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Montego Bay

Round Hill Hotel And Villas

Travelzoo Staff

Why We Love This Hotel

  • 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


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. 

Rooms & Rates

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  • Newspaper / magazines
  • Gym / fitness center
  • Pool bar
  • Restaurant
  • Tennis courts
  • Spa
  • 100% smoke-free


  • 24-hour front desk
  • Airport transfer (fees apply)
  • Baby-sitting service on request
  • Beauty treatments / massages (fees apply)
  • Concierge service
  • Hair salon (fees apply)
  • Laundry / dry cleaning
  • Pillow menu
  • Room service (limited hours)
  • Business center

Room amenities

  • Coffee / tea-making facilities
  • Iron and ironing board
  • Safe
  • Sitting area
  • iPod/iPhone docking station


  • Complimentary Wi-Fi in guest rooms
  • Complimentary Wi-Fi in public areas


  • Bathrobes
  • Hair-dryer
  • Separate shower
  • Luxury toiletries
  • Slippers


Check-in: Standard Time is 4pm.

Checkout: Standard Time is 11am.

Children and additional guests: No rollaway/extra beds available

Pets: Pets not allowed

Additional details:

Know Before You Go

  • This property offers transfers from the airport (surcharges may apply). Guests must contact the property with arrival details 48 hours prior to arrival, using the contact information on the booking confirmation.
  • Some facilities may have restricted access. Guests can contact the property for details using the contact information on the booking confirmation.


The following fees and deposits are charged by the property at time of service, check-in, or check-out.

  • Fee for full breakfast: USD 37.50 for adults and USD 18.75 for children (approximately)
  • Airport shuttle fee: USD 90 per room (roundtrip)
  • Rollaway bed fee: USD 89.0 per day

The above list may not be comprehensive. Fees and deposits may not include tax and are subject to change.

Debit cards not accepted

Have a Question? Contact Travelzoo.

Customer service available Monday - Friday 9am - 6pm GMT + 8.

Rates may vary by date, are subject to availability and are not guaranteed until your purchase is complete.

Please note: Some amenities and services may not be available in all rooms or may incur an additional charge. All prices stated have been verified at the time of publication and may vary at the discretion of the hotel.

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Round Hill Hotel And Villas