim in the pool's clear waters while enjoying the terrace's profusion of flowers and the view of the Caribbean Sea. 

Cliffside Cottage's emerald green lawn is dotted with fragrant fuchsia and colorful bougainvillea. You can take meals out on the covered veranda on the east side of the villa for a view of the lush greenery and the lights of Montego Bay. The villa also has a brand new bar on the veranda. Guests can sip on cocktails and relax on the veranda all day. 

Inside, the villa's living room serves as the main gathering place. The room's vaulted ceiling and tall windows give the room a sunny, open-air atmosphere. The living room has doors that open directly onto the veranda. From the window you can see the still waters of the pool and the waves of the Caribbean Sea. 

The largest of Cliffside Cottage's five bedrooms is in the villa's east wing. This room has a king-size canopy bed of carved mahogany. The en-suite bathroom has a luxurious walk-in shower. Guests of this room has have access to a private, ocean-view balcony. French doors also lead to a side balcony and walkway to the pool deck. 

The second and third bedrooms are connected by an adjoining passage. One bedroom has a queen-size bed of mahogany and an en-suite bathroom with a walk-in shower. This room also French doors that open to an ocean-view terrace, as well as separate doors that open to an interior garden. The other bedroom has the option for a king-size bed or two twin-size beds. The en-suite bathroom has combination shower and bathtub, as well as a double vanity. This room has French doors that lead out to the terrace and a bay window with a gorgeous view of the sunset.

The fourth and fifth bedrooms both have the option for a king-size bed or two twin-size beds. The fourth bedroom has a hall bathroom with a walk-in shower, while the fifth bedroom has an en-suite bathroom with a combination shower and bathtub. Both rooms have a view of the villa's gardens. 

Each of the bedrooms is cooled by air-conditioning. Additionally, each bedroom has a personal safe for guests' use. Guests also have access to Wi-Fi throughout Cliffside Cottage. The villa has a sound system, iPod dock with wireless speakers, and a CD collection. You can also enjoy cable TV, the DVD player, and a large movie collection. 

During your stay at Cliffside Cottage, the villa's professional staff will make sure all of your needs are met. A chef prepares delicious meals, while the butler, housekeeper, laundress, and gardener/night watchman keep the household in perfect order. 

Guests of Cliffside Cottage are also given membership access to the Tryall Club.The exclusive resort offer pools, cocktail hours, water sports, and more. 

Journey to Montego Bay's Cliffside Cottage for an experience of complete luxury and relaxation.
Montego Bay, Jamaica, Caribbean
Vacation Rental
Vacation Rental
Ocean View
Event Allowed
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
5 Bedrooms
10 guests
Master Bedroom (Private East Wing)
Bed: King Bed
·En-Suite Bath with Shower
·Air Conditioning
·Ceiling Fan
·Private Balcony
Bedroom Two
Bed: Queen Bed
·En-Suite Bath with Shower
·Air Conditioning
·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
·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
Bedroom Five
Bed: King Bed w/Option as 2 Twin Beds
·En-Suite Bath with Shower and Bathtub
·Air Conditioning
·Ceiling Fan
Living Room
2 Sofas
·Additional Seating
·High Ceilings
·Direct Access to Veranda
Outdoor Living
·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
·Butler Service
·Chef Service
·DVD Player
·Sound Dock
·Sound System
·IP Telephone (free to US numbers)


We loved all the staff who went above and beyond to see that we were comfortable, happy and safe. Having access to the two clubs was a real bonus for our group of young adults. We could all be together and enjoy a variety of activities. Our first experience with having a staff was a real luxury. Truly makes the vacation a holiday, especially for our Mom.
Superb! Exceeded our expectations. All the staff were friendly and accommodating – they made our trip very special.
My family and friends had a great time at your property in Jamaica. The staff were perfect,,,I would not hesitate to recommend this property to friends and family. Thanks for providing great hospitality!



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
Montego Bay
12 Kilometers
Shopping & Restaurants
Tryall Club
9 Kilometers
Beach, Restaurants, Golf Course, Kids Club