May 29, 2019

Jamaica Luxury Resorts & Villas || Hillside House

If you have been searching for Jamaica luxury resorts and coming up short, look no further than the Hillside House Jamaica.

This incredible house, overlooking a ten-mile stretch of the Carribean Sea, is one of the more spectacular stays Shawn and I have had the chance of enjoying.  Family owned for almost 60 years, the Hillside House has been a destination of choice for high-end guests for decades.  I can certainly see why it is consider one of the best Jamaica luxury resorts.

In today’s post, we will detail our experience, all of the incredible accommodations, the staff (including a butler and a chef!) and so much more!  This is a post you will not want to miss!



Want to know why the Hillside House is considered one Jamaica’s best luxury resorts?  Just look at this incredible view!

When you arrive at the Hillside House, you are greeted by the full staff, including butler and chef, that are on-site.  The staff is there to assist you with every need you and your guests may have during your stay.  You will get a full tour of the house and grounds, as well as a walk through of your meal plan with Natalie, the on-site chef.

TIP: Be sure to be clear about what your party will and will not eat – including any allergies.  You will also want to establish the times you want to eat breakfast, lunch and or dinner as they staff will prepare for the day in advance.  

The wide open Great Room opens to a lavish veranda overlooking the ocean. At night, the lights of Montego Bay across the water welcome guests of the Hillside House to stay out together, sharing drinks, laughter, and memories before retiring to their suites.

During our stay at the Hillside house, we enjoyed exquisite Jamaican meals which rival the finest restaurants on the island.  Although the area is extremely safe, there is a security guard on the premises each night, allowing us to feel completely at ease.


The food and beverages consumed at Hillside House are an additional cost.  Generally speaking, the average cost for three meals a day is approximately $35 per person per day.  This generally does not cover the cost of alcoholic beverages which can also be ordered as part of the food plan.

Jamaican food is fresh and colorful, and the Hillside cook is truly outstanding.  As mentioned above, upon arrival, Natalie will confirm with you about meal options and prepare a shopping list tailored to your family’s preference.  She will purchase the food at a local marker and bring you the receipt.

Dining at the Round Hill Resort is also an option for breakfast, lunch and dinner which Shawn and I did choose to do a few times during our stay.  This can be a great way to linger down at the beach, by the infinity pool or on the magnificent patio overlooking the bay.

The food costs need to be paid to the Chef, Natalie, in cash, as follows:

* An initial installment for food costs are paid in the first couple of days of your stay (in $US).  And, the balance of food costs will be collected at the end of your stay. Depending on your needs, she may or may not need to collect a payment mid-week.

* Because she shops in the open market in Montego Bay with vendors she’s been buying from for years, she consistently gets the very best prices on fresh fish, meat, produce and fruit. In this way the cost and quality of cooking at Hillside is much less expensive than dining out.

* In addition to the cost advantages for meals at Hillside, the dining service is attentive, professional and friendly. This makes for a luxury restaurant experience in the relaxed environs of beautiful Hillside House.



If you’re looking for the ultimate in Jamaica luxury resorts accommodations then the Hillside House will likely answer all of your needs.

The house is a recently renovated five bedroom masterpiece sitting on one of the most spectacular view sites in the Caribbean. Enjoy luxury, elegance and relaxation while lounging by the private pool overlooking Montego Bay.

Hillside House sits within the secluded gates of the award winning Round Hill Resort and  just thirty minutes from the city of Montego Bay and  International airport.  With your stay, you get full access to all of the Round Hill Resort amenities including beach access, spa, tennis courts, shops and restaurants.

All five bedrooms are equipped with remote control quiet air-conditioning, ceiling fans, safes, fiber-optic wifi, cable televisions and en suite bathrooms.  Four of the five bedrooms have their own outdoor sitting areas and spectacular ocean views. The fifth bedroom opens to a private tropical garden which peaks through Pimento and Breadfruit trees to the sea beyond.  It’s truly breathtaking and a one-of-a-kind stay.

Downstairs Pool Terrace Level

This level hosts two master suites (bedrooms 1 & 2).  Both bedrooms are very spacious, private, and can be connected if you wish. Each suite opens directly onto the front terrace, with gorgeous views of the sea.  Both of these master bedrooms offer a traditional Jamaican kingsize bed with en-suite bathrooms with bathtubs and walk-in showers. One of the bedrooms also has a daybed.

Upstairs Entrance Level

Bedroom 3 offers a queen-size bed and an en suite bathroom with a walk-in shower. This room opens to the furnished veranda with a spectacular view of the sea. The 4th bedroom offers an optional king-size or twin beds, en suite bathroom with octagonal walk-in shower which is louvered on three sides to offer a sea view while maintaining privacy. Doors to furnished veranda and that view.  This bedroom connects to Bedroom 5 to create a convenient parent-child suite, if desired.

The 5th bedroom also offers a king-size or twin beds and an en suite bathroom with a walk-in shower. This room is privately located on west side of villa and opens to tropical garden courtyard with sitting area.  It is possible to connect to Bedroom 4 via for a parent-child suite.

There is no shortage of space in any space within the house.  I can almost guarantee the house will take your breath away.

Need a little time to yourself during your stay?  The house offer several great ‘nook’s’ perfect for some peace and quiet or a few hours with your favorite book.  Even better, many of these quiet spaces are just steps outside the doors of several rooms on the resort.

See, one of the best Jamaica luxury resorts indeed!

In the morning, be sure to catch the incredible sunrise!  You will not want to miss it!



What separates the Hillside House from other Jamaica luxury resorts is the staff.  You will lack nothing during your stay at the house thanks for the incredible staff 24 hours a day.

The chef, Natalie, tailors each meal to satisfy the specific tastes of each guest.  And, believe me, the food is incredible and locally sourced.  Then there is Milton, the house butler.  He could not be more compassionate and friendly.  You will truly need for nothing during your visit.  He ensures the stay is one-of-a-kind.

The staff keeps the pool cleaned around the clock, demanded they take care of any ironing even when I said I was happy to do so myself, assisted with travel accommodations, dinner reservations and so much more!

Not to mention, if you want a cocktail by the pool, Milton whips up a mean Stanley’s special – also known as the Jamaican Sunrise.  They were delicious!


You do not need to exchange your USD in Jamaica.  You can use cash and USD all across the island.

As it relates to tips, it is customary to tip the staff at the end of your stay. The recommendation is a tip of $500 – $1,500 (total) depending upon the length of your stay and the amount of people in your party. The tip for the staff needs to be paid in cash and can be put into one envelope which Milton (the House Manager) will distribute to the other staff members.


While we never opted to leave the breathtakingly beautiful resort grounds, there are plenty of options for the more adventurous.

The falls at Ocho Rios? Want to travel to the pristine and calm beaches of Negril?  Or a hummingbird sanctuary in the mountains?  I’d try the world-famous Tryall Golf Club,too, just to name a few.  The Concierge at Round Hill Hotel can also help you with any number of sightseeing excursions and sporting adventures.



The Round Hill Resort is one of the finest old world Caribbean destinations. And,  voted #1 in 2016 as the single finest in Jamaica by Travel and Leisure.

Hillside House guests enjoy membership privileges including access to Round Hill’s beach, water sports, workout facilities, restaurants, bars, and use of the famed Tryall Golf course just five minutes outside Round Hill’s gates. The unique experience of staying in a privately owned villa, while also having access to the Round Hill Resort make one’s stay at Hillside House truly special.

You can view a full review of the Round Hill Resort in our full blog post here.  We included incredible photos of the accommodations, staff and dining.

The Hillside House is just a quick 5 minute walk to the Round Hill Resort and the beach.  Milton will also give you ride to and from, if needed.  The walk is quite nice though.


When you visit this Jamaica luxury resorts, the most difficult decisions you’ll need to make are whether to stay by your private pool or head down to the Round Hill Beach. Or,  to crack open that Red Stripe beer, to schedule a spa treatment or a day trip to Negril, to dine in the villa’s open-air dining patio or on the east balcony to watch the lights of Montego Bay glittering across the water.

Are you as in love with this Jamaica luxury resorts as much as Shawn and I are?  Tell us how you’d spend your time here in the comments below!

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