The Friendliest Island in the Caribbean

Round Hill | Winter Sun & Spring Savings!

Escape the cold and welcome the warmth with an extra night on us. This 4th Night Free offer is perfect for guests planning to luxuriate for four nights or more in any room villa.

Round Hill | Summer & Fall Savings!

Soak up the season and savor more time in paradise with an extra night on us. This 4th Night Free offer is ideal for summer and fall arrivals, inviting guests to relax longer in their villa.

Round Hill | Plan Your Paradise!

The Plan Your Paradise offer invites you to enjoy a seamless three-night escape with 15% off your private villa—the perfect way to experience Round Hill when time is limited, but luxury is essential.

Round Hill | The Perfect Family Escape!

Imagine an extra day all to yourselves in paradise. This exclusive villa offer is perfect for families looking to relax, reconnect, and create unforgettable memories together

• Complimentary Night: Pay for just 3 nights and enjoy 4 nights of luxury
• Kids Stay & Eat Free: kids sleep and dine for free
• Bonus Babysitting: Get 3 complimentary hours of private, in-villa babysitting—the perfect chance for parents to enjoy a quiet dinner or sunset cocktail.
• Complimentary Kids Club - Engaging activities and supervision for kids aged 3–12

Round Hill | Midweek Getaways!

Private Villa Midweek Privilege: Book your 2026 escape and receive 15% off, along with a $150 food and beverage credit.

Jamaica | High Season - Stay 7 Nights, Pay for 6

This villa is participating in this special offer!

Extend your escape—stay seven nights and enjoy one complimentary night at select luxury villas.

Blackout Dates:

All Villas: April 04 to 11, 2026

Allamanda: March 28 to April 11, 2026

Villas with specific travel dates:

Makana on the Beach: January 10 to 24, 2026; February 21 to March 14, 2026

Happy Hour: February 20 to March 21, 2026; March 28 to April 02, 2026; April 07 to 15, 2026

Restrictions:

Windsong: This special offer does not include a complimentary driver

Hillside House on Round Hill | May Getaways

Stay 7 nights for the price of 5 on your May 2026 getaway — the perfect time to travel and save.

Jamaica | Low Season - Luxury for Less!

Book 5 nights or longer and enjoy a complimentary night—because luxury should always come with a little extra.

Stay 5 nights - Pay 4

Stay 6 nights - Pay 5

Stay 7 nights - Pay 6

Jamaica | More Nights, More Luxury!

Stay five, six, or seven nights and receive one complimentary night—stay eight nights or longer and enjoy two nights on us.

Tryall Club | 2026 Caribbean Nights

Turn up the heat at Caribbean Nights 2026 – Stay Longer for Less, where tropical vibes, endless sunsets, and irresistible savings make your getaway last even longer. 🌴✨

Four nights for the price of three nights / Seven nights for the price of five!

*Full payment is required at the time of booking (non-refundable).

Longview Villa on Round Hill | Luxury for Less!

Book four nights or longer and enjoy a complimentary night—because luxury should always come with a little extra.

Extra Value~

Complimentary round-trip transfers when you travel from May 01 to August 30, 2026.

Up to a $750 Concierge Credit

Your villa is just the beginning. With up to $750 in concierge credits, the stay can have built‑in extras that make every day feel carefully planned without you lifting a finger.

When you book a qualifying villa stay, you’ll receive a concierge credit based on the value of your booking:

• Spend $5,000–$14,999: Receive a $200 Concierge Credit
• Spend $15,000–$49,999: Receive a $500 Concierge Credit
• Spend $50,000 or more: Receive a $750 Concierge Credit

Use your concierge credit toward handpicked services and experiences — think private chefs, in‑villa spa treatments, airport transfers, grocery pre‑stocking, and curated local adventures. Our concierge team will handle the details so you can simply arrive, exhale, and enjoy.

The villa is your home away from home. The concierge credit is everything that makes it unforgettable.