RESERVE

Hillside on Round Hill

Montego Bay, Jamaica
‎(5)
5 BEDROOMS
1 King
3 Kings/2 Twins
1 Double
5.0 BATHROOMS
5 En-suite
10 GUESTS
Children Welcome
view photos

Villa Hillside at Round Hill on Jamaica is the ideal choice for Montego Bay vacationers who love their privacy and appreciate the convenience of world-class amenities nearby. This beautiful property was selected for the prevailing tradewinds and glorious views on the east side of Round Hill. Enter the exclusive Round Hill gatehouse and drive under a quarter mile to Villa Hillside tucked away amidst lush island greenery overlooking the deep blue waters of the Caribbean Sea.

White marble floors offset casual furniture in the living room, which is enhanced by a colorful collection of original artwork. A 22-foot window wall opens to the balcony with cooling sea breezes and spectacular sea views. Enjoy al fresco candlelight dinners prepared by your personal chef and served by the butler in the outdoor arbor. Coffee and after dinner drinks are served on the balcony, where you will be enchanted by the twinkling lights of Montego Bay the reflections that dance across the water. Villa Hillside provides a private 40-foot pool with a ten-mile ocean view. Guests will enjoy a full roster of electronics, from the 60-inch satellite Smart TV to the VCR, surround sound system and WiFi Internet service, along with CD and DVD players.

You will be attended by a full staff, including a housekeeper, a laundress and a gardener. Complimentary membership to the exclusive Round Hill and Tryall Clubs is included when you stay at Villa Hillside. A quick tram ride will take you to the private Round Hill Beach Club, and you can take advantage of Round Hill facilities including tennis, a fitness room, a spa, water sports, bars and restaurants. The well-known Tryall Club offers similar amenities as well as preferred rates at the championship Tryall Club Golf Course. Both clubs provide exciting special events like cocktail and beach parties, as well as organized activities for children.

Villa Hillside Villa on Round Hill Staff includes:
Cook
Housekeeper
Laundress
Butler
Gardener
Cost of food and gratuities not included

Villa Hillside Villa on Round Hill additional amenities:
Round Hill Hotel and Beach Club Membership
The Tryall Club Membership includes:
Complimentary beach, tennis, gym, pool, the 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.
For various fees: golf, tennis lessons, Happy Hour, hair salon & spa, bars & restaurants, boutique, motorized water sports, beach parties Mon-Wed-Fri
Location: Round Hill, Montego Bay

Last Renovation Year: 2015

All five bedrooms are air-conditioned.

Bedroom 1: Pool level master bedroom with a king-size bed, spectacular view and en-suite bathroom with bathtub, shower, vanity and WC. 2 guests maximum.

Bedroom 2: Main level bedroom with a king-size bed (can be made up as two single beds), wonderful views, connected door with bedroom 3 and en-suite bathroom with bathtub/shower combination, vanity and WC. 2 guests maximum.

Bedroom 3: Main level bedroom with a double bed, spectacular views, connected door with bedroom 2 and en-suite bathroom with bathtub, shower, vanity and WC. 2 guests maximum.

Bedroom 4: Main level bedroom with a king-size bed (can be made up as two single beds), garden view and en-suite bathroom with bathtub/shower combination, vanity and WC. 2 guests maximum.

Bedroom 5: Main level bedroom with a king-size bed (can be made up as two single beds), garden view and en-suite bathroom with bathtub/shower combination, vanity and WC. 2 guests maximum.

  • Air Conditioning - Bedrooms
  • Alfresco Dining Area
  • Beach Towels
  • Bed and Bath Linens
  • Cable TV
  • CD Player
  • Ceiling Fans
  • Children Welcome
  • Computer
  • Connected Bedrooms
  • Daily Turndown Service
  • Film Library
  • Fitness Room - Community Shared
  • Golf (Nearby)
  • Hair Dryer
  • Internet
  • iPod Dock
  • Library
  • Media Room
  • On-Site Heliport
  • Outdoor Grill
  • Patio/Terrace
  • Phone
  • Playground
  • Resort Privileges
  • Secured Parking
  • View - Ocean/Sea
  • Voltage - 110
  • WiFi
  • Butler/Host
  • Chef/cook
  • Gardener
  • Housekeeper(s)
  • Laundress
Housekeeping: Maid service 7 days a week
Cook
  • Damage Deposit: US$1,000
  • Children Welcome (all ages)
  • No Pets Allowed
  • No Smoking
  • Club Membership
  • Full capacity rate required during Thanksgiving week.
  • Prepayment of staff gratuities required
  • Provisions and groceries are not included
  • Rates are set in US Dollars. Prices in other currencies may fluctuate.
  • Utilities included
  • VAT taxes included in rates.
  • Villa orientation
  • Deposit/Payment: 50% deposit to confirm. Balance due 90 days prior to arrival. Holidays: Balance due 120 days prior arrival
  • Check In: 3pm
  • Check Out: 11am
Do we share the villa? click to close
No. You will not share the villa with another party. The villa is exclusively yours. If a larger villa offers a lower bedroom rate category, the villa will remain exclusively yours but the unrented bedrooms will be locked off.
For example, a 5 bedroom villa that offers a 3 bedroom rate will be the exclusive use of the guest but two bedrooms and their en-suite bathrooms will be locked off. Capacity is capped at 2 guests per bedroom.
Are we protected from fraud? click to open
Yes. Isle Blue stands behind you throughout your entire vacation. Unlike other companies, each property we offer has been hand picked to ensure that our standards are met. All property managers are vetted and payments are required to be held in escrow. Our primary obligation is to ensure your satisfaction and to have an exceptionally memorable vacation.
Can you explain the reservation process? click to open
Once a reservation request is received, Isle Blue will request a contract from the property manager for your dates of interest. Once the dates are confirmed and contract is received from the property manager, a payment will be required to confirm your reservation.
Once a reservation is confirmed, a concierge will welcome you to the planning stages of your vacation to assist with arrival logistics, rental cars, transfers, and a host of concierge services.
What offerings are included with the concierge service? click to open
Our concierge is a complimentary service to our guests. An exceptional benefit. The concierge will assist with your arrival and departure logistics and offer a host of additional services. Services may vary per destination but typically include the following benefits:
  • Transfers
  • VIP Services
  • Chef Services
  • Spa Services
  • Activity and Excursion booking
  • Rental cars
  • Provisioning
Please do not hesitate with any special requests. Our team is here to ensure you dream vacation becomes a grand reality.
Can we arrange an early check in? click to open
Early check in may be possible but is at the sole discretion of the property manager. Early check in permission may not be granted until 24 hours prior to arrival.
Can we arrange a late check out? click to open
A late check out is rarely granted due to the turnover needs of a villa. A late check out may only be granted 24 hours prior to your departure from the property and only when there is no check in scheduled on the day of your check out. If a late check out is urgently needed please contact us.
Are transfers to the property included? click to open
Select villas may include a one way or roundtrip airport transfer while others may provide an escort or meeting point. Arrival logistics will be handled by your dedicated concierge as well as other concierge needs. The property's transfer policy will be listed under the Policies section.
What to expect upon arrival? click to open
In general, a villa orientation will be provided along with a key turnover. During the orientation, information and instructions for the property will be provided. Emergency contact information will be provided. We are available 7 days a week to assist with any urgent needs.
The arrival procedures due vary from villa to villa, select villas may include welcome provisioning while other properties will provide basic arrival information.
What is the cancellation policy? click to open
Since these vacation homes are one of a kind properties, the cancellation policy is strict. We highly recommend considering trip/travel insurance to protect against any unexpected cancellations or issues that may arise.
For more details, please visit Travel Protection
What happens if the property becomes unavailable after I reserve? click to open
In the unlikely event, the rented property becomes unavailable due to a major issue that may affect a guest's experience or a transfer of ownership, Isle Blue will coordinate with the property manager to find an alternate property of equal or superior standard that is subject to the guest's approval. If an alternate property is not acceptable to the guest, the guest will receive a full refund.
Do you accept credit cards (American Express, Mastercard, or Visa)? click to open
Yes, we accept all major credit cards. American Express, Visa, Mastercard and Discover are accepted. Please note that credit card charges may be subject to additional fees. There are no fees with payment by wire transfer or check.
In late 2018, we expect to accept a greater variety of payment methods and currencies via Stripe.
Is housekeeping included? click to open
Housekeeping tends to be a standard among vacation homes but the frequency may vary greatly depending on the property manager’s standards. Most properties will offer daily housekeeping (except Sunday and holidays) while other villas may only provide a mid-week cleaning. Please refer to the Policies section to learn about the housekeeping frequency of the property.
Are towels and linens provided? click to open
Yes. The property will provide bath and pool towels along with linens. Towels and linens will be refreshed as needed.
Are toiletries and tissues provided? click to open
A property may supply an initial supply of soap, shampoo, toilet paper and paper towels but replenishment of supplies once exhausted may be the responsibility of the guest. Each property varies in their handling of toiletries and paper products.
Is a hair dryer available? click to open
A hair dryer is typically available at the property. Upon arrival, please check the bathrooms or closet. Typically, a hair dryer is included in each bathroom.
Is an iron included? click to open
Typically yes, irons tend to be standard equipment for vacation homes. Please ask the property representative upon orientation for the location of the iron.

Isle Blue provides the most in-depth expertise and insight for vacation home rentals and vacation planning. For further helpful tips, answers and recommendations please visit our extensive Knowledge center that hosts articles and answers on general as well as destination specific topics.

SEASON BEDROOMS DAILY WEEKLY
2018 Apr 22 to Nov 17 April 22, 2018 - November 17, 2018 (5 night minimum) 4 5 $1,028.57 $1,142.86 $7,200.00 $8,000.00
2018 Nov 17 to Nov 24 November 17, 2018 - November 24, 2018 (7 night minimum) 5 $2,714.29 $19,000.00
2018 Nov 24 to Dec 15 November 24, 2018 - December 15, 2018 (5 night minimum) 4 5 $1,028.57 $1,142.86 $7,200.00 $8,000.00
2018 Dec 15 to Dec 22 December 15, 2018 - December 22, 2018 (7 night minimum) 5 $2,071.43 $14,500.00
2018 Dec 22 to 2019 Jan 5 December 22, 2018 - January 5, 2019 (10 night minimum) 5 $3,142.86 $22,000.00
2019 Jan 5 to Feb 2 January 5, 2019 - February 2, 2019 (7 night minimum) 4 5 $1,828.57 $2,128.57 $12,800.00 $14,900.00
2019 Feb 2 to Mar 2 February 2, 2019 - March 2, 2019 (7 night minimum) 5 $2,128.57 $14,900.00
2019 Mar 2 to Mar 23 March 2, 2019 - March 23, 2019 (7 night minimum) 5 $2,242.86 $15,700.00
2019 Mar 23 to Mar 30 March 23, 2019 - March 30, 2019 (7 night minimum) 5 $2,471.43 $17,300.00
2019 Mar 30 to Apr 20 March 30, 2019 - April 20, 2019 (7 night minimum) 5 $2,128.57 $14,900.00
2019 Apr 20 to Apr 27 April 20, 2019 - April 27, 2019 (7 night minimum) 5 $2,128.57 $14,900.00
2019 Apr 27 to Nov 23 April 27, 2019 - November 23, 2019 (5 night minimum) 4 5 $1,028.57 $1,142.86 $7,200.00 $8,000.00
2019 Nov 23 to Nov 30 November 23, 2019 - November 30, 2019 (7 night minimum) 5 $3,000.00 $21,000.00
2019 Nov 30 to Dec 14 November 30, 2019 - December 14, 2019 (5 night minimum) 4 5 $1,028.57 $1,142.86 $7,200.00 $8,000.00
2019 Dec 14 to Dec 21 December 14, 2019 - December 21, 2019 (7 night minimum) 5 $1,828.57 $12,800.00
2019 Dec 21 to Dec 28 December 21, 2019 - December 28, 2019 (10 night minimum) 5 $3,357.14 $23,500.00
2019 Dec 28 to 2020 Jan 4 December 28, 2019 - January 4, 2020 (10 night minimum) 5 $3,357.14 $23,500.00
2018 Apr 22 to Nov 17 April 22, 2018 - November 17, 2018 (5 night minimum)
Bedrooms: 4
Daily: $1,028.57
Weekly: $7,200.00
Bedrooms: 5
Daily: $1,142.86
Weekly: $8,000.00
2018 Nov 17 to Nov 24 November 17, 2018 - November 24, 2018 (7 night minimum)
Bedrooms: 5
Daily: $2,714.29
Weekly: $19,000.00
2018 Nov 24 to Dec 15 November 24, 2018 - December 15, 2018 (5 night minimum)
Bedrooms: 4
Daily: $1,028.57
Weekly: $7,200.00
Bedrooms: 5
Daily: $1,142.86
Weekly: $8,000.00
2018 Dec 15 to Dec 22 December 15, 2018 - December 22, 2018 (7 night minimum)
Bedrooms: 5
Daily: $2,071.43
Weekly: $14,500.00
2018 Dec 22 to 2019 Jan 5 December 22, 2018 - January 5, 2019 (10 night minimum)
Bedrooms: 5
Daily: $3,142.86
Weekly: $22,000.00
2019 Jan 5 to Feb 2 January 5, 2019 - February 2, 2019 (7 night minimum)
Bedrooms: 4
Daily: $1,828.57
Weekly: $12,800.00
Bedrooms: 5
Daily: $2,128.57
Weekly: $14,900.00
2019 Feb 2 to Mar 2 February 2, 2019 - March 2, 2019 (7 night minimum)
Bedrooms: 5
Daily: $2,128.57
Weekly: $14,900.00
2019 Mar 2 to Mar 23 March 2, 2019 - March 23, 2019 (7 night minimum)
Bedrooms: 5
Daily: $2,242.86
Weekly: $15,700.00
2019 Mar 23 to Mar 30 March 23, 2019 - March 30, 2019 (7 night minimum)
Bedrooms: 5
Daily: $2,471.43
Weekly: $17,300.00
2019 Mar 30 to Apr 20 March 30, 2019 - April 20, 2019 (7 night minimum)
Bedrooms: 5
Daily: $2,128.57
Weekly: $14,900.00
2019 Apr 20 to Apr 27 April 20, 2019 - April 27, 2019 (7 night minimum)
Bedrooms: 5
Daily: $2,128.57
Weekly: $14,900.00
2019 Apr 27 to Nov 23 April 27, 2019 - November 23, 2019 (5 night minimum)
Bedrooms: 4
Daily: $1,028.57
Weekly: $7,200.00
Bedrooms: 5
Daily: $1,142.86
Weekly: $8,000.00
2019 Nov 23 to Nov 30 November 23, 2019 - November 30, 2019 (7 night minimum)
Bedrooms: 5
Daily: $3,000.00
Weekly: $21,000.00
2019 Nov 30 to Dec 14 November 30, 2019 - December 14, 2019 (5 night minimum)
Bedrooms: 4
Daily: $1,028.57
Weekly: $7,200.00
Bedrooms: 5
Daily: $1,142.86
Weekly: $8,000.00
2019 Dec 14 to Dec 21 December 14, 2019 - December 21, 2019 (7 night minimum)
Bedrooms: 5
Daily: $1,828.57
Weekly: $12,800.00
2019 Dec 21 to Dec 28 December 21, 2019 - December 28, 2019 (10 night minimum)
Bedrooms: 5
Daily: $3,357.14
Weekly: $23,500.00
2019 Dec 28 to 2020 Jan 4 December 28, 2019 - January 4, 2020 (10 night minimum)
Bedrooms: 5
Daily: $3,357.14
Weekly: $23,500.00

Note: The rates above are subject to 15% Tax/Service Charge.
Payments accepted in US Dollars, Euros, British Pound, Canadian Dollars, Swiss Franc, Fijian Dollars, Thai Baht, Australian Dollars, New Zealand Dollars.
Major credit cards accepted in US Dollars.

STARTING AT $1,028.57/Nt
Please try again or contact us for possible waiver at 1.704.256.8327 or [email protected]
Your Estimate:
$0
(Estimate does not include applicable promotions.)
Date Unavailable Availability calendar may not reflect up to date reservation information.
Availability subject to change.

LOCATION

Due to villa's privacy policy, the nearest town is presented on the map

REVIEWS

LEAVE A REVIEW
Kit White Feb, 2017
Source: TripAdvisor/FlipKey

We came with my adult siblings and everyday was paradise. We woke up with the view of the sunrise over the mountains and cocktails at sunset on the veranda. The meals were prepared with consideration to everyone's food requests. My sister, a vegetarian, was delighted with what was prepared for her. From the moment the staff welcomed us on the first day, until we had to leave, all our needs were met. If we needed anything, all we had to do was ask and it happened. Our biggest decision each morning was "do we go to the pool or visit the resort?"

MaryAnn H. Jan, 2017
Source: TripAdvisor/FlipKey

2.0 because 10 years ago we stayed at Hillside House with a party of six, and had the best experience. The home, the views, the access to activities within Round Hill and other area attractions easily available due to the staff. When getting together with the expanded group of now 10, we thought of our previous time at Hillside House, and looked into it. The home has been updated with another suite, and met all our needs with ease. If you think a home would be comfortable with 6, it is now more than comfortable accommodating a larger group. Never do you feel crowded with the expanded patio and outdoor spaces. The staff was able to meet our variable arrival and departures. The chef was seamless in meeting our various dietary requirements. Waking up to the view of Montego Bay allows one to recharge their battery. The staff attends to every need one can have. The value of staying in this home surpasses other options. You have a chef, driver, groundskeeper, laundress - pool, beach, golf access - heaven! Availability to travel anywhere on the island. Highly recommended!

K. Maloney Nov, 2016
Source: TripAdvisor/FlipKey

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!

Gary S. Aug, 2016
Source: HomeAway/VRBO

This is by far the nicest home I have ever rented period! The views are incredible. The moment you enter every care in the world melts away! The home has had extensive renovations and it feels brand new. The 2 master suites are tremendous with unbelievable bathrooms. The home is part of the 5 star Round Hill Resort which is a major plus. The facilities at the resort are amazing, from the recently renovated spa and fitness center to the restaurant and bars, and the amazing seaside infinity pool. Speaking of pools, I think the pool at Hillside House has got to be one of if not the biggest private pool at the resort.

The stay here is so relaxing because every care in the world is taken care of- 3 incredible meals a day, served by a warm and caring staff in such a beautiful setting. Your laundry is done daily. I felt like I died and went to heaven. I will without a doubt be returning to my new favorite vacation destination in the world!

Wayne E. Apr, 2016
Source: HomeAway/VRBO

We spent 5 fabulous days with friends at this spectacular home. From the moment you step on the grounds, the staff is there to take care of your every need. From cooking, to housekeeping, to laundry service to one great meal after the next, they are fantastic. No one had to lift a finger! And the views! The house is lovely and the access to the beach area was wonderful. Our biggest decision of each day was whether to relax at the pool at the house, at the pool at the beach or at the beach. Or to enjoy a workout at the gym or book an appointment at the spa! We had a wonderful time and it was very difficult to leave!

WHAT OUR GUESTS ARE SAYING

"We had a great time and really enjoyed the villa. "
Elaine F
Bella Casa
READ MORE TESTIMONIALS
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