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Jamaica Villa Rentals

Let the sounds of reggae music and the feel of warm ocean breezes put you in instant luxury vacation mode. With great weather, fun and friendly locals, and activities to delight any interest (and any age), you’ll de-stress in no time. Full of great restaurants, unique shops, picturesque beaches, world-class golf, stunning waterfalls, luxury villas and activities galore, Jamaica invites you to be as active or laid back as you want to be. From Montego Bay and Ocho Rios to picturesque Negril and beyond, there is much to discover and experience on this island in the sun.

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Jamaica For Kids

Dunn's River Falls

Ocho Rios’ star attraction, these beautiful cascading falls extend some 180m. Spend the day going from one refreshing pool to the next. There’s a craft market at the top if you’d like to take home a souvenir. Recommended for 7 years old and up.

Chukka Tours

This Jamaican outfitter offers everything from horseback riding and jeep safaris, to ATV tours and a White River kayaking adventure. With something to suit every age and stage, it is your go-to company for fun in the sun.

Black River Safari Cruise

Jamaica’s longest river, it is home to crocodiles, mangroves and lots of exotic birds. Your guide will explain the local ecology and wildlife along the way. You’ll also pass by the beautiful YS Falls, which boasts a 7-tiered cascading waterfall.

Dolphin Cove Jamaica

With locations in Montego Bay and Ocho Rios, this is the perfect place to swim and interact with dolphins, sharks and stingrays in their natural environment. You’ll also see exotic birds, snakes and iguanas, and camels too!

Featured Themes in Jamaica

Weddings & Romance

Luxury villas have long been a feature of the romantic traveler looking to celebrate a special event with friends and family. The privacy not afforded in hotels or resorts sets romantic villa experiences apart. Weddings, vow renewals, anniversaries and our villa experiences are a match made in heaven.

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Golf

It is difficult to explain to the non-golfer the pull of the game, the personal challenge of you versus the course, the ‘aaaargh’ and ‘YEAH!’ moments, but we get it. We have established a portfolio of villas that cater to the avid golfer and provide a challenge to all levels of aspiring 'Tigers'.

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Saint Lucia

Revered by the ancients who fought to preserve her natural beauty in all its glory, Saint Lucia is the perfect place to rent a luxury villa and get out and explore. With gorgeous beaches, lush rainforest and of course, those iconic Pitons, this island is perfection.

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Soft and pristine, Punta Cana’s famed white-sand beaches await! Home base to some quality R&R, sun-drenched days and gorgeous surf, Caribbean living doesn’t get much better than in a luxury villa in the Dominican Republic. Explore and discover or do nothing at all – this destination delivers.

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62 Villas

Villas in Jamaica

Caribbean / JamaicaSunDown Villa 7

Per Night From US $2,519
Max Group Size

14

Bedrooms

7

Bathrooms

7

A private stretch of white sand beach on Discovery Bay highlights this seven bedroom sanctuary of open-aired living.

Caribbean / JamaicaSunDown Villa 5

Per Night From US $1,799
Max Group Size

10

Bedrooms

5

Bathrooms

5

A private stretch of white sand beach on Discovery Bay highlights this five bedroom sanctuary of open-aired living.

Caribbean / JamaicaHalf Moon 7 Bedroom – Half Moon Resort

Per Night From US $2,529
Max Group Size

14

Bedrooms

7

Bathrooms

7

The enjoyment of your own private villa combined with the boundless amenities of a world-class resort.

Caribbean / JamaicaZion Hill – The Tryall Club

Per Night From US $2,569
Max Group Size

10

Bedrooms

5

Bathrooms

5

First-class amenities abound in this stunning five bedroom villa. Days can be filled with activities or spent in blissful relaxation.

Caribbean / JamaicaPalm Villa – Idle Awhile Negril

Per Night From US $1,499
Max Group Size

10

Bedrooms

5

Bathrooms

5

Enjoy your time in the spacious outdoor living room that is the focal point of this five-bedroom oceanfront villa.

Caribbean / JamaicaHaystack – The Tryall Club

Per Night From US $3,279
Max Group Size

20

Bedrooms

10

Bathrooms

10

Haystack is an enormous ten bedroom villa located amidst rolling lawns and gardens and offers an array of activities with huge open spaces and perfect appointments.

Caribbean / JamaicaCreate Abundance – The Tryall Club

Per Night From US $3,389
Max Group Size

20

Bedrooms

10

Bathrooms

10

Commanding views of a lush forest and the blue sea beyond, This massive ten bedroom Colonial style villa allows you to get active or simply do nothing at all.

Caribbean / JamaicaVista Del Mar – The Tryall Club

Per Night From US $1,039
Max Group Size

6

Bedrooms

3

Bathrooms

3

Vista Del Mar is a three bedroom villa filled with Jamaican charm that includes mahogany louvred windows and vaulted ceilings.

Caribbean / JamaicaYellowbird – The Tryall Club

Per Night From US $789
Max Group Size

8

Bedrooms

4

Bathrooms

4

Surrounded by lush gardens and perfectly manicured lawns, Yellowbird is a treat for the senses.

Caribbean / JamaicaNo Le Hace – The Tryall Club

Per Night From US $1,289
Max Group Size

10

Bedrooms

5

Bathrooms

5

A gazebo and thatched-roof bar compliment the infinity pool that seems to spill into the ocean beyond.

Caribbean / JamaicaAvalon – The Tryall Club

Per Night From US $779
Max Group Size

8

Bedrooms

4

Bathrooms

4

Wrapped in beautiful gardens, Avalon is a private oasis of luxury and tranquility.

Caribbean / JamaicaEureka – The Tryall Club

Per Night From US $1,299
Max Group Size

8

Bedrooms

4

Bathrooms

4

With perfect details throughout, this four bedroom home speaks of a time when luxury and privilege were the order of the day.

Caribbean / JamaicaMa’Moura – The Tryall Club

Per Night From US $1,299
Max Group Size

8

Bedrooms

4

Bathrooms

4

The ultimate in unobstructed views, Ma Moura is centered around the luxurious circular pool and spacious verandah.

Caribbean / JamaicaRose Cottage – The Tryall Club

Per Night From US $2,339
Max Group Size

12

Bedrooms

6

Bathrooms

6

This special home away from home is elegant and comfortable in its style and detail. Caribbean breezes drift throughout the six pavilions that make up this home.

Caribbean / JamaicaBali Hai – The Tryall Club

Per Night From US $1,429
Max Group Size

10

Bedrooms

5

Bathrooms

5

A slice of Bali comes to Jamaica with this one of a kind luxury villa. Peace and tranquility are evident throughout this five bedroom home and no detail has been left out.

Caribbean / JamaicaSunDown Villa 9

Per Night From US $2,519
Max Group Size

18

Bedrooms

9

Bathrooms

9

A private stretch of white sand beach on Discovery Bay highlights this nine bedroom sanctuary of open-aired living.

Caribbean / JamaicaSomeday Soon – The Tryall Club

Per Night From US $2,069
Max Group Size

10

Bedrooms

5

Bathrooms

5

Gorgeous Jamaican art and furnishings adorn this five bedroom villa that encapsulates the local charm and flair.

Caribbean / JamaicaThe Cliff Villa 4

Per Night From US $599
Max Group Size

8

Bedrooms

4

Bathrooms

4

Spacious and open, Villa 4 at The Cliff combines the ultimate in sleek contemporary style with open-aired luxury.

Caribbean / JamaicaAlmond Villa – Idle Awhile Negril

Per Night From US $1,199
Max Group Size

8

Bedrooms

4

Bathrooms

4

Enjoy your time in the spacious outdoor living room that is the focal point of this four bedroom oceanfront villa.

Caribbean / JamaicaSea Salt – The Tryall Club

Per Night From US $1,949
Max Group Size

10

Bedrooms

5

Bathrooms

5

Situated on five acres of beautiful gardens with stunning views across the valleys and the sea, Sea Salt is the perfect blend of luxury, privacy and tranquility.

Caribbean / JamaicaPoint of View – The Tryall Club

Per Night From US $2,569
Max Group Size

10

Bedrooms

5

Bathrooms

5

With sweeping East to West views of lush tropical valleys and the deep blue of the sea beyond, this five-bedroom home will leave you truly inspired.

Caribbean / JamaicaJubilation – The Tryall Club

Per Night From US $1,949
Max Group Size

12

Bedrooms

6

Bathrooms

6

With a huge pool and enormous terrace and deck space, Jubilation is the perfect luxury home to entertain in.

Caribbean / JamaicaFollowing Seas – The Tryall Club

Per Night From US $2,269
Max Group Size

12

Bedrooms

6

Bathrooms

6

With landscaped gardens and unending sea views, this seven acre masterpiece of glamour and charm will stay in your memory long after you’ve left.

Caribbean / JamaicaDragonfly – The Tryall Club

Per Night From US $3,199
Max Group Size

14

Bedrooms

7

Bathrooms

7

Luxury and comfort combine in this seven bedroom villa that showcases unobstructed views of of the lush valleys and the sea beyond. No detail was overlooked in Dragonfly.

Caribbean / JamaicaBumper’s Nest – The Tryall Club

Per Night From US $2,269
Max Group Size

6

Bedrooms

12

Bathrooms

6

Natural light and fresh tropical breezes flow through this six bedroom villa located on three acres at the peak of Mahogany Hill .

Caribbean / JamaicaHanover Grange – The Tryall Club

Per Night From US $3,049
Max Group Size

18

Bedrooms

9

Bathrooms

9

Nine bedrooms of contemporary chic made this spacious and tranquil villa a special spot among celebrities and business leaders looking for the perfect getaway.

Caribbean / JamaicaBougainvillea House – The Tryall Club

Per Night From US $1,759
Max Group Size

10

Bedrooms

5

Bathrooms

5

Private outdoor showers and verandahs blend with gorgeous gathering areas to offer both blissful privacy and group activities.

Caribbean / JamaicaPhoenix – The Tryall Club

Per Night From US $3,139
Max Group Size

14

Bedrooms

7

Bathrooms

7

The epitome of luxury, Phoenix is a seven bedroom “ home away from home” that offers large groups the ultimate in privacy and beachside living.

Caribbean / JamaicaSunset – The Tryall Club

Per Night From US $2,139
Max Group Size

10

Bedrooms

5

Bathrooms

5

This five bedroom villa boasts an incredible beachfront location. Enjoy your private pool while the full staff takes care of your every need.

Caribbean / JamaicaBye the Way – The Tryall Club

Per Night From US $529
Max Group Size

4

Bedrooms

2

Bathrooms

2

The 67 ft. veranda is the focal point of this gorgeous colonial style bungalow. From here you will enjoy panoramic ocean views surrounded by beautiful landscaped gardens.

Caribbean / JamaicaThe Cliff Villa 5

Per Night From US $749
Max Group Size

10

Bedrooms

5

Bathrooms

5

If you are looking for the perfect blend of hotel living, exclusivity and uninterrupted privacy, look no further than The Cliff Villa 5. This beautiful 2-storey, 5-bedroom home offers spectacular ocean views from just about every corner.

Caribbean / JamaicaLime Acre

Per Night From US $1,129
Max Group Size

10

Bedrooms

5

Bathrooms

5

Located on Jamaica’s tranquil South Coast, Lime Acre is a luxury villa perfect for those in search of some off-the-beaten-track adventures that transport you to another time and place. Offering a rugged, unspoiled beauty, this 5-bedroom sanctuary sits on 4 acres of land.

Caribbean / JamaicaHalf Moon 5 Bedroom ~ Half Moon Resort

Per Night From US $2,999
Max Group Size

10

Bedrooms

5

Bathrooms

5

Located on the grounds of one of Jamaica’s most iconic resort destinations, this 5-bedroom villa is the tropical sanctuary you’ve been craving. Nestled in a neighbourhood known for privacy, and with access to the various resort experiences, this villa has all the amenities you want or need.

Caribbean / JamaicaHalf Moon 6 Bedroom – Half Moon Resort

Per Night From US $3,699
Max Group Size

12

Bedrooms

6

Bathrooms

6

Located in a neighbourhood known and loved for its luxury and privacy, this 6-bedroom villa is an excellent choice for a larger group of friends or family. Step onto the terrace and soak in the sunshine and the gorgeous ocean views.

Caribbean / JamaicaMonticello

Per Night From US $1,299
Max Group Size

6/10

Bedrooms

3/5

Bathrooms

3/5

Newly refurbished, Monticello Villa is set on an 8-acre estate surrounded by gorgeous manicured lawns and the golf course at Upton, St. Ann. Originally built in the early 1950s for a European aristocrat, today the villa retains all of its Old World charm while offering guests a modern experience.

Caribbean / JamaicaFrankfort

Per Night From US $2,999
Max Group Size

12

Bedrooms

6

Bathrooms

7

Originally a 17th-century fortress, today Frankfort has been brilliantly restored to be one of the most sought-after private villas on the island. Set overlooking a 300-foot private beach, the villa features 6 bedrooms, along with an old stone verandah that is perfect for al fresco dining.

Caribbean / JamaicaCanoe Cove

Per Night From US $2,569
Max Group Size

14

Bedrooms

7

Bathrooms

9

Uncomplicated and loaded with amenities, Canoe Cove sits on 3 acres of land in Old Fort Bay. Boasting 180 feet of beachfront bliss, here you are encouraged to be as restful or as active as you see fit. Here earth tones help blend the indoors and outdoors seamlessly, creating an ambiance of grandeur.

Caribbean / JamaicaRio Chico

Per Night From US $8,199
Max Group Size

16

Bedrooms

8

Bathrooms

8.5

This magnificent 14-acre oceanfront estate is surrounded by lush vegetation, creeks and even waterfalls… not to mention 2 private beaches for you to call your own. To cool off, there’s a main pool with a cliff-side infinity area, a beach-side pool and a natural waterfall pool.

Caribbean / JamaicaTek Time

Per Night From US $999
Max Group Size

10

Bedrooms

5

Bathrooms

5.5

Enjoy a pampered life at this glamorous villa located on Rosehall Estates. Overlooking the 12th hole of Cinnamon Hill golf course, Tek Time offers everything you could want in your vacation: privacy, luxury and pampering from the dedicated staff of five.

Caribbean / JamaicaCaribbean Jewel

Per Night From US $859
Max Group Size

8

Bedrooms

4

Bathrooms

4

This 5,000 sq. ft. Mediterranean-style villa easily lives up to its name. Offering four ocean view bedrooms, inside it is classic Caribbean elegance – vaulted ceilings, warm wood accents – and when you open the doors to the terrace, the space fills with light and those gorgeous ocean breezes.

Caribbean / JamaicaAqua Bay – The Tryall Club

Per Night From US $2,569
Max Group Size

8

Bedrooms

4

Bathrooms

6

Located at ocean’s edge, this villa redefines the concept of ocean style. Reflecting the sea inside and out, Aqua Bay boast not only a zero-edge heated pool with spa, but two swimming holes on the coastal strip that are fed with sea water and are adjacent to an elevated white sand beach.

Caribbean / JamaicaTradewinds On The Sea – The Tryall Club

Per Night From US $2,279
Max Group Size

8

Bedrooms

4

Bathrooms

4.5

Set right on the shore and built in classic Caribbean style, Tradewinds is just one of a handful of private villas on the sprawling Tryall Estate. Offering spectacular sea views and private beach (depending on the tide), life here is the epitome of modern beachfront living.

Caribbean / JamaicaLolita – The Tryall Club

Per Night From US $2,429
Max Group Size

10

Bedrooms

5

Bathrooms

5

With its breathtaking setting, sensational views and meticulous attention to detail, Villa Lolita is certainly one of the finest villas on the island. Comprised of 14,000 sq. ft. of free-flowing living space and built over three levels, Lolita is the answer for those who seek only the very best.

Caribbean / JamaicaVilla Infinity – The Tryall Club

Per Night From US $2,139
Max Group Size

10

Bedrooms

5

Bathrooms

5.5

Named for its spectacular pool, Infinity was built to maximize its setting while also exuding an atmosphere that is elegant and comfortable. From its elevated perch, this premier, 5-bedroom villa offers spacious rooms and a large outdoor area that lends itself so perfectly to barefoot living.

Caribbean / JamaicaKarma Bay – The Tryall Club

Per Night From US $1,429
Max Group Size

12

Bedrooms

6

Bathrooms

6.5

For a taste of paradise where the waves lap the shore and the warm Caribbean breezes caress the surrounding palms, Karma Bay is a waterfront villa that has all the attributes for an unforgettable experience. With an emphasis on luxurious tropical living, the villa features 6 private bedrooms.

Caribbean / JamaicaAnticipation – The Tryall Club

Per Night From US $1,369
Max Group Size

12

Bedrooms

6

Bathrooms

6.5

The name says it all… as you turn into the driveway and begin to ascend, your anticipation grows as you wonder how much more of the stunning ocean panorama will be seen once you arrive at the top. You will not be disappointed – 180 degrees of uninterrupted seascape await.

Caribbean / JamaicaHummingbird House – The Tryall Club

Per Night From US $2,569
Max Group Size

14

Bedrooms

7

Bathrooms

7.5

With one of the most panoramic views, this sprawling 14,000 sq. ft. residence sits amidst 4 acres of lush gardens on Barnes Hill. Among its many highlights, it features a spectacular 50-foot infinity pool and has been built in a modern, open style.

Caribbean / JamaicaSugar Hill – The Tryall Club

Per Night From US $2,999
Max Group Size

16

Bedrooms

8

Bathrooms

8

This stunning, 8-bedroom private villa sits perched atop a lush 3-acre property that overlooks the Caribbean Sea. Built in traditional plantation style, the beautifully appointed 4-bedroom main villa and 4-bedroom guest house, are surrounded by exquisitely manicured gardens and tropical trees.

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