Showing

PreviousNext property

$1,429

6 BR / 6 BA / Sleeps 12

Karma Bay - Montego Bay vacation rentals
1 / 17

$1,429

Inquire

Karma Bay

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

Details

Karma Bay is a 6 bedroom Premier property on a spectacular water front location in the historic Tryall Club. The villa was totally renovated into a series of pavilions with separate living room/dining room and 6 bedrooms all connected by covered walkways lined with spectacular art and landscaping. Karma Bay prides …
  • Waterfront
  • Ocean or water views
  • Shared outdoor pool (unheated)
  • Hot Tub/Jacuzzi
  • Patio
  • Suitable for children - ask
  • Suitable for the elderly - ask

PreviousNext property

$708

4 BR / 4 BA / Sleeps 8

Sunrise Villa - Montego Bay vacation rentals
1 / 12

$708

Inquire

Sunrise Villa

Montego Bay house
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's…
  • Waterfront
  • Ocean or water views
  • Shared outdoor pool (unheated)
  • Hot Tub/Jacuzzi
  • Microwave
  • Suitable for children - ask
  • Suitable for the elderly - ask

PreviousNext property

$1,075

6 BR / 5 BA / Sleeps 12

2 Reviews

$1,075

Inquire

Pavilion Villa

Montego Bay villa
6 BR / 5 BA / Sleeps 12 | Quick view
“ Excellent ” 2 Reviews

Details

Reviews

(2)

Pavilion is a gorgeous villa located at the end of a cul-de-sac with stunning views of the Caribbean Sea to the north and a tranquil viewa of the mountains to the south. The villa is very spacious and beautiful. The home is designed as five separate 400 square foot octagons located in separate wings. All five bedrooms…
  • Hot Tub/Jacuzzi
  • Washing Machine
  • Clothes Dryer
  • Fitness Room
  • Dishwasher
  • Suitable for children
  • Suitable for the elderly - ask
  • Wheelchair accessible

Details

Reviews

(2)

Pavilion - Our Dream Vacation

Left on Aug 29, 2013 for a stay in August 2013

Pavilion – Half Moon

Aug 17-24, 2013. After much anticipation, our one year of planning this dream vacation was finally arriving! My husband and I went on this vacation with three other couples. We chose this villa because of the master bedrooms, the unlimited golfing, the pool, and access to Half Moon Resort. And, it did not disappoint us at all.

Once getting through customs, some of…

PreviousNext property

$940

7 BR / 9 BA / Sleeps 14

Stylish 7 Bedroom with Private Pool in Montego Bay - Montego Bay vacation rentals
1 / 30

$940

Inquire

Stylish 7 Bedroom with Private Pool in Montego Bay

Montego Bay villa
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

PreviousNext property

$2,000

7 BR / 7 BA / Sleeps 14

Whispering Waters - Montego Bay vacation rentals
1 / 31

$2,000

Inquire

Whispering Waters

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

Details

From the homeowner who created the wonderful villa Keely Villa comes its new sister house, Whispering Waters Villa. Located side by side, these neighboring villas combine to offer 13 bedrooms, 2 swimming pools, 2 private beaches and 2 tennis courts lit for night play. Each villa has its own private coral cove 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

PreviousNext property

$1,169

6 BR / 8 BA / Sleeps 12

6 Bedroom Villa with View in Montego Bay - Montego Bay vacation rentals
1 / 28

$1,169

Inquire

6 Bedroom Villa with View in Montego Bay

Montego Bay villa
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

PreviousNext property

$643

4 BR / 4 BA / Sleeps 8

1 Reviews

$643

Inquire

None VL TTC

Montego Bay house
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.

PreviousNext property

$1,000

5 BR / 6 BA / Sleeps 10

1 / 17

$1,000

Inquire

Great River House

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

Details

Great River House - featured in "Caribbean Travel and Life" and selected one of Luxury Retreats favorite Jamaican villas; Great River House tops the luxury list for privacy & exceptional staff! Set on over four acres of rolling lawns, the house commands sweeping views of the sea with included amenities …
  • Ocean or water views
  • Mountain Views
  • Hot Tub/Jacuzzi
  • Outdoor Dining Area
  • A/C or climate control
  • Suitable for children - ask
  • Suitable for the elderly - ask

PreviousNext property

$707

6 BR / 7 BA / Sleeps 13

1 / 40

$707

Inquire

Glamorous 6 Bedroom Villa in Montego Bay

Montego Bay villa
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

PreviousNext property

$786

5 BR / 6 BA / Sleeps 10

1 / 18

$786

Inquire

Marvelous 5 Bedroom Villa with View in Montego Bay

Montego Bay villa
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

$2,571

6 BR / 14 BA / Sleeps 17

7 Reviews

$2,571

Inquire

Flower Hill Retreat in prestigious Spring Farm - Elegance Defined

Montego Bay villa
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.…

PreviousNext property

$1,108

4 BR / 4 BA / Sleeps 8

1 / 25

$1,108

Inquire

None VL SRB

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

Details

Villa VL SRB is a 4-bedroom private home on a jewel-like location by the sea. VL SRB is one of the most beloved and often revisited villas on Jamaica's beautiful north coast. Its prize location is a waterfront acre, 8 miles west of Montego Bay. Complimentary Round Hill and Tryall Beach Club memberships are included …
  • Waterfront
  • 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

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

Montego Bay villa
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

PreviousNext property

$730

4 BR / 4 BA / Sleeps 8

1 / 13

$730

Inquire

Beautiful Beachfront Villa with Private Pool

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

Details

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

PreviousNext property

$1,624

6 BR / 8 BA / Sleeps 12

1 / 26

$1,624

Inquire

None VL WWT

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

Details

Villa VL WWT is among the newest and most stylish villas in the award-winning, gated community, The Tryall Club. Its has been meticulously designed for a family lifestyle in a healthy indoor-outdoor environment. Generously furnished with multiple sitting areas make for easy living throughout the villa. Tryall is a …
  • Hot Tub/Jacuzzi
  • Internet Access
  • A/C or climate control
  • Fitness Room
  • Stereo or CD player
  • Pet friendly - ask
  • Smoking allowed - ask
  • Suitable for children - ask
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask

PreviousNext property

$550

7 BR / 7 BA / Sleeps 14

1 / 15

$550

Inquire

Thomas House

Montego Bay house
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
  • Mountain Views
  • Hot Tub/Jacuzzi
  • Internet Access
  • Outdoor Dining Area
  • Suitable for children - ask
  • Suitable for the elderly - ask

PreviousNext property

$1,142

6 BR / 0 BA / Sleeps 12

1 / 30

$1,142

Inquire

BEACH ACCESS! BUTLER! STAFF! POOL! Endless Summer

Montego Bay house
6 BR / Sleeps 12 | Quick view

Details

Resort Membership to Half Moon Resort for all guests staying at Endless Summer Villa. This full membership offers the following to our guests. Resort Membership Benefits Use of Sunrise Beach, Hibiscus & Oleander Pools, Jacuzzi, tennis courts, Fitness Centre, Croquet, Miniature putting green. FAMILY FRIENDLY…
  • Ocean or water views
  • Hot Tub/Jacuzzi
  • Internet Access
  • Outdoor Dining Area
  • A/C or climate control
  • Smoking allowed - ask
  • Suitable for the elderly - ask

PreviousNext property

$1,371

6 BR / 8 BA / Sleeps 14

8 Reviews

$1,371

Inquire

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

Montego Bay villa
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

PreviousNext property

$2,571

6 BR / 14 BA / Sleeps 14

1 / 47

$2,571

Inquire

Extraordinary 6 Bedroom Villa in Montego Bay

Montego Bay villa
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

PreviousNext property

$458

3 BR / 3 BA / Sleeps 7

1 / 10

$458

Inquire

Elegant 3 Bedroom Villa with Private Pool in Montego Bay

Montego Bay villa
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

PreviousNext property

$1,169

5 BR / 5 BA / Sleeps 12

1 / 22

$1,169

Inquire

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

Montego Bay villa
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

PreviousNext property

$786

4 BR / 4 BA / Sleeps 8

1 / 27

$786

Inquire

None VL YTC

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

Details

Perched on a remarkable site at the excellent, gated community The Tryall Club, VL YTC is a delightful home for a family or for any group wanting a wonderful week of golf, tennis, and water sports while being pampered by an excellent personal staff. Tryall is a private club with amenities such as a private beach, …
  • 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

PreviousNext property

$1,540

6 BR / 7 BA / Sleeps 12

1 / 15

$1,540

Inquire

None VL PIM

Montego Bay house
6 BR / 7 BA / Sleeps 12 | Quick view

Details

Villa VL PIM is a sprawling, glamorous 9,000-square-foot private estate on six landscaped acres. The villa was built in the late 1950's for French Count and Countess Jacques and Vera di Sibour in the period when Jamaica was a glamorous party destination for the early jet set. Today, VL PIM is a spacious private home …
  • Shared outdoor pool (unheated)
  • Hot Tub/Jacuzzi
  • Internet Access
  • Outdoor Dining Area
  • Fitness Room
  • Pet friendly - ask
  • Smoking allowed - ask
  • Suitable for children - ask
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask

PreviousNext property

$1,786

7 BR / 7 BA / Sleeps 14

1 / 24

$1,786

Inquire

Tremendous 7 Bedroom Villa with View in Montego Bay

Montego Bay villa
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

6 BR / 6 BA / Sleeps 12

1 / 23

$1,286

Inquire

Endless Summer at Montego Bay, Jamaica - Ocean View, Pool

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

Details

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 dome of this home's highest turret. From the gallery, as from all …
  • Ocean or water views
  • Hot Tub/Jacuzzi
  • Internet Access
  • Outdoor Dining Area
  • Grill
  • Pet friendly - ask
  • Smoking allowed - ask
  • Suitable for children - ask
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask

PreviousNext property

$2,078

7 BR / 8 BA / Sleeps 14

1 / 15

$2,078

Inquire

None VL PTC

Montego Bay house
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

PreviousNext property

$1,071

9 BR / 9 BA / Sleeps 18

1 / 24

$1,071

Inquire

Summerhill

Montego Bay villa
9 BR / 9 BA / Sleeps 18 | Quick view

Details

Summerhill is one of the newest villas located in the Spring Farm area, just past the exclusive Half Moon Golf & Country Club and just ten minutes east of Montego Bay. It is located on lush tropical grounds that offer flowering trees, a massive well-manicured lawn, walking paths and a garden sitting area designed for …
  • Hot Tub/Jacuzzi
  • Internet Access
  • Washing Machine
  • Clothes Dryer
  • Books
  • Suitable for children
  • Suitable for the elderly - ask

PreviousNext property

$643

5 BR / 5 BA / Sleeps 1

1 / 19

$643

Inquire

Drambuie

Montego Bay house
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

PreviousNext property

$1,010

7 BR / 9 BA / Sleeps 16

1 / 31

$1,010

Inquire

Fairway Manor

Montego Bay villa
7 BR / 9 BA / Sleeps 16 | Quick view

Details

Stunning for its massive renovation and outstanding new features. Today’s Fairway Manor is a stylish multi-faceted 10,000-square-foot private home. Its rooms feature cool marble floors and overlook the famous Half Moon 18-hole Robert Trent Jones golf course and a dramatic panorama of the Caribbean Sea. Additional …
  • 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

PreviousNext property

$786

3 BR / 3 BA / Sleeps 1

1 / 12

$786

Inquire

Sunset

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

Details

Sunset is a three-bedroom beachfront villa located in Tryall Club . This beautiful villa sits on the edge of the Caribbean Sea with its own sand beach. Sunset is ideal for snorkeling enthusiasts, and for families with children who love to play in sea and sand. Breathtaking vistas of Montego Bay and the island’s …
  • Waterfront
  • Ocean or water views
  • Hot Tub/Jacuzzi
  • Safe
  • Satellite or cable TV
  • Suitable for children - ask
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask

PreviousNext property

$1,299

6 BR / 8 BA / Sleeps 12

1 Reviews

$1,299

Inquire

Viviana at the Tryall Club

Montego Bay villa
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, …

PreviousNext property

$1,071

9 BR / 9 BA / Sleeps 18

1 / 24

$1,071

Inquire

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

Montego Bay villa
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

PreviousNext property

$700

7 BR / 7 BA / Sleeps 18

1 Reviews

$700

Book

Celebrity Villa Jamaica

Montego Bay villa
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…

PreviousNext property

$750

3 BR / 4 BA / Sleeps 1

1 / 9

$750

Inquire

Serenity

Montego Bay house
3 BR / 4 BA / Sleeps 1 | Quick view

Details

The inviting cobblestone driveway leads you to the most delightful ambiance of Serenity Villa ; a three bedroom hillside property located on the world’s acclaimed Tryall Club resort. Serenity, perched on Copperwood Ridge, has astounding views of the Caribbean Sea and is surrounded by beautiful lush landscaping …
  • Hot Tub/Jacuzzi
  • A/C or climate control
  • Safe
  • Satellite or cable TV
  • Stereo or CD player
  • Suitable for children - ask
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask

PreviousNext property

$1,010

7 BR / 8 BA / Sleeps 14

4 Reviews

$1,010

Inquire

Fairway Manor

Montego Bay villa
7 BR / 8 BA / Sleeps 14 | Quick view
“ Excellent ” 4 Reviews

Details

Reviews

(4)

Fairway Manor is a glamorous seven-bedroom villa overlooking the famous Half Moon Golf Course and the Caribbean Sea. Nestled on a hillside, its rooms open onto an 85' verandah, where the sweeping 120-degree views of manicured grounds, golf course, sea and sky are truly breathtaking. The villa is less than a five …
  • Hot Tub/Jacuzzi
  • Internet Access
  • Washing Machine
  • Clothes Dryer
  • Patio
  • Suitable for children
  • Suitable for the elderly - ask

Details

Reviews

(4)

Great Family Vacation

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

Our family vacation at Fairway Manor was the most enjoyable and enriching experience of a lifetime. Our children were enveloped by the friendly and attentive service of your staff throughout our stay, providing them with a cultural, safe and culinary experience that I\'m certain they will never forget. The property was maintained at a level beyond our expectations and the food that was served to …

PreviousNext property

$1,559

6 BR / 8 BA / Sleeps 14

1 / 21

$1,559

Inquire

Rose Cottage at the Tryall Club

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

Details

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

PreviousNext property

$708

4 BR / 4 BA / Sleeps 1

1 / 18

$708

Inquire

Fairwinds

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

Details

Located in the Tryall Golf and Beach Club, Fairwinds Villa offers the best of both worlds; the privacy and personalized attention of villa living, and the amenities of the Tryall resort. With its spectacular views, lush gardens with waterfall, fountains and lily ponds, this beautiful villa is truly the place at which …
  • Ocean or water views
  • Hot Tub/Jacuzzi
  • A/C or climate control
  • Satellite or cable TV
  • Stereo or CD player
  • Suitable for children - ask
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask

PreviousNext property

$485

5 BR / 7 BA / Sleeps 10

1 Reviews

$485

Inquire

Datura Villa

Montego Bay villa
5 BR / 7 BA / Sleeps 10 | Quick view
“ Very Good ” 1 Reviews

Details

Reviews

(1)

Your stay at Datura is one that can be tailored to fit almost anyone's needs, from couples and families to groups and retreats. Your accommodations can be as inclusive as an all-inclusive or as casual as a luxury hotel or resort. The only difference is that your visit will always feel personal and intimate with none …
  • Hot Tub/Jacuzzi
  • Fireplace
  • Washing Machine
  • Clothes Dryer
  • Outdoor Dining Area
  • Suitable for children
  • Suitable for the elderly - ask
  • Wheelchair accessible

Details

Reviews

(1)

Beautiful home with excellent views

Left on Jul 02, 2011 for a stay in April 2011

Amazing view from any area of this property. Large house with many full bathrooms and an onsite staff of cooks, house and ground keepers. Excellent pool and hot tub, fruit trees on the property.

Being at the top of a hill there is nothing within walking distance. A taxi or private driver will be needed to leave the house. If you are looking to do nothing but relax then there is really no …

PreviousNext property

$1,371

6 BR / 6 BA / Sleeps 12

1 / 34

$1,371

Inquire

Greatview

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

Details

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 …
  • Ocean or water views
  • Hot Tub/Jacuzzi
  • Outdoor Dining Area
  • A/C or climate control
  • Balcony or terrace
  • Suitable for children - ask
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask

PreviousNext property

$1,949

6 BR / 8 BA / Sleeps 12

1 / 25

$1,949

Inquire

None VL VVT

Montego Bay house
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

PreviousNext property

$358

1 BR / 2 BA / Sleeps 4

1 / 36

$358

Inquire

Mirador at the Tryall Club ~ A Great House Villa Suite

Montego Bay villa
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

PreviousNext property

$1,428

6 BR / 6 BA / Sleeps 12

1 / 30

$1,428

Inquire

Anticipation

Montego Bay house
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
  • Outdoor Dining Area
  • A/C or climate control
  • Deck
  • Suitable for children - ask
  • Suitable for the elderly - ask

PreviousNext property

$1,000

5 BR / 5 BA / Sleeps 12

1 / 18

$1,000

Inquire

Wild Orchid - Jamaica

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

Details

Wild Orchid is located on 220 private of acres of former banana and coconut plantations. The Georgian design captures the ambiance of the original plantation. The interiors are spacious and feature Oriental rugs, hand laid tiled and custom cedar accents. An extensive covered veranda is comfortably furnished with …
  • Hot Tub/Jacuzzi
  • Washing Machine
  • Clothes Dryer
  • A/C or climate control
  • Fitness Room
  • Suitable for children
  • Suitable for the elderly - ask

PreviousNext property

$785

3 BR / 3 BA / Sleeps 9

1 / 55

$785

Inquire

Goat Hill

Montego Bay villa
3 BR / 3 BA / Sleeps 9 | 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 nearby Great River while the west view provides an equally lovely view toward the Round Hill …
  • Hot Tub/Jacuzzi
  • Internet Access
  • Washing Machine
  • Clothes Dryer
  • Fitness Room
  • Suitable for children
  • Suitable for the elderly - ask

PreviousNext property

$730

4 BR / 4 BA / Sleeps 8

1 Reviews

$730

Inquire

Calypso Shores on the Beach

Montego Bay villa
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 …

PreviousNext property

$1,285

5 BR / 6 BA / Sleeps 13

2 Reviews

$1,285

Inquire

Knockando on Round Hill

Montego Bay villa
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 …

PreviousNext property

$150

1 BR / 2 BA / Sleeps 4

3 Reviews

$150

Book

One Bedroom Luxury Condo Montego Bay Jamaica,

Montego Bay condo
1 BR / 2 BA / Sleeps 4 | Quick view
“ Very Good ” 3 Reviews

Details

Reviews

(3)

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

(3)

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 …

PreviousNext property

$1,143

6 BR / 6 BA / Sleeps 12

1 / 23

$1,143

Inquire

Endless Summer

Montego Bay villa
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

PreviousNext property

$1,285

7 BR / 9 BA / Sleeps 14

1 / 37

$1,285

Inquire

Belle Abri

Montego Bay villa
7 BR / 9 BA / Sleeps 14 | Quick view

Details

Completed in 2006, Belle Abri ("beautiful sanctuary") is a large home overlooking the Half Moon golf course and Caribbean Sea offering breathtaking views. A deluxe home, it offers 12,000 square feet and seven bedrooms as well as a private pool and private tennis court. Located in the prestigious Spring Farm area, the …
  • Hot Tub/Jacuzzi
  • Internet Access
  • Clothes Dryer
  • Fitness Room
  • Grill
  • Suitable for children
  • Suitable for the elderly - ask

PreviousNext property

$1,948

7 BR / 7 BA / Sleeps 12

4 Reviews

$1,948

Inquire

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

Montego Bay villa
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.

1 23
page 1 of 3
Load more