Cliffside Cottage, Jamaica
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Cliffside Cottage

Montego Bay, Jamaica
‎(6 reviews)
5 BEDROOMS
1 King
3 Kings/2 Twins
1 Queen
5 BATHROOMS
5 En-suite
10 GUESTS
Children Welcome

Villa Cliffside Cottage on Jamaica is a luxurious five-bedroom home in desirable Montego Bay that affords every amenity for a memorable tropical vacation. The name says it all to describe this glorious location where the villa is perched overlooking panoramic vistas of the blue Caribbean Sea.

Enjoy 5,000 square feet of living space both outdoors and indoors situated on four beautiful acres. The inviting living room is decorated in soft tones of island colors with stylish sofas and tile flooring. A soaring rafter-and-beam ceiling with lazy ceiling fans cools the room and adds a dramatic architectural touch. Wide doorways open to admit sea breezes and a profusion of natural light. Step outside to the wrap-around verandah, the perfect spot to appreciate jaw-dropping water views. Dine in style in the formal dining room, or opt to be served delicious home cooked meals prepared by your personal chef on the east verandah. Upon request, you may also take your meals under the stars on the cut stone pool terrace that surrounds the 40-foot private pool. Linger over an after-dinner coffee and a Tia Maria, and watch the lights of Montego Bay come up as the sun goes down. The magic of the natural environment is rejuvenating as you enjoy exotic tropical flowers and lush mountain vegetation set against the azure blue of the bay.

Guests at Villa Cliffside Cottage will have the advantage of a full staff, including a housekeeper, a laundress and a night watchman in addition to the chef. Modern electronics including WiFi Internet service are at your fingertips. 

The Tryall Club Membership: 
All guests must pay a resort entry fee of US$34 per person per day plus a 15% tax to have access to the resort amenities at the Tryall Club.  Children 13-15 years of age pay a discounted rate of 50% off plus 15% tax and children 12 & under are complimentary.
​After paying the Temporary Membership Fee, members may use most Club facilities at no charge with the exception of the tennis shop, ball boys, bar & restaurant, spa, grocery, motorized water sports, nanny services, and golf.  Complimentary amenities include the beach, non-motorized water sports, tennis, the excellent gym, the Hummingbird Kids Club, Great House afternoon tea, the Manager's Cocktail Party, and various special events.
Please Note: Tryall Club membership is guaranteed for guests traveling through November 1, 2025.

Lot Size: 4 acres Interior Area Size: 5000 ft²
Karlecka Party Jan, 1970

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!

Source: Guest Book

Terri B. Jan, 1970

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!

Source: Guest Book

Robert B. Jan, 1970

A wonderful week for our family of 10. Perfect for ages 4-67!

The staff was completely warm and welcoming from the moment we arrived. We felt completely taken care of. Delicious meals! We left every menu up to Chef Benford and each one was wonderful.

We could not have had a better week. The house and grounds are well cared for and beautiful, very comfortable.

Source: Guest Book

Walker Jan, 1970

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!

Source: Guest Book

Sheila O. Jan, 1970

Exceptional staff!! Enjoyed being with them. Accommodations were excellent. Cliffside exceeded our expectation and will plan to return!

Source: Guest Book

Jason N. Jan, 1970

Superb! Exceeded our expectations. All the staff were friendly and accommodating – they made our trip very special.

Source: Guest Book

Bedroom 1: Master bedroom with a king-size bed, balconies with ocean views and access to the pool and en-suite bathroom with walk-in shower, vanity and WC. 2 guests maximum.

Bedroom 2: Bedroom with a queen-size bed, access to terrace with ocean view, access to interior garden and en-suite bathroom with bathtub/shower combination, vanity and WC. 2 guests maximum

Bedroom 3: Bedroom with a king-size bed (can be made up as two single beds), access to terrace with ocean and pool view and en-suite bathroom with bathtub/shower combination, vanity and WC 2 guests maximum.

Bedroom 4 : Bedroom with a king-size bed (can be made up as two single beds), daybed, garden views and hall bathroom with walk-in shower, vanity and WC 2 guests maximum.

Bedroom 5: Bedroom with a king-size bed (can be made up as two single beds), garden views and private hall bathroom with bathtub/shower combination, vanity and WC 2 guests maximum.

Note: An interior passageway connects Bedroom 2 and Bedroom 3 for a convenient parent-child combination if desired. Connecting door can remain open or closed.

  • Air Conditioning - Bedrooms
  • Air Conditioning - Living Area
  • Alfresco Dining Area
  • Beach Towels
  • Bed and Bath Linens
  • Cable TV
  • CD Player
  • Chef Service
  • Children Welcome
  • Coffee Maker
  • Computer
  • Daily Turndown Service
  • DVD Player
  • Film Library
  • Fitness Room - Community Shared
  • Free Calls to the USA and Canada
  • Golf (Nearby)
  • Hair Dryer
  • Internet
  • iPod Dock
  • Kids Club
  • Library
  • Media Room
  • Outdoor Bar
  • Outdoor Grill
  • Patio/Terrace
  • Phone
  • Safe
  • Secured Parking
  • Smart TV
  • Tryall Club Membership
  • View - Ocean/Sea
  • Voltage - 110
  • WiFi
  • Butler/Host
  • Chef/cook
  • Gardener
  • Housekeeper(s)
  • Laundress
  • Security Guard
Housekeeping: Maid service 7 days a week
Chef : 3 meals per day
Cost of food and beverage is not included. Average budget is $70 per day per adult and $35 per day per child.

Suggested staff gratuity is 15% of the rental rate during low season and 10% of the rental rate during high season.
* Unless stated otherwise, the expenses for food and beverages are excluded and will be invoiced separately by the property.
  • Outdoor
  • Private
SEASON BEDROOMS DAILY WEEKLY
2024 Dec 1 to Dec 15 December 1, 2024 - December 15, 2024 (5 night minimum)
3 $786.00 $5,500.00
5 $1,000.00 $7,000.00
2024 Dec 15 to Dec 19 December 15, 2024 - December 19, 2024 (7 night minimum)
3 $1,129.00 $7,900.00
5 $1,272.00 $8,900.00
2024 Dec 19 to Dec 27 December 19, 2024 - December 27, 2024 (7 night minimum)
5 $1,858.00 $13,000.00
2024 Dec 27 to 2025 Jan 3 December 27, 2024 - January 3, 2025 (7 night minimum)
5 $2,000.00 $14,000.00
2025 Jan 3 to Apr 19 January 3, 2025 - April 19, 2025 (7 night minimum)
3 $1,129.00 $7,900.00
5 $1,272.00 $8,900.00
2025 Apr 19 to Apr 27 April 19, 2025 - April 27, 2025 (7 night minimum)
5 $1,272.00 $8,900.00
2025 Apr 27 to Nov 22 April 27, 2025 - November 22, 2025 (5 night minimum)
3 $786.00 $5,500.00
5 $1,000.00 $7,000.00
2025 Nov 22 to Nov 30 November 22, 2025 - November 30, 2025 (7 night minimum)
5 $1,143.00 $8,000.00
2025 Nov 30 to Dec 15 November 30, 2025 - December 15, 2025 (5 night minimum)
3 $786.00 $5,500.00
5 $1,000.00 $7,000.00
2025 Dec 15 to Dec 19 December 15, 2025 - December 19, 2025 (7 night minimum)
3 $1,129.00 $7,900.00
5 $1,272.00 $8,900.00
2025 Dec 19 to Dec 27 December 19, 2025 - December 27, 2025 (7 night minimum)
5 $1,858.00 $13,000.00
2025 Dec 26 to 2026 Jan 3 December 26, 2025 - January 3, 2026 (7 night minimum)
5 $2,000.00 $14,000.00
2024 Dec 1 to Dec 15 December 1, 2024 - December 15, 2024 (5 night minimum)
Bedrooms: 3
Daily: $786.00
Weekly: $5,500.00
Bedrooms: 5
Daily: $1,000.00
Weekly: $7,000.00
2024 Dec 15 to Dec 19 December 15, 2024 - December 19, 2024 (7 night minimum)
Bedrooms: 3
Daily: $1,129.00
Weekly: $7,900.00
Bedrooms: 5
Daily: $1,272.00
Weekly: $8,900.00
2024 Dec 19 to Dec 27 December 19, 2024 - December 27, 2024 (7 night minimum)
Bedrooms: 5
Daily: $1,858.00
Weekly: $13,000.00
2024 Dec 27 to 2025 Jan 3 December 27, 2024 - January 3, 2025 (7 night minimum)
Bedrooms: 5
Daily: $2,000.00
Weekly: $14,000.00
2025 Jan 3 to Apr 19 January 3, 2025 - April 19, 2025 (7 night minimum)
Bedrooms: 3
Daily: $1,129.00
Weekly: $7,900.00
Bedrooms: 5
Daily: $1,272.00
Weekly: $8,900.00
2025 Apr 19 to Apr 27 April 19, 2025 - April 27, 2025 (7 night minimum)
Bedrooms: 5
Daily: $1,272.00
Weekly: $8,900.00
2025 Apr 27 to Nov 22 April 27, 2025 - November 22, 2025 (5 night minimum)
Bedrooms: 3
Daily: $786.00
Weekly: $5,500.00
Bedrooms: 5
Daily: $1,000.00
Weekly: $7,000.00
2025 Nov 22 to Nov 30 November 22, 2025 - November 30, 2025 (7 night minimum)
Bedrooms: 5
Daily: $1,143.00
Weekly: $8,000.00
2025 Nov 30 to Dec 15 November 30, 2025 - December 15, 2025 (5 night minimum)
Bedrooms: 3
Daily: $786.00
Weekly: $5,500.00
Bedrooms: 5
Daily: $1,000.00
Weekly: $7,000.00
2025 Dec 15 to Dec 19 December 15, 2025 - December 19, 2025 (7 night minimum)
Bedrooms: 3
Daily: $1,129.00
Weekly: $7,900.00
Bedrooms: 5
Daily: $1,272.00
Weekly: $8,900.00
2025 Dec 19 to Dec 27 December 19, 2025 - December 27, 2025 (7 night minimum)
Bedrooms: 5
Daily: $1,858.00
Weekly: $13,000.00
2025 Dec 26 to 2026 Jan 3 December 26, 2025 - January 3, 2026 (7 night minimum)
Bedrooms: 5
Daily: $2,000.00
Weekly: $14,000.00

Rates based on 10 guests.

Note: The rates above are subject to 0% Tax/Service Charge.
Payments accepted in US Dollars, Canadian Dollars, Euros, British Pound, Swiss Franc, Australian Dollars, New Zealand Dollars.
Major credit cards accepted in US Dollars.
Rates are subject to change without prior notice.

  • Reservation deposit is 30%. Full balance is due 90 days prior to arrival.
  • Holiday/Festive Booking Condition: 50% deposit required. Balance due by August 1st.
  • Thanksgiving Booking Condition: 50% deposit required. Balance due by August 1st.
  • Cancellation Policy: General Conditions: For cancellations greater than 61 days prior to arrival, 25% of the deposit paid is forfeited. Cancellations within 60 days, 100% of gross rental is forfeited. Thanksgiving Conditions: For cancellations greater than 91 days prior to arrival, 25% of the deposit paid is forfeited. Cancellations within 90 days, 100% of gross rental is forfeited. Please note for Thanksgiving week all payment are non refundable for the following villas: Rio Chico, Lime-Acre, and Sundown. Holidays/Festive Conditions: For cancellations greater than 121 days prior to arrival, 25% of the deposit paid is forfeited. Cancellations within 120 days, 100% of gross rental is forfeited. Please note for Festive season all payment are non refundable for the following villas: Rio Chico, Lime-Acre, Sundown, Whispering Waters, Keela Wee, Happy Hour, and Sea Grapes.
  • Check In / Check Out: 3pm / 11am
  • Damage Deposit: Mandatory US$149.00 fee covering up to US$2,500 worth of damage
  • Children Welcome (all ages)
  • No Pets Allowed
  • No Smoking
  • Club Membership
  • Full capacity rate required during Thanksgiving week.
  • Kids Club
  • Provisions and groceries are not included
  • Rates are set in US Dollars. Prices in other currencies may fluctuate.
  • Staff gratuity is 10% of the gross rental rate in High Season, 15% in Low Season, divided among the staff members. Amount to be paid in cash at the villa.
  • Utilities included
  • VAT taxes included in rates.
  • Villa orientation
  • Tryall Club Temporary Membership Fee for stays of less than 7 days - $34 + 15% tax per guest per day
  • Jamaica fee - US$ 50
  • Mandatory US$149.00 fee covering up to US$2,500 worth of damage

Once a vacation home is selected, the pampered adventure begins. Our concierge team will assist with creating a magical and immersive vacation experience. Our services include

* at select destinations

While available for advanced requests, the concierge team connects with guests 30 days prior to arrival to coordinate arrivals and to reserve desired services and experiences. Guests with scheduled Christmas/New Year stays will be contacted 90 days prior to arrival.

Advice, Answers and Tips
Explore our support articles for answers to your questions
Common Questions
Do we share the villa? click to close
No. You will not share the villa with another party. The villa is exclusively yours. If a larger villa offers a lower bedroom rate category, the villa will remain exclusively yours but the unrented bedrooms will be locked off.
For example, a 5 bedroom villa that offers a 3 bedroom rate will be the exclusive use of the guest but two bedrooms and their en-suite bathrooms will be locked off. Capacity is capped at 2 guests per bedroom.
Are we protected from fraud? click to open
Yes. Isle Blue stands behind you throughout your entire vacation. Unlike other companies, each property we offer has been hand picked to ensure that our standards are met. All property managers are vetted and payments are required to be held in escrow. Our primary obligation is to ensure your satisfaction and to have an exceptionally memorable vacation.
Can you explain the reservation process? click to open
Once a reservation request is received, Isle Blue will request a contract from the property manager for your dates of interest. Once the dates are confirmed and contract is received from the property manager, a payment will be required to confirm your reservation.
Once a reservation is confirmed, a concierge will welcome you to the planning stages of your vacation to assist with arrival logistics, rental cars, transfers, and a host of concierge services.
Can we arrange an early check in? click to open
Early check in may be possible but is at the sole discretion of the property manager. Early check in permission may not be granted until 24 hours prior to arrival.
Can we arrange a late check out? click to open
A late check out is rarely granted due to the turnover needs of a villa. A late check out may only be granted 24 hours prior to your departure from the property and only when there is no check in scheduled on the day of your check out. If a late check out is urgently needed please contact us.
Are transfers to the property included? click to open
Select villas may include a one way or roundtrip airport transfer while others may provide an escort or meeting point. Arrival logistics will be handled by your dedicated concierge as well as other concierge needs. The property's transfer policy will be listed under the Policies section.
What to expect upon arrival? click to open
In general, a villa orientation will be provided along with a key turnover. During the orientation, information and instructions for the property will be provided. Emergency contact information will be provided. We are available 7 days a week to assist with any urgent needs.
The arrival procedures vary from villa to villa, select villas may include welcome provisioning while other properties will provide basic arrival information.
What is the cancellation policy? click to open
Since these vacation homes are one of a kind properties, the cancellation policy is strict. We highly recommend considering trip/travel insurance to protect against any unexpected cancellations or issues that may arise.
For more details, please visit Travel Protection
What happens if the property becomes unavailable after I reserve? click to open
In the unlikely event, the rented property becomes unavailable due to a major issue that may affect a guest's experience or a transfer of ownership, Isle Blue will coordinate with the property manager to find an alternate property of equal or superior standard that is subject to the guest's approval. If an alternate property is not acceptable to the guest, the guest will receive a full refund.
Do you accept credit cards (American Express, Mastercard, or Visa)? click to open
Yes, we accept all major credit cards. American Express, Visa, Mastercard and Discover are accepted. Please note that credit card charges may be subject to additional fees. There are no fees with payment by wire transfer or check.
In the near future, we expect to accept a greater variety of payment methods and currencies via Stripe.
Is housekeeping included? click to open
Housekeeping tends to be a standard among vacation homes but the frequency may vary greatly depending on the property manager’s standards. Most properties will offer daily housekeeping (except Sunday and holidays) while other villas may only provide a mid-week cleaning. Please refer to the Staff section to learn about the housekeeping frequency of the property.
Are towels and linens provided? click to open
Yes. The property will provide bath and pool towels along with linens. Towels and linens will be refreshed as needed.
Are toiletries and tissues provided? click to open
A property may supply an initial supply of soap, shampoo, toilet paper and paper towels but replenishment of supplies once exhausted may be the responsibility of the guest. Each property varies in their handling of toiletries and paper products.
Is a hair dryer available? click to open
A hair dryer should be available at the property. Upon arrival, please check the bathrooms or closet. Typically, a hair dryer is included in each bathroom.
Is an iron included? click to open
Typically yes, irons tend to be standard equipment for vacation homes. Please ask the property representative upon orientation for the location of the iron.

Plan your dream destination wedding or special Caribbean event. The villa is available for wedding receptions and special events.   

Maximum guests: 50 guests

Rental rates:
The villa requires seven nights minimum rental of villa at the full house rental rates. A $30 per person surcharge applies to outside guests (in excess of double occupancy per bedroom) who attend a rehearsal dinner, the wedding reception, brunch, or any other hospitality event at the wedding villa.

Refundable security deposit: USD $1,000.00
NB the security deposit is not released until two (2) weeks after even

Clients are also required to hire outside caterers as well as rent chairs, tables, tents, glasses, cutlery, and crockery.

Terms and conditions:
The villa does not allow unregistered guests to stay overnight. Overnight guests are restricted to 2 guests per rented bedroom and must be declared. If extra guests require accommodations, we recommend the rental of neighboring "sister" villas. For "sister" villas where additional guests are accommodated, there is a seven-night minimum in High Season and a five-night minimum in Low Season. Guests are responsible for the set-up and clean-up of the event. The event may not occur within 24 hours of departure. For example, with a Saturday departure guests must hold the event on Thursday or sooner. 

Please contact our villa specialists to assist you in selecting the perfect wedding venue for your special occasion.

PROMOTIONS

  • Escape to Paradise with Our Villa Promotion!

    Book a 5-night stay or longer with a minimum of US$ 10000 rental rate, between December 20, 2024 and January 5, 2025, and we'll pamper you with a US$500 Concierge Credit that can be used towards a range of exclusive services to make your stay truly unforgettable.

    Use Your US$ 500 Concierge Credit for:

    • Spa Services: Relax and rejuvenate with a wide range of spa treatments right in the comfort of your villa. Indulge in massages, facials, and more.
    • Charters: Set sail on a private yacht or boat charter and explore the pristine waters of your destination. Discover hidden coves, snorkel in crystal-clear waters, and soak up the sun in style.
    • Tours: Explore the local culture and attractions with our curated tours. From historical sites to culinary adventures, we've got you covered.
    • Excursions: Dive into thrilling adventures with our exciting excursions.

    Don't miss out on this incredible opportunity to elevate your villa experience! Book your 5-night stay or longer and take advantage of our US$500 Concierge Credit.

    Terms and Conditions:
    - Promotion valid for new bookings made between  December 4, 2024 and December 31, 2024.
    -.Not combinable with other promotions.
    - Concierge Credit is non-transferable and has no cash value.
    - Concierge Credit does not apply to car rental or chef service.
    - Services are subject to availability and must be booked in advance.
    - Other terms and conditions may apply.

    Offer ends: December 31, 2024

    Offer cannot be combined with other offers | Offer based on availability | Minimum night stay required | Non-transferrable | No cash value | Promotion is only valid on new reservations | Black-out dates may apply | Rates subject to tax and service charge | Credit can only be used on one selected service and cannot be split between multiple services.

  • Escape to Paradise with Our Villa Promotion!

    Book a 5-night stay or longer with a minimum of US$5000 rental rate, and we'll pamper you with a US$200 Concierge Credit that can be used towards a range of exclusive services to make your stay truly unforgettable.

    Use Your US$200 Concierge Credit for:

    • Spa Services: Relax and rejuvenate with a wide range of spa treatments right in the comfort of your villa. Indulge in massages, facials, and more.
    • Charters: Set sail on a private yacht or boat charter and explore the pristine waters of your destination. Discover hidden coves, snorkel in crystal-clear waters, and soak up the sun in style.
    • Tours: Explore the local culture and attractions with our curated tours. From historical sites to culinary adventures, we've got you covered.
    • Excursions: Dive into thrilling adventures with our exciting excursions.

    Don't miss out on this incredible opportunity to elevate your villa experience! Book your 5-night stay or longer and take advantage of our US$200 Concierge Credit.

    Terms and Conditions:
    - Promotion valid for new bookings made between  December 4, 2024 and January 31, 2025.
    - Not applicable for Holiday dates (December 20, 2024 to January 5, 2025)

    - Concierge Credit is non-transferable and has no cash value.
    - Concierge Credit does not apply to car rental or chef service.
    - Services are subject to availability and must be booked in advance.
    - Other terms and conditions may apply.


    Blackout Dates: December 20, 2024 - January 5, 2025
    Offer ends: January 31, 2025

    Offer cannot be combined with other offers | Offer based on availability | Minimum night stay required | Non-transferrable | No cash value | Promotion is only valid on new reservations | Black-out dates may apply | Rates subject to tax and service charge
(Updated Daily)
Date Unavailable Availability calendar may not reflect up to date reservation information.
Availability subject to change.

Location, Directions & Nearby Villas

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WHAT OUR GUESTS ARE SAYING

"Isle Blue is everything they say they are. They were a pleasure to deal with and were very responsive and informative. The pictures on their website are exactly what you end up getting and they provide full concierge service throughout your stay. My family and I had an amazing time and before we even returned home, we went to the Isle Blue website to check out their inventory for our next vacation. They really are just that good!"
Marc W.
Emvie
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