Jamaica Villas by Linda Smith

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Summerland on Round Hill • Montego Bay, Jamaica Villa

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About Summerland on Round Hill

Perched atop glamorous, private Round Hill, Summerland is a fully staffed private home sited for its dramatic view over the sea. The view is simply mesmerizing day and night.

  • 4-bedroom private villa on 1 acre within the prestigious Round Hill Resort & Spa compound
  • 3,500 square feet of indoor and outdoor living space
  • full staff: cook, butler, housekeepers, laundress, gardener
  • child friendly: connecting bedrooms, 2 Pack n Plays, high chair
  • outdoor tree swing, supervised Kids Club at the hotel
  • 20' x 50' private swimming pool
  • wireless Internet access (bring your laptop)
  • cable television, CD and DVD players, library of DVDs, iPod dock
  • Round Hill Membership: complimentary use of the new Round Hill gym and $25 daily fee is waived for Summerland guests (paid by the homeowner), complimentary beach, two connecting heated pools for parents & children, jogging trail. For various additional fees: Pineapple Kids Club, 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.

Perched atop glamorous, private Round Hill, Summerland is a fully staffed private home sited for its dramatic view over the sea.  The east verandah captures views of the sunrise, the deep blue Caribbean Sea, and later the magical lights of Montego Bay twinkling across the sea. The view is simply mesmerizing day and night. All meals are served al fresco in this breathtaking spot. Table service of Villeroy & Boch and Aynsley china enhance home-cooked meals.

Interiors at Summerland are a tasteful blending of comfortable casual furniture and elegant Georgian antiques. Original art, highlighted by an excellent collection of Eve Foster, enriches the interiors and echoes old Jamaica and a former grace. See http://www.harmonyhall.com/Gallery/artist/artist.php?id=21

Service at Summerland is designed to pamper guests while never intruding on privacy. This is a staff who adore having children in the house.  Chef Chubby is legend not only for her true Jamaican cooking (jerk pork simmered all day in pimento leaves, curried chicken, seasoned rice and more) but also for her whacky humor and bottomless bowl of homemade cookies always available on the corner of the kitchen counter. The housekeeper keeps all rooms immaculate and adorned by fresh blooms from Summerland's gardens.  Laundresses look after household linens and also all guests' personal laundry so everyone can fly home with suitcases full of clean clothes at the end of their stay. Gardener Shavaun maintains the grounds and pool.  The butler is on the property 24/7 to serve you early morning coffee, help you plan your daily activities, and answer questions about the island and all it has to offer.  He is just a request away to make your favorite afternoon tea, or bring you a refreshing cocktail at days end.


South Wing
Master Bedroom

Kingsize four-poster bed, newly remodeled and enlarged en-suite bath which dons a walk-in shower with a rainfall showerhead. An extra large, custom built armoire with a 37" cable television, and plenty of room for your wardrobe.  French doors to private patio and short stone walkway to pool terrace.  Also connects through interior door to the living room.

North Wing
Bedrooms 2, 3 and 4 interconnect through passage doors that can be left open for parents with small children in the adjoining rooms or closed for complete privacy of guests in each bedroom. Each bedroom has its own private bathroom.

Bedroom 2
Optional king or twin beds, en-suite bathroom with tub-shower combination, 37" cable television, very large bedroom great for parents or children.  Connects to Bedroom 3.

Bedroom 3
Optional king or twin beds, en-suite bath with tub-shower combination. Connects to Bedrooms 2 and 4.

Bedroom 4
Queensize bed, en-suite bathroom with tub-shower combination. Connects to Bedroom 3.

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

Season Bedrooms Weekly Rate
Low Season 2018
April 16 - December 14
1–4 $6,000
Thanksgiving 2018
November 17 - November 24
1–4 $11,500
Christmas 2018
December 19 - December 26
1–4 $18,500
New Year's 2018-2019
December 26 - January 2
1–4 $19,800
High Season 2019
December 15 - April 27
1–4 $11,500
Easter 2019
April 20 - April 27
Easter week is any 7 nights that includes Easter Sunday
1–4 $11,500
Link to Calendar

Booking Calendar

Guest Reviews

  • Blessed to be here and served by the wonderful staff. Everything was great! Thank you so much for being so nice.

    Shawn W - July 2015

  • Staff was fantastic.

    JD - June 2015

  • The staff was excellent, by far the best one we have had. The food was unbelievable and Chubby accommodated all of our food issues and made us believe in wonderful food again! This is a wonderful cottage with a beautiful setting. The pool was the best and somehow always warm.

    Lorelei G - April 2015

  • Everyone was helpful, attentive, kind, thoughtful and caring. Excellent job!

    Susannah T - March 2015

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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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