Luxury rentals in Westmoreland Parish

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Top-rated vacation rentals in Westmoreland Parish

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Villa in Montego Bay

4.61 out of 5 average rating, 31 reviews

Caribbean Jewel

Nestled in a secluded coastal neighborhood of Jamaica’s gorgeous Montego Bay, Caribbean Jewel is a villa that easily lives up to its name. With four ocean-view en-suite bedrooms, a full staff, and several amazing golf courses and beaches within a few kilometers, your Jamaican vacation will be relaxing, rejuvenating, and unforgettable. All of the traditional elements of luxurious Caribbean architecture are covered and updated, on this modern villa. Details like the low profile terracotta roof, exposed-beam vaulted ceilings, warm wood trim, and wide openings to the terrace are classic examples of Caribbean design. Open those doors, and this villa instantly fills with a fresh ocean breeze and natural sunlight, creating a relaxing, tropical atmosphere throughout. The living room is decorated with plush furniture, state of the art electronics, and plenty of local plants to add a splash of color and freshness. And the kitchen, which switches to a clean white color scheme, is outfitted with high-end appliances and dark granite countertops. Caribbean Jewel’s staff included overnight security, a butler, private chef, laundress, and a housekeeper. There’s formal dining inside and an alfresco set on the terrace, both with seating for twelve. The villa is located within a gated community, and it includes parking. Inside, Caribbean Jewel is equipped with Wi-Fi, cable television, air conditioning, an office space, and a sound system. And, on the terrace, you’ll love the ocean views, the swimming pool, and the spacious backyard garden. Just thirteen kilometers away, Montego Bay’s downtown area is rich with boutique and retail shopping, restaurants, beachfront bars, nightlife, and adventure tourism. Montego Bay’s surrounding area is well adorned with beautiful public and private beach clubs, which you’ll receive complimentary access to Rose Hall and Doctor Cave beach clubs. It’s also a golfer’s paradise. With Half Moon, Cinnamon Hill, and White Witch golf courses all within five kilometers of Caribbean Jewel. Copyright © Luxury Retreats. All rights reserved. BEDROOM & BATHROOM Upper Level • Bedroom 1- Primary: King size bed, Ensuite bathroom with stand-alone shower & bathtub, Dual vanity, Dressing area, Walk-in closet, Television, Air conditioning, Private veranda, Ocean view Main Level • Bedroom 2: King size bed (or 2 Twin size beds), Ensuite bathroom with stand-alone rain shower, Television, Air conditioning, Shared balcony, Ocean view • Bedroom 3: Queen size bed, Ensuite bathroom with shower/bathtub combo, Television, Air conditioning, Access to terrace, Ocean view • Bedroom 4: King size bed (or 2 Twin size beds), Ensuite bathroom with stand-alone rain shower, Dual vanity, Television, Air conditioning, Access to terrace, Ocean view Additional Bedding • Den: Sofa bed, Air conditioning, Shared access to powder room FEATURES & AMENITIES • Ocean view • More under “What this place offers” below Extra Cost (advance notice may be required): • Babysitting service • More under “Add-on services” below

May 28 – Jun 4

G$238,495 GYD per night

Villa in Montego Bay

4.5 out of 5 average rating, 4 reviews

Serendipity

Otherwise known as “the occurrence of events by chance in a beneficial way,” Serendipity villa happens to be one of those places that guests are just so happy to stumble upon. The villa provides a casually elegant atmosphere minutes from the airport. Situated on the “Elegant Corridor” in Montego Bay, Serendipity has been modeled to relax the senses and soothe the spirit. The villa features a refreshing swimming pool, water toys and private tennis court. The villa is family friendly and includes a home entertainment system with iPod dock, a music and movie library, Wi-Fi access and baby gear. The villa is also partially wheelchair accessible. A gated property, Serendipity villa provides a full staff, including security. Provide the groceries and enjoy the tasty dishes freshly prepared by your chef, formal dining or casual alfresco - it is all up to you. The spacious and comfortable living areas provide lovely views of the tropical tree tops and turquoise sea from almost every angle. Archways connect the open living spaces and dining areas, thus maintaining a cooling draft and a clear ocean view throughout. Many of the spaces lead to covered terraces where you can enjoy a postcard perfect sunrise. Six stately and breezy bedrooms with ocean vistas accommodate up to twelve guests at Serendipity. Each bedroom includes en-suite bathroom, air conditioning, ceiling fan and TV. The decor in each themed bedroom has been chosen to reflect the clean, modern atmosphere of the villa. Serendipity boasts spectacular 180 degree views that showcase the pristine Half Moon Golf Course and glimmering Caribbean Sea. The villa is also close to a number of other top quality golf courses including the Hyatt Ziva/Zilara and the famed Tryall Club. Or a day trip to the nearby outdoor museum Columbus Park provides clues into an era of exploration through the Spanish colonial artifacts on display. However you spend your getaway, Serendipity happily welcomes you to days of luxury in the warm Jamaican sun. Copyright © Luxury Retreats. All rights reserved. BEDROOM & BATHROOM • Bedroom 1: King size bed, Ensuite bathroom with shower and bathtub, Air conditioning, Ceiling fan, Safe, Television • Bedroom 2: 2 Twin size beds, Ensuite bathroom with shower and bathtub, Air conditioning, Ceiling fan, Television • Bedroom 3: 2 Twin size beds, Ensuite bathroom with shower and bathtub, Air conditioning, Ceiling fan, Television • Bedroom 4: King size bed, Ensuite bathroom with shower and bathtub, Air conditioning, Ceiling fan, Television • Bedroom 5: 2 Twin size beds, Ensuite bathroom with shower and bathtub, Air conditioning, Ceiling fan, Television • Bedroom 6: 2 Twin size beds, Ensuite bathroom with shower and bathtub, Air conditioning, Ceiling fan,Television FEATURES & AMENITIES • More under “What this place offers” below Included: • Gardener • More under “What this place offers” below Extra Cost – advance notice may be required: • Activities and excursions • Babysitting service • More under “Add-on services” below

May 19 – 26

G$479,911 GYD per night

Villa in Montego Bay

5.0 out of 5 average rating, 9 reviews

Seaside Cottage

Find luxury waterfront living in an exclusive location at Seaside Cottage. This perfectly named Jamaica vacation rental boasts a spectacular Round Hill setting and equally covetable views that stretch from Montego Bay in the east to sunsets over the Caribbean Sea in the west. Its five-star staff and four bedrooms make it an ideal holiday retreat for groups of up to eight friends or an extended family. Your stay at the cottage includes the services of a chef, butler, housekeeper and gardener who live on-site. When you’re not sampling local specialties or sipping cocktails and lounge by the infinity pool. The villa also features a streaming TV, Wi-Fi and an integrated sound system. The villa’s newly remodeled interiors let you enjoy the views along with the breeze from a beautiful open-concept great room. The sitting area has a chic all-white color scheme, while the dining area uses wood paneling to dramatic effect. The chef service is part of your stay There are two bedrooms in the cottage’s main house and two in a separate pavilion. All four have king beds and en-suite bathrooms, and features like al-fresco showers or bathtubs and private entrances give the bedrooms in the pavilion honeymoon-suite-worthy appeal. Guests of Seaside Cottage receive a complimentary Round Hill membership, which gives you access to the resort’s infinity pool, tennis court, spa and fitness areas, yoga center, restaurants and bars. It’s a 3-minute walk to the beach and oceanfront bar at Round Hill, and a 5-minute golf-cart ride to the rest of the resort’s amenities. Beyond the resort, it’s a short drive from the villa to the Tryall Golf Club and the activities in and around Montego Bay. Copyright © Luxury Retreats. All rights reserved. BEDROOM & BATHROOM • Bedroom 1 - Primary: King size bed, Ensuite bathroom with stand-alone rain shower and bathtub, Alfresco shower, Television, Safe, Air conditioning, Private garden, Direct access to pool, Ocean view • Bedroom 2 - Primary: King size bed, Ensuite bathroom with stand-alone rain shower, Television, Safe, Air conditioning, Private garden, Direct access to pool, Ocean view Pavilion • Bedroom 3: King size bed, Ensuite bathroom with alfresco shower and bathtub, Television, Air conditioning, Private balcony, Private entrance, Ocean view • Bedroom 4: King size bed, Ensuite bathroom with stand-alone rain shower and alfresco bathtub, Television, Air conditioning, Private entrance, Ocean view Features & Amenities • Wine fridge Outdoor Features • Wine fridge • 6 Seater golf cart Staff & Services Included: Please note that the staff lives on-site • Gardener • Complimentary Round Hill Resort membership • Laundry service At Extra Cost – advance notice may be required: • Activities and excursions SHARED ACCESS TO AMENITIES AT THE ROUND HILL RESORT (some may be at extra cost) • Round Hill beach • Infinity pool • Pool bar • Restaurants • Bars • Watersport activities • Spa centre • Fitness centre • yoga pavilion • Kids club and activities

Sep 19 – 26

G$1,204,861 GYD per night

Villa in Spring Farm

4.5 out of 5 average rating, 12 reviews

Nianna Eden

Take a morning stroll through the Spring Farms Estate’s 2-acres of private tropical gardens, set just outside Montego Bay in an upscale seaside community. Think about how to spend your afternoon. Is it a trip to the beach? A round of golf? You could do both; they’re only a few minutes away. Don’t decide yet. Head back to Nianna Eden and enjoy your morning coffee while you gaze upon the sparkling Caribbean Sea, it will come to you. Jamaica’s natural features make it an incredible vacation destination. That’s why Nianna Eden invites the fresh sea breeze, warm natural sunlight, and epic ocean views inside to inspire. Merging modern architecture with those features is Nianna Eden’s specialty, as you’ll find intricate stonework, exposed-wood, and carefully integrated tech gadgets. And, the vibrant colors and textures of Jamaican works of art placed throughout the villa are sure to spark conversation on nights in. Grab a book and explore the gardens, play bartender and whip up some fancy new cocktails, or stretch out in a sun lounger and see where the day takes you. On special occasions, get dressed up and enjoy the air conditioning in the formal dining room or commit to the bathing suit, hopping in and out of the pool as you sample freshly grilled treats from the barbeque. And, don’t worry about upkeep, the villa’s staff has got you covered. 6 minutes from home, the prestigious Rose Hall Beach Club, a private club, is easily one of the country’s best beaches. Decorated with coconut trees and pristine white sand, this exclusive beach is a picture of perfection. Wave breaking rocks ensure calm waters, ideal for kids and first-time snorkelers. While the kids play, relax at the poolside grill. After, head 15 minutes West for an exciting night in Montego Bay. Copyright © Luxury Retreats. All rights reserved. BEDROOM & BATHROOM • Bedroom 1 - Primary: King size bed, Ensuite bathroom with stand-alone rain shower, Dual vanity, Television, Safe, Lounge area, Air conditioning, Ocean view • Bedroom 2: King size bed, Ensuite bathroom with stand-alone shower, Television, Safe, Air conditioning, Garden view • Bedroom 3: 2 Twin size beds, Ensuite bathroom with stand-alone rain shower, Television, Safe, Lounge area, Air conditioning, Direct access to pool, Ocean view • Bedroom 4: King size bed, Ensuite bathroom with stand-alone rain shower, Television, Safe, Lounge area, Air conditioning, Direct access to pool, Ocean view • Bedroom 5: King size bed, Ensuite bathroom with stand-alone rain shower, Dual vanity, Television, Safe, Lounge area, Air conditioning, Garden view Features & Amenities • Ocean view • More under “What this place offers” below Extra Cost (advance notice may be required): • Activities and excursions • More under “Add-on services” below

Aug 9 – 16

G$416,073 GYD per night

Villa in White House

Villa Bamidele

Please note this host requires a supplemental contract be signed at the time of booking. Orchids float above their pots and fruit trees scent the air at this waterfront home on Jamaica’s south coast. Beyond the living room, an open veranda beckons to pool terrace and white-sand beach just below. Interior design firm Ishka sourced sourced guango millwork from trees on the property and mahogany furnishings from local artisans. It’s a few minutes’ drive to the village of White House. Copyright © Luxury Retreats. All rights reserved. BEDROOM & BATHROOM Main House • Bedroom 1 - Primary: King size bed, Ensuite bathroom with stand-alone shower & bathtub, Walk-in closet, Balcony, Ocean view • Bedroom 2: King size bed, Ensuite bathroom with stand-alone shower & bathtub, Walk-in closet, Ocean view • Bedroom 3: King size bed, Ensuite bathroom with stand-alone shower & bathtub, Walk-in closet, Balcony, Ocean view • Bedroom 4: King size bed, Ensuite bathroom with stand-alone shower & bathtub, Walk-in closet, Ocean view • Bedroom 5: Queen size bed, Ensuite bathroom with stand-alone shower, Walk-in closet • Bedroom 6: Queen size bed, Ensuite bathroom with stand-alone shower, Walk-in closet Cozy-Dayz Cottage • Bedroom 7: Queen size bed, Ensuite bathroom with stand-alone shower, Terrace Beach Stroll Cottage • Bedroom 8: Queen size bed, Ensuite bathroom with stand-alone shower, Terrace Seaclusion Cottage • Bedroom 9: King size bed, Ensuite bathroom with stand-alone shower, Alfresco bathtubs, Alfresco shower, Terrace, Ocean view Seaduced Cottage • Bedroom 10: King size bed, Ensuite bathroom with stand-alone shower & bathtub, Walk-in closet, Terrace, Ocean view FEATURES & AMENITIES Main House • Wine cooler • Home theater OUTDOOR FEATURES • Terrace STAFF & SERVICES Extra Cost (advance notice may be required): • Activities and excursions

Apr 12 – 19

G$1,788,609 GYD per night

Villa in Montego Bay

Oceans 8

The vibrant Caribbean Sea ripples just beyond this Montego Bay villa. Soaring ceilings and natural light compliment the home’s lavish décor. A capacious pool, with sunbeds, an adjoining hot tub, and a fire feature, is the focal point of the backyard. Craving a taste of local cuisine? A personal chef is included. Coral reefs entice you to dive, snorkel, or simply boat atop the vibrant marine life. Copyright © Luxury Retreats. All rights reserved. BEDROOM & BATHROOM • Bedroom 1 - Primary: King size bed, Ensuite bathroom with stand-alone shower & bathtub, Walk-in closet, Television, Balcony, Ocean view • Bedroom 2: King size bed, Ensuite bathroom with stand-alone shower, Walk-in closet, Television, Balcony, Ocean view • Bedroom 3: King size bed, Ensuite bathroom with stand-alone shower, Walk-in closet, Television, Balcony, Ocean view • Bedroom 4: King size bed, Ensuite bathroom with stand-alone shower, Walk-in closet, Television, Balcony, Ocean view • Bedroom 5: King size bed, Ensuite bathroom with stand-alone shower, Walk-in closet, Television, Balcony, Ocean view • Bedroom 6: 2 Queen size beds, Ensuite bathroom Additional bedding: • Game room: Murphy bed FEATURES & AMENITIES • Home theater • More under “What this place offers” below STAFF & SERVICES Extra Cost (advance notice may be required): • Activities and excursions • More under “Add-on services” below

Jan 24 – 31

G$1,953,719 GYD per night

Villa in Rose Hall

BougainVilla

Nestled amongst lush greenery and mature trees, this breezy villa enjoys a scenic perch just off the coast of Montego Bay. Swing open the terrace and bedroom doors to fill the interior with fresh ocean air. Step outside to relax by the pool and enjoy the ocean view. When sunset approaches, head to the terrace bar for a tropical cocktail or pick a beach bar along the sandy coast. Copyright © Luxury Retreats. All rights reserved. BEDROOM & BATHROOM • Bedroom 1 - Primary: King size bed, Ensuite bathroom with stand-alone shower & bathtub, Walk-in closet, Television, Terrace, Ocean view • Bedroom 2: King size bed, Ensuite bathroom with stand-alone shower, Television, Terrace, Ocean view • Bedroom 3: King size bed, Ensuite bathroom with stand-alone shower, Television, Ocean view • Bedroom 4: King size bed, Ensuite bathroom with stand-alone shower, Television, Ocean view • Bedroom 5: Queen size bed, Shared access to hallway bathroom, Stand-alone shower, Television • Bedroom 6: 2 Twin size beds (can be converted to a king), Ensuite bathroom with stand-alone shower, Television STAFF & SERVICES Included • Daily Chef services (breakfast, lunch and dinner; groceries not included) • 2 Gardeners Extra Cost (advance notice may be required): • Activities and excursions

Jul 10 – 17

G$542,509 GYD per night

Villa in White House

Lime Acre

Famous for its rugged, unspoiled coast, the southern shores of jamaica are the perfect place to reconnect with nature. Spend your days picking fresh mangos, guava, plantain, and lime around this lush 4-acre plantation-house property. Follow the stone path to your own private strip of beach. The nearby coral reef is bustling with sealife and perfect for first-time snorkelers. Copyright © Luxury Retreats. All rights reserved. BEDROOM & BATHROOM Main House • Bedroom 1: Four Poster king size bed, En-suite bathroom with stand-alone shower and bathtub, Television, Safe, Balcony, Ocean view • Bedroom 2: Four Poster king size bed, Ensuite bathroom with stand-alone shower and bathtub, Television • Bedroom 3: 2 Double size beds, Ensuite bathroom with stand-alone shower, Television, Terrace Guesthouse • Bedroom 4: Four Poster king size bed, Ensuite bathroom with stand-alone shower, Television, Terrace • Bedroom 5: 2 Twin size beds, En-suite bathroom with stand-alone shower and bathtub, Television STAFF & SERVICES Included: • Water sports captain • Groundskeepers Extra Cost (advance notice may be required): • All inclusive package (Food and drink) • Vehicle rental • Masseuse • Yoga • Event fee

Jan 25 – Feb 1

G$750,748 GYD per night

Villa in Spring Farm

5.0 out of 5 average rating, 5 reviews

Villa Rosa

Modern tropical treehouse near Half Moon Beach Open the wooden gates to a palm-lined allée leading to tropical modernism above the sea. A terrace and balconies lined with loungers all face the heated pool with a diving board, and the fitness room opens to a treetop deck for yoga. Settle in for a massage while the chef and butler work the scene, and feel the ocean breeze on a chevron-patterned armchair by the TV. Half Moon is a 2-minute drive. Copyright © Luxury Retreats. All rights reserved.

Sep 15 – 22

G$655,809 GYD per night

Villa in Montego Bay

4.75 out of 5 average rating, 4 reviews

Calypso Shores

Set within the Lagoons, a gated community near Montego Bay, this exclusive villa enjoys its own private beach and stunning ocean views. In the area, you’ll find some of the country’s best golf courses, restaurants, and Lagoon’s amazing waterfront gym. Your stay includes the services of a cook, butler, gardener, and housekeeper. And there’s a 13-foot sailboat for you to explore the lagoon with. Copyright © Luxury Retreats. All rights reserved.

Feb 6 – 13

G$321,455 GYD per night

Villa in Whitehouse

5.0 out of 5 average rating, 10 reviews

Santosha - 10 B/R luxury Villa w/ Private Beach

Waves ripple on the walls and in the views from this sleek retreat near White House on Jamaica’s southwest coast. Saltwater spray is nearly close enough to kiss the edges of a pool terrace with loungers and a covered dining area. White and blue interiors nod to the coastal setting in bright, airy living rooms. It’s steps to a private sandy beach and a 1-hour drive to Montego Bay. Copyright © Luxury Retreats. All rights reserved.

Jan 31 – Feb 7

G$614,347 GYD per night