Cliffside Cottage

Caribbean / Jamaica / Montego Bay

Dramatically perched on a lush green hillside above the sea, Cliffside Cottage commands stunning views of the deep blue Caribbean Sea by day and romantic lights that glisten across Montego Bay after sunset. Sunrise and sunset vistas from this vantage point are mesmerizing.

up to 5
Bedrooms
up to 10
Guests
5
Bathrooms
Min. Nights Upon Request

Overview

  • Five-bedroom five-bath private villa with a remarkable view
  • 5,000 square feet of indoor and outdoor living space on four acres
  • 20' x 40' private pool and large cut stone pool terrace
  • The new bar is located on the veranda with an outdoor dining area
  • Air conditioning in all bedrooms
  • Private safes in each bedroom
  • The staff of 5: chef, butler, housekeeper, laundress, gardener/night watchman
  • Cable television with a large plasma screen, DVD, and video library
  • Sound system, CD library, and iPod dock with wireless speakers
  • Complimentary calls to the US and Canada
  • Wireless Internet
  • Magnificent panorama of Montego Bay, the Caribbean Sea, sunrises, sunsets
  • Cliffside Cottage has a membership to the Tryall Club

Entering this pretty cottage is the large living room with a high rafter-and-beam ceiling. This space opens wide to a wrap-around verandah that captures the breathtaking view and refreshing tradewinds.

Wonderful home-cooked meals are served on the breezy covered east verandah with a view of Montego Bay across the water ... or in the cozy and colorful indoor dining room. The staff will also create romantic poolside dinner parties under the stars at guests’ request.

Accommodations-

Master Bedroom
In the private east wing. King-size mahogany canopy bed, French doors to a private balcony with ocean view, French doors to side balcony and walkway to pool, en-suite bathroom with large walk-in shower.

Bedroom 2
Queen-size mahogany bed, French doors to terrace with ocean view, en-suite bathroom with large walk-in shower. French doors to the interior garden with landscape lights and a walkway to the living room. Adjoining passageway with Bedroom 3.

Bedroom 3
King-size or twin beds at the guest's option. French doors to terrace with ocean and pool view. Large bay window with sunset views. En-suite bathroom with double vanity and tub-shower combination. Adjoining passageway with Bedroom 2.

Bedroom 4
King-size or twin beds at the guests' option along with a day bed. Garden view. Hall bath with walk-in shower.

Bedroom 5
King-size or twin beds at the guest’s option. Garden view. En-suite bathroom with tub-shower combination.

Tryall Membership

All guests of Cliffside Cottage must pay a resort entry fee of US$34 per person per day plus a 15% service charge 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 a 15% service charge 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 30, 2024.  There may be occasions when some or all the facilities of the hotel may be closed for membership guest services due to a private hotel event. The Tryall Club reserves the right to change or alter its membership packages with no advance notice.

 

 

Amenities

5 Bedrooms, 5 Bathrooms

Sleeps 10 Guests

5000 Interior Square Ft.

  • Bedrooms Only
  • Child Friendly: Connecting Bedroom(s)
  • Child Friendly: Kids Club Membership
  • Golf and Tennis: Golf on Site or Nearby
  • Audio: iPod Dock(s)
  • Communications: Complimentary Calls to the US, UK and Canada
  • Communications: Wireless Internet Access
  • Distant ocean view
  • Golf and Tennis: Tennis Nearby
  • Chef
  • Butler
  • Housekeeper
  • Gardener
  • Night Watchman
  • Fitness Equipment: Full Gym Nearby (walk, drive or take golf cart)
  • Beach Club & Resort Membership: Tryall Club (outside the gate)
  • Other: Spa on Site or Nearby
  • Weddings (up to 50 people)
  • Bathrooms: Hair Dryers

Details

Bedroom Details

Master Bedroom
In private east wing. Kingsize mahogany canopy bed, French doors to private balcony with ocean view, French doors to side balcony and walkway to pool, en-suite bathroom with large walk-in shower.

Bedroom 2
Queensize mahogany bed, French doors to terrace with ocean view, en-suite bathroom with large walk-in shower. French doors to interior garden with landscape lights and walkway to living room. Adjoining passageway with Bedroom 3.

Bedroom 3
Kingsize or twin beds at guests' option. French doors to terrace with ocean and pool view. Large bay window with sunset views. En-suite bathroom with double vanity and tub-shower combination. Adjoining passageway with Bedroom 2.
Bedroom 4
Kingsize or twin beds at guests' option along with day bed. Garden view. Hall bath with walk-in shower.
Bedroom 5
Kingsize or twin beds at guests’ option. Garden view. En-suite bathroom with tub-shower combination.

Distance Details

Beach: 13 minutes to the Tryall Club
Town: 20 minutes via driver
Airport: 20 minutes

Rates

Travel Dates Bedrooms Min. Night Stay Nightly Rates

High Season: 7-night minimum stay required
Low Season: 5-night minimum stay required
Holidays: A 7-night, full-house rate is required for all holiday weeks which include Easter Sunday, Thanksgiving, Christmas, and New Year’s Eve.
*Rates are subject to change without notice. Please check with your villa specialist to confirm.

December 19, 2024 - December 26, 2024
Christmas HolidayChristmas - Dec 19-26 or 20-27 or any 7 nights that includes Dec 25th. Additionally any 7 nights (eg. Dec 17-24) that prevents a Christmas reservation will be invoiced at the Christmas rate. 		5 7 $ 1,858 *
December 27, 2024 - January 02, 2025
New Year's HolidayNew Year - Dec 26-Jan 2 or Dec 27-Jan 3 or any 7 nights that includes Dec 31st. 		5 7 $ 2,000 *
January 03, 2025 - April 18, 2025
High Season 		3 7 $ 1,129 *
January 03, 2025 - April 18, 2025
High Season 		5 7 $ 1,272 *
April 19, 2025 - April 26, 2025
Easter - Any 7 nights that includes Easter Sunday 		5 7 $ 1,272 *
April 27, 2025 - November 21, 2025
Low Season 		3 5 $ 786 *
April 27, 2025 - November 21, 2025
Low Season 		5 5 $ 1,000 *
November 22, 2025 - November 29, 2025
Thanksgiving Holiday 		5 7 $ 1,143 *
November 30, 2025 - December 14, 2025
Low Season 		3 5 $ 786 *
November 30, 2025 - December 14, 2025
Low Season 		5 5 $ 1,000 *
December 15, 2025 - December 18, 2025
High Season 		3 7 $ 1,129 *
December 15, 2025 - December 18, 2025
High Season 		5 7 $ 1,272 *
December 19, 2025 - December 26, 2025
Christmas HolidayChristmas - Dec 19-26 or 20-27 or any 7 nights that includes Dec 25th. Additionally any 7 nights (eg. Dec 17-24) that prevents a Christmas reservation will be invoiced at the Christmas rate. 		5 7 $ 1,858 *
December 26, 2025 - January 02, 2026
New Year's HolidayNew Year - Dec 26-Jan 2 or Dec 27-Jan 3 or any 7 nights that includes Dec 31st. 		5 7 $ 2,000 *
USD rates above based on approximate currency conversion. Holiday dates may not be listed in rate chart. Rates are subject to change without notice. Please confirm rate, holiday dates, and currency with your Villa Specialist at time of booking.

Wedding Details

Maximum guests: 50

Villas in Proximity: Blue Heaven, Serenity on the Beach
 

Check In Times

Check in: 03:00 PM - Check out: 11:00 AM

Minimum Stay Details

High Season: 7-night minimum stay required
Low Season: 5-night minimum stay required
Holidays: A 7-night, full-house rate is required for all holiday weeks which include Easter Sunday, Thanksgiving, Christmas, and New Year’s Eve.
5% surcharge for festive bookings

Accidental Damage Waiver

A $149 Accidental Damage Waiver applies to every reservation.

Calendar

00
Booked
00
Check-in
Available
00
Check-out
Available
00
On Hold
00
Check-in
On Hold
00
Check-out
On Hold
December
MonTueWedThuFriSatSun
 
 
 
 
 
 
01
02
03
04
05
06
07
08
09
10
11
12
13
14
15
16
17
18
19
20
21
22
23
24
25
26
27
28
29
30
31
 
 
 
 
 
January
MonTueWedThuFriSatSun
 
 
01
02
03
04
05
06
07
08
09
10
11
12
13
14
15
16
17
18
19
20
21
22
23
24
25
26
27
28
29
30
31
 
 
February
MonTueWedThuFriSatSun
 
 
 
 
 
01
02
03
04
05
06
07
08
09
10
11
12
13
14
15
16
17
18
19
20
21
22
23
24
25
26
27
28
 
 
March
MonTueWedThuFriSatSun
 
 
 
 
 
01
02
03
04
05
06
07
08
09
10
11
12
13
14
15
16
17
18
19
20
21
22
23
24
25
26
27
28
29
30
31
 
 
 
 
 
 
April
MonTueWedThuFriSatSun
 
01
02
03
04
05
06
07
08
09
10
11
12
13
14
15
16
17
18
19
20
21
22
23
24
25
26
27
28
29
30
 
 
 
 
May
MonTueWedThuFriSatSun
 
 
 
01
02
03
04
05
06
07
08
09
10
11
12
13
14
15
16
17
18
19
20
21
22
23
24
25
26
27
28
29
30
31
 
June
MonTueWedThuFriSatSun
 
 
 
 
 
 
01
02
03
04
05
06
07
08
09
10
11
12
13
14
15
16
17
18
19
20
21
22
23
24
25
26
27
28
29
30
 
 
 
 
 
 
July
MonTueWedThuFriSatSun
 
01
02
03
04
05
06
07
08
09
10
11
12
13
14
15
16
17
18
19
20
21
22
23
24
25
26
27
28
29
30
31
 
 
 
August
MonTueWedThuFriSatSun
 
 
 
 
01
02
03
04
05
06
07
08
09
10
11
12
13
14
15
16
17
18
19
20
21
22
23
24
25
26
27
28
29
30
31
September
MonTueWedThuFriSatSun
01
02
03
04
05
06
07
08
09
10
11
12
13
14
15
16
17
18
19
20
21
22
23
24
25
26
27
28
29
30
 
 
 
 
 
October
MonTueWedThuFriSatSun
 
 
01
02
03
04
05
06
07
08
09
10
11
12
13
14
15
16
17
18
19
20
21
22
23
24
25
26
27
28
29
30
31
 
 
November
MonTueWedThuFriSatSun
 
 
 
 
 
01
02
03
04
05
06
07
08
09
10
11
12
13
14
15
16
17
18
19
20
21
22
23
24
25
26
27
28
29
30
December
MonTueWedThuFriSatSun
01
02
03
04
05
06
07
08
09
10
11
12
13
14
15
16
17
18
19
20
21
22
23
24
25
26
27
28
29
30
31
 
 
 
 

Location

Reviews

Staff & Service: Excellent - Thank you so much!
Accommodations: Excellent - We really enjoyed our stay.
Ground Transportation: Excellent
Overall Expectation: Exceeded
Will you return: Yes

-Zaft Party

Hi Barbara ,
We had a wonderful stay at Cliffside. We've been telling all of our friends and family about the villa. The breathtaking views, the wonderful, kind, caring, and friendly staff who tended to all of our needs. The food was delicious as well. We wish we could have stayed longer and missed the staff once we left. Even the kids enjoyed it and still talk about the villa and the staff. They were so wonderful.

The only thing that we had an issue with was the water pressure in most of the bathrooms. It was low especially on the 1st day but it was fixed. If that could be rectified then there should be no other complaints.

We would love to return in 2025 but we are going to Europe. When we are returning to Jamaica we will definitely be in touch.

-Ennis Party

Staff & Service: Excellent - Staff and service were exceptional. They were kind, warm, helpful, and went above & beyond.
Accommodations: Excellent - Villa was lovely
Overall Expectation: Exceeded
Will you return: Yes
Additional Comments: Will definitely recommend. 5-Star!!

-Ennis 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!

-Karlecka Party

Staff and service was great. Great food, lots of variety.

We loved our stay would love to return.

Crispin C.

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!

Terri B.

The staff is very warm, friendly. Everything is perfect. Excellent meals.

Ken T.

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.

Robert B.

We had such an awesome time while in Jamaica!! The staff that was there 18 yrs ago when I first visited were just as kind and loving as the first time that I met them!! I am excited to start planning my vacation for next year!!!

Thanks again for all your help!

Kim W.

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

Sheila O.

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

Jason N.

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!

Walker

Staff, Service & accommodations were excellent!

Sarah H.

All of the staff were amazing. Michael, Clifford & Pat were outstanding. We loved the villa and will recommend to our friends!

Mark S.

Wonderful service & beautiful villa! We had such a great time that we will be definitely returning!

Alliya M.

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.

Connie D.

Staff are all excellent! Taking them all home!!

Clifford C.

Absolutely wonderful! Superb! The staff is amazing and attended to our every need. Cliffside will be recommended.

Perry C.

Dear Linda,

The entire staff was amazing! We were welcomed and treated with love for our entire visit. The house is updated and beautiful all around - pool and grounds. So tidy and clean,laundry was wonderful too! Clifford was kind, reliable and always on time with a smile. I would return and recommend absolutely!

Annu G.

Dear Linda,

The staff made our trip special.

Shirley R.

Dear Linda,

The staff is amazing. Hope to be back soon.

Raymond D.

Dear Linda,

Had a wonderful stay. The staff is awesome. Loved all of them. We will hopefully return soon.

Barry F.

Dear Linda,

I will not hesitate to recommend this villa to anyone who wants to visit Jamaica! We have enjoyed every minute. We love the staff. Ms. Patricia is by far more than anyone could ever ask. She displays grace and elegance when serving guests. Cliffside Cottage is a 5 star villa. You can't ask for anything better. Great location & great view.

Kimberly W.

Dear Linda,

Such a nice, warm welcome that continued throughout the entire stay. The house is beautiful and filled with an excellent staff. Can't wait to return and bring a group.

Anne and Nathan J.

Dear Linda,

This was a wonderful stay! The staff was around when we needed them, and everything was thought of ahead of time! Awesome chef! Beautiful views! We recommend Cliffside Cottage. It exceeded our expectations and we hope to return!

John & Lisa E.

Dear Linda,

The staff is excellent and they make things so easy! The villa is perfectly situated and appointed. This is the best "Linda Smith" villa yet!

John E.

Dear Linda,

The entire staff made us feel at home! We had a great time and thank you and the local staff for everything!

Nedra H.

Dear Linda,

This staff is very friendly, helpful and polite and create an extremely pleasant atmosphere. We want to take the staff home with us because we love them do much - where did you find such nice people? The villa is exceptionally clean, the view is spectacular and we had a very relaxing vacation

Neema F.

Very comfortable. Five star service!

Slade party

Staff & Service: Excellent - I love everybody
Accommodations: Excellent
Ground Transportation: Excellent
Overall Expectation: Exceeded
Will Return: Yes
Additional Comments: We will definitely return soon

-Unaka Party

Staff & Service: Excellent
Accommodations: Excellent
Ground Transportation: Excellent
Overall Expectation: Exceeded
Will Return: Yes
Additional Comments: Amazing villa and wonderful staff!!

-Criner Party

Staff & Service: Excellent - Excellent is not enough to rate the service we received. Our staff deserves 10 stars for the service we received.
Accommodations: Excellent
Ground Transportation: Excellent
Overall Expectation: Exceeded
Will Return: Yes
Additional Comments: Cliffside Villa crew is the best!!!

-Boyd Party

Staff & Service: Excellent - Just incredible!
Accommodations: Excellent - Beyond awesome!
Ground Transportation: Excellent
Overall Expectation: Exceeded
Will Return: Yes
This was an awesome vacation. The staff went beyond to make our stay the best ever! I would not want to stay anywhere else in Jamaica but Cliffside! We will be back. Please have the same staff here.

-Johnson Party

Staff & Service: Excellent - The staff was so welcoming and helpful. They made us feel at home.
Accommodations: Excellent - The rooms were very spacious and comfortable.
Ground Transportation: Excellent
Overall Expectation: Exceeded
Will Return: Yes

-McCoy Party

Staff & Service: Excellent - All staff was extremely accommodating and helpful with the kids & guests
Accommodations: Excellent - The property was beautiful and so serene. Breathtaking views
Ground Transportation: Excellent
Overall Expectation: Exceeded
Will Return: Yes

-Ashman Party

Staff & Service: Excellent - This was a WOW experience
Accommodations: Excellent
Ground Transportation: Excellent
Overall Expectation: Exceeded
Will Return: Yes - Great vacation and wonderful staff.

-Gaust Party

Staff & Service: Excellent - We were treated amazing. Such a wonderful experience!
Accommodations: Excellent - Everything was working perfectly.
Ground Transportation: Excellent-
Overall Expectation: Exceeded - This was one of the best stays I have experienced. Thank you will be back soon!!!
Will Return: Yes

-Oruke Party

Lovely group of people who were warm and helpful.
The dinners were delicious! Table presentation & service...excellent!
The view is divine. The fresh flowers were lovely
Staff & Service: Excellent
Accommodations: Excellent
Ground Transportation: Excellent
Overall Expectation: Exceeded

-Kelsey Party

The chef was very excellent!
Everyone was very nice towards us.
I would recommend this place to anyone.

-Paye Party

Everyone was fantastic!
It was beautiful.
Staff was great.
We loved it here!

-Kelsey Party

Staff & Service: Excellent
Accommodations: Excellent
Will return and recommend to others

-Bolton Party

Staff & Service: Excellent
Accommodations: Excellent
We will be back each year.

-Gayle Party

Staff & Service: A+/Wonderful
Accommodations: A+/Excellent Vacation
I love it here!

-Sewrattan Party

Overall amazing staff!! We left very spoiled. Met above our expectations!!

-Skauge Party

House and staff were amazing! Five stars!

Moulton & Montazeni Party

Patricia - Great house mom
Benford - Respectful chef and gentleman
Derrick - The face to our Jamaican vacation
Renville - Our kindly watchman
Tristan - Helpful & a ready smile
Moulette - Always there for all of us.

Nevitt Party

We couldn't have been any happier with the staff!! Great people! We felt very welcome and comfortable - would love to have stayed another week. Perfect views too! Would absolutely return to this villa and recommend to others.

Treadwell/ Santimauro/Loggins Party

The staff and service and accommodations were outstanding! Our expectations were exceeded and we would return & recommend the villa to others.

Bersano/ Janish party

The staff was perfect. They were very attentive. Every meal we requested was made. All the food was delicious. Everything was very clean. Clifford the driver was great. He made sure we stayed safe and gave us good ideas to visit. I have been to Jamaica 2 times, but this is the first time I stayed at a villa. Patricia, Benford, & Renville made this the best vacation ever because of the staff. I will only be vacationing at Cliffside Cottage.

Chardonay

The staff was amazing, like family almost. Personable, kind, & made our stay just like home. Beautiful property - clean comfy, & the grounds were beautiful as well. Excellent driver, Clifford was awesome, knowledgeable, & very attentive & kind.

Davis Party

Staff was excellent. We will definitely be back.

Russell Party

Excellent service. I would return to the villa and recommend to others.

Burton Family

The staff exceeded our expectations in every way. The attention to detail surpasses any 5 star hotel. They were inviting and treated us like family. Truly unforgettable. We are grateful for their efforts. Accommodations felt like a home away from home. Clifford was phenomenal as a driver. We also appreciated his recommendations. The only thing that's upsetting is having to leave.

Chef Benford - His culinary skills had us eager to come back home. His meals made our trip more memorable. We all were amazed how he was able to accommodate every request. Ms. Patricia - I instantly felt comfortable around her. Ms. Patricia's energy was always inviting and positive. I valued her maternal guidance and oversight. Mr. Derrick - we are truly grateful for everything Derrick did for us. He was always available with a warm smile. He was courteous and a phenomenal bartender. Mr. Renville - We felt secure knowing Mr. Renville watched over us. No matter the time of night our family could sleep well with him around. Mr. Moullett- Her efforts behind the scenes wasn't unnoticed. We appreciated having fresh laundry every day. We didn't have to worry about anything staying here. Thank you.

Collings Party

I was so relaxed at the villa. The service was amazing.

Hagood party

Everyone went above and beyond. Patricia is very hospitable and addressed all needs asap. Benford made great good and executed beatifically. Derrick was professional and made great drinks. Clifford A+ driver. Allison did a herculean job and Renville made us feel safe and kept the grounds immaculate.

Wertheimer Party

Excellent service. Friendly staff who anticipated all our needs.

Gibson and Spencer Families

We found everyone so kind and wonderful and attentive to all our needs...super friendly!!

DeMuth/ Sapir

Amazing! Fabulous! Wonderful! Loved it. Renville does an excellent job. Clifford was on top of every detail. House was very comfortable. View spectacular! Staff was great.

Ross

Excellent staff and service and we felt like we were in heaven! Exceeded expectations. As our kid said, it's the best cook of the world! Cliffside Cottage is a real jewel. Driver Clifford delivered an excellent service. Excellent overall experience and wonderful holiday.

Scharer Family

This was the best experience ever!

Capers Party

All Meals were spectacular. Everything was always kept clean. Staff always friendly and available to help! The staff took extra care of our 4 year old to be sure he was happy! The grounds are impeccable! Just lovely! Would love to return and will recommend.

Wing Family

We loved it, it was fabulous. The only reason we would not return is if there were no access to Tryall. Our kids really enjoyed being able to go to Tryall and enjoy beach activities there.

Doolittle Party

We enjoyed everyone. Everyone was great. Thank you for everything! We loved Cliffside!

Villa information may change without notice and should be confirmed with our villa rental specialists.

Similar Villas You Might Like
Blue Heaven Montego Bay
Drambuie Estate Montego Bay
Noble House on the Beach Montego Bay
Pimento Hill Montego Bay