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$730

4 BR / 4 BA / Sleeps 8

Beautiful Beachfront Villa with Private Pool - Montego Bay vacation rentals
1 / 13

$730

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Beautiful Beachfront Villa with Private Pool

4 BR / 4 BA / Sleeps 8 | Quick view

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Welcome to Calypso Shores, a stunning fully staffed, waterfront villa with its own private beach and pool. Ten minutes from the airport in beautiful Montego Bay. Exclusive VIP service at the airport upon arrival. Located in a lovely gated community with round the clock security, tennis courts, work out facilities, and…
  • Shared outdoor pool (unheated)
  • Hot Tub/Jacuzzi
  • Internet Access
  • Clothes Dryer
  • Balcony or terrace
  • Suitable for children
  • Suitable for the elderly - ask
  • Wheelchair accessible

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$1,559

6 BR / 8 BA / Sleeps 14

Rose Cottage at the Tryall Club - Montego Bay vacation rentals
1 / 21

$1,559

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Rose Cottage at the Tryall Club

6 BR / 8 BA / Sleeps 14 | Quick view

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Rose Cottage is a large and lavish new home with glorious views of the lush Jamaican mountains and the deep blue Caribbean Sea. Its design is a stylish blend of Jamaican, Asian and European elements with an emphasis on extraordinary comfort. Additional amenities include: ping pong table, piano, snorkel gear, golf on …
  • Heated Pool
  • Hot Tub/Jacuzzi
  • Internet Access
  • A/C or climate control
  • Pet friendly - ask
  • Smoking allowed - ask
  • Suitable for children
  • Suitable for the elderly - ask
  • Wheelchair accessible

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$730

4 BR / 4 BA / Sleeps 8

1 Reviews

$730

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Calypso Shores on the Beach

4 BR / 4 BA / Sleeps 8 | Quick view
“ Excellent ” 1 Reviews

Details

Reviews

(1)

Located in a lovely California-style residential neighborhood named Lagoons, Calypso Shores is one of the newest homes in this collection. Its prize location is a beachfront acre on a calm lagoon. Lovers of water sports will revel in this location. Additional amenities include: poolside shower, golf available, beach …
  • Waterfront
  • Shared outdoor pool (unheated)
  • Hot Tub/Jacuzzi
  • Internet Access
  • A/C or climate control
  • Pet friendly - ask
  • Smoking allowed - ask
  • Suitable for children
  • Suitable for the elderly - ask
  • Wheelchair accessible

Details

Reviews

(1)

The best vacation trip yet!

Left on May 28, 2014 for a stay in May 2014

Everything about this trip was fabulous!!! From the time we got off the plane and had VIP treatment thru customs, till the time we arrived at the house all the way up to the time we had to depart and go home!!!

The house is wonderful, the staff was very professional, friendly, and catered to all of our needs. No matter what we needed it was "no problem". The food was great and the service was …

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$1,285

5 BR / 6 BA / Sleeps 13

2 Reviews

$1,285

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Knockando on Round Hill

5 BR / 6 BA / Sleeps 13 | Quick view
“ Excellent ” 2 Reviews

Details

Reviews

(2)

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 …
  • Shared outdoor pool (unheated)
  • Hot Tub/Jacuzzi
  • Internet Access
  • A/C or climate control
  • Pet friendly - ask
  • Smoking allowed - ask
  • Suitable for children
  • Suitable for the elderly - ask
  • Wheelchair accessible

Details

Reviews

(2)

Knockando villa is delightful with a spectacular view and a warm

Left on Jun 14, 2013 for a stay in January 2013

This was our 10th stay in Linda Smith's villas and 5th time at Knockando which is our favorite. Trip #11 is already reserved at Knockando in 2014. The view is magnificent down the coastline and changes as the sun moves across the sky each day. The villa is perfect for our group of 8 women with lots of spots to gather or just relax and read a book. And the Staff!!! They're the best!! After 5 …

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$700

7 BR / 7 BA / Sleeps 18

1 Reviews

$700

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Celebrity Villa Jamaica

7 BR / 7 BA / Sleeps 18 | Quick view
“ Excellent ” 1 Reviews

Details

Reviews

(1)

Come to Celebrity Villa Jamaica where the luxurious accommodations and impeccable service are fit for a STAR celebrity! The beautiful mansion is a NEW CONSTRUCTION 6,000 sq ft 7 BR/ 7 BA plush estate home nestled on an ocean view mountain in the prestigious Iron Shore resort community in Montego Bay, Jamaica. The …
  • Ocean or water views
  • Mountain Views
  • Shared outdoor pool (unheated)
  • Hot Tub/Jacuzzi
  • Internet Access
  • Suitable for children
  • Suitable for the elderly
  • Wheelchair accessible

Details

Reviews

(1)

A Gem from all aspects of vacation travel and needs!

Left on Mar 22, 2015 for a stay in March 2015

The layout and condition of the Villa was perfect! The staff were great; Chef Michael always had a wonderful meal primed and ready! Richard drive us to the best spots on the island and served as a personal Concierge telling us what was good and the price we should pay. Jason and Nick was always around, like a personal body guard! When we went to dancing, they were right there with extra eyes…

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$150

1 BR / 2 BA / Sleeps 4

2 Reviews

$150

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One Bedroom Luxury Condo Montego Bay Jamaica,

1 BR / 2 BA / Sleeps 4 | Quick view
“ Very Good ” 2 Reviews

Details

Reviews

(2)

These units are hardly ever put up for rent. This is one of the large one bedroom condos at the Palmyra with a more expansive kitchen. The unit has 2 full bathrooms, high ceilings, air condition throughout which is not universal to all condos now. The patio is large enough to accommodate ten persons and the view is …
  • Hot Tub/Jacuzzi
  • Sauna
  • Internet Access
  • Washing Machine
  • Clothes Dryer
  • Pet friendly - ask
  • Smoking allowed - ask
  • Suitable for children
  • Suitable for the elderly
  • Wheelchair accessible

Details

Reviews

(2)

Great Scenery

Left on Oct 12, 2014 for a stay in October 2014

My husband and I visited this property for our 5th Wedding Anniversary, and though some parts of the property were going through renovation or up-keep, majority of what we saw was beautiful. The ocean views are breath-taken, and the private breach was very quiet. We were told that the property was experiencing a change of ownership - which may have been the reasons why we had some issues more …

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$643

4 BR / 4 BA / Sleeps 8

1 Reviews

$643

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None VL TTC

4 BR / 4 BA / Sleeps 8 | Quick view
“ Excellent ” 1 Reviews

Details

Reviews

(1)

Villa VL TTC sits on two acres in the famous gated community of The Tryall Club, directly on the Caribbean Sea. 300 feet of waterfront form the north perimeter of the property. The water here is excellent for swimming and snorkeling. Sometimes the sea is as smooth as glass, and other times its waves break dramatically…
  • Shared outdoor pool (unheated)
  • Hot Tub/Jacuzzi
  • Internet Access
  • Outdoor Dining Area
  • A/C or climate control
  • Pet friendly - ask
  • Smoking allowed - ask
  • Suitable for children - ask
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask

Details

Reviews

(1)

The best vacation ever.

Left on Jun 06, 2014 for a stay in May 2014

The tradewinds is perfect, from location to amities. We went for a girls trip and loved being pampered by the staff and enjoying the grounds of the tryall country club. We could have stayed at our location for the whole week and been happy. Can't wait to come back. This would also be a great vacation property for families.

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$135

1 BR / 1 BA / Sleeps 4

11 Reviews

$135

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Luxurious 1 BdRm Ocean Front Condo in Montego Bay

1 BR / 1 BA / Sleeps 4 | Quick view
“ Excellent ” 11 Reviews

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Reviews

(11)

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. It's located 15 minutes from the airport. It has breathtaking view from balconies of the caribbean sea/pool area. Guests have full access to the Palmyra grounds with …
  • Waterfront
  • Ocean or water views
  • Shared outdoor pool (unheated)
  • Hot Tub/Jacuzzi
  • Internet Access
  • Suitable for children
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask

Details

Reviews

(11)

Great Place To Stay

Left on Feb 20, 2012 for a stay in February 2012

We had a wonderful time and experience. The staff was very friendly and helpful, everything was clean and well kept. The beach and location were great . I would come back in a heart beat.

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$1,143

6 BR / 6 BA / Sleeps 12

1 / 23

$1,143

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Endless Summer

6 BR / 6 BA / Sleeps 12 | Quick view

Details

One of the most glamorous villas in Jamaica, Endless Summer is a turreted mansion with breathtaking views of the Caribbean Sea. Additional amenities include: poolside shower, available for large groups, connecting bedroom(s), golf available, beach club, complimentary calls to the us, uk and canada, cook or chef …
  • Shared outdoor pool (unheated)
  • Hot Tub/Jacuzzi
  • Internet Access
  • A/C or climate control
  • Pet friendly - ask
  • Smoking allowed - ask
  • Suitable for children
  • Suitable for the elderly - ask
  • Wheelchair accessible

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$150

3 BR / 3 BA / Sleeps 6

1 / 6

$150

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SEA CASTLES PENTHOUSE

3 BR / 3 BA / Sleeps 6 | Quick view

Details

HEY MON ! I WANNA WISH YOU A VERY WARM WELCOME TO JAMAICA AND THE TROPICAL SHORES OF MONTEGO BAY A NICE BEAUTIFUL PENTHOUSE LOCATED IN A BEAUTIFUL AREA CALLED ROSEHALL MONTEGO BAY 15 MINUTES AWAY FROM AIRPORT.... PENTHOUSE INCLUDES *3 BEDROOMS *3 BATHROOMS *LIVING AND DINING *FULLY EQUIPED KITCHEN *DOUBLE SUN …
  • Waterfront
  • Ocean or water views
  • Mountain Views
  • Hot Tub/Jacuzzi
  • Housekeeping Optional
  • Smoking allowed
  • Suitable for children
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask

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$358

1 BR / 2 BA / Sleeps 4

1 / 36

$358

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Mirador at the Tryall Club ~ A Great House Villa Suite

1 BR / 2 BA / Sleeps 4 | 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. Additional amenities include: golf available, beach club, …
  • Hot Tub/Jacuzzi
  • 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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$550

7 BR / 7 BA / Sleeps 14

1 / 15

$550

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Thomas%20House

7 BR / 7 BA / Sleeps 14 | Quick view

Details

Thomas House is a spacious, beautiful, fully staffed 7-bedroom/71/2-bathroom private hillside villa located in the exclusive Spring Farm area. Overlooking the Caribbean Sea this villa provides the both spectacular views and privacy. Thomas House is located on the east side of Montego Bay, approximately 15 minutes from…
  • 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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$125

7 BR / 2 BA / Sleeps 4

1 Reviews

$125

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Waters Edge Guest House

7 BR / 2 BA / Sleeps 4 | Quick view
“ Excellent ” 1 Reviews

Details

Reviews

(1)

Waters Edge Guest house is a very luxurious Guest house located on the Unity hall main road, its taste of luxury will far reach all guest expectation, the Guest house boast eleven (11) 50 inches Samsung Smart Television , state of the art bathroom fixtures by Moen, exquisite furnishing by Thomasville Furniture …
  • Waterfront
  • Ocean or water views
  • Mountain Views
  • Hot Tub/Jacuzzi
  • Internet Access
  • Suitable for children

Details

Reviews

(1)

AMAZING

Left on Mar 05, 2015 for a stay in February 2015

me and my girlfriend stayed at the Waters Edge guest house for 4 days, and honestly it is one of the best places places I have ever stayed, the location is perfect the view is beyond beautiful and the rooms are extremely clean, l love this place.

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$2,571

6 BR / 14 BA / Sleeps 17

7 Reviews

$2,571

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Flower Hill Retreat in prestigious Spring Farm - Elegance Defined

6 BR / 14 BA / Sleeps 17 | Quick view
“ Excellent ” 7 Reviews

Details

Reviews

(7)

This elegant retreat nestled in the prestigious Spring Farm gated community is the ideal setting for a large gathering. At 18,000 square feet it perfectly accommodates five couples, with additional bedding available for groups of up to 17 guests. Once you drive in through the palm tree-lined entrance, step inside this…
  • Shared outdoor pool (unheated)
  • Hot Tub/Jacuzzi
  • Internet Access
  • A/C or climate control
  • Fitness Room
  • Pet friendly - ask
  • Smoking allowed - ask
  • Suitable for children - ask
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask

Details

Reviews

(7)

A little piece of heaven

Left on Mar 18, 2013 for a stay in March 2013

We have traveled quite a bit over the years, staying in condos, resorts and villas with and without staff. Our stay at Flower Hill was by far our favourite trip.The view from the villa is unforgettable, rain or shine. Chef Ardel exceeded our expectations each and every day. He is truly a talented chef. Our butlers, William and Keneil had a wonderful way of making our day relaxing and fun.…

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$1,429

6 BR / 6 BA / Sleeps 12

1 / 30

$1,429

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Anticipation

6 BR / 6 BA / Sleeps 12 | Quick view

Details

Anticipation is privately nestled on the hillside of the world renowned Tryall Club with an uninterrupted 180 degree panoramic view of the Caribbean Ocean. It is arguably one of the best positioned locations at Tryall Club. The six bedroom contemporary villa is an elegant merger of Caribbean architecture and European …
  • Ocean or water views
  • Hot Tub/Jacuzzi
  • Microwave
  • Satellite or cable TV
  • DVD Player
  • Suitable for children - ask
  • Suitable for the elderly - ask

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$2,571

6 BR / 14 BA / Sleeps 14

1 / 47

$2,571

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Extraordinary 6 Bedroom Villa in Montego Bay

6 BR / 14 BA / Sleeps 14 | Quick view

Details

Gym: incliner trainer treadmill, double-sided half-cage with Olympic bars and weights bench, elliptical bike, cybex trainer, cable cross, punch kettle bells, fitness balls and yoga mats. Spa with two tables and cedar steam room: massage, facial, body scrub, manicure, pedicure. 100"projection theater in Serengeti …
  • Shared outdoor pool (unheated)
  • Hot Tub/Jacuzzi
  • Wireless Internet
  • A/C or climate control
  • Television
  • Pet friendly - ask
  • Smoking allowed - ask
  • Suitable for children
  • Suitable for the elderly
  • Wheelchair accessible

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$1,169

5 BR / 5 BA / Sleeps 12

1 / 22

$1,169

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Modern 5 Bedroom Villa with Private Terrace & Pool in Montego Bay

5 BR / 5 BA / Sleeps 12 | Quick view

Details

Highest Premier rating named villa of the year 2009. Onsite staff includes chef, butler, housekeepers, gardeners and laundress. Excellent multi-speaker sound system and Sirius radio. Private air conditioned gym and steam room. The Tryall Club Temporary Membership Fee (see paragraph below). The Tryall Club …
  • Shared outdoor pool (unheated)
  • Hot Tub/Jacuzzi
  • Wireless Internet
  • A/C or climate control
  • Books
  • Pet friendly - ask
  • Smoking allowed - ask
  • Suitable for children
  • Suitable for the elderly - ask
  • Wheelchair accessible

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$1,169

6 BR / 8 BA / Sleeps 12

1 / 28

$1,169

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6 Bedroom Villa with View in Montego Bay

6 BR / 8 BA / Sleeps 12 | Quick view

Details

Highest premier rating. Onsite staff includes chef, butler, housekeepers, gardeners and laundress. Personal gym. Laptop, printer, copier and scanner. Free overseas calls to United States, United Kingdom and Canada. The Tryall Club Temporary Membership Fee (see paragraph below). The Tryall Club Membership: …
  • Shared outdoor pool (unheated)
  • Hot Tub/Jacuzzi
  • Internet Access
  • A/C or climate control
  • Balcony or terrace
  • Pet friendly - ask
  • Smoking allowed - ask
  • Suitable for children
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask

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$929

5 BR / 6 BA / Sleeps 10

1 / 12

$929

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None VL PAV

5 BR / 6 BA / Sleeps 10 | Quick view

Details

VL PAV 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. A complimentary Half Moon Golf, Tennis & Beach Club Membership make villa VL …
  • Shared outdoor pool (unheated)
  • Hot Tub/Jacuzzi
  • Internet Access
  • 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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$1,949

6 BR / 8 BA / Sleeps 12

1 / 25

$1,949

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None VL VVT

6 BR / 8 BA / Sleeps 12 | Quick view

Details

Villa VL VVT has a quarter-mile driveway with brilliant bougainvillea on all sides and leads to a Travertine-paved Italianate courtyard, and dramatic entrance. On a remarkable six private acres at the prestigious Tryall Club, VL VVT is uniquely private, wonderfully quiet, and tranquil while just minutes away by …
  • Hot Tub/Jacuzzi
  • Internet Access
  • Outdoor Dining Area
  • A/C or climate control
  • Fitness Room
  • Pet friendly - ask
  • Smoking allowed - ask
  • Suitable for children - ask
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask

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$2,078

7 BR / 8 BA / Sleeps 14

1 / 15

$2,078

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None VL PTC

7 BR / 8 BA / Sleeps 14 | Quick view

Details

Villa VL PTC sits on a spectacular seascape on Jamaica's lush North Coast at the luxurious Tryall Club 12 miles west of Montego Bay. The beach club, pro shop, first tee, and driving range are within walking distance of the villas front door. Nine Laykold tennis courts are just a golf cart ride up the hill. Tryall …
  • Shared outdoor pool (unheated)
  • 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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$708

4 BR / 4 BA / Sleeps 8

1 / 12

$708

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Sunrise%20Villa

4 BR / 4 BA / Sleeps 8 | Quick view

Details

Sunrise is a lovely four bedroom, comfortably furnished, villa located beach front in Tryall Club. The villas splendid location looks out over a private beach and the clear-blue shallows of the Caribbean Sea to a snorkeling reef and the indigo waters beyond. Just across the lane are the green fairways of Tryall Club&…
  • Waterfront
  • Ocean or water views
  • Shared outdoor pool (unheated)
  • Hot Tub/Jacuzzi
  • Microwave
  • Suitable for children - ask
  • Suitable for the elderly - ask

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$1,429

5 BR / 5 BA / Sleeps 10

1 / 16

$1,429

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Villa%20Lolita

5 BR / 5 BA / Sleeps 10 | Quick view

Details

Villa Lolita is one of Tryall's newest and most fabulously equipped Premier luxury villas! It is 14,000 square feet of dramatically designed new construction, built in the fall of 2008. You'll be surrounded by beautiful panoramic views of the ocean and mountains found only in the Caribbean. This 5 bedroom home is …
  • 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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$1,299

6 BR / 8 BA / Sleeps 12

1 Reviews

$1,299

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Viviana at the Tryall Club

6 BR / 8 BA / Sleeps 12 | Quick view
“ Excellent ” 1 Reviews

Details

Reviews

(1)

On a remarkable six private acres on a plum site at the prestigious Tryall Club, Viviana is distinguished by the top rank of Premier. Uniquely private, the feeling is being in a world of your own, wonderfully quiet and tranquil while just minutes away by complimentary golf cart are the amenities that have defined the …
  • Shared outdoor pool (unheated)
  • Hot Tub/Jacuzzi
  • Internet Access
  • A/C or climate control
  • Pet friendly - ask
  • Smoking allowed - ask
  • Suitable for children
  • Suitable for the elderly - ask
  • Wheelchair accessible

Details

Reviews

(1)

Completely Wonderful Experience

Left on Jun 14, 2013 for a stay in February 2013

If anyone asks me to recommend a villa expert in the Caribbean, Villas By Linda Smith is where I would send them. And my entire family would do the same. Our representatives (we have had more than one over the years) have always exceeded our expectations in service, timeliness, and advice. We are lucky to have a group with both a professional and friendly approach. The home we stayed in, …

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$1,371

6 BR / 8 BA / Sleeps 14

8 Reviews

$1,371

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Greatview Villa - Fully Staffed, Treehouse, Kids Club, Golf Course

6 BR / 8 BA / Sleeps 14 | Quick view
“ Excellent ” 8 Reviews

Details

Reviews

(8)

Almost like an illusion perched on the side of a mountain is Greatview, a magnificent villa in the Montego Bay area of Jamaica. The cliffhanging swimming pools at differing levels make a splendid sight from across the valley. The guiding hand of Greatviews creator and the commitment of its staff are evident in the …
  • Hot Tub/Jacuzzi
  • Internet Access
  • Housekeeping Optional
  • A/C or climate control
  • Fitness Room
  • Pet friendly - ask
  • Smoking allowed - ask
  • Suitable for children - ask
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask

Details

Reviews

(8)

Our Stay at Greatview

Left on Oct 27, 2010 for a stay in August 2010

great time at greatview, lovely family vacation

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$707

6 BR / 7 BA / Sleeps 13

1 / 40

$707

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Glamorous 6 Bedroom Villa in Montego Bay

6 BR / 7 BA / Sleeps 13 | 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 & spa, bars & restaurants, gift shops, water sports, Internet room, beach parties Mon-Wed-…
  • Shared outdoor pool (unheated)
  • Hot Tub/Jacuzzi
  • Wireless Internet
  • A/C or climate control
  • Television
  • Pet friendly - ask
  • Smoking allowed - ask
  • Suitable for children
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask

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$1,071

9 BR / 9 BA / Sleeps 18

1 / 24

$1,071

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Multi-level Summerhill Villa features Spanish architecture, freshwater pool & full staff

9 BR / 9 BA / Sleeps 18 | Quick view

Details

Summerhill Villa is a gated luxury destination located in the Springfarm area of Montego Bay. A private driver meets you upon your arrival at the airport. The scenic fifteen minute drive to your villa then takes you through several seaside resorts, the entrance of the world class Half Moon Golf Course and Country Club…
  • Shared outdoor pool (unheated)
  • Hot Tub/Jacuzzi
  • Internet Access
  • A/C or climate control
  • Books
  • Pet friendly - ask
  • Smoking allowed - ask
  • Suitable for children - ask
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask

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$1,948

7 BR / 7 BA / Sleeps 12

4 Reviews

$1,948

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Sugar Hill at Tryall Club with gym, pool, amazing ocean view and maid service

7 BR / 7 BA / Sleeps 12 | Quick view
“ Excellent ” 4 Reviews

Details

Reviews

(4)

Sugar Hill is an archetypal Jamaican villa that captures spectacular views of the shimmering Caribbean Sea, the edges of the northwest coastline and the lush surrounding hillside. Beautiful flowers and exotic birds inhabit the manicured tropical gardens. This golfer’s paradise is located at the famed Tryall Club in …
  • Hot Tub/Jacuzzi
  • A/C or climate control
  • Television
  • DVD Player
  • Ceiling Fans
  • Pet friendly - ask
  • Smoking allowed - ask
  • Suitable for children - ask
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask

Details

Reviews

(4)

Our Stay at Sugar Hill at Tryall

Left on Oct 14, 2011 for a stay in February 2011

The villa is wonderful, including the staff, whom we viewed as part of the family. The Tryall facilities are wonderful. From the time we were picked up at Sangster to the time, one week later, that we were dropped off there, we felt that we were being looked after by people who really cared that everything was going well for us.

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$940

7 BR / 9 BA / Sleeps 14

1 / 30

$940

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Stylish 7 Bedroom with Private Pool in Montego Bay

7 BR / 9 BA / Sleeps 14 | Quick view

Details

Today's Fairway Manor is a stylish multi-faceted 10,000 square foot private home, massively renovated with upgrades throughout. Its rooms overlook the famous Half Moon 18 hole Robert Trent Jones golf course and a dramatic panorama of the Caribbean Sea. Fairway Manor's well planned rooms open onto terraces and …
  • Shared outdoor pool (unheated)
  • Hot Tub/Jacuzzi
  • Internet Access
  • A/C or climate control
  • Balcony or terrace
  • Pet friendly - ask
  • Smoking allowed - ask
  • Suitable for children
  • 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

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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$858

4294967295 BR / 5 BA / Sleeps 2

1 / 29

$858

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Allamanda

5 BA / Sleeps 2 | Quick view

Details

Allamanda Villa completed in 2012, is an elegant five bedroom Caribbean vacation home. All on one level, the villa boasts a dramatic fifteen hundred square foot great room with soaring twenty foot ceilings and fifty feet of sliding glass doors that open up onto an expansive covered terrace.Master Bedroom 1 - (20Â&…
  • Ocean or water views
  • Hot Tub/Jacuzzi
  • Microwave
  • Satellite or cable TV
  • DVD Player
  • 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

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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$1,285

5 BR / 5 BA / Sleeps 12

1 / 20

$1,285

Inquire

5 Bedroom Villa with Pool in Montego Bay

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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$643

5 BR / 5 BA / Sleeps 1

1 / 19

$643

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Drambuie

5 BR / 5 BA / Sleeps 1 | Quick view

Details

Drambuie Estate is a spectacular 35 acre hilltop villa with extraordinary views of the sea and Montego Bay. The villa was built in the 1940's by the Duke of Malborough as their private winter residence. Using cut stone walls brought from England over 200 years ago as ships ballast, the villa is constructed to resemble…
  • Ocean or water views
  • Hot Tub/Jacuzzi
  • Patio
  • Satellite or cable TV
  • DVD Player
  • 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

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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$458

3 BR / 3 BA / Sleeps 7

1 / 10

$458

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Elegant 3 Bedroom Villa with Private Pool in Montego Bay

3 BR / 3 BA / Sleeps 7 | Quick view

Details

Deluxe private villa with a sweeping view of the blue Caribbean Sea and Montego Bay. Three bedrooms, two and a half bathrooms, there is also one daybed in children's play room. 16' x 32' private pool. Onsite staff includes a cook, housekeeper/laundress, gardener and butler. Digital satellite system, televisions, …
  • Shared outdoor pool (unheated)
  • Hot Tub/Jacuzzi
  • 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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$99

16 BR / 16 BA / Sleeps 32

2 Reviews

$99

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Sea View Heights Villa Montego Bay

16 BR / 16 BA / Sleeps 32 | Quick view
“ Excellent ” 2 Reviews

Details

Reviews

(2)

Located in Barrette Town - Rose Hall, Montego Bay Recently Completed in 2007, Sea View Heights Villa 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 …
  • Ocean or water views
  • Mountain Views
  • Shared outdoor pool (unheated)
  • Hot Tub/Jacuzzi
  • Internet Access
  • Pet friendly
  • Smoking allowed
  • Suitable for children
  • Suitable for the elderly
  • Wheelchair accessible

Details

Reviews

(2)

A Charming Home From Home in Rose Hall Jamaica

Left on Dec 12, 2011 for a stay in November 2011

Having spent a week at an all-inclusive we really wanted to experience something more authentic, the real Jamaica, and you cannot find more authentic a home than Sea View Heights in the charming little rural village of Barrette Town, Rose Hall, close to Montego Bay.

We had tired of the bland food and decor  of our all inclusive hotel. Tired of the constant flow of hustlers on the beach and …

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$1,428

5 BR / 5 BA / Sleeps 10

1 / 24

Details

With a sweeping view of the Caribbean Sea, Pineapple House is a spacious villa located on Copper Ridge, along Jamaicas exclusive North Shore. Distinctive in its architecture, Pineapple Houses extensive fret-work and Oliver Messel design is defined by its Messel-green shutters, coral stone exterior, authentic Saltillo …
  • Hot Tub/Jacuzzi
  • Internet Access
  • A/C or climate control
  • Fitness Room
  • Grill
  • Pet friendly - ask
  • Smoking allowed - ask
  • Suitable for children - ask
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask

PreviousNext property

$2,071

5 BR / 7 BA / Sleeps 10

1 / 17

$2,071

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Ocean view Trinity Villa at Tryall- infinity pool, near beach- award-winning golf

5 BR / 7 BA / Sleeps 10 | Quick view

Details

Located at the famed Tryall Club, Trinity Villa is a deluxe luxury destination situated high above the Caribbean Sea that boasts breathtaking views of the ocean, tropical forests and a championship eighteen hole golf course. The infinity pool itself is a feat of architecture with the stairs from the balcony above …
  • Shared outdoor pool (unheated)
  • Hot Tub/Jacuzzi
  • Internet Access
  • Washing Machine
  • Clothes Dryer
  • Pet friendly - ask
  • Smoking allowed - ask
  • Suitable for children - ask
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask

PreviousNext property

$1,299

6 BR / 6 BA / Sleeps 0

1 / 22

$1,299

Inquire

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

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

PreviousNext property

$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

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

PreviousNext property

$786

3 BR / 4 BA / Sleeps 6

1 / 30

$786

Inquire

Gleaming 3 Bedroom Villa with View of the Bay in Montego Bay

3 BR / 4 BA / Sleeps 6 | 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
  • Internet Access
  • A/C or climate control
  • Television
  • Pet friendly - ask
  • Smoking allowed - ask
  • Suitable for children - ask
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask

PreviousNext property

$1,143

6 BR / 6 BA / Sleeps 12

1 / 23

$1,143

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6 Bedroom Villa with Panoramic View of Golf Course & Ocean in Montego Bay

6 BR / 6 BA / Sleeps 12 | Quick view

Details

Endless Summer is a turreted mansion with views of the Caribbean Sea. From the porte cochere, beveled glass doors open to a dramatic 80' columned space. A sweeping white stone staircase curves gracefully from the foyer to a balustraded gallery encircling and overlooking the sunken living room, topped high above by the…
  • Shared outdoor pool (unheated)
  • Hot Tub/Jacuzzi
  • Internet Access
  • A/C or climate control
  • Balcony or terrace
  • 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

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

PreviousNext property

$929

5 BR / 5 BA / Sleeps 11

1 / 20

$929

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5 Bedroom Villa with Private Terrace in Montego Bay

5 BR / 5 BA / Sleeps 11 | Quick view

Details

A massive whole-house 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 immediately apparent. The view becomes…
  • Shared outdoor pool (unheated)
  • Hot Tub/Jacuzzi
  • Wireless Internet
  • A/C or climate control
  • Books
  • Pet friendly - ask
  • Smoking allowed - ask
  • Suitable for children
  • Suitable for the elderly - ask
  • Wheelchair accessible - 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

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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$1,786

7 BR / 7 BA / Sleeps 14

1 / 24

$1,786

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Tremendous 7 Bedroom Villa with View in Montego Bay

7 BR / 7 BA / Sleeps 14 | Quick view

Details

Seven bedrooms (four bedroom main house and three bedroom cottage) and seven en suite bathrooms. Onsite staff includes butler, cook, housekeeper, laundress and gardeners. Round Hill Membership: Complimentary beach, fitness room, two connecting heated pools for parents and children, jogging trail, Manager's …
  • 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 - ask
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask

PreviousNext property

$1,286

7 BR / 9 BA / Sleeps 14

1 / 19

$1,286

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Extraordinary 7 Bedroom Villa in Montego Bay

7 BR / 9 BA / Sleeps 14 | Quick view

Details

EXTRAORDINARY NEW HALF MOON TENNIS & BEACH MEMBERSHIP FOR BELLE ABRI GUESTS! * Five minutes from beaches and three world class golf courses: Half Moon, White Witch and Cinnamon Hill. Complimentary beach membership at Half Moon, five minutes down the hill. Full staff onsite including a chef, butler, housekeeper, …
  • Shared outdoor pool (unheated)
  • Hot Tub/Jacuzzi
  • Internet Access
  • A/C or climate control
  • Grill
  • Pet friendly - ask
  • Smoking allowed - ask
  • Suitable for children
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask

PreviousNext property

$786

5 BR / 6 BA / Sleeps 10

1 / 18

$786

Inquire

Marvelous 5 Bedroom Villa with View in Montego Bay

5 BR / 6 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. For …
  • Shared outdoor pool (unheated)
  • Hot Tub/Jacuzzi
  • Wireless Internet
  • A/C or climate control
  • Fitness Room
  • Pet friendly - ask
  • Smoking allowed - ask
  • Suitable for children
  • Suitable for the elderly
  • Wheelchair accessible - ask

PreviousNext property

$1,299

6 BR / 7 BA / Sleeps 14

1 / 9

$1,299

Inquire

Spectacular 4 Bedroom Villa with Private Pool in Montego Bay

6 BR / 7 BA / Sleeps 14 | Quick view

Details

On three acres of land with a commanding view of the Caribbean Sea, lush green mountains and golf course, Bumper's Nest was designed by distinguished architect Kasimir Korybut. Completed in 1995, it is still one of the most glamorous homes at the Tryall Club. Here is an extraordinary private home with simply the best …
  • Shared outdoor pool (unheated)
  • Hot Tub/Jacuzzi
  • Internet Access
  • A/C or climate control
  • Microwave
  • Pet friendly - ask
  • Smoking allowed - ask
  • Suitable for children
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask
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