Hillside Villa at Round Hill

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Sleeps: 8 - 10 Bedrooms: 5 Bathrooms: 5


Wedding Venue Pool Ideal for Kids Walk to Beach All Bedrooms En-Suite

It’s no surprise that Hillside House on Round Hill has been hailed as possessing one of the most spectacular views in all of the Caribbean. The villa, which sits on top of a glorious hill overlooks the island and provides striking views of Jamaica lit up at night, where the sky meets the horizon.

The villa is styled with vibrant royal blue and turquoise touches of colour throughout. The living room has wide doors that open out onto a large furnished outside living room. Guests will be able to lounge inside while relishing the warmth and tropical scents of the garden. What better way to watch the sun go down than in your own outdoor living room? This space will make evenings worth staying in for. The living room boasts crisp white chairs adorned with patterned blue cushions, a bookshelf full of books and vibrant wall art.

The bedrooms see neutral tones paired with bright bursts of colour. You’re guaranteed to get a restful night’s sleep with the large comfy beds complemented by the tranquillity of your surroundings. The bedrooms also contain pretty house flowers and lots of space. Guests will be happy to discover that one of the additions to the home during its renovation – the master bedroom, is on the same level as the pool terrace. One of the bedrooms opens out to a quaint and private tropical garden.

The home’s wonderful pool is surrounded by indigenous plants and trees and will provide the ultimate relaxing experience, swimming the days away. Royal blue sun loungers sit beside the pool for when you want to peacefully take in the hot climate.

Oliver Approved

What you should know…

  • It will be super-hot during your stay at Hillside House, so luckily all five bedrooms benefit from remote-control air-conditioning and ceiling fans

Property Features

Private Pool Internet Air-Con BBQ All Bedrooms En-Suite Tennis Court Ground Floor Bed & Bath Cable TV DVD Ceiling Fans Waterfront

The Villa

Hillside Villa is a truly remarkable holiday home within the Round Hill Estate. This 5-bedroom villa also has access to Tryall Club Beach Club & Resort and Beach Club & Resort  at Round Hill.

Ground Floor

- Two king bedrooms, with en-suite bathroom
- Utility room

First Floor
- King bedroom, with en-suite bathroom & balcony
- Queen bedroom, with en-suite bathroom & balcony
- Twin bedroom, with en-suite bathroom
- Dining & living area
- Fully equipped kitchen
- Terrace


- Private swimming pool, with Roman steps & ladder access
- Hammock
- Lawn area
- Outdoor dining & furniture
- Parasols
- Poolside shower
- Private Parking
- Sun loungers


About the surrounding area of Hillside Villa at Round Hill
Walk to Beach Walk to Restaurant <1hr to Airport Watersports Golf Nearby Tennis Nearby Horse Riding Outstanding Landscapes Outdoor Pursuit & Activities Tourist Towns & Villages
Loading map

Situated nearby the gorgeous Montego Bay, you won’t find yourself short of things to do. Whether it’s partaking in the city’s exhilarating outdoor activities or simply sun-soaking on one of the blissful beaches, you’ve come to one of the island’s most sparkling locations.

While staying at this wonderful holiday home, why not visit Sky Beach Bar & Seafood Grill? It’s a fantastic venue with brilliant sea views and even better seafood, and it’s only a 5-minute drive away. Guests will have the option of dining under a quaint and private Palapa. The fish is outstanding and includes shrimp, conch, octopus and more, all served amongst the charming ambience. The restaurant is situated on a lovely beach, offering views of the surrounding nature and the tranquil sounds of the sea waves crashing. The setting even has DJ’s blasting out party music on some evenings.

By embarking on a short and scenic 30-minute drive, you will discover the enchanting Rastafari Indigenous Village Museum. Rastafari is a spiritual movement native to Jamaica and this is the ideal place to connect with the movement and learn what it means to the country. You will enjoy the fresh coconut water and informative guide while you go on the tour, journeying through the captivating bamboo glade and arriving at the Rasta village. You will discover Rastafari philosophy and watch the community’s members make soap, jewellery, art and musical instruments. This is the place to go to connect with nature.

Local Amenities
Nearest Airport Sangster International Airport


Nearest Town/City Montego Bay


Nearest Restaurant

(Walking Distance)

Nearest Bar/Pub

(Walking Distance)

Nearest Beach

(Walking Distance)

Nearest Golf Tryall Golf Club


Nearest Tennis

(Walking Distance)

About the Island & Getting There

About Jamaica

We have assembled a guide on some of our Jamaica highlights, so please check it out!

Prior to Booking

Please be aware that Jamaica is an island nation that experiences weather patterns dictated by the Atlantic Ocean to the north of the island and the Caribbean Sea to the south of the island. This tropical rainforest climate results in the island experiencing a hurricane season, which usually occurs between June to November. When thinking about booking your holiday to Jamaica, please consult Foreign travel advice for more information.

Entry Requirements

Tourists who are British Citizens will not require a visa upon arrival and Departure Tax is included in most flight costs. Please check Entry Requirements before departure.

Local Public Holidays

14th February - Ash Wednesday
23rd May - Labour Day
1st August - Emancipation Day
6th August 2019 - Independence Day
15th October 2019 - National Heroes' Day

Getting There

Jamaica has two international airports, Donald Sangster in Montego Bay and Norman Manley, Kingston.

From the US:
There are many direct flights with Jet Blue, Caribbean, Delta, American and United from cities including New York, Chicago, Miami, Atlanta, Charlotte, Dallas, Houston and Philadelphia.

From the UK:
There are direct flights to Montego Bay from Gatwick and Manchester with American Airlines, British Airways or Virgin Atlantic. Glasgow and Belfast passengers can also fly via the US with United Airlines.

A. Sangster International Airport, Montego Bay,
B. Norman Manley International Airport, Kingston, Kingston Parish:

View large map


Best Suited For: All Ages
Ideal for Kids Ideal for Teens

While staying at Hillside House, young children will have the option of sleeping in suites that connect to their parent’s bedroom. The home also offers the opportunity for kids to get involved with all the fun at theRound Hill’s Pineapple Kids Club and Hummingbird Kids Club at the Tryall Club. Activities at the club include water sports, tennis, afternoon tea and more.

The Animal Farm & Nature Reserve is a 40-minute drive away in Montego Bay. Described as a ‘rainforest adventure,’ the park is a treat for bird watchers. Kids will love touring this magical piece of nature. Tour guides will take you through the rainforest where you will see a range of rare birds and local herbs that are traditionally used as natural remedies.

Kids Activities Close-by

  • Beach Nearby
  • Walk to Beach
  • Walk to Restaurant
  • <1hr to Airport
  • Watersports
  • Tennis Nearby
  • Horse Riding
  • Outdoor Pursuit & Activities
  • Tourist Towns & Villages

Onsite Facilities

  • Tennis Court
  • DVD
  • Waterfront

Services Available

  • Chef/Cook Available
  • Maid Service Available


Oliver's Extras

  • Chef/Cook Available
  • Maid Service Available
  • Butler Available
  • Butler Included
  • Round Hill Gym Access Included
  • Tryall Club Beach Club & Resort Membership and Beach Club & Resort Membership at Round Hill Included
  • Gardener Included

At Oliver’s Travels we pride ourselves on going that little bit further for our guests. From private chefs to babysitters we can help you arrange those little extras that make it a truly memorable holiday. Simply fill in the concierge request form or contact the Oliver’s Concierge Team who will be happy to help. We can typically help you arrange any of the following:

- Maid service/extra cleaning
- Private chef/cook/catering
- Welcome hamper/pre-stocked fridge
- Local day-trips or tours
- Airport pick-up/drop-off
- Babysitting/childcare services

Simply fill in the concierge request form or contact the Oliver’s Concierge Team.

Please note that all extras are subject to availability and must be requested in advance of the holiday (prices on request). Due to some rural/remote locations, not all services will be available at all properties. However, we will always do our best to fulfil your requests!



Terms & Conditions

Villa Conditions
- Prices may be subject to local taxes and service charges where applicable and may change without notice.
- Holiday rates may vary.
- A 50% Client Deposit may be requested during Festive Bookings.

These terms and conditions may be amended from time to time.

Security deposit Credit cards details requested as guarantee
Arrival time 3.00 p.m.
Departure time 11.00 a.m.
Energy costs included? Included in the rental price
Linen & towels included? Included in the rental price
End of stay cleaning included? Included in the rental price
Tax Taxes & Fees of 10% must be applied to the villa rental rate, due to General Government Consumption Tax
Changeover day Flexible
Minimum stay 7 nights
Internet access? Wi-Fi connection included
Pets welcome? Pets are not allowed
Smoking Allowed? Smoking & Vaping is not permitted inside the villa
Insurance It is recommended that all guests take out insurance to cover against potential cancellation and any accidental damage caused during your stay at the property.

Rental Rates

Please note: All rates below are subject to 10% Government General Consumption Tax

Prices based on an occupancy of 8 people:

Rental period Weekly
Aug 22nd 2019 - Jan 2nd 2020 £11,308
Jan 2nd 2020 - Dec 31st 2020 £11,308
Dec 31st 2020 - Feb 22nd 2021 £11,308

Prices based on an occupancy of 10 people:

Rental period Weekly
Aug 22nd 2019 - Jan 2nd 2020 £13,163
Jan 2nd 2020 - Dec 31st 2020 £13,163
Dec 31st 2020 - Feb 22nd 2021 £13,163

Prices based on an occupancy of 8 people:

Rental period Weekly
Aug 22nd 2019 - Jan 2nd 2020 €11,838
Jan 2nd 2020 - Dec 31st 2020 €11,838
Dec 31st 2020 - Feb 22nd 2021 €11,838

Prices based on an occupancy of 10 people:

Rental period Weekly
Aug 22nd 2019 - Jan 2nd 2020 €13,780
Jan 2nd 2020 - Dec 31st 2020 €13,780
Dec 31st 2020 - Feb 22nd 2021 €13,780

Prices based on an occupancy of 8 people:

Rental period Weekly
Aug 22nd 2019 - Jan 2nd 2020 $13,124
Jan 2nd 2020 - Dec 31st 2020 $13,124
Dec 31st 2020 - Feb 22nd 2021 $13,124

Prices based on an occupancy of 10 people:

Rental period Weekly
Aug 22nd 2019 - Jan 2nd 2020 $15,276
Jan 2nd 2020 - Dec 31st 2020 $15,276
Dec 31st 2020 - Feb 22nd 2021 $15,276

Please note that prices may not be 100% accurate for dates outside of the current calendar year. For an accurate quote, please enquire.


  • Stunning views

    Posted by Shoshana on 20/09/2018

    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.


    Posted by Ophelia on 08/02/2017

    We all want the same things when we go on vacation...beautiful place to stay, great food, impeccable service surrounded by spectacular views . Sounds like a dream..doesn't it? We actually experienced all these and more at the Hillside House at Round Hill! Our family of 9 including 3 small children, celebrated our 50th wedding anniversary and the 40th birthday of my daughter in law.

  • Truly Amazing....

    Posted by Kelly on 15/11/2016

    This private residence within the Round Hill resort is truly amazing - from the upgraded bedrooms and baths, to the unbeatable views, the refreshing swimming pool and the amazing staff. We were treated to a week away with the owners of the residence and we enjoyed three wonderful meals each day rotating from the garden dining area, to the beautiful veranda to a casual poolside meal. We enjoyed easy access via golf cart to the Round Hill resort for fun theme nights, daily tea, the beautiful beach, and the spa. I can not say enough positive things about this house!

  • Hillside Villa at Round Hill Jamaica is to die for!

    Posted by Anonymous on 09/04/2010

    My family along with another family rented a villa called, 'Hillside Villa,' at Round Hill Jamaica. The villa was spectacular. It feel like a throwback to old Hollywood with it's 1950's-60's architecture. The view of Montego Bay is stunning and unique in the Round Hill Villa resort. The staff were perfect -- providing friendly yet not intrusive service. The food was phenomenal. Although a vacation at Round Hill is a pricy endeavor I felt that it was worth every penny.

    We have stayed at a lot of resorts in Jamaica, St Johns, Dominica Republic and Mexico but Round Hill is by far my favorite because of the intimate size and of course the beauty!

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