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Hillside House at Round Hill 3,4, or 5 luxurious bedrooms Ocean View Full Staff

Bedrooms 5
Property type villa
Minimum Stay 7 nights


About the property

Private Villa, 5 Bedrooms, 5 Baths, Montego Bay, Jamaica

You may rent Hillside either as a 3 bedroom, 4 bedroom or 5 bedroom villa. Rates differ based on low or high season, and number of bedrooms rented. Please inquire about special rates and promotions.

Hillside House, a crown jewel at Round Hill Resort, has been fully renovated and had a grand reopening in October of 2015. This lavish extraordinary private villa is located inside the secluded gates of the exclusive award winning Round Hill Resort in Montego Bay, Jamaica where princesses, presidents, rock stars and dignitaries have enjoyed private hideaway vacations for six decades. There you will find sitting on one of the finest view sites in the Caribbean, a multi-million dollar island home owned by the same family for 60 years. Offered is a Maffessanti/Williams designed five bedroom ensuites with private patios and balconies overlooking Montego Bay with the city lights far off in the distance. There is truly no private view like this one on the island. The fully staffed home includes a butler, maids, a laundress, gardener and your private five star cook that will exceed all your epicurean expectations. Play golf, tennis or jog along the lush trails situated right outside your villa. Sit by your own enormous pool and take in the balmy easterly winds in total privacy, luxury, elegance and relaxation. Wonderful for families, weddings or romantic getaways, or celebrity hideaways. Enjoy all the amenities Round Hill has to offer as your rental includes membership to the resort. You will have access to the “Kids Club,” a new million dollar spa to work out or luxuriate with health treatments, enjoy after dinner music at the Ralph Lauren designed Round Hill bar, take off site excursions to waterfalls, zip lines, or river rafting. Whatever your pleasure, this will be THE villa you will return to time and again. Hillside Villa at Round Hill Resort. Come take in this unparalleled view at this luxurious yet comfortable Caribbean home and experience a truly sumptuous vacation.

Just over 50 years ago when Round Hill was an undeveloped, lush jungle rising over the sea, one man had the good fortune and discernment to select the most treasured lot of all. This priceless piece of land, which was favored by the sun and prevailing trade winds, also featured one of the most spectacular views in all of the Caribbean.

The home was built with a vision of joyful family gatherings, romantic getaways and friends celebrating the complete vacation experience. Thus, Hillside was born. The result is a home privately tucked into the east side of Round Hill yet minutes from the amenities of the famous resort.

The large living room opens to a spacious veranda overlooking the pool and ten-mile stretch of sea that separates Round Hill from the town of Montego Bay. Each night the lights of Montego Bay dance across the water, forming part of the magic of Hillside.

Candlelight dinners are served in the outdoor dining arbor adjacent to the lighted garden. Later, Stanley, the butler, serves coffee and after-dinner drinks on the veranda, giving guests another experience of the mesmerizing view and ocean breezes before retiring.

Hillside Villa boasts one of the finest staffs on the North Coast of Jamaica. Natalie, the cook, is gifted with talents that rival the island's finest chefs. Hillside's Butler, Stanley, serves meals and has been with the house for over 25 years. The Housekeeper performs daily maid service and decorates with fresh tropical flowers. The laundress washes clothes and towels daily, and the gardener maintains the pool and grounds in immaculate condition.

The Round Hill beach and hotel are a short walk down the tree-lined lane, just outside Hillside's door. The hotel offers free tram service for the one-minute ride to the beach. Hillside renters enjoy the security and full amenities offered by Round Hill Resort as well as the complete privacy of their own fully staffed villa. A complimentary golf cart is available for rental should you desire it.

Hillside Villa has full membership at Round Hill hotel and enjoys all of its amenities, including beach access. Hillside also enjoys membership at Tryall club for world-class golf only a short drive away.

Please note if you have a smaller group and wish only 3 of the 5 bedrooms, we are happy to offer you a discount.

More Details

Member since: 2009
Speaks: english
Response time:
Within a few hours
Response rate:
Calendar last updated:
November 3, 2017

About Misty

The house is owned by multiple people.

Please note rates quoted are 4 bedroom rates. Rates for 5 bedrooms slightly higher. All rates to include an additional 8% resort fee surcharge.

Misty purchased this villa in 1959

Why Misty chose Montego Bay

Just over 50 years ago when Round Hill was an undeveloped, lush jungle rising over the sea, one man had the good fortune and discernment to select the most treasured lot of all. This priceless piece of land, which was favored by the sun and prevailing trade winds, also featured one of the most spectacular views in all of the Caribbean.

What makes this villa unique

•5 bedroom, 5 bath private villa on one of the most magnificent sites in Jamaica

•Staff of 5: cook, butler, chambermaid, laundress, and gardener

•20' x 40' private pool with breathtaking 10-mile ocean view

•Air conditioning in all bedrooms

•Cable television, WiFi, DVD, sound system with CD player, iPod connection, and CD’s

•Access to Round Hill Beach Club and its amenities (just a short walk or tram ride away)

•Complimentary wireless internet access (bring your own computer)


Montego Bay Villa Accommodation and Amenities

Property Type:
  • villa
  • Guests provide their own meals
  • Housekeeper Included
House Rules:
  • Max. occupancy: 10
  • children welcome
  • non smoking only
Location Type:
  • Beach View
  • Ocean View
  • Air Conditioning
  • Broadband Access
  • Clothes Dryer
  • Linens Provided
  • Telephone
  • Towels Provided
  • Washing Machine
  • Wireless Internet
  • Catering Available
  • Cooking Utensils
  • Dishwasher
  • Ice Maker
  • Kitchen
  • Microwave
  • Refrigerator
  • Dining Area
  • 5 Bathrooms
  • Bathroom 1 -
    Bathroom 2 -
    Bathroom 3 -
    Bathroom 4 -
    Bathroom 5 -
  • 5 Bedrooms, Sleeps 10
  • Five beautiful bedrooms. Villa can be rented as a 4 bedroom or 5 bedroom.
  • CD Player
  • DVD Player
  • Music Library
  • Satellite / Cable
  • Stereo
  • Television
  • VCR
  • Video Library
  • Balcony
  • Deck / Patio
  • Lanai / Gazebo
  • Outdoor Grill
  • wheelchair accessible
Pool / Spa:
  • Private Pool
Onsite Services:
  • Private Chef
  • Staff
  • health/beauty spa
  • restaurants
Leisure Activities:
  • antiquing
  • boating
  • scenic drives
  • shelling
  • shopping
  • sight seeing
  • walking
  • wildlife viewing
Local Services & Businesses:
  • fitness center
Sports & Adventure Activities:
  • basketball court
  • fishing
  • golf
  • hiking
  • kayaking
  • rafting
  • sailing
  • snorkeling/diving
  • spelunking
  • swimming
  • tennis
  • water skiing
  • wind-surfing
Staff of 5: cook, butler, chambermaid, laundress, and gardener


Exceptional! 5/5 -
(13 traveler reviews)

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Hillside House at Round Hill 3,4, or 5 luxurious bedrooms Ocean View Full Staff
average rating of 5.0 based on 13 reviews


  • 5 of 5

We all want the same things when we go on vacation...beautiful place to stay, great food, impeccable service surrounded by spectacular views . Sounds like a dream..doesn't it? We actually experienced all these and more at the Hillside House at Round Hill! Our family of 9 including 3 small children, celebrated our 50th wedding anniversary and the 40th birthday of my daughter in law.

We unanimously agreed Hillside was the PERFECT place:

. the house sits on a hill affording us fantastic views'

. rooms were all tastefully decorated with fresh flowers provided by the dedicated staff

. every meal prepared exquisitely by our talended and creative chef, Natalie..even baked special cakes for

our special events.

. Stanley, the butler, ensured that every need was met; even made special treats for children and spec.drinks

for adults

. Ruth & Shielah attended to the housekeeping and clean laundry with Sharon helping out

. Milton maintained the well manicured lawn and lovely flowers; kept the family sized pool always inviting

. Golf cart is provided

. Hillside guests are welcome to use many of the Round Hill amenities plus enjoyed a complimentary

afternoon tea and scones everyday.

We were so relaxed and comfortable in the house plus Round Hill that we only ventured out once to go to Negril..very nice beach. We had everything we needed at Hillside...gave the family time to bond and just enjoy each others company.

We're already talking about our next visit. We will definitely share our experience with others. Thank you for sharing your home with us.

  • Submitted: Mar 3, 2017
  • Stayed: February 2017
  • Source: VRBO, from HomeAway
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  • 5 of 5

This is by far the nicest home I have ever rented period! The views are incredible. The moment you enter every care in the world melts away! The home has had extensive renovations and it feels brand new. The 2 master suites are tremendous with unbelievable bathrooms. The home is part of the 5 star Round Hill Resort which is a major plus. The facilities at the resort are amazing, from the recently renovated spa and fitness center to the restaurant and bars, and the amazing seaside infinity pool. Speaking of pools, I think the pool at Hillside House has got to be one of if not the biggest private pool at the resort.

The stay here is so relaxing because every care in the world is taken care of- 3 incredible meals a day, served by a warm and caring staff in such a beautiful setting. Your laundry is done daily. I felt like I died and went to heaven. I will without a doubt be returning to my new favorite vacation destination in the world!

  • Submitted: Dec 2, 2016
  • Stayed: August 2016
  • Source: VRBO, from HomeAway
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Boston, MA, USA

Ideal in every way...

  • 5 of 5

Hillside House is an incredible retreat with breath taking views over Montego Bay. An easy ride from Sangster Airport to Round Hill, you are immediately surrounded by the beautiful scenery of the private resort when you pass the guard house. The house sits on a hill and the first thing you see is the endless ocean view and tropical scenery. You stand in the spacious, open house and admire the common areas with comfortable seating, gentle breezes and stylish furnishings. Walking down to the pool lets you see all the sun bathing areas both around the large pool, and among the plantings, with the world class view of the bay. Five bedrooms of varying sizes accommodated our party ranging from 14 to 70+ years old, and the beds were all comfortable along with private baths for each. The staff are the nicest and highest quality around. The house is maintained on a daily basis, home cooked meals are local fare that are delicious, and special requests are accommodated within reason. The partnership with the Round Hill resort gives you an entirely new experience of a vintage, five-star feeling resort. A short walk over the hill and you are greeted by friendly staff to guide you to the private beach, infinity pool, bars, restaurant, spa and water activities. It is a very cozy size and at no point did you feel any sort of crowding. Afternoon tea is highly recommended as are the evening entertainment shows. We enjoyed our week in Jamaica very much and would definitely visit again.

  • Submitted: Dec 2, 2016
  • Stayed: August 2016
  • Source: VRBO, from HomeAway
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Timeless Elegance, Intoxicating Views, Tropical Paradise.

  • 5 of 5

The ride to Hillside House from the Airport is only 18 minute and when you arrive, you are greeted with cold towelettes and a cold rum punch. You will then be guided into the absolutely stunning villa with what has to be the most romantic and spectacular view on the Island of Jamaica. Everything at that point is like a dream. The staff takes care of everything, laundry pressed, hung and put away, three deliciously prepared meals each day out on the garden patio or facing the sea, fresh cut flowers and cold water in each bedroom which is its own suite with flat screen, a 40' swimming pool that hangs on the edge of the hill facing the sea. You have complete use of the famous Round Hill Resort Hotel and Spa where you can luxuriate on the beach, play tennis, eat meals, have the best fruit drinks at the beach bar, snorkel or take in various beauty and relaxation treatments at the Spa which also features a world class fitness center. Our group found it hard to leave Hillside House. One of the best vacations we have ever had and plan on going back next year. You will fall in love with Stanley, the butler of 35 years!!! and the entire staff. Natalie, the chef is a marvel and so sweet! Whether you want to go as a group of friends or a family or two, this house at this spot is extraordinary. GO! Don't even think about looking at other options. This is IT!

  • Submitted: Dec 1, 2016
  • Stayed: July 2016
  • Source: VRBO, from HomeAway
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Truly Amazing....

  • 5 of 5

This private residence within the Round Hill resort is truly amazing - from the upgraded bedrooms and baths, to the unbeatable views, the refreshing swimming pool and the amazing staff. We were treated to a week away with the owners of the residence and we enjoyed three wonderful meals each day rotating from the garden dining area, to the beautiful veranda to a casual poolside meal. We enjoyed easy access via golf cart to the Round Hill resort for fun theme nights, daily tea, the beautiful beach, and the spa. I can not say enough positive things about this house!

  • Submitted: Nov 18, 2016
  • Stayed: November 2016
  • Source: VRBO, from HomeAway
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Charlotte, NC, USA


  • 5 of 5

What's not to like? This is a beautiful recently updated and upgraded space that lacks nothing in wonderful details included to make your stay that much more enjoyable. Not only is the inside space beautiful but also puts you at ease the minute you walk into it with the comfortable furniture, calming colors and the natural views of the ocean from almost every vantage point at the house. The staff are incredibly warm and one step ahead of you in service. These people are so kind and it feels like they enjoy taking care of you and you are extremely well taken care of. From the huge amount of delicious many course meals which are served to you, to a choice of beautiful settings to eat, to daily laundry and cleaning service, access to a my title said, "Perfection!" The facilities at Round Hill are 5 star and we loved taking advantage of them- the beautiful workout room with ocean views, night time entertainment, the 4:00PM tea at the club, the beautiful beaches and the infinity pool, the hammocks and chairs placed all-around with ocean views-I have never felt so relaxed! What a great getaway that is an instant stress reliever. I cannot recommend Hillside enough. There are not enough superlatives to describe it. My husband and I travel quite a bit and this is by far our best vacation spot!

  • Submitted: Jun 11, 2016
  • Stayed: April 2016
  • Source: VRBO, from HomeAway
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Round Hill Membership, Beach Access


Rates & Availability

Taxes and fees are additional

Additional information about rental rates

Refundable damage deposit $1,000

Owner's Cancellation Policy

Please ask the owner or check their rental agreement when booking the property.