Luxury rentals in Montego Bay

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Top-rated luxury vacation rentals in Montego Bay

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Luxe
Villa in Montego Bay
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
Jul 8 – 15
$1,143 per night
4.61 out of 5 average rating, 31 reviews
Luxe
Villa in Montego Bay
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
Apr 20 – 27
$2,300 per night
4.5 out of 5 average rating, 4 reviews
Luxe
Villa in Montego Bay
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
Aug 12 – 19
$5,060 per night
5.0 out of 5 average rating, 9 reviews

Popular amenities for Montego Bay luxury vacation rentals

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Flower Hill
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Following Seas at Tryall Club
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Villa in Montego Bay
Sugar Hill at Tryall Club
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All about Montego Bay

Planning a Montego Bay vacation? We’re here to help!

Jamaica means beaches, reggae, jerk chicken and chilled Red Stripe beer – a sun-soaked Caribbean vacation where you can kick back and let the good vibes soothe your work-weary soul. Yes, the beaches, such as Montego Bay’s Doctor’s Cave Beach with its crystal-clear sea and powder-soft sand, are gorgeous, and we suggest you schedule plenty of time to make the most of their golden charms. But there’s plenty of other stuff to do too.

Relaxed river rafting

 When sugar was king in Jamaica, during the plantation era, Martha Brae River – one of the country’s largest – was a vital artery connecting the inland sugar estates to the trading ports on the coast. The crop was transported on long bamboo rafts, ready to be loaded onto ships bound for Europe. Today, the bamboo rafts remain, but their cargo has changed to chime with the times – now that tourism is one of Jamaica’s biggest sources of income, it’s curious visitors who float downstream on the 30-foot rafts, taking in the beauty of the jungle scenery as they go. The Martha Brae Rafting Village is only 20 miles from Montego Bay, and there’s round-trip transport available if you need it, making this an easy afternoon excursion. A knowledgeable local guide will bring you along three miles of lazily flowing river, regaling you with the legend of Martha Brae – said to be a Taino witch who knew the location of a hidden stash of gold – and telling you about the abundant flora and fauna as you pass. Make sure to pack your swimsuit, because there’s a pool at the Rafting Village, and the calm river waters are also safe to swim in and the perfect cool retreat from the tropical heat.

 

Ghosts of the past

 

A Garden of Eden

Experience the luxury of our villas in Montego Bay

The deep-green hills around Montego Bay and the shores bathed by the gently lapping Caribbean Sea – both are equally alluring options for a perfect Jamaican vacation. Perhaps you’d like a property with views across the treetops from the spacious terrace, your own pool and tennis court and a barbecue grill for those balmy evenings – although you can also have your own chef to rustle up delicious Jamaican dishes.

Or is the ocean calling your name? In that case, may we suggest one of our Montego Bay beach villas ? Stone floors, vaulted ceilings, and white walls make for a cool, calm retreat at the end of a long day in the sun – choose a home where the sand is just steps from your veranda, and where beach toys, kayaks, and snorkeling gear are all on hand to help your day go swimmingly. With villas ranging from 4 bedrooms all the way up to 12, there’s plenty of room for everyone, so take your friends, take the whole family, take your wedding party – then sit back and take it easy.

Destinations to explore

  1. Airbnb
  2. Jamaica
  3. St. James Parish
  4. Montego Bay
  5. Luxury rentals