So, you’ve decided on Jamaica’s most popular travel destination, Montego Bay, for your next holiday. We can picture it now: Laid out on the powder-soft sand, clutching a Red Stripe, reggae tunes on the speakers. Magic. Chowing down on jerk chicken while lazily rolling down the Martha Brae River. Splendid. Or navigating ruins and waterfalls with well-shaped golf shots on one of MoBay’s historic courses. Glorious. These new Montego Bay vacation homes make all this possible — and don’t be surprised if you spend more time at your villa than you had planned.
Villa Christina is a beauty. She portrays an undeniably European flair, but is Jamaican at heart. Her build completed in 2019, the architecture is rather Tuscan, which you’ll notice upon entry into its monasterial entranceway with earthy tones. Its decor is reminiscent of old-style Spanish villas, from terracotta tile floors to Colonial style ceramic roofing. The sheer size and remoteness of the gated-community property gives it shades of Euro country estate. Yet the surroundings are classically Caribbean, and there’s beach, golf, and resort living all within close proximity.
Villa Christina is on-site at Cinnamon Hill Golf Course, between the 10th green and 11th tee box. For golfers, what more could you ask for? Just when you think it doesn’t get much better, you find out the course actually allows Villa Christina guests to begin their round on the 11th hole. Stroll through your private pool terrace, and your caddy will meet you at the tee for your first shot. Eighteen holes later, finish up your round on 10, where your non-playing family and friends can cheer you on from the villa’s evening dining terrace and infinity edge pool, which overlooks that hole’s fairway and green.
Life is a breeze at Christina, which has its own guest-only saltwater infinity pool and alfresco dining set-up with a barbecue. An indoor wellness center sports a steam room, massage table, and hot tub, along with an exercise room. Liven up any evening in the bar room, which has a pool table. The villa has a private chef, housekeeper, and villa manager all on-site to service you, and you can also decide to stock the fridge and cook for yourselves in the fully-equipped kitchen. The master bedroom has direct access to an outdoor jetted plunge pool, and another of the five bedrooms has its own kitchenette. Half Moon Resort is only eight minutes away, and a stay at Villa Christina provides you with a full membership at no charge. Nearby Montego Bay, Luminous Lagoon, and Rockland’s Bird Sanctuary all beckon.
It’s all good at Everything Nice. Set on Montego Bay’s northwest shore waterfront on a peninsula leading into the Caribbean Sea, this two-story villa provides everything you love about a resort vacation without the crowds. Substitute lineups and shared amenities for a two-steps-ahead butler waiting on your every whim. With your own private, resort-style swimming pool, you’ll never have to rush to get your own lounge chair. Empty chairs will be waiting patiently for you, and cold drinks will already be on their way. The pool faces stunning views of the sea. One favorite spot for enjoying the lookout is a set of three in-water lounge chairs with side tables, directly facing outwards and sitting in inches of water with a waterfall providing the soundtrack behind you — talk about refreshing!
More to get excited about: At Everything Nice, guests have their own personal chef working out of the home’s gourmet kitchen. Sure, there’s an elegant dining table with seating for all 10 guests (plus a kids’ table) in the dining room, but we have a feeling you’ll opt for one of two alfresco dining setups. A rustic picnic-style table sits on the veranda above the pool and has easy access to the bar, and a temporary table in the sand on the adjacent beach is a guest favorite. The small stretch of sand just beyond the swimming pool is a nice spot for sunbathing. Though located on a marine sanctuary filled with fish and stingrays and generally not swimmable, watersports are encouraged. The good news is kayaks and paddleboards are included with your stay.
Still more fun to be had: Take advantage of the ping pong and pool tables for some friendly competition, or curl up with a movie. The home has a media room with a large TV for escaping the sun, but of course, being Jamaica, there is an outdoor TV on the veranda too. Guests at Everything Nice benefit from complimentary access to Hard Rock Cafe and Beach Club, just a three-minute jaunt from door to door. Also nearby: Aqua Sol Theme Park, Royal Decameron Montego Beach, and the Montego Bay Cruise Port.
Trade Winds is a treat for a couple, a small group, or multiple families. The layout of the gated, multi-house property makes it such that any travel group can enjoy togetherness and privacy to their desire. The main house has three spacious bedrooms. The master has a private veranda while the two other rooms share a patio. The cottage house has two ocean view bedrooms with a shared patio, and each has a private alfresco shower.
There are also many common spaces in which to congregate. For one, the large infinity-edge swimming pool faces the Caribbean Sea and has sun-kissed poolside seating with a view. The pool terrace has a full bar with pull-up seating and a TV. There are stay-cool outdoor living areas too: a shaded lounge has comfy patio furniture in a living room setting, and a large covered but exposed colorful living space with tropical prints fits right into the Jamaican lifestyle. Plus, large retractable floor-to-ceiling glass doors bring the outdoors in.
Trade Winds is ideal for a honeymoon or romantic getaway as well. Lovers can enjoy an outdoor couples massage facing the golf course or an intimate candlelit dinner under the stars. With the services of a personal chef, butler, housekeeper, and even a chauffeur for cruising the island stress-free, you can focus all your time and energy on each other. Guests at Trade Winds have golf privileges at Half Moon, White Witch, and Cinnamon Hill, and member access at Half Moon Resort.
A Seaside Cottage, indeed. West of Montego Bay, this relaxed four-bedroom vacation home welcomes guests with ease. Its centerpiece is an oceanfront, three-level infinity pool that bleeds right into the Caribbean Sea just steps away. From there, it’s all seaside living — footwear optional — in a setting that knows how to balance Jamaica’s warm sun with cool shaded spots. There’s a covered outdoor living area behind the pool, perfect for spending lazy afternoons with a book, a cocktail, or both. Behind that, the exposed indoor living area sits beyond large sliding glass doors that are just a suggestion.
A small cabana beside the pool houses an intimate alfresco dining set up for a meal that you can have prepared and served to you by on-site staff. A private chef, butler, and housekeepers all remain on the premises for the duration of your stay. In the evenings, connect your favorite vacation playlist to the home’s integrated sound system and retreat to the outdoor wet bar for a sunset sip.
Seaside Cottage’s main house has two bedrooms, each with direct pool access and a private garden. Its guest pavilion has a separate entrance, its own open-concept living area and two bedrooms with alfresco bathtubs. Guests receive a complimentary membership at the Round Hill resort, which includes access to its tennis court, spa, fitness center, restaurant, oceanfront bars, and more.