Starting at $1,142.00 a night
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?

  • 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 fire pit
  • new coral stone floors
  • complimentary Wi-Fi throughout
  • 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 beach, two connecting heated pools for parents & children, jogging trail, Manager's Cocktail Party every Wednesday. For various fees: Pineapple Kids Club, tennis, hair salon & spa, bars & restaurants, gift shops, water sports, Internet room, beach parties Mon-Wed-Fri

The Tryall Club membership: complimentary beach, tennis, gym, pool, Hummingbird Kids Club, non-motorized water sports, Internet room, new Usain Bolt Games Room for kids, teens & adults, jogging trail, afternoon tea & Manager's Cocktail Party every Monday night. For various fees: golf, tennis lessons, Happy Hour, hair salon & spa, bars & restaurants, boutique, motorized water sports & Reggae Night on the Beach Thursday night.

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.

Onsite Services:

  • Daily Maid Service
  • Concierge

Local Features:

  • Groceries


  • DVD Player
  • Satellite/Cable TV


  • Outdoor Pool


  • Wireless Internet
  • Hair Dryer
  • Internet
  • Air-Conditioning
  • Safe
  • Dryer
  • Linens


  • Lawn / Garden
  • Deck/Patio
  • Patio Furniture

Kitchen & Dining:

  • Kitchen
  • Refrigerator
  • Microwave
  • Oven
  • 4 Ring Stove
  • Coffee Maker
  • Toaster

Attractions & Activities:

  • Ocean
  • Beach
  • Restaurants

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