Luxury rentals in Montego Bay

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Top-rated luxury vacation rentals in Montego Bay

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Luxe
A spacious outdoor terrace surrounds a refreshing swimming pool, with lounge chairs positioned nearby. The setting is enhanced by lush tropical greenery and a sunset sky, creating a serene atmosphere. The villa stands in the background, featuring a light-colored façade and elegant architectural details.
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

Luxe
A modern villa is framed by lush greenery and palm trees, featuring a spacious pool at the center. Outdoor lounge areas with seating surround the pool, while large glass doors invite natural light into the interior. Mountains rise majestically in the background.
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

Luxe
A well-kept pathway leads to a villa, surrounded by vibrant tropical plants and flowers. The driveway is bordered with neatly arranged stones, and lush greenery creates a serene atmosphere. The clear blue sky enhances the inviting curb appeal of the property.
Villa in St. James Parish

Abacus Villa

Set atop the verdant hills of Montego Bay's exclusive Spring Farm Estate, Abacus Villa is a refined Caribbean sanctuary designed for discerning travelers who seek privacy, comfort, and style in equal measure. Montego Bay is renowned for its stunning coastline, featuring beautiful beaches and clear, inviting waters that truly capture the island's allure. With sweeping views over the shimmering waters of Half Moon Bay and a design ethos that celebrates indoor - outdoor living, Abacus combines cont

Luxe
The villa's elegant exterior showcases a spacious pool surrounded by lounge chairs. Large sliding doors open to a welcoming living area, while a statue adds artistic flair to the landscape. The two-story structure offers a blend of architectural style and serene outdoor living space.
Villa in Montego Bay

Villa Indigo

Villa Indigo- majestic, panoramic views of the Caribbean Sea and lush valleys. Practically a private resort unto itself, fully staffed with butlers, a chef and sous chef, and housekeepers anticipating your every need. Peloton gym, media room, mahogany bar. Villa and Bamboo Cottage each have five en-suite bedrooms, infinity pool and bar. Terraced estate lush gardens, koi ponds, a hot tub, driftwood playhouse. Membership to world-class Half Moon luxury resort and three championship golf courses.

Luxe
A modern two-story treehouse structure is visible, featuring large glass doors and an open layout. A spacious pool area is highlighted in the foreground, with lounge chairs positioned beside the water. Stone walls surround the pool, while tropical greenery complements the setting.
Villa in Spring Farm
5 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.

Luxe
A shaded outdoor seating area features a comfortable couch with decorative cushions, accompanied by a glass coffee table. The scenic view includes shimmering water, lush greenery, and distant hills, creating a serene and inviting environment for relaxation.
Villa in Montego Bay
4.95 out of 5 average rating, 19 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... Your stay includes the services of a cook, butler, gardener, and housekeeper. PLEASE NOTE: While chef services are available as part of your experience, groceries are NOT INCLUDED in the booking. You’re welcome to bring your own, or we can assist with pre-stocking if arranged in advance, with reimbursement provided at check-in.

Luxe
A spacious outdoor area features a clear blue pool complemented by a hot tub. Lounge chairs are positioned around the pool, providing a relaxing atmosphere. The home's exterior showcases a modern design with large windows and a covered balcony, surrounded by tropical landscaping.
Place to stay in Runaway Bay

Breakaway

Wavelets kiss white sand on the grounds of this lush Jamaica home. The acre of land is ringed by private beach perfect for swimming or kayaking, and there’s also a pool and hot tub. Plants fill an atrium and living areas like a rainforest, and details like slipcovered chairs and live-edge tables add to the relaxed feel. It’s a short drive to other beaches and caves in Runaway Bay. Copyright © Luxury Retreats. All rights reserved.

Luxe
A sparkling outdoor swimming pool reflects the surrounding tropical landscape. Lounge chairs are arranged beside the pool, offering a comfortable spot for relaxation. Lush greenery and colorful flowers create a vibrant backdrop, enhancing the serene atmosphere of the outdoor space.
Villa in Montego Bay
5 out of 5 average rating, 16 reviews

Oceanview 6-BR Villa| Beach Access, Chef Available

Nutmeg Oceanview villa - 6Br - Sleeps 13. Lower rates for fewer bedrooms may be available upon request.

Luxe
The exterior of the villa showcases a Tuscan-inspired design with warm stucco walls and a terracotta-tiled roof. Multiple outdoor seating areas surround the saltwater infinity pool, while lush greenery and potted plants add natural beauty to the landscape.
Villa in Rose Hall

Villa Christina

Tuscan architecture overlooking Cinnamon Hill golf

Luxe
A serene view of the villa complex reflects in the tranquil waters of a swimming pool. Each villa showcases elegant architecture with sloped roofs and inviting outdoor spaces, framed by lush greenery and soft lighting from within.
Place to stay in St. James
5 out of 5 average rating, 3 reviews

Silent Waters Villa - 9 Bedroom Estate - Two Pools

Eastern-influenced villa with ocean views

Luxe
A multi-level villa is surrounded by lush greenery, with a tropical pool area in the foreground. The exterior features a combination of wooden and textured white walls, large windows, and an inviting patio set for outdoor dining under shaded umbrellas.
Villa in Cornwall County
5 out of 5 average rating, 6 reviews

Idle Awhile Villa Palm - 5 bedroom Villa, Negril

Palm-lined garden estate on 7-Mile Beach

Luxe
The spacious living area features high, vaulted ceilings and is furnished with comfortable seating arrangements. Bright accent cushions add color to the neutral tones. Large windows allow natural light to illuminate the space, while lush greenery is visible through the openings.
Villa in Sandy Bay

Hummingbird House

Oceanview resort villa atop Barnes Hill

Popular amenities for Montego Bay luxury vacation rentals

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. Saint James
  4. Montego Bay
  5. Luxury rentals