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Jamaica Villa Rentals

Let the sounds of reggae music and the feel of warm ocean breezes put you in instant 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 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.

Destination Villas (21)

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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Jamaica
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Golf
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’.

Villas
Weddings & Romance
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.

Villas
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Arts & Culture

Travel experiences touch us in many different ways, often finding the incredible while in pursuit of the amazing. World-famous works of art and local cultures sit in equality in their ability to inspire us to the WOW moment every journey should include.

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Food & Drink
Food & Drink

Immerse yourself in everything your chosen destination has to offer; experiencing the gastronomic delights accompanied by a glass of the local specialty. Whether a Michelin-star restaurant in Spain, a wine tour in France, or a rum festival in Barbados, our Food & Drink experiences will create lasting memories for all our connoisseur guests.

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Villas in Jamaica

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Caribbean / JamaicaHalf Moon 5 Bedroom ~ Half Moon Resort

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

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

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

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' private beach, the villa features 6 bedrooms, along with an old stone verandah that is perfect for al fresco dining.

Caribbean / JamaicaCanoe Cove

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' 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

Max Group Size

16 / 24

Bedrooms

8 / 12

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

Max Group Size

10

Bedrooms

5

Bathrooms

5.5

Enjoyed 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

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 / JamaicaVilla Starstruck ~ Round Hill Resort

Max Group Size

6

Bedrooms

3

Bathrooms

3

You may remember Round Hill’s Villa Star Struck from the movie “How Stella Got Her Groove Back.” Nestled into the hillside, this villa makes the most of the view by ensuring you can see it almost everywhere you go. With more than 3,000 sq. ft. of space, and 3 bedrooms, this villa is definitely a star.

Caribbean / JamaicaVilla Hideaway ~ Round Hill Resort

Max Group Size

12

Bedrooms

5

Bathrooms

5

Beautifully appointed, this recently renovated villa sits at the edge of an undeveloped tropical forest – the perfect hideaway for your next escape. Featuring 4 bedrooms in the main house and another in the guesthouse, this can be a great choice for families and honeymooners alike.

Caribbean / JamaicaVilla Seclusion ~ Round Hill Resort

Max Group Size

10

Bedrooms

4

Bathrooms

4

Surrounded by a gorgeous tropical garden, Round Hill’s Villa Seclusion boasts a level of secluded luxury one often dreams about. Recently renovated, this premium luxury villa offers 4 bedrooms – 3 in the main villa and 1 in the detached guesthouse – with plenty of living space to stretch out and enjoy.

Caribbean / JamaicaVilla Green Edge ~ Round Hill Resort

Max Group Size

14

Bedrooms

6

Bathrooms

8

Described as “the epitome of excellence,” Round Hill’s Villa Green Edge is situated at the edge of a tropical forest, affording maximum privacy and some of the best ocean views. Recently renovated, this villa offers 6 bedrooms and features multiple balconies that overlook the main pool.

Caribbean / JamaicaDiamond Villa ~ Round Hill Resort

Max Group Size

14

Bedrooms

6

Bathrooms

6

Exuding the utmost in luxurious appointments, incredible views and meticulous attention to detail, Diamond Villa is truly the crème-de-la-crème of villa living. From the tropical gardens that greet you, opening up to views of the ocean that seem to stretch out endlessly in front of you, this is paradise.

Caribbean / JamaicaAqua Bay – The Tryall Club

Max Group Size

10

Bedrooms

4

Bathrooms

5.5

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 – The Tryall Club

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

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 / JamaicaInfinity – The Tryall Club

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

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

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

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

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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