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

Montego Bay, Montego Bay

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.


Sports And Adventure Activities

  • Swimming
  • Tennis
  • Sailing
  • Fishing
  • Golf
  • Wind-surfing
  • Water Skiing
  • Hiking
  • Rafting
  • Spelunking
  • Basketball Court
  • Kayaking
  • Snorkeling/diving

Leisure Activities

  • Walking
  • Antiquing
  • Sight Seeing
  • Scenic Drives
  • Boating
  • Shelling
  • Shopping
  • Wildlife Viewing

Local Services And Businesses

  • Fitness Center


  • Restaurants
  • Health/beauty Spa

Location Type

  • Beach View
  • Ocean View

Catering Options

  • Guests Provide Their Own Meals


  • Telephone
  • Air Conditioning
  • Linens Provided
  • Washing Machine
  • Clothes Dryer
  • Internet
  • Towels Provided
  • Broadband Access
  • Wireless Internet
  • Iron & Board
  • Hair Dryer


  • Dishwasher
  • Refrigerator
  • Microwave
  • Grill
  • Cooking Utensils
  • Ice Maker
  • Catering Available
  • Kitchen


  • Television
  • Satellite / Cable
  • VCR
  • Stereo
  • CD Player
  • DVD Player
  • Music Library
  • Video Library


  • Balcony
  • Outdoor Grill
  • Deck / Patio
  • Lanai / Gazebo


  • Pets Not Allowed
  • Wheelchair Accessible
  • Children Welcome
  • Non Smoking Only


  • Dining Area

Onsite Services

  • Staff
  • Private Chef

Pool / Spa

  • Private Pool

House Cleaning

  • Housekeeper Included

Houses Rules

  • 04:00 PM
  • 11:00 AM
  • No parties/events
  • Smoking allowed
  • Pets allowed
  • Children allowed
  • Max occupancy: 10


Cancellation Policy

  • 100% refund if canceled at least 60 days before arrival date.

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