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Exceptional Villas


#346128 · Villa Rental in , St. James Parish,

5 Bedrooms
10 guests
5 Full Bathrooms
Villa Rental

Property Description

Welcome to Hillside Villa, a luxury 5 bedroom villa located on Round Hill near Montego Bay on one of the most stunning locations in Jamaica. Hillside villa as the name suggests sits on height overlooking Round Hill resort and offers some of the most magnificent views of the Caribbean Sea.

The villa is set in a wonderfully manicured garden and has its own private pool for you to enjoy. The terrace features an outdoor dining area – perfect for dining alfresco with family and friends. The deck has lounge chairs and umbrellas to relax and enjoy the Caribbean sunshine and the wonderful sea views.

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 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

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 • safes in every bedroom

• 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 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 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.


When you stay at Hillsid

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House Rules

Check In Time: 16:00
Check Out Time: 10:00
Max occupancy: 10


Rate Name Nightly Weekend Weekly Monthly
Default Rate
5 Nights Minimum
- - $13214 CAD -
High Season 2018
01/03/18 - 04/21/18
7 Nights Minimum
- - $18115 CAD -
Low Season 2018
04/22/18 - 11/17/18
5 Nights Minimum
- - $9998 CAD -
Thanksgiving 2018
11/18/18 - 11/25/18
7 Nights Minimum
- - $23748 CAD -
Low Season 2018
11/26/18 - 12/15/18
5 Nights Minimum
- - $9998 CAD -
Christmas 2018
12/16/18 - 12/26/18
7 Nights Minimum
- - $26240 CAD -



Board Games
Internet Access


Heated Pool


Sandy Beach
Tennis Court
Deck / Patio


Gym / Fitness Centre
Restaurant On Site
Maid Service

Availability Calendar

January 2018

  • Unavailable
  • Check In Available
  • Check Out Available
Availability last updated Jan 21, 2018
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