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$1,258

5 BR / 6 BA / Sleeps 13

Knockando at Round Hill - Montego Bay vacation rentals
1 / 18

$1,258

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Knockando at Round Hill

Ironshore house
5 BR / 6 BA / Sleeps 13 | Quick view

Details

More than 50 years ago, a visionary named John Pringle dreamed of turning a magical Jamaican hillside and waterfront into a luxurious retreat and he named it Round Hill. He sat upon the hill, gazed over the deep blue sea and selected the site for his own home, the genesis of what was to become a renowned resort for …
  • Internet Access
  • A/C or climate control
  • Pet friendly - ask
  • Smoking allowed - ask
  • Suitable for children - ask
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask

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$1,948

6 BR / 7 BA / Sleeps 12

Viviana at the Tryall Club - Montego Bay vacation rentals
1 / 25

$1,948

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Viviana at the Tryall Club

Ironshore house
6 BR / 7 BA / Sleeps 12 | Quick view

Details

Enter a quarter-mile driveway, beautifully landscaped with brilliant bougainvillea on all sides. Then see the Travertine-paved Italianate courtyard which is the dramatic entrance to Viviana. You're home.On a remarkable six private acres on a plum site at the prestigious Tryall Club, Viviana is distinguished by the top…
  • Internet Access
  • A/C or climate control
  • Pet friendly - ask
  • Smoking allowed - ask
  • Suitable for children - ask
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask

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$1,172

5 BR / 5 BA / Sleeps 10

Mahogany Hill at the Tryall Club - Montego Bay vacation rentals
1 / 20

$1,172

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Mahogany Hill at the Tryall Club

Montego Bay house
5 BR / 5 BA / Sleeps 10 | Quick view

Details

N/A
  • Private Pool
  • A/C or climate control
  • Pet friendly - ask
  • Smoking allowed - ask
  • Suitable for children - ask
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask

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$929

5 BR / 5 BA / Sleeps 10

Nutmeg - Montego Bay vacation rentals
1 / 21

$929

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Nutmeg

Montego Bay house
5 BR / 5 BA / Sleeps 10 | Quick view

Details

A massive whole-house renovation has created this lovely vacation villa in the upscale residential neighborhood of Spring Farm just five minutes from three world-class golf courses, designer shops, bars, restaurants and beaches. Through carved entrance doors with antique brass fittings, the magnificent view is …
  • Internet Access
  • A/C or climate control
  • Pet friendly - ask
  • Smoking allowed - ask
  • Suitable for children - ask
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask

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$1,893

5 BR / 5 BA / Sleeps 1

Trinity - Montego Bay vacation rentals
1 / 28

$1,893

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Trinity

Montego Bay house
5 BR / 5 BA / Sleeps 1 | Quick view

Details

Completed in January of 2007, Trinity Villa is an ultra-luxurious paradise. The 4 acre estate is home to royal palms, numerous fruit trees, and indigenous flowers. Grand in luxury and in scale, Trinity is comprised of 13,000 square feet of living space under the roof, and an additional 6000 square feet of pool and …
  • Ocean or water views
  • Patio
  • Safe
  • Microwave
  • Satellite or cable TV
  • Suitable for children - ask
  • Suitable for the elderly - ask

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$2,598

6 BR / 6 BA / Sleeps 12

Windrush at the Tryall Club - Montego Bay vacation rentals
1 / 16

$2,598

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Windrush at the Tryall Club

Montego Bay house
6 BR / 6 BA / Sleeps 12 | Quick view

Details

This entirely renovated luxury villa is beautifully situated on five acres of lush gardens and the offers utterly stunning views of the Carribean Sea.It features an air-conditioned master bedroom with a four-poster Jamaican mahogany king-size bed and mahogany floors, en-suite bathroom with separate shower and dressing…
  • Internet Access
  • Pet friendly - ask
  • Smoking allowed - ask
  • Suitable for children - ask
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask

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$1,299

6 BR / 6 BA / Sleeps 0

1 / 22

$1,299

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6 Bedroom Villa with Panoramic View of the Caribbean Sea in Montego Bay

Montego Bay villa
6 BR / 6 BA / | Quick view

Details

8,000-square-foot, 6-bedroom villa on 7 acres at the prestigious Tryall Clubhighest Premier ratinglarge private poolstaff of 7: chef, butler, housekeepers, gardeners, laundressocean and mountain views from one of the highest points at the Tryall Clubindoor and outdoor diningcable television in all bedrooms and …
  • Shared outdoor pool (unheated)
  • Hot Tub/Jacuzzi
  • Internet Access
  • A/C or climate control
  • Pet friendly - ask
  • Smoking allowed - ask
  • Suitable for children - ask
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask

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$715

5 BR / 5 BA / Sleeps 14

1 / 8

$715

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Pavilion

Montego Bay house
5 BR / 5 BA / Sleeps 14 | Quick view

Details

Pavilion is an exquisite villa privately located at the end of a cul-de-sac with magnificent views of the Caribbean Sea to the north and a tranquil 10-mile view of the mountains to the south. It is spacious, quiet, peaceful and beautiful. Architecturally, Pavilion is designed as five 400-square-foot octagons in …
  • Hot Tub/Jacuzzi
  • Internet Access
  • A/C or climate control
  • Pet friendly - ask
  • Smoking allowed - ask
  • Suitable for children - ask
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask

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$358

2 BR / 2 BA / Sleeps 4

1 / 27

$358

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La Casita

Montego Bay house
2 BR / 2 BA / Sleeps 4 | Quick view

Details

N/A
  • Private Pool
  • Internet Access
  • A/C or climate control
  • Pet friendly - ask
  • Smoking allowed - ask
  • Suitable for children - ask
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask

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$452

4 BR / 4 BA / Sleeps 8

1 / 28

$452

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Calypso at the Tryall Club

Ironshore house
4 BR / 4 BA / Sleeps 8 | Quick view

Details

Calypso is a charming open-air villa adjacent to the 16th fairway of the championship The Tryall Golf Course. Its lush grounds are graced by palm, lime, avocado, grapefruit, papaya, and poinciana trees, brilliant hibiscus and bougainvillea, and a beautiful lavender orchid tree. The beautiful living room has four deep-…
  • Internet Access
  • Pet friendly - ask
  • Smoking allowed - ask
  • Suitable for children - ask
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask

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$1,559

8 BR / 8 BA / Sleeps 16

1 / 22

$1,559

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Haystack at the Tryall Club

Montego Bay house
8 BR / 8 BA / Sleeps 16 | Quick view

Details

Haystack is the only eight-bedroom villa at the posh Tryall Club. Among the newest, its architecture defines spacious bedroom suites, a long furnished verandah perfect for dining outdoors, a striking red inside dining room and large family play room - all enhanced by overviews of the long private pool, acres of …
  • Internet Access
  • A/C or climate control
  • Pet friendly - ask
  • Smoking allowed - ask
  • Suitable for children - ask
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask

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$75

1 BR / 1 BA / Sleeps 3

1 / 20

$75

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Mobay Club Studio Hip Strip, Beach Pool Nightlife

Montego Bay condo
1 BR / 1 BA / Sleeps 3 | Quick view

Details

Quiet studio apartment with own patio on Hip Strip, in a middle of everything in Montego Bay. Nightclubs, beaches, restaurants, shopping, deep sea fishing The studio has a fully equipped kitchen, air conditioning and ceiling fan, cable TV, Wi-Fi, towels, linen, a swimming pool, tennis courts and restaurants.
  • Shared outdoor pool (unheated)
  • Wireless Internet
  • Outdoor Dining Area
  • A/C or climate control
  • Balcony or terrace
  • Pet friendly - ask
  • Suitable for children - ask
  • Suitable for the elderly - elevator access
  • Wheelchair accessible

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$100

4294967295 BR / 1 BA / Sleeps 2

1 / 14

$100

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Skytop Beach Studio

Montego Bay studio
1 BA / Sleeps 2 | Quick view

Details

This small apartment has all the essentials; air conditioning, balcony/terrace, daily maid service, free on-site parking and kitchen There is a uniformed security guard at the front entrance of the building. The Montego Bay Club is found on the Hip Strip in Montego Bay City, an attractive part of Jamaica that is a …
  • Ocean or water views
  • Mountain Views
  • Shared outdoor pool (unheated)
  • Outdoor Dining Area
  • A/C or climate control
  • Suitable for children
  • Suitable for the elderly - elevator access
  • Wheelchair accessible

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$1,554

6 BR / 6 BA / Sleeps 12

1 / 17

$1,554

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Half Moon - 6br Royal Villas

Montego Bay villa
6 BR / 6 BA / Sleeps 12 | Quick view

Details

Located on the grounds of the deluxe Half Moon Golf, Tennis and Beach Club the Royal Villas are truly luxurious and cater to the most discerning travelers. The Royal Villas are surrounded by magnificent gardens and designed with impressive Georgian architecture with elegantly appointed living and dining areas. There …
  • Washing Machine
  • Clothes Dryer
  • Grill
  • Safe
  • Dishwasher
  • Suitable for children
  • Suitable for the elderly - ask

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$1,715

7 BR / 7 BA / Sleeps 14

1 / 29

$1,715

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Sugar Hill

Montego Bay house
7 BR / 7 BA / Sleeps 14 | Quick view

Details

Sugar Hill is an elegant new island home perched atop a manicured 3-acre property overlooking the breathtaking Caribbean Sea and magnificent Tryall Club Resort. The one level floor plan allows views of the glittering turquoise sea and curvaceous coastline from every room. It is built in the traditional Jamaican …
  • Ocean or water views
  • Shared outdoor pool (unheated)
  • Hot Tub/Jacuzzi
  • Internet Access
  • Fitness Room
  • Suitable for children - ask
  • Suitable for the elderly - ask

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$1,720

5 BR / 5 BA / Sleeps 1

1 / 22

$1,720

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Bougainvillea

Montego Bay house
5 BR / 5 BA / Sleeps 1 | Quick view

Details

Bougainvillea House completed in the Fall of 2007 is one of Tryall’s newest villas which is quickly apparent in the unsurpassed luxury it provides. Designed by one of Jamaica’s best known architects, it is built in classic Caribbean Georgian style but discreetly includes every 21st century luxury. It …
  • Ocean or water views
  • Mountain Views
  • Hot Tub/Jacuzzi
  • Wireless Internet
  • Outdoor Dining Area
  • Suitable for children - ask
  • Suitable for the elderly - ask

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$728

4 BR / 4 BA / Sleeps 8

1 / 14

$728

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Hillside Villa

Montego Bay villa
4 BR / 4 BA / Sleeps 8 | Quick view

Details

When Round Hill was only an undeveloped lush green hillside rising over the sea, one man had the good fortune to have his choice of lots, and the vision to choose that piece of land most favored by the sun and prevailing tradewinds ... which also happened to have one of the most spectacular views in all the Caribbean…
  • Internet Access
  • Washing Machine
  • Clothes Dryer
  • Grill
  • Dishwasher
  • Suitable for children
  • Suitable for the elderly - ask

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$1,500

4 BR / 4 BA / Sleeps 8

1 / 38

$1,500

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Villa Janus

Montego Bay villa
4 BR / 4 BA / Sleeps 8 | Quick view

Details

Villa Janus is located on the highest point at the exclusive Round Hill Resort. The home provides exceptional panoramic views of the Caribbean. An stunning home, the villa was named for the Roman God "Janus" who was the God of entrances, doors as well as endings. Janus was represented by a double faced head with each …
  • Internet Access
  • Washing Machine
  • Clothes Dryer
  • Grill
  • Dishwasher
  • Suitable for children
  • Suitable for the elderly - ask

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$1,298

5 BR / 5 BA / Sleeps 10

1 / 40

$1,298

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Breathtaking 5 Bedroom Villa with Private View in Montego Bay

Montego Bay villa
5 BR / 5 BA / Sleeps 10 | Quick view

Details

Tryall Club Membership: Complimentary beach, tennis, gym, pool, Hummingbird Kids Club, non-motorized water sports, internet room, new Usain Bolt Games Room for kids, teens and adults, jogging trail, afternoon tea and Manager's Cocktail Party. For various fees: golf, tennis lessons, Happy Hour, hair salon and spa, …
  • Shared outdoor pool (unheated)
  • Internet Access
  • A/C or climate control
  • Satellite or cable TV
  • Stereo or CD player
  • Pet friendly - ask
  • Smoking allowed - ask
  • Suitable for children
  • Suitable for the elderly - ask
  • Wheelchair accessible

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$2,014

5 BR / 5 BA / Sleeps 10

1 / 13

$2,014

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Round Hill 5br

Montego Bay villa
5 BR / 5 BA / Sleeps 10 | Quick view

Details

There are 27 individually owned villas with 74 suites surrounded by 30 acres of tropical gardens. Villas or cottages contain 2, 3, 4 and 5 suites, each with private, complete villa with private pool or suites in villas with a shared pool; 23 villas have their own pool. The villas are beautifully decorated individual …
  • Safe
  • Television
  • Stereo or CD player
  • Suitable for children
  • Suitable for the elderly - ask

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$728

4 BR / 4 BA / Sleeps 8

1 / 8

$728

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Spectacular 4 Bedroom Villa with View of the Caribbean Sea in Montego Bay

Montego Bay villa
4 BR / 4 BA / Sleeps 8 | Quick view

Details

When Round Hill was only an undeveloped knob of lush green hillside rising over the sea, one man had the good fortune to have his choice of lots, and the wisdom to choose that piece of land most favored by the sun and prevailing tradewinds, which also happened to have one of the most spectacular views in all the …
  • Shared outdoor pool (unheated)
  • Internet Access
  • A/C or climate control
  • Balcony or terrace
  • Fitness Room
  • Pet friendly - ask
  • Smoking allowed - ask
  • Suitable for children
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask

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$1,300

4 BR / 4 BA / Sleeps 8

1 / 18

$1,300

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Seaside Cottage on Round Hill

Montego Bay villa
4 BR / 4 BA / Sleeps 8 | Quick view

Details

Seaside Cottage is a four-bedroom private home at famous Round Hill. Its exquisite location provides one of the most spectacular views in the Caribbean. Hidden from the awareness of others ... this cottage is only minutes from all amenities of posh Round Hill Hotel and beach club. Additional amenities include: golf …
  • Waterfront
  • Shared outdoor pool (unheated)
  • Internet Access
  • A/C or climate control
  • Pet friendly - ask
  • Smoking allowed - ask
  • Suitable for children
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask

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$1,000

5 BR / 6 BA / Sleeps 10

1 / 24

$1,000

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Contemporary 5 Bedroom Villa in Montego Bay

Montego Bay villa
5 BR / 6 BA / Sleeps 10 | Quick view

Details

Five bedroom, five bathroom private villa on 220 private acres. 7,000 square feet of indoor and outdoor living space. 20' x 40' private pool. Tennis court lit for night play. Five cable televisions in all bedrooms. 42'' LCD cable television with Direct TV, VCR, DVD in living room. Bose music sound system. …
  • Shared outdoor pool (unheated)
  • Hot Tub/Jacuzzi
  • Internet Access
  • A/C or climate control
  • Pet friendly - ask
  • Smoking allowed - ask
  • Suitable for children - ask
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask

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$1,948

6 BR / 6 BA / Sleeps 12

1 / 30

$1,948

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Villa Viviana at Tryall, 6 acres of land-golf carts to explore it and full staff

Montego Bay villa
6 BR / 6 BA / Sleeps 12 | Quick view

Details

Majestic ocean views and a lion’s head water fountain await you at Villa Viviana. The property is part of the famed Tryall Club, ranked by Condé Nast as one of the best places to stay in the world. A true golfer’s paradise, this villa provides all the perks required for a relaxing and rejuvenating stay. The villa…
  • Shared outdoor pool (unheated)
  • Internet Access
  • Television
  • DVD Player
  • VCR
  • Pet friendly - ask
  • Smoking allowed - ask
  • Suitable for children - ask
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask

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$1,558

6 BR / 8 BA / Sleeps 12

1 / 25

$1,558

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Astonishing 6 Bedroom Villa in Montego Bay

Montego Bay villa
6 BR / 8 BA / Sleeps 12 | Quick view

Details

Onsite staff includes chef, butlers, housekeeper, laundress and gardener. Two acres of spacious, landscaped grounds with soccer goals and lawn games. Sirius XM radio with 200 channels. Handicap accessible: 36" doorways, seamless entrances to large showers - perfect family home, extremely child friendly Option of …
  • Shared outdoor pool (unheated)
  • Wireless Internet
  • A/C or climate control
  • Television
  • Stereo or CD player
  • Pet friendly - ask
  • Smoking allowed - ask
  • Suitable for children
  • Suitable for the elderly
  • Wheelchair accessible

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$280

3 BR / 5 BA / Sleeps 6

1 / 28

$280

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Windfall Villas... FREE TRANSPORTATION !

Montego Bay villa
3 BR / 5 BA / Sleeps 6 | Quick view

Details

Hello I'm Mel, Thank you for looking at Windfall Villas, I'm sure you will enjoy your stay with us. While deciding on a place to stay, your comfort and safety is first, It also has to be cost friendly….within your budget. With that in mind lets talk about what you get. Free transportation to A fully equipped, user …
  • Ocean or water views
  • Mountain Views
  • Wireless Internet
  • Housekeeping Optional
  • Washing Machine
  • Pet friendly - ask
  • Smoking allowed
  • Suitable for children
  • Suitable for the elderly
  • Wheelchair accessible - ask

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$200

1 BR / 1 BA / Sleeps 3

1 / 22

$200

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Caribbean Soul Guest House with Private Driver

Montego Bay condo
1 BR / 1 BA / Sleeps 3 | Quick view

Details

Caribbean Soul is located in the newly built gated community of Miramar in Unity Hall, Montego Bay. The location is 5 minutes from downtown Montego Bay with ample shopping and dining experiences to choose from. Our property has a state of the art swimming pool and thermal controlled hot tub with sea and mountain view…
  • Shared outdoor pool (unheated)
  • Hot Tub/Jacuzzi
  • Internet Access
  • Washing Machine
  • Clothes Dryer
  • Suitable for children - ask
  • Wheelchair accessible - ask

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$1,430

6 BR / 0 BA / Sleeps 12

1 / 25

$1,430

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BEACH CLUB! TENNIS! GOLF! POOL! Following Seas

Montego Bay house
6 BR / Sleeps 12 | Quick view

Details

Following Seas at the Tryall Club is a fabulous private villa in Montego Bay, with premier rating among villa rentals in Jamaica. The 8,000 square foot villa has recently been renovated with tasteful décor, thoughtful amenities and every imaginable comfort. The villa's architecture is classic Jamaican, with all the …
  • Private Beach
  • Ocean or water views
  • Mountain Views
  • Internet Access
  • Washing Machine
  • Smoking allowed - ask
  • Suitable for the elderly - ask

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$1,215

4 BR / 4 BA / Sleeps 8

1 / 20

$1,215

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SPECTACULAR! BEACH MEMBERSHIP! Destiny Villa

Montego Bay house
4 BR / 4 BA / Sleeps 8 | Quick view

Details

Destiny Villa in Montego Bay offers some of the most spectacular views of the sparkling Caribbean Sea, the densely wooded great river valley, dramatic mountains and Montego Bay. The villa itself has the most dramatic architecture, beautifully landscaped gardens, lovely décor and very spacious rooms, making it unique …
  • Ocean or water views
  • Mountain Views
  • Internet Access
  • Outdoor Dining Area
  • A/C or climate control
  • Suitable for children
  • Suitable for the elderly
  • Wheelchair accessible

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$130

18 BR / 15 BA / Sleeps 36

1 / 28

$130

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Sea View Heights Villa Montego Bay

Montego Bay villa
18 BR / 15 BA / Sleeps 36 | Quick view

Details

Sea View Heights Villa Montego Bay, is a lovely private home surrounded by real authentic Jamaican homes, and luscious countryside. The villa is tastefully decorated in colorful recreational fabrics, satellite TV, VCR, Stereo and comfortable furniture inside and out. The spacious bedrooms are similarly furnished, …
  • Waterfront
  • Ocean or water views
  • Hot Tub/Jacuzzi
  • Internet Access
  • Housekeeping Optional
  • Suitable for children - ask
  • Suitable for the elderly - ask

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$786

3 BR / 3 BA / Sleeps 6

1 / 27

$786

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Goat Hill

Montego Bay house
3 BR / 3 BA / Sleeps 6 | Quick view

Details

Goat Hill sits on a remarkable site, located specifically to benefit from the spectacular view of the Caribbean Sea and the most favorable trade-winds day and night. The east view captures the sunrise, Montego Bay and the Great River ~ the west view is an equally lovely vista toward Round Hill, the Caribbean Sea and …
  • Ocean or water views
  • Shared outdoor pool (unheated)
  • Hot Tub/Jacuzzi
  • Microwave
  • Satellite or cable TV
  • Suitable for children - ask
  • Suitable for the elderly - ask

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$1,715

5 BR / 5 BA / Sleeps 1

1 / 23

$1,715

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Sundance

Montego Bay house
5 BR / 5 BA / Sleeps 1 | Quick view

Details

Sundance is a stunning five bedroom, traditional Palladian style villa completed in 2006, extending to 6,000 square feet and occupying a quiet two-acre site, off Mahogany Drive, with views of the Caribbean. Antique brick and Italian tiled terraces, pathways and extensive planted areas create a magnificent setting for …
  • Ocean or water views
  • Hot Tub/Jacuzzi
  • Safe
  • Microwave
  • Satellite or cable TV
  • Suitable for children - ask
  • Suitable for the elderly - ask

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$140

1 BR / 1 BA / Sleeps 4

1 / 29

$140

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Affordable Elegance in Luxurious Beach Front Condo

Montego Bay condo
1 BR / 1 BA / Sleeps 4 | Quick view

Details

This luxurious well appointed one bedroom condominium is located at the Palmyra in an exclusive part of Montego Bay. It has its own private beach. Imagine the pristine white sand beaches of the Caribbean, cradled by lush tropical mountains and the warm ocean air, and you will picture The Palmyra. On the northeast …
  • Waterfront
  • Hot Tub/Jacuzzi
  • Internet Access
  • Washing Machine
  • Clothes Dryer
  • Suitable for children - ask
  • Suitable for the elderly - ask

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$1,429

5 BR / 3 BA / Sleeps 10

1 / 21

$1,429

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Someday Soon

Montego Bay house
5 BR / 3 BA / Sleeps 10 | Quick view

Details

Someday Soon has recently undergone a major renovation and has reopened as a stunning new Premier villa. This secluded villa is located on a gentle sloping hillside, has spectacular views of the Caribbean Sea and is also conveniently located near Tryall's tennis courts and the Great House. This is a most charming …
  • Ocean or water views
  • Shared outdoor pool (unheated)
  • Hot Tub/Jacuzzi
  • Microwave
  • Satellite or cable TV
  • Suitable for children - ask
  • Suitable for the elderly - ask

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$1,299

5 BR / 5 BA / Sleeps 10

1 / 33

$1,299

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Lolita at the Tryall Club

Ironshore house
5 BR / 5 BA / Sleeps 10 | Quick view

Details

Lolita is a remarkable new architectural achievement: a 14,500-square-foot modern villa on a four-acre site chosen for its breathtaking view of the deep blue Caribbean Sea! In textures of rich mahogany, Italian Travertine and handsome granite, Lolita was designed by noted Chicago architect Tom Reed (see also Silent …
  • Hot Tub/Jacuzzi
  • Internet Access
  • Pet friendly - ask
  • Smoking allowed - ask
  • Suitable for children - ask
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask

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$565

4 BR / 4 BA / Sleeps 8

1 / 8

$565

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Almond Hill

Montego Bay house
4 BR / 4 BA / Sleeps 8 | Quick view

Details

Designed by Prince Kasimir Korybut in 1993, Almond Hill is a lovely private home located on a former coconut plantation just 20 minutes from Montego Bay and one minute from posh Round Hill where guests enjoy complimentary resort membership. The villa is tastefully decorated with comfortable furniture inside and out. …
  • Internet Access
  • A/C or climate control
  • Satellite or cable TV
  • DVD Player
  • Pet friendly - ask
  • Smoking allowed - ask
  • Suitable for children - ask
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask

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$786

5 BR / 5 BA / Sleeps 10

1 / 25

$786

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Cielo at the Tryall Club

Ironshore house
5 BR / 5 BA / Sleeps 10 | Quick view

Details

The villa's layout in three wings and a separate cottage is marvelous for two and three generation families. Cielo is notable for not only its breathtaking views but also for its spacious bedrooms, very large lawns for kids to play and its marvelous, much-lauded Chef Valrie who knows her stuff brilliantly when it …
  • Hot Tub/Jacuzzi
  • Internet Access
  • A/C or climate control
  • Satellite or cable TV
  • Pet friendly - ask
  • Smoking allowed - ask
  • Suitable for children - ask
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask

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$643

6 BR / 6 BA / Sleeps 15

1 / 29

$643

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Pimento Hill

Montego Bay house
6 BR / 6 BA / Sleeps 15 | Quick view

Details

Pimento Hill is a spacious private home with a legendary history. The villa overlooks the Caribbean Sea and is located just five minutes from chic Round Hill where guests enjoy complimentary membership.It was originally built in the late 1950’s for French Count and Countess Jacques and Vera di Sibour in the period …
  • Hot Tub/Jacuzzi
  • Internet Access
  • A/C or climate control
  • Pet friendly - ask
  • Smoking allowed - ask
  • Suitable for children - ask
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask

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$1,429

5 BR / 5 BA / Sleeps 10

1 / 24

$1,429

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Sea Salt

Montego Bay house
5 BR / 5 BA / Sleeps 10 | Quick view

Details

Sea Salt is a brand new addition to the exclusive Tryall Club, built in 2007, Sea Salt is one of the most welcoming private homes that grace the northern coast of this Caribbean paradise. Inside, you'll find classic Jamaican architecture and 7,700 sq. ft. of living, dining and entertaining space. Outside, you're …
  • Ocean or water views
  • Shared outdoor pool (unheated)
  • Hot Tub/Jacuzzi
  • A/C or climate control
  • Microwave
  • Suitable for children - ask
  • Suitable for the elderly - ask

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$1,371

7 BR / 7 BA / Sleeps 12

3 Reviews

$1,371

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Greatview

Montego Bay villa
7 BR / 7 BA / Sleeps 12 | Quick view
“ Excellent ” 3 Reviews

Details

Reviews

(3)

Greatview is one of the newest and most luxurious of the Montego Bay, Spring Farm villas overlooking the Half Moon Bay golf course and the Caribbean Sea. It is immediately apparent why the owners chose this name for their villa. From the colorful blue hues of the Caribbean Sea to the green mountains beyond, the …
  • Hot Tub/Jacuzzi
  • Sauna
  • Internet Access
  • Washing Machine
  • Clothes Dryer
  • Suitable for children
  • Suitable for the elderly - ask
  • Wheelchair accessible

Details

Reviews

(3)

Spring Farms Finest

Left on Mar 20, 2013 for a stay in March 2005

This villa was absolutely amazing. Our compliments to the owner and architect. The view is as true as the villa name. The house was furnished impecably and the staff was outstanding. This house is a 5 star resort with the privacy of your own villa. We couldnt say enough about this villa!

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$1,285

5 BR / 5 BA / Sleeps 12

1 / 20

$1,285

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5 Bedroom Villa with Pool in Montego Bay

Montego Bay villa
5 BR / 5 BA / Sleeps 12 | Quick view

Details

Round Hill membership: complimentary beach, tennis, two connecting heated pools for parents and children, jogging trail, Manager's Cocktail Party. For various fees: Pineapple Kids Club, fitness room, tennis lessons, hair salon and spa, bars and restaurants, gift shops, water sports, Internet room, beach parties Mon-…
  • Shared outdoor pool (unheated)
  • Hot Tub/Jacuzzi
  • Wireless Internet
  • A/C or climate control
  • Satellite or cable TV
  • Pet friendly - ask
  • Smoking allowed - ask
  • Suitable for children
  • Suitable for the elderly
  • Wheelchair accessible - ask

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$1,428

4 BR / 4 BA / Sleeps 8

1 / 26

$1,428

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Round Hill 4br

Montego Bay villa
4 BR / 4 BA / Sleeps 8 | Quick view

Details

There are 27 individually owned villas with 74 suites surrounded by 30 acres of tropical gardens. Villas or cottages contain 2, 3, 4 and 5 suites, each with private, complete villa with private pool or suites in villas with a shared pool; 23 villas have their own pool. The villas are beautifully decorated individual …
  • Fitness Room
  • Safe
  • Ceiling Fans
  • Suitable for children
  • Suitable for the elderly - ask

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$1,559

5 BR / 5 BA / Sleeps 10

1 / 35

$1,559

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None VL SST

Montego Bay house
5 BR / 5 BA / Sleeps 10 | Quick view

Details

Villa VL SST is one of the most stylish additions to the gated Tryall community. Tryall is a private club with amenities such as a private beach, water sports, tennis, an excellent gym, the Hummingbird Kids Club, Great House afternoon tea, the Manager's Cocktail Party, and various special events. Golf, food and …
  • Hot Tub/Jacuzzi
  • Internet Access
  • A/C or climate control
  • Fitness Room
  • Satellite or cable TV
  • Pet friendly - ask
  • Smoking allowed - ask
  • Suitable for children - ask
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask

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$1,715

5 BR / 5 BA / Sleeps 10

1 / 18

$1,715

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Villa Stella

Montego Bay house
5 BR / 5 BA / Sleeps 10 | Quick view

Details

Villa Stella, just recently completely renovated, offers breathtaking views of the Caribbean Sea and the Tryall Club estate from Copperwood Ridge. Stylish interiors, attention to details, travertine marble, wooden floors and a gorgeous terrace with oversized swimming pool and deck overlooking the sea make Villa Stella…
  • Ocean or water views
  • Shared outdoor pool (unheated)
  • Patio
  • Safe
  • Satellite or cable TV
  • Suitable for children - ask
  • Suitable for the elderly - ask

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$786

4 BR / 4 BA / Sleeps 10

1 / 30

$786

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Fabulous 4 Bedroom Villa with private Pool & Garden in Montego Bay

Montego Bay villa
4 BR / 4 BA / Sleeps 10 | Quick view

Details

The Tryall Club Temporary Membership Fee (see paragraph below). The Tryall Club Membership: Complimentary beach, tennis, gym, pool, Hummingbird Kids Club, non-motorized water sports, internet room, new Usain Bolt Games Room for kids, teens and adults, jogging trail, afternoon tea and Manager's Cocktail Party. …
  • Shared outdoor pool (unheated)
  • Internet Access
  • A/C or climate control
  • Fitness Room
  • Satellite or cable TV
  • Pet friendly - ask
  • Smoking allowed - ask
  • Suitable for children - ask
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask

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$786

3 BR / 3 BA / Sleeps 6

1 / 19

$786

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Goat Hill

Montego Bay house
3 BR / 3 BA / Sleeps 6 | Quick view

Details

Goat Hill sits on a remarkable site, located specifically to benefit from the spectacular view of the Caribbean Sea and the most favorable tradewinds day and night. The east view captures the sunrise, Montego Bay and the Great River - the west view is an equally lovely vista toward Round Hill, the Caribbean Sea and …
  • Hot Tub/Jacuzzi
  • Internet Access
  • A/C or climate control
  • Pet friendly - ask
  • Smoking allowed - ask
  • Suitable for children - ask
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask

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$2,000

6 BR / 14 BA / Sleeps 12

1 / 39

$2,000

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Flower Hill

Montego Bay house
6 BR / 14 BA / Sleeps 12 | Quick view

Details

Flower Hill - This breathtaking and luxurious 18,000 sq. ft. villa completed in the summer of 2012 is located in the Montego Bay, Spring Farm villas overlooking the Half Moon Resort golf course and the Caribbean Sea. The 6-bedroom 14-bathroom villas was constructed using the finest materials and with immaculate …
  • Ocean or water views
  • Shared outdoor pool (unheated)
  • Hot Tub/Jacuzzi
  • A/C or climate control
  • Patio
  • Suitable for children - ask
  • Suitable for the elderly - ask

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$358

1 BR / 2 BA / Sleeps 2

1 / 35

$358

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Attractive 1 Bedroom Villa in Montego Bay

Montego Bay villa
1 BR / 2 BA / Sleeps 2 | Quick view

Details

Mirador is a stylish one bedroom apartment at the posh Tryall Club. Its prize location provides both proximity to the elegant Tryall Club Great House and a breathtaking view over the deep blue Caribbean Sea and the manicured championship golf course. Guests are provided free overseas calls to the United States, …
  • Hot Tub/Jacuzzi
  • Internet Access
  • Washing Machine
  • Clothes Dryer
  • A/C or climate control
  • Pet friendly - ask
  • Smoking allowed - ask
  • Suitable for children - ask
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask

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$786

4 BR / 4 BA / Sleeps 8

1 / 12

$786

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Coo Yah

Montego Bay house
4 BR / 4 BA / Sleeps 8 | Quick view

Details

Coo Yah is a deluxe four-bedroom villa located in the renowned Tryall Club on the west side of Montego Bay. Coo yah is Jamaican patois for Look here. And what you will find is a spectacular newly renovated (2009) villa overlooking the golf course and Caribbean Sea. The villa is architect designed and is uniquely …
  • Ocean or water views
  • Shared outdoor pool (unheated)
  • Hot Tub/Jacuzzi
  • Microwave
  • Satellite or cable TV
  • Suitable for children - ask
  • Suitable for the elderly - ask

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$1,372

6 BR / 8 BA / Sleeps 14

1 / 37

$1,372

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6 Bedroom Villa with Veranda overlooking the Pool in Montego Bay

Montego Bay villa
6 BR / 8 BA / Sleeps 14 | Quick view

Details

Seventh very private bedroom available on request; ask us for rates and availability. Onsite staff includes two butlers, chef, housekeepers, gardener laundress and 24 hour concierge service. Air conditioned gym with recumbent bicycle, treadmill, stair master, free weights, exercise balls, mats and television. …
  • Shared outdoor pool (unheated)
  • Hot Tub/Jacuzzi
  • Internet Access
  • A/C or climate control
  • Books
  • Pet friendly - ask
  • Smoking allowed
  • Suitable for children
  • Suitable for the elderly
  • Wheelchair accessible
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