up to 5
up to 10
Min. Nights

About Villa

When Round Hill was only an undeveloped knob of lush green hillside rising over the sea, one man had the good fortune to have his choice of lots, and the wisdom to choose that piece of land most favored by the sun and prevailing tradewinds ... which also happened to have one of the most spectacular views in all the Caribbean. Today, an extensive renovation of the original house was just completed by the same family who captured the site 60 years ago and named their first house Hillside Cottage.

Introducing the all new Hillside House on Round Hill!

This new jewel now crowns the top of legendary Round Hill.  The site has always been a show-stopper, unrivaled in its views and trade winds.  What’s new is the villa itself, recreated as a marvelous 5-bedroom home by one of Jamaica’s most in-demand design teams. Everything old is new again!

  • Architect Nancy Maffessanti
  • Interior Designer Sue Williams

Thoughtfully designed for families … inviting, unpretentious, relaxed luxury for the good life

The charm of Old Jamaica … the luxury of modern amenities

What’s New as of December 2015?

  • brand new 5th bedroom … original 4 bedrooms completely renovated
  • new Great Room opening to fabulous furnished balcony and world-class breathtaking view
  • large new master bedroom on pool terrace level
  • new bedroom balconies
  • connecting suites for parents and children
  • 2 new dining areas
  • new outdoor shower
  • new coral stone floors
  • complimentary Wi-Fi in villa and throughout Round Hill
  • tasteful new color palette of pure whites and blues
  • polished mahogany furniture
  • pickled shingle ceilings
  • expanded collection of fine art
  • new flat-screen Smart TV’s throughout 
  • safes in every bedroom
  • complimentary 4-seater transportation cart
  • the same seasoned staff of 5: excellent cook, longtime butler, housekeeper, laundress, gardener
  • the same wonderful 20' x 40' private pool with 10-mile ocean view
  • Round Hill membership: complimentary use of the new Round Hill gym and $25 daily fee is waived for Hillside House guests (paid by the homeowner), complimentary WiFi throughout Round Hill (daily fee waived/paid by  the homeowner), complimentary beach, two connecting heated pools for parents & children, jogging trail. For various additional fees: Pineapple Kids Club, gym, tennis, hair salon & spa, afternoon tea, Manager's Cocktail Party, bars & restaurants, gift shops, water sports, Internet room, beach parties Mon-Wed-Fri.
  • Tryall Club membership: complimentary beach, tennis, gym, pool, Hummingbird Kids Club, non-motorized water sports, Internet room, Usain Bolt Games Room for all ages, jogging trail, afternoon tea, and Manager's Cocktail Party every Monday night. For various additional fees: golf, tennis lessons, Happy Hour, hair salon & spa, bars & restaurants, boutique, motorized water sports, and every Thursday Reggae Night on the Beach with live entertainment.

    *NOTE: Tryall Club membership is guaranteed for guests travelling through November 30, 2019. Some villa beach memberships are not guaranteed if travel dates are beyond November 30, 2019. Ask our Villa Specialists if you have any questions.

For six decades, Round Hill has been the destination of choice for princesses, presidents and rock stars.  Privately tucked into the east side of the hill, away and apart from all others, this extraordinary location is literally minutes from the amenities of the famous resort and less than half an hour from the international airport and Montego Bay.

A new Great Room opens wide to the piece-de-resistance, a broad furnished balcony verandah overlooking a breathtaking ten-mile stretch of sea all the way to the distant view of the town of Montego Bay. Each night the lights of Montego Bay dance across the water, forming magic at this prize location. Candlelight dinners and after-dinner drinks on the new balcony tempt guests to linger long to memorize the mesmerizing view and balmy trade winds before retiring to their individual suites.


All five bedrooms provide state-of-the-art remote-control quiet air-conditioning, ceiling fans, safes, cable televisions and en suite bathrooms with walk-in showers.  

Four bedrooms open wide to spectacular views of the Bay and city lights of the town of Montego Bay across the water. The fifth bedroom opens to a small, private tropical garden.

Downstairs Pool Terrace Level

Master Bedrooms 1 & 2
This level is dedicated to two master suites which can connect at guests’ option.  Both suites are private, each with a glorious 10-mile view over the sea.  Each suite opens directly onto the lawn and pool terrace … and an even greater view of sky and sea.  Truly breathtaking day and night.

Both of these rooms near the pool terrace offer traditional Jamaican kingsize beds. Both have identical glamorous en-suite bathrooms with double vanities in custom mahogany cabinets, deep tubs and large glass-walled walk-in showers.  The pair of bathrooms connect to form a passageway between the two downstairs bedrooms, forming a convenient family suite if desired.

Upstairs Entrance Level

Bedroom 3
Queensize bed, en suite bathroom with walk-in shower.  Doors to furnished balcony and spectacular view of the sea.

Bedroom 4
Optional kingsize or twin beds, en suite bathroom with octagonal walk-in shower louvered on three sides to enable both sea view and privacy. Double doors to furnished balcony and that view.  This bedroom connects to Bedroom 5 for convenient parent-child suite if desired.

Bedroom 5
Optional kingsize or twin beds, en suite bathroom with walk-in shower. Privately located on west side of villa.  Opens to tropical garden courtyard with sitting area.  Optional connection to Bedroom 4 via the private garden for convenient parent-child suite.


5 Bedrooms, 5 Bathrooms

Sleeps 10 People

0 Interior Square Ft.

Air Conditioning

Children Welcome


Fully Staffed Villa

Golf Available



Audio: iPod Dock(s)

Beach Club & Resort Membership: Round Hill (inside the gate)

Beach Club & Resort Membership: Tryall Club (outside the gate)

Child Friendly: Connecting Bedroom(s)

Child Friendly: Kids Club Membership

Communications: Computer or Laptop

Golf and Tennis: Golf on Site or Nearby

Golf and Tennis: Tennis Nearby

Other: Available for Weddings

Other: Spa on Site or Nearby

Communications: Wireless Internet Access

Bathrooms: Hair Dryers

Fitness Equipment: Complimentary use of the new Round Hill Gym

Fitness Equipment: Full Gym Nearby (walk, drive or take golf cart)


Travel Dates Bedrooms Min. Night Stay Nightly Rates

Hillside House has very limited availability for 2018, now through January 19, 2019. Please inquiry for rates.

December 19, 2018 - December 26, 2018
5 7 $3143
December 27, 2018 - January 02, 2019
New Year's
5 7 $3143
January 03, 2019 - February 02, 2019
4 7 $1829
January 03, 2019 - February 02, 2019
5 7 $2129


Villa Unavailable