Montego Bay
Round Hill Hotel And Villas
Casey Gasinowski
Deal Expert
Why We Love It
- Legendary oceanfront hotel on former pineapple plantation
- Hosted JFK and Jackie, Paul McCartney and other A-list celebs
- Villas include personal maids, chefs and private pools
- Complimentary afternoon tea for all guests
"A west shore institution, Round Hill is one of the places that put Jamaican tourism on the map" -- Travel + Leisure
Map & Directions
Rooms & Rates
Overview
Five-star luxury was introduced to Montego Bay when the Round Hill Hotel & Villas opened in 1953 on a private peninsula that was once a pineapple plantation. Over the decades, the resort has hosted professional athletes, Hollywood royalty and presidents -- including JFK and Jackie on their honeymoon. It was in Villa 12 that Oscar Hammerstein met Maria von Trapp and was inspired to write "The Sound of Music." Sir Paul McCartney vacations with his family in Villa 17.
The two-story Pineapple House has 36 white-on-white guest rooms with views of the infinity pool and beach. Ralph Lauren, who owns property on the grounds, personally outfitted the spaces with dark wood, bamboo and rattan for an upscale Caribbean vibe. To rub shoulders with celebrities, upgrade to one of the 27 private villas scattered among coconut trees and allspice groves with personal maids and cooks serving made-to-order breakfast. Most villas have private pools and can sleep up to eight people; nannies are available for traveling families.
All guests are treated to complimentary afternoon tea, and the James Beard Award-winning chef creates daily menus from the hotel’s organic vegetable garden and fruit orchard. Guests can enjoy the tropical sunshine from palm-shaded chaise lounges overlooking the infinity pool and ocean beyond. For further relaxation, book a massage or facial treatment in the spa built within the remains of the plantation’s original stone manor house. Visitors also have access to the hotel’s gym with yoga classes, tennis courts and water sports.
From the press:
- "A favorite of celebrities and other wealthy people thanks to its private, elegant villas" -- Fodor’s
- "Round Hill aims for that private island feel, and is a place to relax" -- Frommer’s
Amenities
Policies
Have a Question? Contact Travelzoo.
- 1-877-966-0000 U.S. and Canada (toll-free)
- +44 (0) 20 3564 9000 U.K. and Europe
- Email Us
Customer Service available Mon-Sun, 9am-12 midnight ET
Rates may vary by date, are subject to availability and are not guaranteed until your purchase is complete.
The room rates listed are for double occupancy per room unless otherwise stated and exclude tax recovery charges and service fees.
It is the responsibility of the hotel chain and/or the individual property to ensure the accuracy of the photos displayed. Travelzoo is not responsible for any inaccuracies in the photos.
*Unless otherwise stated, Travelzoo-exclusive extras are valid once per stay (based on two adults sharing). Value is an estimate based on double occupancy. Extras are only included with Member Rates and may not be available on all dates. Extras are non-transferable and have no cash value. Total value may vary depending on time of booking and availability. When included, breakfast may be limited to 2 guests per stay subject to hotel’s discretion. Other restrictions may apply; see our T&Cs for details.
