Hillside House on Round Hill

Caribbean / Jamaica / Montego Bay

Perched atop the legendary Round Hill Estate, Hillside House embodies the timeless charm of Old Jamaica paired seamlessly with modern luxury. This crowning jewel has long been a show-stopper, celebrated for its breathtaking panoramic views and cooling trade winds that sweep effortlessly through the property. Thoughtfully designed with families in mind, Hillside House offers inviting, unpretentious elegance — a relaxed yet refined retreat created for savoring the very best of island living.

up to 5
Bedrooms
up to 10
Guests
5
Bathrooms
Min. Nights Upon Request

Overview

  • Five-bedroom villa
  • The Great Room opens to a fabulous furnished balcony and a world-class, breathtaking view
  • Two Master Bedrooms on the pool terrace level
  • Upper-level bedroom balconies
  • Connecting suites for parents and children
  • Two dining areas
  • Outdoor shower
  • Fire pit
  • Coral stone floors
  • Complimentary Wi-Fi in the villa and throughout Round Hill
  • Flat-screen Smart TV’s throughout
  • Safes in every bedroom
  • Complimentary 6-seater transportation cart (for transport throughout Round Hill)
  • Fully staffed: excellent cook, butler, housekeeper, laundress, gardener
  • Large 20 x 40-foot private pool with 10-mile ocean view
  • Round Hill membership: complimentary beach access, two connecting heated swimming pools for parents & children, Afternoon tea, tennis, Pickleball,l and jogging trail. For various additional fees: Pineapple Kids Club, gym, tennis, pickle ball, 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.

The Great Room opens wide to the pièce de résistance, 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 prime 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.

Accommodations

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

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. 

Both of these Master Bedrooms offer traditional Jamaican king-size 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 a furnished verandah and a 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 the furnished verandah and that view. This bedroom connects to Bedroom 5 for a convenient parent-child suite if desired.

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

Round Hill 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, and unforgettable long sunsets from the waterfront terrace.

Guests receive complimentary use of the Round Hill gym; the $25 daily fee is waived for Hillside House guests (paid for by the homeowner). Hillside House guests also receive complimentary WiFi throughout Round Hill (daily fee waived/paid by the homeowner).

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

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 pros 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.


Features

5 Bedrooms, 5 Bathrooms

Sleeps 10 People

Bedrooms Only

Connecting Suites

Complimentary Wi-Fi

Ocean View Pool (20x40 feet)

Gardener

Laundress

Housekeeper

Butler

Cook

Round Hill Membership

Tryall Club Membership

Hair Dryers

Six-Seater Transportation Cart

Outdoor Shower

Fire Pit

Terrace/Balcony

Room Safes (each bedroom)

iPod Docks

Flat-Screen TVs


Details

Pool Details

20 x 40-foot private pool with breathtaking 10-mile ocean view

Distance Details

Beach: 1 minute to Round Hill beach via comp shuttle
Tryall Club: 10 minute drive
Town: 22 minutes via driver
Airport: 22 minutes

Staff and Services

Butler
Cook
Gardener
Housekeeper
Laundress


Rates

Travel Dates Bedrooms Min. Night Stay Nightly Rates

High Season: 7-night minimum stay required
Low Season: 5-night minimum stay required
Holidays: 7-night minimum stay required
* Rates & minimum stay requirements are subject to change without notice. Please check with your villa specialist to confirm.

April 01, 2026 - April 03, 2026
High Season
5 7 $4,142 *
April 04, 2026 - April 11, 2026
Easter - Any 7 nights that includes Easter Sunday
5 7 $4,428 *
April 12, 2026 - April 15, 2026
High Season
5 7 $4,142 *
April 16, 2026 - November 20, 2026
Low Season
5 5 $3,428 *
November 21, 2026 - November 28, 2026
Thanksgiving Holiday
5 7 $4,428 *
November 29, 2026 - December 14, 2026
Low Season
5 5 $3,428 *
December 15, 2026 - December 18, 2026
High Season
5 7 $4,142 *
December 19, 2026 - December 26, 2026
Christmas - Dec 19-26 or 20-27 or any 7 nights that includes Dec 25th. Additionally, any 7 nights (eg. Dec 17-24) that prevents a Christmas reservation will be invoiced at the Christmas rate.
5 0 $6,071 *
December 27, 2026 - January 03, 2027
New Year - Dec 26-Jan 2 or Dec 27-Jan 3 or any 7 nights that include Dec 31st.
5 0 $6,071 *
USD rates above based on approximate currency conversion. Holiday dates may not be listed in rate chart. Rates are subject to change without notice. Please confirm rate, holiday dates, and currency with your Villa Specialist at time of booking.

Check In Times

Check in: 03:00 PM - Check out: 11:00 AM

Minimum Stay Details

High Season: 7-night minimum stay required
Low Season: 5-night minimum stay required
Holidays: 7-night minimum stay required

Accidental Damage Waiver

A $149 Accidental Damage Waiver applies to every reservation.

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Location

Reviews

Our family of eight had a perfect vacation at the Hillside House. The villa itself was beautiful, spacious and peaceful, with stunning views of the water and Montego Bay city lights across the way. The staff members were professional, responsive, and friendly. We loved our gourmet meals prepared by chef Natalie. Half of our family is vegetarian, and she was able to accommodate our preferences without a problem. We hope to return next year.

Shoshana B.

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

Toni B.

The friendliest people ever and the house is beautiful!

Marcee H.

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

Kelly E.

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.

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.

Villa information may change without notice and should be confirmed with our villa rental specialists.

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