Swimsuit

The Round Hill Hotel and Villas is the Perfect Retreat in Montego Bay

It may be the Jamaican resort’s designs by Ralph Lauren and natural beauty that attract visitors, but it’s the people who make them stay.

Alisandra Puliti

Round Hill Hotel and Villas

The Round Hill Hotel and Villas is utterly breathtaking. Located on a private beach enclave set on a 110-acre peninsula in Montego Bay, Jamaica, once guests check in, there is no reason to leave until departure. It is a true retreat within a gated community that offers exclusive access to one of the most pristine beaches in the Caribbean, as seen in the Sports Illustrated Swimsuit 2025 photoshoots of Alix Earle, Nazanin Mandi, Nicole Williams English, Denise Bidot, Parris Goebel, Rayna Vallandingham and Christen Goff.

There really is no detail forgotten at this true legacy brand. Established in 1953, Round Hill was one of the first boutique resorts in the region, designed to cater to discerning travelers seeking privacy, exclusivity and natural beauty like Grace Kelly, Audrey Hepburn, John F. Kennedy and Jacqueline Kennedy to a more recent stay of Prince Harry and Meghan Markle. Over the decades, the resort has maintained its reputation as a haven of elegance, blending classic Caribbean hospitality with modern amenities while preserving its rich heritage.

Round Hill Hotel and Villas pool
The Round Hill Hotel and Villas

The resort recently completed an enhancement to many of its common areas and shared spaces, including its iconic Ralph Lauren Bar. In fact, the American designer, who has a villa on property, is responsible for reimagining the resort’s interiors complementing the surrounding lush greenery and palm trees and adding to the vibrancy of the place.

It may be the resort’s design and natural beauty that attracts visitors, but it’s the people who make them stay and return. The true heart of Round Hill lies in its remarkable staff, whose warmth and dedication elevate every guest’s experience. Many team members have devoted decades of service to the resort, with some proudly continuing a legacy started by their parents and grandparents. Hospitality is in their genes and this generational expertise and heartfelt commitment have made the staff exceptionally attuned to anticipating and exceeding guest needs.

It’s also the convenience of a direct flight from most US East Coast cities and then a quick 25-minute drive from Montego Bay International Airport (MBJ) or a short helicopter ride from Kingston.

Stay

A villa at The Round Hill Hotel and Villas
The Round Hill Hotel and Villas

Guests may choose from 36 ocean-view rooms and suites or from 27 two- to five-bedroom villas, most with private pools. (Stays start from $700 per night.) The aesthetic in all is quintessentially Ralph but with Jamaican flare. Only steps away from the golden sand beach and infinity pool, the two-floor building has secluded balconies on the lower levels and cathedral ceilings up top.

 An all-new villa also debuted in late 2024. Villa 14 comprises three distinct villas as well as a dedicated staff building. The two-story Main House spans 4,800 square feet, the two-story One Bedroom South offers 2,000 square feet, and the three-story Tree House covers 2,650 square feet. Each is a masterpiece of design, featuring high ceilings, floor-to-ceiling folding glass doors and breathtaking views. 

The Round Hill Hotel and Villas room
The Round Hill Hotel and Villas

Dining

Round Hill offers an exceptional culinary experience with 11 diverse food and beverage outlets, ranging from fine dining restaurants to casual beach bars. Led by award-winning Executive Chef Martin Maginley, the team reimagines local Caribbean cuisine with a modern twist, emphasizing fresh, organic ingredients sourced from the on-site garden.

Whether you prefer a gourmet meal or a light bite, the hotel’s commitment to sustainable practices and accommodating dietary needs ensures a memorable dining experience. For a truly personalized culinary journey, private chefs can be booked during a stay in one of the villas.

The Georgian Room is where guests start their day with a large assortment of breakfast items. For lunch and dinner, it doesn’t get more romantic than dining at The Seaside Terrace. Whether it be during the day to take in the lush scenery or at night under the stars, the restaurant has an a la carte menu, plus special themed menus like Jamaica or Curry Night.  

It wouldn’t be a true trip to Jamaica without a chocolate and rum tasting. Inspired by Liz Pringle, co-founder of Round Hill and the late wife of Round Hill Founder John Pringle, Liz’s Rum Punch is not to be missed. The flavor combination of citrus goodness and warm Jamaican spirit is equally as good without the rum.  

Wellness & Fitness

The Round Hill Spa is a place to be worry-free, at least for the duration of your treatment. Elemis brand aromatherapy products are used as a part of the extensive treatment menu focusing on natural and indigenous influences. A relaxation pool sets it apart from other spas in Jamaica and the bespoke services bring relaxing and beautifying rituals to the perfect place of your choosing.

If movement is something that can’t wait until you return home, the gym is complete with Cybex Fitness equipment, technologically enhanced cardio machines and innovative strength lines. Personal trainers are available should you need a bit of extra motivation. The Round Hill Resort also has tennis and pickleball courts for those craving a different kind of workout.

The Round Hill Hotel and Villas aerial view from a drone
The Round Hill Hotel and Villas

Activities

Beyond the gates of the property, Montego Bay offers historical landmarks, beautiful beaches, duty-free shopping, rivers, and waterfalls for exploration. Some of the most popular excursions include snorkeling and sailing on the Caribbean Sea, tubing down pristine tropical rivers, ziplining through lush island foliage and dancing the night away on a private sunset cruise. 

For more information, please visit the hotel’s website.

Published
Alisandra Puliti
ALISANDRA PULITI

Alisandra Puliti is a NYC-based entertainment journalist with over 15 years of experience. Before joining the SI Swimsuit team as a contributing editor, the Penn State alum held several positions at HELLO! and HOLA! Media, Us Weekly and OK! Magazine. Throughout her tenure, she has been a fixture at events such as the Golden Globes to the Cannes Film Festival and has interviewed the likes of Jennifer Lopez, Taylor Swift, Zoe Saldana and more of Hollywood’s elite. A self-professed ‘social homebody,’ when she isn’t home binge-watching the newest streaming series or perfecting pasta dishes, her constant wanderlust has her packing her bags and heading out for a new adventure –most likely back to Italy!

Home/Hotspot Destinations