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Hillside House on Round Hill • Montego Bay, Jamaica Villa

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A Star is Re-Born Atop Round Hill!

In October 2015, a stunning renovation will be complete!

About Hillside House on Round Hill

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 is underway 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 soon will crown 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.

  • 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
  • 2 new glamorous master bedrooms on private downstairs level near pool
  • new bedroom verandahs
  • 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 
  • 4-seater transportation cart available for a fee
  • 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 beach, two connecting heated pools for parents & children, jogging trail, Manager's Cocktail Party. For various fees: Pineapple Kids Club, fitness room, 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. For various fees: golf, tennis lessons, Happy Hour, hair salon & spa, bars & restaurants, boutique, motorized water sports, beach parties Mon-Wed-Fri

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 will open wide to the piece-de-resistance, a broad furnished verandah overlooking an incredible 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 verandah tempt guests to linger long to memorize the mesmerizing view and the joy of sea breezes before retiring to their individual suites.


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

Four bedrooms will have their own outdoor sitting areas and spectacular views of the Bay and city lights of the town of Montego Bay across the water. The fifth bedroom opens to a private tropical garden with views through towering Pimento and Breadfruit trees to the sea beyond.

Downstairs Pool Terrace Level

Bedrooms 1 & 2
This level is dedicated to two large master suites which can connect at guests’ option.  Both suites are spacious and 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 Master Bedrooms offer traditional Jamaican kingsize beds. Both will have en-suite bathrooms with bathtubs and walk-in showers.

Upstairs Entrance Level

Bedroom 3
Queensize bed, en suite bathroom with walk-in shower.  Doors to furnished verandah 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. Doors to furnished verandah 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.

The Tryall Club Membership

A significant amenity for guests in this villa is membership at the excellent Tryall Club.  On 2,200 acres, Tryall’s golf course is among the most beautiful in the world.  Its 18 hillside and seaside fairways have been home to the Johnnie Walker, Mazda and other PGA championship events.  The resident pro offers workshops and private lessons.   The Tryall tennis club features nine Nova Cushion courts, some lit for night play, with world-class pro’s on call.  All white attire required.

The beach is well planned for parents and children. Have lunch at the beach bar.  Work out in the well-equipped gym and compete in the new Usain Bolt Games Room at the Great House (teens love it).  Jog the marked trails. Snorkeling, kayaking, Hobie Cat and sunfish are complimentary.  Glass bottom boats, charter fishing, a boat to the reef and any captained craft attract various fees.  Enjoy weekly events like  complimentary Manager’s Cocktail Party on Mondays, as well as Beach BBQ and Reggae Night beach parties for an additional fee.

On the hill, enjoy the historic Great House for daily 4:00 tea and sweets. Shop at the convenient commissary and chic boutique, and meet for happy hour and snacks at the casual bar.  Also at the Great House is the new Usain Bolt Games Room open all day and night for ping pong, pool, air hockey, foosball, shuffleboard, chess and checkers, board games, comfy reclining chairs and HDTV. And don’t miss the massive Tryall pool. The Tryall Club is thoughtfully designed to please toddlers, preteens, tweens, moms, dads and everyone from teens to octogenarians.

For a great write-up of the Tryall Club, see Dana Vachon's article Club Jamaica in Departures Magazine.

The Tryall Club was chosen by Condé Nast Traveler for its Gold List of "the best places to stay in the whole world.”

Round Hill Hotel and Beach Club Membership

A special amenity available to guests in this villa is membership at Round Hill ... just minutes from the villa and one of the finest private resorts on Jamaica's North Coast.  Round Hill offers a beach, pool, chaise lounges, towels, jogging trail, gift shop, logo shop, library with computer, bar, afternoon tea and Wednesday Manager's Cocktail Party ... and unforgettable long sunsets from the waterfront terrace.  For additional charges, members may enjoy the spa, tennis courts, Pineapple Kids Club, fitness center, salon, a range of water sports and parties (Monday beach party and Friday Jamaica Night).

Note: Round Hill will be closed September 8 to October 14, 2015.  Membership amenities are subject to change without notice.  

Round Hill was chosen by Condé Nast Traveler for its Gold List of "the best places to stay in the whole world."

Rental Rates

Season Bedrooms Weekly Rate
Low Season
April 16 - December 14
1–4 $6,500
Low Season
April 16 - December 14
5 $7,500
November 21 - November 28
1–5 $13,750
December 19 - December 26
1–5 $15,000
New Year
December 26 - January 2
1–5 $15,000
High Season
December 15 - April 15
1–4 $10,750
High Season
December 15 - April 15
5 $12,850
March 26 - April 2
1–5 $13,750
Thanksgiving (2016 Holiday)
November 19 - November 26
1–5 $16,000
Christmas (2016 Holiday)
December 19 - December 26
1–5 $18,500
New Years (2016/17)
December 26 - January 2
1–5 $18,500

A Star is Re-Born Atop Round Hill!

In October 2015, a stunning renovation will be complete!

Link to Calendar

Booking Calendar

Guest Reviews

  • Dear Linda,

    To you and all the folks at Linda Smith villas. Thank you soooo much for a wonderful week. Our only hope is to return some day soon. Everything was wonderful. We were totally spoiled, especially Leon down at Seaside who was constantly making the children pina coladas and strawberry daiquiris and even a new one called a Miami Vice (all virgin, of course). I could go on and on but I'm sure you know how well they treat you there. Stanley, of course was at hand at every turn to take us wherever we wanted to go. Again, we had a great time and would recommend your services to anyone who will listen to us. Or even some who would rather we did not go on expounding on the virtues.”

    Connie H. - June 2012

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