Jessie Randall

Round Hill

  • Where:
  • Why:Holiday get away with my three young sons and husband.
  • When:December 2013
  • Who:Me, husband Brian Murphy, twin sons Casper and Liam (6) and Harry (3)
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Round Hill The highlight of our trip was Santa arriving on Christmas afternoon by speedboat. That's my son Casper in the striped rash guard holding Santa's hand.

The highlight of our trip was Santa arriving on Christmas afternoon by speedboat. That's my son Casper in the striped rash guard holding Santa's hand.

Round Hill Walkway down to the pool and beach.

Walkway down to the pool and beach.

Round Hill My baby walking up a bougainvillea covered walkway <br data-src=

My baby walking up a bougainvillea covered walkway
at Round Hill.

Round Hill A pair of sandals from my line worn with a cut out dress from Zimmermann. My beach vacation wardrobe…mostly white, airy dresses and jumpers plus a ton of sandals too.

A pair of sandals from my line worn with a cut out dress from Zimmermann. My beach vacation wardrobe…mostly white, airy dresses and jumpers plus a ton of sandals too.

Round Hill View from the hotel room out to the ocean. The rooms are very simple and chic. Designed by Ralph Lauren, who owns two homes on the property, they are cool, relaxing retreats from the blazing heat outside.

View from the hotel room out to the ocean. The rooms are very simple and chic. Designed by Ralph Lauren, who owns two homes on the property, they are cool, relaxing retreats from the blazing heat outside.

Round Hill I love the shape of these palm leaves out by the pool.

I love the shape of these palm leaves out by the pool.

Round Hill This was taken of my son two seconds after we arrived from the airport in the infinity pool overlooking the ocean. So beautiful.

This was taken of my son two seconds after we arrived from the airport in the infinity pool overlooking the ocean. So beautiful.

Round Hill Tropical fruit salad for breakfast.

Tropical fruit salad for breakfast.

Round Hill I am a sucker for a frozen drink brought to my pool chair. Especially if it is a margarita.

I am a sucker for a frozen drink brought to my pool chair. Especially if it is a margarita.

Round Hill My husband captured this incredible shot of my youngest running through the beautiful plants and flowers with sunlight streaming down on the property.

My husband captured this incredible shot of my youngest running through the beautiful plants and flowers with sunlight streaming down on the property.

Round Hill The open-air lobby at Round Hill with its iconic black and white checkerboard tiles and green striped awnings. This is where Kingsley, the unofficial

The open-air lobby at Round Hill with its iconic black and white checkerboard tiles and green striped awnings. This is where Kingsley, the unofficial "mayor" of the resort, holds court in his turquoise blazer, welcoming guests, chatting with kids and generally running the show.

Round Hill Photo taken through a leaf of the little covered daybed outside our room where we could nap, relax or eat breakfast.

Photo taken through a leaf of the little covered daybed outside our room where we could nap, relax or eat breakfast.

Round Hill View from the infinity pool where my boys loved to swim each day.

View from the infinity pool where my boys loved to swim each day.

Round Hill This is a picture of the man who paints each day outside the kids club at the resort. He gives painting lessons to the kids and sells his pieces to the guests. Here is a picture of the hotel pool. I love his leaf used as a palette.

This is a picture of the man who paints each day outside the kids club at the resort. He gives painting lessons to the kids and sells his pieces to the guests. Here is a picture of the hotel pool. I love his leaf used as a palette.

Highs & Lows

  • My favorite parts about this hotel are the beautiful beach and pools. I have never felt so relaxed. Such a beautiful view everywhere you look.

  • The kids club is awesome – it’s not just a bunch of kids sitting around playing video games – it’s a real Jamaican experience from painting classes taught by their local artist to basket weaving out of palm leaves.

  • Our room was designed by Ralph Lauren. I love the clean, white look of the hotel rooms, which are big and open. I just felt relaxed when I step inside. Bonuses are the beautiful big tubs and patios with views out to the ocean.

  • The staff is incredible from the bellmen who are happy to give a 3 year old a golf cart ride at 6:30am, to the sweet women who run the kids club to all the beach staff who know everyone’s names and are so happy to help in any way possible.

  • Christmas is an incredible time at Round Hill with little presents left outside the door for each guest on Christmas morning and Santa arriving by speedboat.

  • I can’t think of any cons other than going through customs in the hot airport is no fun. I recommend paying extra for a service called Mobay Club, which significantly reduces time in customs and immigration.

The Barometer

  • Design

  • Website

  • Mini Bar

  • Environmental Consciousness

  • Night's Sleep

  • Service

  • Amenities

  • Takeable Treats

  • Refer a Friend

  • Overall Value

  • Life Changing

Total: 40/50

Important Bits

  • Type

    Luxury resort.

  • Vibe

    Comfortable, old school luxury.

  • Location

    We take a car to the resort and then never leave until it’s time to go home. I love just plunking down in one place and not needing to go anywhere but the beach. It’s such a relaxing place.

  • Rooms

    110

  • Music

    Live music at dinner including a cappella carols on Christmas. Out at the beach it’s just relaxing quiet, no tunes necessary.

  • Year Opened

    1953

  • Designed By

    The original architecture of this notable Montego Bay resort was designed by William Ballard and the signature décor was conceived by Guy Roop. One cottage owner, Ralph Lauren, has taken a personal interest in redesigning parts of Round Hill, enhancing its quintessential character.

  • Health & Wellness

    Yes.

  • Restaurant

    There are two restaurants at the hotel plus several bars around the beach and pool serving good, island fare.

  • Bar

    Everything here is very laid back.

  • Children

    Round Hill is perfect for children. I love the kids club, which has very crafty activities like weaving, stone painting, tie dying and basket weaving. Every employee here makes a point to learn each child’s name and they genuinely seem to be delighted to engage and interact with kids.

  • Price

    Expensive.

Jump Around

Jump Around

Pimento Way, Jamaica

Get a massage at the hotel spa

Get a massage at the hotel spa

John Pringle Drive, Montego Bay, Jamaica

See the traditional dance show on Friday nights

See the traditional dance show on Friday nights

John Pringle Drive, Montego Bay, Jamaica

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