Do you like style, class, and historical glamour? Round Hill Hotel and Villas in Montego Bay, Jamaica is all 3 of these! Built in 1953, this resort has hosted numerous celebrities including Taye Diggs (Stella got her Grove Back here), Cindy Crawford, Sir Noel Coward, Adele Astaire, Ralph Lauren (owns a villa or two), Jackie-O and JFK just to name a few.

The property is located on 110 acres about 20 minutes from the airport (MBJ). I highly recommend purchasing the VIP arrival and departure service to save time in customs upon arrival and to use the departure lounge while waiting on your flight. It’s not cheap but so worth it.
The resort consists of 27 villas ranging from 2-6 bedrooms in four different categories. The Classic villas range from 800 – 1000 square feet and offer basic decor. Deluxe offer upgraded decor and ensuite bathrooms, luxury villas are 3-6 bedrooms with private pools and offer indoor/outdoor living, and premium luxury are 4-6 bedrooms with game rooms, upgraded interiors, and the best of the best.

All bedding in each villa is either a king bed or 2 doubles. Each villa comes with it’s own staff which will clean up around the property, fix any housekeeping issues, and serve breakfast each morning. The breakfast is served family style and each night before you go to bed you fill out a card with the desired meal and time for the next morning.

Breakfast set up in our villa

Fruit at breakfast

Breakfast bread basket

Toast and an assortment of jellies
I stayed in villa #16 which is a Premium Luxury 6 bedroom villa. Each villa had it’s own living space, bedroom and bath, and outdoor dining area. The pool area is shared with the other 5 bedroom and there’s a partially stocked kitchen where the staff prepares the morning breakfast. We had ample supply of soft drinks, beer, and water along with any breakfast leftovers.

Exterior view of villa #16

Foyer in villa #16

My bedroom in villa #16

My private living room with views of the Caribbean in villa #16

My bathroom in villa #16

My bathroom in villa #16

Game room in villa #16

Villa #16 pool

Sitting area at villa #16
Villa #25 is a 3 bedroom luxury villa with each bedroom having its own bedroom, bath and living area. The pool is also shared with all 3 bedrooms.

Bedroom in villa #25

Villa #25 pool
Villas #20 and 21 are the newest and are premium luxury. At the time of my visit (10/14) they were still under construction.
If a couple is traveling along then the resort will do its best unless it’s completely booked to be sure there is an empty villa between you and another couple since there are no individual villas.
There are no washers/dryers in the villas but laundry service is available 24 hours a day, dry cleaning takes 2 days.
In addition to the villas there’s the Pineapple House with 36 ocean front rooms designed by Ralph Lauren. 18 rooms are upstairs with no balcony, just a large picture window overlooking the sea and 18 downstairs with a patio. These are closer to the pool area and are not as isolated as the villas. The rooms are 460 square feet with a separate shower and tub. Bedding options are either a King or 2 doubles with connecting options for families.

View from 2nd floor room at Pineapple House

Double room at Pineapple House

Bathroom at Pineapple House
Meal plans are available and all the food is locally sourced and authentic. The property has a 1 acre garden that provides some fruits and vegetables to the resort. The platinum food plan includes all meals, beverages, airport transfers, as well as an off-site activity. Each afternoon high tea is served and it’s not to be missed.

Tea menu

Afternoon tea
You can be as active or inactive as you want on your trip. Some of the activities include kayak, paddleboard, Hobie cat, snorkeling, jogging trails, tennis (pro available), golfing at Tryall (10 minutes away – complimentary shuttle), sport fishing, scuba diving, speed boat, and more.

There’s a Kids Club for the kids daily from 9am – 5pm for kids ages 3 and up (must be potty trained). The services are complimentary but there will be a charge for food.

Kids Club

Kids Club
If you are concerted about your health during your stay, there is a nurses station on property open from 9am – 5pm, a doctor on call that’s 5 minutes away, and the local hospital is only 20 minutes away.





This was my first trip to Jamaica and I was told to think of it as a country, not an island. The people are very happy and everyone must finish high school. The Kingston area is known for it’s high crime and is located 4-5 hours from Montego Bay. Some of the foods they are know for are jerk everything, festival (sweet breadsticks), yams, sweet potatoes, rice, and beans. I’ve recently fallen in love with Caribbean cooking and Jamaica certainly does not disappoint.



We ventured out one night to a local restaurant, Scotchies, which is about 30 minutes from the resort that is known for having the best jerk on the island. Be sure to have plenty of beverages around because it’s spicy. Good, but spicy! Just 3 minutes from the resort is Lobster Pot that serves dinner only and only 2 entrees which are lobster and the freshly caught fish of the day.

Dinner at Scotchies

The best limeade I’ve ever tasted at Scotchies
Round Hill is a Virtuoso resort and when you book with McAlpin Travel, an independent affiliate of Brownell, I can offer you the following added amenities:
Virtuoso Amenities:
- Upgrade on arrival, subject to availability
- Daily full breakfast, for up to two in room guests
- $100 USD Equivalent Spa Services credit,
- to be utilized during stay (not combinable, no cash value if not redeemed in full)
- Early check-in/late check-out
- subject to availability