Montego Bay Vacation Rentals, Villas, & More

Montego Bay (285) Filter Cancel

1-50 of 285 Montego Bay Rentals

| View All
Sort:
1  2  3  4  5  View All
Montego Bay Jamaica Vacation Rentals - Apartment
1 / 30

Montego Bay Apartment
1 Bedroom / 1 Bathroom / Sleeps 3
Apartment / 1 Bedroom / Sleeps 3

from

$140

/ night

Email Owner
Bedrooms:1
Bathrooms:1
Sleeps:3
Type:Apartment
Per night:$140 - $180
Per week:$1,000
Pets allowed:No
Internet:Yes

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...

See more

Close x

Montego Bay Jamaica Vacation Rentals - Home
1 / 15

Montego Bay Home
4 Bedrooms / 4 Bathrooms / Sleeps 1
Home / 4 Bedrooms / Sleeps 1

from

$350

/ night

Email Owner
Bedrooms:4
Bathrooms:4
Sleeps:1
Type:Home
Per night:$350
Per month:$10,500
Pets allowed:No
Internet:No

Skylark Villa is a beautiful 4 bedroom, 4 bathroom villa located in the exclusive Spring Farm neighborhood of Montego Bay on two acres of lush tropical gardens with flowering plants, palms and fruit trees. The property is very private and secure. The villa overlooks the Half Moon...

See more

Close x

1 / 11

Montego Bay Home
2 Bedrooms / 1 Bathroom / Sleeps 4
Home / 2 Bedrooms / Sleeps 4

from

$79

/ night

Email Owner
Bedrooms:2
Bathrooms:1
Sleeps:4
Type:Home
Per night:$79
Per month:$2,370
Pets allowed:Yes
Internet:No

Tthis is a 2 bedroom fully furnished house, most of our furniture has been imported with influence from the UK. At our home in Montego Bay, there is a good size kitchen/dining area and a bathroom. We live in a small community which is local to shops. Montego Bay is the second ...

See more

Close x

Keep cool and relax!
1 / 28

Montego Bay Cottage
2 Bedrooms / 1 Bathroom / Sleeps 4
Cottage / 2 Bedrooms / Sleeps 4

(2)“ Excellent ”2 Reviews

Bedrooms:2
Bathrooms:1
Sleeps:4
Type:Cottage
No rental rates available - please contact the owner
 
Pets allowed:No
Internet:Yes

Explore beyond the stereotypical tourist traps such as the hotel star systems and Sandals resort experience. A newly built two- bedroom bungalow on the oversubscribed Bogue Village, in the St James Parish, Montego Bay. It has eco friendly solar powered hot water supplying a ...

See more

Close x

Nice property for a getaway!

“ Excellent ”
January 1, 2011
We stayed in this property for 5 days, it's a nice little house in Bogue village, close to the airport and the hip street. The neighborhood is safe and quiet. The property managers were very helpful and accommodating. They picked up and dropped us off on time at the airport. We had a good time
Neha, Austin, TX

See all reviews

Close x

Poolside !
1 / 46

Montego Bay Villa
3 Bedrooms / 3 Bathrooms / Sleeps 6
Villa / 3 Bedrooms / Sleeps 6

(1)“ Excellent ”1 Review

from

$429

/ night

Email Owner
Bedrooms:3
Bathrooms:3
Sleeps:6
Type:Villa
Per night:$429 - $572
Per week:$3,000 - $4,000
Pets allowed:No
Internet:Yes

Star Apple House is a luxurious private villa, a comfortable retreat on a hill overlooking the Caribbean Sea and Montego Bay on the Jamaican north coast. The Villa comes fully staffed, ( Cook, housekeeper and a butler) We offer superior accommodation and service for up to 6 guests....

See more

Close x

Star Apple is a sublime, relaxing villa.. love it!

“ Excellent ”
January 23, 2015
I have stayed at Star Apple three times so far, it's a villa I hope to holiday in again (and again). From the minute you arrive and see the setting- lush tropical ondulating gardens, a lovely pool, fantastic sea views across Montego Bay- you will be smitten by this special place! The staff are charming, humble, accomodating people who tend to your every need. A pot of coffee arrives secretly on the terrace the minute you rise. Then effortlessly, you'll be told by Michael that breakfast is served on tbe spacious terrace, surrounded by lush tropical plants. A day relaxing by the pool, afternoon tea will be srved around 4pm. Then out comes the ice bucket as a G&T will be served as a sundowner as you laze on the comfy sunbeds as the sun sets on the horizon. Not far away is Roundhill if you fancy a day at their beach or an evening cocktail. Not far are interesting villages, lovely beaches, places to explore. It's nice to venture oit but nicer sill to return to Star Apple and be cocooned in this special villa. It's just lovely. It's a place you'll leave feeling totally chilled after a week or two in such a great place.
Ann Cunliffe, Manchester, England

See all reviews

Close x

Montego Bay Jamaica Vacation Rentals - Apartment
1 / 21

Montego Bay Apartment
1 Bedroom / 1 Bathroom / Sleeps 3
Apartment / 1 Bedroom / Sleeps 3

(37)“ Excellent ”37 Reviews

from

$85

/ night

Email Owner
Bedrooms:1
Bathrooms:1
Sleeps:3
Type:Apartment
Per night:$85
Per week:$560
Pets allowed:No
Internet:Yes

Within 5 minutes of the airport, and right next to the finest beaches, entertainment, and the area's commerce, this accommodation is suitable for a relaxing vacation getaway, or for business travel. The apartment featured here is optimized for a quiet restful vacation just steps...

See more

Close x

awesome place to stay!!

“ Excellent ”
April 3, 2015
I stayed at the montego bay club in March for 9 nights and it was amazing! it was clean, air conditioning worked, the view from the balcony was unforgettable and to make things even better we were right across the street from the famous doctors cave beach. Glover and Mrs. James were very hospitable from day 1. I was even given some Helpful tips on where to eat and what to do around the area. I will definitely be staying here again!!!!
Monique Diimplez, toronto, on

See all reviews

Close x

Sea view from backyard
1 / 22

Montego Bay Villa
3 Bedrooms / 3 Bathrooms / Sleeps 8
Villa / 3 Bedrooms / Sleeps 8

(2)“ Excellent ”2 Reviews

from

$201

/ night

Email Owner
Bedrooms:3
Bathrooms:3
Sleeps:8
Type:Villa
Per night:$201 - $212
Per week:$1,406 - $1,484
Pets allowed:No
Internet:No

Swarm villa is a gorgeous one storey villa. Why not come home to swarm villa and relax by your private pool or check out the tropical plants and birds in our well kept gardens. Remember, this is a sea view property so your sure to see a luxury cruise ship pull into harbour in the...

See more

Close x

New Divine Camp 2011,camper

“ Excellent ”
August 29, 2011
Well lets say our stay at Villa Swarm was DIVINE,we were welcome with of course great island greeting, the hospitality was excellent.The property is well maintained and the pool was very relaxing,if your planning a get away make Villa Swarm your place of choice and it will truly be your home away from home.
Eunice Williams, USA

See all reviews

Close x

Montego Bay Jamaica Vacation Rentals - Villa
1 / 21

Montego Bay Villa
4 Bedrooms / 4 Bathrooms / Sleeps 8
Villa / 4 Bedrooms / Sleeps 8

from

$800

/ night

Email Owner
Bedrooms:4
Bathrooms:4
Sleeps:8
Type:Villa
Per night:$800 - $1,300
Per week:$5,600 - $9,100
Pets allowed:No
Internet:Yes

Summerland is a beautiful private home situated on 2 acres within the luxurious Round Hill Hotel compound. Its unique location atop Round Hill offers magnificent views of Montego Bay, pleasant tropical breezes and spectacular sunsets. The furnishings reflect the colonial ambiance...

See more

Close x

1 / 13

Montego Bay Villa
6 Bedrooms / 5 Bathrooms / Sleeps 12
Villa / 6 Bedrooms / Sleeps 12

from

$118

/ night

Email Owner
Bedrooms:6
Bathrooms:5
Sleeps:12
Type:Villa
Per night:$118 - $141
Per week:$825
Pets allowed:Yes
Internet:Yes

"Soon Come" Villa has 6 air- conditioned bedrooms with Cable TV, private bathrooms and ceiling fan, Living Room with Stereo, Cable TV, DVD and CD players. High speed internet . Formal Dining Room, Kitchen, private swimming pool, sun porch accented with beautiful tropical flowers,...

See more

Close x

1 / 23

Montego Bay Villa
18 Bedrooms / 15 Bathrooms / Sleeps 36
Villa / 18 Bedrooms / Sleeps 36

from

$100

/ night

Email Owner
Bedrooms:18
Bathrooms:15
Sleeps:36
Type:Villa
Per night:$100 - $130
Per week:$700
Pets allowed:No
Internet:No

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, satellites TV, VCR, stereo and comfortable furniture inside and outside. Te spacious bedrooms...

See more

Close x

1 / 15

Montego Bay Townhouse
2 Bedrooms / 1.5 Bathrooms / Sleeps 4
Townhouse / 2 Bedrooms / Sleeps 4

(9)“ Excellent ”9 Reviews

from

$140

/ night

Email Owner
Bedrooms:2
Bathrooms:1.5
Sleeps:4
Type:Townhouse
Per night:$140 - $150
Per week:$1,000
Pets allowed:No
Internet:No

Brand new furnished two bedroom townhouse with central air/cable internet, hot water available for weekly monthly rental. Five minutes from Sangster Internation airport, entertainment, beach, and shopping/ business area. Gated community, 24hour security with pool on site. Housekeeper,...

See more

Close x

Great vacay spot

“ Excellent ”
August 1, 2012
It's was beautiful the house was very roomy and clean... The security was very good at lettin us know wen visitor came...the pool was open 24 hours so we went for a a lot of late night swims. The neighbors r friendly..it's very close to the hip strip and beaches and very easy to get a cab. The house is beautiful and can sleep up to five..I would definitely stay there again
Tiana White, Philadelphia pa

See all reviews

Close x

Montego Bay Jamaica Vacation Rentals - Condo
1 / 21

Montego Bay Condo
1 Bedroom / 1 Bathroom / Sleeps 5
Condo / 1 Bedroom / Sleeps 5

(1)“ Excellent ”1 Review

from

$145

/ night

Email Owner
Bedrooms:1
Bathrooms:1
Sleeps:5
Type:Condo
Per night:$145
Per week:$1,015
Pets allowed:No
Internet:Yes

SEE PHOTOS - THIS IS A Front Facing Beach View ONE BEDROOM SUITE ( not a Studio or side view and perfectly positioned as not too high or too low ) . I waited many years to be able to purchase "this" Condo " ! Email me - for photos and details for both condos to Henry Clemons ...

See more

Close x

Jamaica Paradise

“ Excellent ”
December 13, 2013
I can't say enough great things about this property. The location is perfect. Right on the hip strip and across the street from the warm water of the Caribbean. The view from the condo is spectacular. The condo is clean and equipped with all the necessary items one might need. I only stayed a couple of nights, but I will definitely stay longer next time. Henry had a wealth of information to make my stay more enjoyable. Not only that, but he called me shortly after we arrived to make sure all was well.
Jennie Wright, Hillsboro, OR

See all reviews

Close x

1 / 29

Montego Bay Villa
18 Bedrooms / 15 Bathrooms / Sleeps 36
Villa / 18 Bedrooms / Sleeps 36

from

$130

/ night

Email Owner
Bedrooms:18
Bathrooms:15
Sleeps:36
Type:Villa
Per night:$130
Per month:$3,900
Pets allowed:No
Internet:Yes

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 ...

See more

Close x

Montego Bay Jamaica Vacation Rentals - Home
1 / 15

Montego Bay Home
7 Bedrooms / 8 Bathrooms / Sleeps 14
Home / 7 Bedrooms / Sleeps 14

Bedrooms:7
Bathrooms:8
Sleeps:14
Type:Home
Per night:$2,078
Per week:$14,545
Pets allowed:No
Internet:Yes

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 ...

See more

Close x

Montego Bay Jamaica Vacation Rentals - Home
1 / 25

Montego Bay Home
6 Bedrooms / 8 Bathrooms / Sleeps 12
Home / 6 Bedrooms / Sleeps 12

Bedrooms:6
Bathrooms:8
Sleeps:12
Type:Home
Per night:$1,949 - $3,897
Per week:$13,640 - $27,275
Pets allowed:No
Internet:Yes

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...

See more

Close x

Montego Bay Jamaica Vacation Rentals - Home
1 / 8

Montego Bay Home
5 Bedrooms / 5 Bathrooms / Sleeps 10
Home / 5 Bedrooms / Sleeps 10

Bedrooms:5
Bathrooms:5
Sleeps:10
Type:Home
Per night:$2,759 - $3,539
Per week:$19,313 - $24,773
Pets allowed:No
Internet:No

Beautifully appointed, open, and airy, the private villas of Round Hill are known worldwide as some of the finest villas in Jamaica, garnering numerous awards and accolades for excellence, including the World Travel Award for World's Leading Villa for eight years running. The...

See more

Close x

Montego Bay Jamaica Vacation Rentals - Home
1 / 25

Montego Bay Home
4 Bedrooms / 4 Bathrooms / Sleeps 8
Home / 4 Bedrooms / Sleeps 8

Bedrooms:4
Bathrooms:4
Sleeps:8
Type:Home
Per night:$1,108 - $2,160
Per week:$7,750 - $15,120
Pets allowed:No
Internet:Yes

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...

See more

Close x

Montego Bay Jamaica Vacation Rentals - Home
1 / 8

Montego Bay Home
4 Bedrooms / 4 Bathrooms / Sleeps 8
Home / 4 Bedrooms / Sleeps 8

Bedrooms:4
Bathrooms:4
Sleeps:8
Type:Home
Per night:$1,875 - $2,515
Per week:$13,125 - $17,605
Pets allowed:No
Internet:Yes

Beautifully appointed, open, and airy, the private villas of Round Hill are known worldwide as some of the finest villas in Jamaica, garnering numerous awards and accolades for excellence, including the World Travel Award for World's Leading Villa for eight years running. The...

See more

Close x

Montego Bay Jamaica Vacation Rentals - Home
1 / 28

Montego Bay Home
3 Bedrooms / 4 Bathrooms / Sleeps 6
Home / 3 Bedrooms / Sleeps 6

from

$715

/ night

Email Owner
Bedrooms:3
Bathrooms:4
Sleeps:6
Type:Home
Per night:$715
Per week:$5,000
Pets allowed:No
Internet:No

VL SBT is a charming three- bedroom beach house on a fabulous site, a double lot absolutely on the edge of the beach and the sea. The wide blue all- day view is topped off by a sunset sky and a stunning nighttime view of the sparkling lights of the town of Montego Bay 12 miles across...

See more

Close x

Montego Bay Jamaica Vacation Rentals - Home
1 / 6

Montego Bay Home
3 Bedrooms / 3 Bathrooms / Sleeps 6
Home / 3 Bedrooms / Sleeps 6

from

$558

/ night

Email Owner
Bedrooms:3
Bathrooms:3
Sleeps:6
Type:Home
Per night:$558 - $1,000
Per week:$3,900 - $7,000
Pets allowed:No
Internet:Yes

Villa VL BLU is a simply beautiful three- bedroom private villa with a breathtaking panorama of sea and sky. Wide glass doors and cedar louvers open to the wrap- around verandah and spectacular view. The pretty living room has extraordinarily comfortable overstuffed sofas and chairs...

See more

Close x

Montego Bay Jamaica Vacation Rentals - Home
1 / 8

Montego Bay Home
3 Bedrooms / 3 Bathrooms / Sleeps 6
Home / 3 Bedrooms / Sleeps 6

Bedrooms:3
Bathrooms:3
Sleeps:6
Type:Home
Per night:$1,551 - $2,011
Per week:$10,857 - $14,077
Pets allowed:No
Internet:Yes

Beautifully appointed, open, and airy, the private villas of Round Hill are known worldwide as some of the finest villas in Jamaica, garnering numerous awards and accolades for excellence, including the World Travel Award for World's Leading Villa for eight years running. The...

See more

Close x

Montego Bay Jamaica Vacation Rentals - Home
1 / 18

Montego Bay Home
2 Bedrooms / 2 Bathrooms / Sleeps 4
Home / 2 Bedrooms / Sleeps 4

Bedrooms:2
Bathrooms:2
Sleeps:4
Type:Home
Per night:$1,347 - $1,757
Per week:$9,429 - $12,299
Pets allowed:No
Internet:Yes

Beautifully appointed, open, and airy, the private villas of Round Hill are known worldwide as some of the finest villas in Jamaica, garnering numerous awards and accolades for excellence, including the World Travel Award for World's Leading Villa for eight years running. The...

See more

Close x

Montego Bay Jamaica Vacation Rentals - Home
1 / 21

Montego Bay Home
6 Bedrooms / 7 Bathrooms / Sleeps 12
Home / 6 Bedrooms / Sleeps 12

Bedrooms:6
Bathrooms:7
Sleeps:12
Type:Home
Per night:$2,598 - $3,897
Per week:$18,185 - $27,275
Pets allowed:No
Internet:Yes

Villa VL WTC offers 6 bedrooms, is located in the gated community of the Tryall Club and overlooks the golf course and the Caribbean Sea. Tryall is a private club with amenities such as a private beach, water sports, tennis, an excellent gym, the Hummingbird Kids Club, Great...

See more

Close x

Montego Bay Jamaica Vacation Rentals - Home
1 / 18

Montego Bay Home
5 Bedrooms / 5 Bathrooms / Sleeps 10
Home / 5 Bedrooms / Sleeps 10

Bedrooms:5
Bathrooms:5
Sleeps:10
Type:Home
Per night:$1,143 - $2,358
Per week:$8,000 - $16,500
Pets allowed:No
Internet:Yes

VL NUT is a 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 immediately...

See more

Close x

Montego Bay Jamaica Vacation Rentals - Home
1 / 35

Montego Bay Home
5 Bedrooms / 5 Bathrooms / Sleeps 10
Home / 5 Bedrooms / Sleeps 10

Bedrooms:5
Bathrooms:5
Sleeps:10
Type:Home
Per night:$1,559
Per week:$10,910
Pets allowed:No
Internet:Yes

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 ...

See more

Close x

Montego Bay Jamaica Vacation Rentals - Home
1 / 9

Montego Bay Home
3 Bedrooms / 3 Bathrooms / Sleeps 6
Home / 3 Bedrooms / Sleeps 6

Bedrooms:3
Bathrooms:3
Sleeps:6
Type:Home
Per night:$1,040
Per week:$7,275
Pets allowed:No
Internet:Yes

Villa VL VTC offers a magnificent view of the deep blue Caribbean Sea and peaceful, private location. On a prize site above the sea, it is only minutes by complimentary shuttle or private golf cart from the Tryall Club Great House and shops, private beach, and golf and tennis ...

See more

Close x

Montego Bay Jamaica Vacation Rentals - Villa
1 / 36

Montego Bay Villa
8 Bedrooms / 10 Bathrooms / Sleeps 16
Villa / 8 Bedrooms / Sleeps 16

Bedrooms:8
Bathrooms:10
Sleeps:16
Type:Villa
Per night:$1,351 - $3,377
Per week:$9,455 - $23,637
Pets allowed:No
Internet:Yes

From the moment one approaches its colorful entrance, the eponymous architecture of Round House is intriguing. Spiral stairways and balconies connect multiple living, dining and sleeping areas in this eight- bedroom staffed villa at the Tryall Club. Additional amenities include:...

See more

Close x

Montego Bay Jamaica Vacation Rentals - Villa
1 / 33

Montego Bay Villa
7 Bedrooms / 8 Bathrooms / Sleeps 14
Villa / 7 Bedrooms / Sleeps 14

Bedrooms:7
Bathrooms:8
Sleeps:14
Type:Villa
Per night:$2,598 - $6,358
Per week:$18,182 - $44,500
Pets allowed:No
Internet:Yes

If the only sounds you want to hear while you’re on vacation are the birds, wind and the sea, come to Seaclusion. Completed in February 2015, Seaclusion is one of the newest and most distinctive villas in the posh Tryall Club. Perhaps the most astonishing feature is the oxymoron...

See more

Close x

Montego Bay Jamaica Vacation Rentals - Villa
1 / 20

Montego Bay Villa
5 Bedrooms / 5 Bathrooms / Sleeps 12
Villa / 5 Bedrooms / Sleeps 12

Bedrooms:5
Bathrooms:5
Sleeps:12
Type:Villa
Per night:$1,286 - $3,000
Per week:$9,000 - $21,000
Pets allowed:No
Internet:Yes

ALLAMANDA is a brilliant new contemporary private villa with large heated pool, an excellent staff including top- rated chef, and nearby memberships at Round Hill and the Tryall Golf, TennisAdditional amenities include: pool table, ping pong table, complimentary use of the new...

See more

Close x

Montego Bay Jamaica Vacation Rentals - Home
1 / 25

Montego Bay Home
6 Bedrooms / 6 Bathrooms / Sleeps 12
Home / 6 Bedrooms / Sleeps 12

Bedrooms:6
Bathrooms:6
Sleeps:12
Type:Home
Per night:$2,140 - $4,285
Per month:$64,200 - $128,550
Pets allowed:No
Internet:No

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 dé cor, thoughtful amenities and every imaginable comfort. The villa’...

See more

Close x

Montego Bay Jamaica Vacation Rentals - Home
1 / 17

Montego Bay Home
6 Bedrooms / 6 Bathrooms / Sleeps 12
Home / 6 Bedrooms / Sleeps 12

Bedrooms:6
Bathrooms:6
Sleeps:12
Type:Home
Per night:$2,140 - $4,285
Per month:$64,200 - $128,550
Pets allowed:No
Internet:No

Viviana Villa is one of Tryall's newest luxury deluxe editions located in the picturesque Montego Bay. The brand new Tryall villa is a glamorous mansion with Tryall club facilities for all guests. The very luxurious interiors and magnificent views offered by this villa rental in Jamaica...

See more

Close x

Montego Bay Jamaica Vacation Rentals - Villa
1 / 40

Montego Bay Villa
5 Bedrooms / 6 Bathrooms / Sleeps 10
Villa / 5 Bedrooms / Sleeps 10

Bedrooms:5
Bathrooms:6
Sleeps:10
Type:Villa
Per night:$1,299 - $3,897
Per week:$9,091 - $27,273
Pets allowed:No
Internet:Yes

Sea Salt is one of the most stylish villas in this collection. Exquisite classic Jamaican architecture defines 7, 700 square feet of living, dining, entertaining and relaxation spaces. Exteriors are lushly landscaped with native trees and a host of flowering plants. Additional ...

See more

Close x

Montego Bay Jamaica Vacation Rentals - Home
1 / 26

Montego Bay Home
5 Bedrooms / 6 Bathrooms / Sleeps 10
Home / 5 Bedrooms / Sleeps 10

Bedrooms:5
Bathrooms:6
Sleeps:10
Type:Home
Per night:$1,710 - $3,570
Per month:$51,300 - $107,100
Pets allowed:No
Internet:No

Anticipation Villa in Tryall Club is one of the newest and most contemporary villas in Jamaica. The fabulous luxury villa Jamaica is rated premier class, the highest rating in Tryall Club and is located within the club’ s gated community. Being positioned directly over the...

See more

Close x

Montego Bay Jamaica Vacation Rentals - Villa
1 / 16

Montego Bay Villa
4 Bedrooms / 4 Bathrooms / Sleeps 8
Villa / 4 Bedrooms / Sleeps 8

from

$858

/ night

Email Owner
Bedrooms:4
Bathrooms:4
Sleeps:8
Type:Villa
Per night:$858 - $1,965
Per week:$6,000 - $13,750
Pets allowed:No
Internet:Yes

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 ...

See more

Close x

Montego Bay Jamaica Vacation Rentals - Villa
1 / 18

Montego Bay Villa
4 Bedrooms / 4 Bathrooms / Sleeps 8
Villa / 4 Bedrooms / Sleeps 8

Bedrooms:4
Bathrooms:4
Sleeps:8
Type:Villa
Per night:$1,300 - $2,858
Per week:$9,100 - $20,000
Pets allowed:No
Internet:Yes

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....

See more

Close x

Montego Bay Jamaica Vacation Rentals - Home
1 / 45

Montego Bay Home
3 Bedrooms / 6 Bathrooms / Sleeps 6
Home / 3 Bedrooms / Sleeps 6

from

$710

/ night

Email Owner
Bedrooms:3
Bathrooms:6
Sleeps:6
Type:Home
Per night:$710 - $855
Per month:$21,300 - $25,650
Pets allowed:No
Internet:No

Wait! Why you should book this villa?You have found a villa that has a first class Tryall Club Beach and Resort membership available for all guests! (Direct bookings with Jamaican Treasures )The Tryall Club is one of Jamaica’ s premier private resort club offering:Complimentary...

See more

Close x

Montego Bay Jamaica Vacation Rentals - Home
1 / 24

Montego Bay Home
8 Bedrooms / 8 Bathrooms / Sleeps 16
Home / 8 Bedrooms / Sleeps 16

(2)“ Excellent ”2 Reviews

Bedrooms:8
Bathrooms:8
Sleeps:16
Type:Home
Per night:$2,855 - $5,710
Per month:$85,650 - $171,300
Pets allowed:No
Internet:No

Haystack Villa is one of the newest villas within the celebrated and exclusive Tryall Club estate. The highest rated premier villa in Tryall Club, the gorgeous and very welcoming Haystack Villa provides an unmatched vacation experience in elegance and serenity. Brilliant views of...

See more

Close x

Montego Bay Jamaica Vacation Rentals - Home
1 / 24

Montego Bay Home
6 Bedrooms / 6 Bathrooms / Sleeps 12
Home / 6 Bedrooms / Sleeps 12

Bedrooms:6
Bathrooms:6
Sleeps:12
Type:Home
Per night:$1,500 - $2,843
Per week:$10,500 - $19,900
Pets allowed:No
Internet:Yes

Villa VL TRB is a stunning 4, 800- square- foot beachfront home on a sweeping acre of soft, beautifully landscaped lawn with a stone walkway that leads through the lush garden to the beach. 100 yards offshore is Holden's Reef, a continuation of the barrier reef complex that fronts...

See more

Close x

Montego Bay Jamaica Vacation Rentals - Villa
1 / 28

Montego Bay Villa
6 Bedrooms / 8 Bathrooms / Sleeps 12
Villa / 6 Bedrooms / Sleeps 12

(1)“ Excellent ”1 Review

Bedrooms:6
Bathrooms:8
Sleeps:12
Type:Villa
Per night:$1,299 - $3,897
Per week:$9,091 - $27,273
Pets allowed:No
Internet:Yes

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...

See more

Close x

Montego Bay Jamaica Vacation Rentals - Villa
1 / 20

Montego Bay Villa
3 Bedrooms / 4 Bathrooms / Sleeps 8
Villa / 3 Bedrooms / Sleeps 8

(1)“ Excellent ”1 Review

from

$715

/ night

Email Owner
Bedrooms:3
Bathrooms:4
Sleeps:8
Type:Villa
Per night:$715 - $1,858
Per week:$5,000 - $13,000
Pets allowed:No
Internet:Yes

Pinnacle is a casual open- air Caribbean- style villa overlooking the historic Tryall Great House, golf course and the sea. Nine tennis courts (with pro’s standing by) are within walking distance. The golf pro shop is four minutes down the hill in Pinnacle's complimentary golf ...

See more

Close x

Montego Bay Jamaica Vacation Rentals - Villa
1 / 34

Montego Bay Villa
3 Bedrooms / 4 Bathrooms / Sleeps 6
Villa / 3 Bedrooms / Sleeps 6

(2)“ Excellent ”2 Reviews

from

$715

/ night

Email Owner
Bedrooms:3
Bathrooms:4
Sleeps:6
Type:Villa
Per night:$715
Per week:$5,000
Pets allowed:No
Internet:Yes

Sunset is a charming three- bedroom beach house on a fabulous site: a double lot absolutely on the edge of the beach and the sea. The wide blue all- day view is topped off by a sunset sky and a stunning nighttime view of the sparkling lights of the town of Montego Bay 12 miles across...

See more

Close x

Montego Bay Jamaica Vacation Rentals - Villa
1 / 9

Montego Bay Villa
6 Bedrooms / 7 Bathrooms / Sleeps 14
Villa / 6 Bedrooms / Sleeps 14

Bedrooms:6
Bathrooms:7
Sleeps:14
Type:Villa
Per night:$1,299 - $3,896
Per week:$9,093 - $27,272
Pets allowed:No
Internet:Yes

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...

See more

Close x

Montego Bay Jamaica Vacation Rentals - Villa
1 / 40

Montego Bay Villa
5 Bedrooms / 6 Bathrooms / Sleeps 11
Villa / 5 Bedrooms / Sleeps 11

Bedrooms:5
Bathrooms:6
Sleeps:11
Type:Villa
Per night:$1,299 - $3,247
Per week:$9,091 - $22,727
Pets allowed:No
Internet:Yes

Rated Premier, the highest category. Heated pool ~ 25' x 70' with fiber optic night lighting. Private putting green and shuffleboard court on the large lawn. Onsite staff includes chef, butler, housekeepers, laundress and gardeners. Two complimentary golf carts for transport...

See more

Close x

Montego Bay Jamaica Vacation Rentals - Villa
1 / 16

Montego Bay Villa
5 Bedrooms / 5 Bathrooms / Sleeps 10
Villa / 5 Bedrooms / Sleeps 10

from

$715

/ night

Email Owner
Bedrooms:5
Bathrooms:5
Sleeps:10
Type:Villa
Per night:$715 - $1,786
Per week:$5,000 - $12,500
Pets allowed:No
Internet:Yes

Dramatically perched on a lush green hillside above the sea, Cliffside Cottage commands stunning views of the deep blue Caribbean Sea by day and romantic lights that glisten across Montego Bay after sunset. Sunrise and sunset vistas from this vantage point are mesmerizing. The ...

See more

Close x

Montego Bay Jamaica Vacation Rentals - Villa
1 / 21

Montego Bay Villa
5 Bedrooms / 6 Bathrooms / Sleeps 10
Villa / 5 Bedrooms / Sleeps 10

from

$858

/ night

Email Owner
Bedrooms:5
Bathrooms:6
Sleeps:10
Type:Villa
Per night:$858 - $2,643
Per week:$6,000 - $18,500
Pets allowed:No
Internet:Yes

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...

See more

Close x

Montego Bay Jamaica Vacation Rentals - Villa
1 / 24

Montego Bay Villa
4 Bedrooms / 4 Bathrooms / Sleeps 8
Villa / 4 Bedrooms / Sleeps 8

from

$452

/ night

Email Owner
Bedrooms:4
Bathrooms:4
Sleeps:8
Type:Villa
Per night:$452 - $1,624
Per week:$3,159 - $11,364
Pets allowed:No
Internet:Yes

CALYPSO is a charming open air villa adjacent to the 16th hole of the championship Tryall golf course. Four bedroom private villa at the famous Tryall Club. Uniquely located next to the 16th hole of the championship Tryall golf course. Onsite staff includes butler, cook, housekeeper,...

See more

Close x

Montego Bay Jamaica Vacation Rentals - Villa
1 / 10

Montego Bay Villa
3 Bedrooms / 3 Bathrooms / Sleeps 7
Villa / 3 Bedrooms / Sleeps 7

from

$458

/ night

Email Owner
Bedrooms:3
Bathrooms:3
Sleeps:7
Type:Villa
Per night:$458 - $1,000
Per week:$3,200 - $7,000
Pets allowed:No
Internet:Yes

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....

See more

Close x

Montego Bay Jamaica Vacation Rentals - Villa
1 / 37

Montego Bay Villa
6 Bedrooms / 8 Bathrooms / Sleeps 14
Villa / 6 Bedrooms / Sleeps 14

Bedrooms:6
Bathrooms:8
Sleeps:14
Type:Villa
Per night:$1,372 - $3,858
Per week:$9,600 - $27,000
Pets allowed:No
Internet:Yes

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,...

See more

Close x

Montego Bay Jamaica Vacation Rentals - Villa
1 / 23

Montego Bay Villa
6 Bedrooms / 6 Bathrooms / Sleeps 12
Villa / 6 Bedrooms / Sleeps 12

Bedrooms:6
Bathrooms:6
Sleeps:12
Type:Villa
Per night:$1,143 - $2,786
Per week:$8,000 - $19,500
Pets allowed:No
Internet:Yes

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...

See more

Close x

Montego Bay Jamaica Vacation Rentals - Villa
1 / 20

Montego Bay Villa
5 Bedrooms / 5 Bathrooms / Sleeps 12
Villa / 5 Bedrooms / Sleeps 12

Bedrooms:5
Bathrooms:5
Sleeps:12
Type:Villa
Per night:$1,285 - $3,000
Per month:$38,550 - $90,000
Pets allowed:No
Internet:Yes

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...

See more

Close x

1  2  3  4  5  View All
12345View All
page 1 of 6
Loading...
Click for larger map
Loading...
Show Big Map
  • Price

  • Bedrooms

    Guests

  • Amenities

    • More