Jamaica Villas by Linda Smith

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Hillside House on Round Hill • Montego Bay, Jamaica Villa

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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 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.

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.

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, Wednesday Manager's Cocktail Party ... and unforgettable long sunsets from the waterfront terrace.

For additional charges, members may enjoy the spa, tennis courts, afternoon tea, Pineapple Kids Club, fitness center, salon, a range of water sports and beach parties.

Internet access is $22 per day for up to 3 devices. This may be paid at reception. The internet service can be upgraded to Premium (faster speed) for $33 per day for up to 3 devices.

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

Note: Round Hill will be closed September 4 - October 11, 2018 for their annual maintenance.

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.”

*NOTE: Tryall Club membership is guaranteed for guests travelling through November 30, 2018. Some villa beach memberships are not guaranteed if travel dates are beyond November 30, 2018. Ask our Villa Specialists if you have any questions.

Rental Rates

  • Hillside House 15% Surcharge must be applied to the villa rental rate (Resort Fee of 10% + 5% Administration Fee)
Season Bedrooms Weekly Rate
Low Season
April 21 - December 15
1–4 $7,200
Low Season
April 21 - December 15
5 $8,000
November 17 - November 24
1–5 $19,000
December 22 - December 29
1–5 $22,000
New Year's
December 30 - January 6
1–5 $22,000
High Season 2019
December 15 - February 16
1–4 $12,800
High Season 2019
December 15 - February 16
5 $14,500
High Season 2019
February 16 - April 27
Premium High Season - only 5 bedroom available
1–5 $14,500
Easter 2019
April 20 - April 27
Easter week is any 7 nights that includes Easter Sunday
1–5 $14,500
Link to Calendar

Booking Calendar

Guest Reviews

  • Our staff was amazing. We can’t wait to come back again. Thank you!

    Toni B - November 2015

  • The friendliest people ever and the house is beautiful!

    Marcee H - November 2015

  • Amazing staff, house is beautiful beyond words!! We will be back.

    Kelly E - October 2015

  • Wow what a wonderful place with the BEST staff I have ever met! We had the best time. It was so hard to leave!

    I know we will be coming back some time...All my friends are still talking about it!

    The house , grounds , Fay's cooking , off the charts! Stanley was so interesting and taught us about the culture. Sheila and Ruth were wonderful and Milton always had a smile!

    I have never experienced anything like it and I travel all the time! I will return !!

    Karen C - October 2015

  • 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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Jamaica Villas by Linda Smith 100 Fordham Road, Bldg. C Wilmington, MA, 01887 Tel 301.229.4300 Email info@jamaicavillas.com
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