Rialto
Montego Bay

Round Hill Hotel & Villas

Rialto Score 9+

A The Set hotel. Rialto is a The Set Collection agency: book this hotel direct at the VIP rate for benefits that can include priority room upgrades, hotel credits, and more.

Round Hill Hotel and Villas is not merely a resort; it is a place you call home, a sanctuary where guests arrive and leave as part of the family. This genuine warmth and loyalty are guaranteed by an exceptional 40% repeater guest rate and the staff's impressive average tenure of 20 years, ensuring every visit is marked by familiar, heartwarming service. This deeply personalized environment makes Round Hill the definitive choice for all life's cherished moments, from romance and honeymoons to breathtaking weddings, private celebrations, and memorable multigenerational trips.

John Pringle Dr, JMDWD14 Montego Bay, Jamaica
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Round Hill Hotel & Villas
One offer
4th Night Free
Stays until May 30, 2027

About Round Hill Hotel & Villas

Insider tip

You can watch the sunset by the beach and sunrise from Lizzie's Point, or stop by the bar to view photos of legendary past guests, from John F. Kennedy to Paul Newman and Paul McCartney.

In the hotel’s own words

Round Hill Hotel & Villas: Timeless Caribbean Luxury

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Welcome to Round Hill Hotel and Villas, an authentic Caribbean icon and a storied retreat where a glamorous past meets timeless luxury. Since the 1950s, this destination, nestled on a spectacular 110-acre private peninsula in Montego Bay (25 minutes from MBJ airport), has defined Caribbean elegance, hosting presidents, artists, and legends. Here, a pristine shoreline offers an unparalleled sense of space and tranquility.

Luxurious Accommodations

Your sanctuary awaits in curated perfection:

The Pineapple House: 36 Oceanview and oceanfront hotel rooms, each a coastal chic masterpiece designed by the legendary Ralph Lauren.

Signature Villas: 27 unique villas (2-6 bedrooms). Each is a secluded haven with its own dedicated staff who prepare a personalized breakfast daily. Select villas also offer

Exclusive Private Pool Suites for the ultimate in seclusion and indulgence.

Distinctive Dining & Gastronomy

Our dining is a celebration of local, organic flavors, featuring the "Light Clean Caribbean Cuisine" of our Executive Chef.

We redefine luxury gastronomy with our exclusive limited-time Michelin-Star Pop-Up dining events, the Culinary Constellation Series. This celebrated series brings world-renowned, innovative chefs to our shores, offering an unforgettable, multi-sensory journey that blends global excellence with vibrant Jamaican ingredients.

Wellness, Activities, and Family

Find peace at our award-winning spa set in an 18th-century plantation house. Enjoy daily yoga, explore the coastline by boat, or indulge in tennis and an array of exhilarating land and sea activities.

Though a legacy of romance, Round Hill is a haven for all ages and generations. Our complimentary Kids Clubs (Pineapple Club for younger children and the 7-Up Club for tweens) ensure memorable adventures, while the resort’s array of activities guarantees enjoyment for the entire family.

Exclusivity for Your Significant Occasion

Beyond leisure, Round Hill is the premier choice for life’s most important moments.

Our estate is the perfect backdrop for breathtaking weddings and for corporate leaders, our venue is ideal for discrete, high-level C-Level corporate events, with private villas curated for exclusivity and focus.

www.roundhill.com

VIP Hotel Program · Invitation-only

Book direct at the The Set Collection VIP rate, instantly

All 13 The Set Collection hotels →

A direct booking with the hotel, confirmed instantly on Rialto — no contact form or middleman. Hotel loyalty points and elite status apply where applicable.

The Set Collection is The Set Collection's invitation-only VIP program, open to a small group of luxury travel agencies. VIP rates generally meet or beat the hotel's website rates and include the amenities below.

  • Daily breakfast for two
  • $100-200 hotel credit per stay
  • Room upgrade on arrival, based on availability
  • Early check-in and late check-out, based on availability
  • Welcome amenity

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Rooms and suites

7 room types, as described by the hotel.
Rooms
1Oceanview Room
Impeccably designed by villa-owner Ralph Lauren to evoke a crisp, clean Caribbean ambiance, the Oceanfront Rooms at Round Hill are as stunning as they are comfortable.
2Ocean Front Balcony Room
3Oceanfront Room with Patio or Balcony
Suites
4One Bedroom Suite
Offering the ultimate in privacy and seclusion, our free standing one-bedroom suites are nestled in lush and tropical surroundings.
Villas
5Classic Villas
These secluded and picturesque villas embody the resort’s original style of timeless enchantment, while serving as the perfect home-away-from-home. The Classic Villas come with your own dedicated staff and are equipped with two to five bedrooms, and multiple indoor and outdoor spaces.
6Signature Villa
The Signature Villas boast beautiful views of the ocean, more spacious outdoor areas, and beautifully landscaped lawns line with vibrant tropical flowers. Furnishings are upgraded, and larger bedrooms with ensuite bathrooms may be closed off and air-conditioned for comfort - offering ample space for guests.
7Estate Villa
Round Hill's crown jewel, the Estate Villa is located next to a tropical rainforest, offering an unmatched level of privacy and seclusion. The villa includes five or six bedrooms, two pools, multiple open-air living spaces, bar, and waterfall with sweeping views of Round Hill Bay.

Book with your AI assistant

Set up the connector →
  1. 1Connect Rialto to Claude or ChatGPT: it is an MCP server, added from the connector settings in one step.
  2. 2Ask for Round Hill Hotel & Villas on your dates. The assistant returns live VIP, corporate and public rates with the benefits named per rate.
  3. 3Finish on a secure Rialto page. The booking is instant and direct with the hotel; card details never pass through the chat.

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Frequently Asked Questions

Does booking through Rialto cost more than booking with the hotel?

No - VIP rates under The Set Collection always meet or beat hotel's public, flexible rate, and provide valuable amenities and possible upgrades. Rialto also provides the hotel's non-VIP and corporate rates, so you can compare with full transparency.

Can my AI assistant book this hotel?

Yes. Connect Rialto to Claude or ChatGPT with our AI hotel booking MCP server and ask for rates. You finish the booking instantly on a secure Rialto page, direct with the hotel. Card details are not sent through the AI chat, so either you would approve the final checkout step and reconfirm all the information, or if you authorize your agent with Computer-Use permissions, it can fill out the checkout form as well.

What is the value of the VIP benefits?

Daily breakfast for two plus the $100-200 hotel credit come with every stay at this hotel - adding $100-200/day in value. A room upgrade could also be worth a substantial amount, in addition to early check-in / late check-out benefits when available.

What room types does Round Hill Hotel & Villas offer?

Round Hill Hotel & Villas lists Oceanview Room, Ocean Front Balcony Room, Oceanfront Room with Patio or Balcony, One Bedroom Suite, Classic Villas, Signature Villa and 1 more. Sizes and bed options for each are in the rooms table above.

How does this compare to other programs, like through AMEX Fine Hotels & Resorts, or Chase Edit?

Using a hotel's own VIP program may provide higher upgrade priority, additional VIP benefits and promotional rate offers, and a direct relationship with the hotel for special requests. Rialto offers more VIP hotels than any credit card program. In addition, Chase Edit rates can be substantially more expensive as they rarely run promotions whereas AMEX rates are often comparable but do not offer programs such as Upgrade at Booking.

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