• 

  Jamaica Villa
  Bougainvillea
  Tryall
  5 bedroom
  $1,715–$2,858 / night
• 

  Tennis Villas
  Makana on the Beach
  Discovery Bay
  6 bedroom
  $1,858–$2,429 / night

• 

  Golf Villas
  Villas at Half Moon, A
  Montego Bay
  7 bedroom
  $1,175–$3,999 / night

By Steve Lassman, Vice President & General Manager

As the heart of winter set in, I started counting down the days to my next escape. Jamaica in January certainly has its appeal! I quickly learned why it’s known as one of the most popular villa rental destinations in the Caribbean. After departing from the snowy Northeast, I arrived in sunny Jamaica within a few hours. Not only was the air warm and inviting, but the locals were too! The sun, sand, and slow pace certainly cater to a laid-back, relaxing lifestyle.

Upon arriving in Montego Bay, we stayed in the nearby Nutmeg villa – a stately oasis with spectacular views, conveniently located just minutes from three world-class golf courses, designer shops, bars, restaurants, and gorgeous white-sand beaches. Thankfully, my team and I were able to make enough time during our villa business schedule to explore this glorious natural landscape and a few of its adventures. While many vacationers venture to Jamaica to sunbathe on the beaches, the island has much more to offer – especially if you’re looking for more activity. Golfers have their pick of Jamaica’s well-known courses, considered by many to be the best in the Caribbean. Windsurfers, scuba divers, and deep-sea fishermen will find plenty to do in Jamaica's crystal-clear blue waters. Hikers and horseback riders will discover numerous trails to explore. Sightseers will enjoy a scenic train tour of the island or a gentle river rafting trip on the Martha Brae River.

My Favorite Excursions:

• Round Hill & The Palmyra Resorts – Some of the Island Hideaways villas offer guests access to a few resorts in the area like this one. We had our fill of its spa facility, fitness center, and many watersports. In addition, many of our villas offer kids’ club membership here.
• The Tryall Club – We also enjoyed access to this resort’s amazing facilities: an 18-hole, par-72 championship golf course designed by Ralph Plummer; Hobie Cat and sunfish sailing; private beach; tennis courts; spa; and gym.
• Dunn’s River Falls – Don’t miss a challenging climb up the soaking steps of this 600-foot-high waterfall. We had a blast and the view was spectacular!

Discovering all these hotspots really worked up our appetites for some authentic island dishes. Jamaica has cuisine with a flavor all its own, including its world-famous jerk chicken, and a wide array of restaurants in which to enjoy it. My favorite venue we visited was Rick’s Café in Negril. They sure do serve some delicious Caribbean specialties, but it’s also the best place on the island to watch the spectacular Jamaican sunset. It is definitely a must see.

We were able to see several other villas during our trip, and each visit made it clearer why villa rentals are so popular in Jamaica – they offer unbeatable luxury, convenience, and value in a sublime setting. In addition to daily maid service, most retreats also come with your very own cook. Imagine indulging in authentic Jamaican cuisine – or any of your favorite foods – in the privacy of your tropical home without lifting a finger!

My Top Villa Recommendations:

• Half Moon Royal Villas
  The 32 immaculately decorated Half Moon Royal villas are conveniently located in Montego Bay as part of the full-service RockResort. Each villa offers a personal butler, housekeeper, cook, private swimming pool, and two golf carts to get around the property and the 18 holes designed by Robert Trent Jones just around the corner.
• Bougainvillea
  This contemporary villa is definitely one of the more stylish homes in the Tryall Club collection. Prepare to be pampered at Bougainvillea by your own cook, butler, housekeeper, gardener, and laundress. With complimentary shuttles and two personal golf carts, taking advantage of the pro fairways, tennis courts, beach, and bevy of watersports will be a breeze.
• Makana
  This was my favorite villa that we toured. The staff greeted us with fresh lime-aid upon our arrival, which was much appreciated on a warm January day! Makana, located on Discovery Bay, is quite private and exceptionally glamorous. It has a private beach, tennis court, gym, and spa.

All in all, I had a wonderful stay in Jamaica, and definitely plan to go back. When it comes to upscale villas on this “in” island, expect fleeting availability and unforgettable adventures – it always pays to plan months in advance. For me, there’s perhaps no better time to go than January since the warm sea breezes and sunny skies are a welcome escape from the whipping winter winds of the Northeast. But Jamaica is a great destination year-round, especially when you’ve got a luxurious villa just for you and your family or friends!