Montego Bay Vacation Rentals, Villas, & More

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1-50 of 223 Montego Bay Rentals

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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...

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1 / 30

Montego Bay Apartment
1 Bedroom / 1 Bathroom / Sleeps 4
Apartment / 1 Bedroom / Sleeps 4

from

$140

/ night

Email Owner
Bedrooms:1
Bathrooms:1
Sleeps:4
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...

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Montego Bay Jamaica Vacation Rentals - Villa
1 / 48

Montego Bay Villa
6 Bedrooms / 7 Bathrooms / Sleeps 15
Villa / 6 Bedrooms / Sleeps 15

(2)“ Excellent ”2 Reviews

from

$707

/ night

Email Owner
Bedrooms:6
Bathrooms:7
Sleeps:15
Type:Villa
Per night:$707 - $2,700
Per week:$4,950 - $18,900
Pets allowed:No
Internet:Yes

Pimento Hill is a beautiful home with a legendary history. The home overlooks the Caribbean Sea and is conveniently located just a five minute drive from the exclusive Round Hill Resort where guests enjoy complementary beach membership. The villa was originally built in the late 1950's...

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Keep cool and relax!
1 / 28

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

(2)“ Excellent ”2 Reviews

from

$78

/ night

Email Owner
Bedrooms:2
Bathrooms:1
Sleeps:4
Type:Cottage
Per night:$78
Per week:$546
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 ...

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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

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Montego Bay Jamaica Vacation Rentals - Home
1 / 18

Montego Bay Home
6 Bedrooms / 6 Bathrooms / Sleeps 1
Home / 6 Bedrooms / Sleeps 1

from

$680

/ night

Email Owner
Bedrooms:6
Bathrooms:6
Sleeps:1
Type:Home
Per night:$680
Per month:$20,400
Pets allowed:No
Internet:Yes

Serendipity Villa is located in the prestigious Spring Farm neighborhood above and overlooking Half Moon Bay resort and the blue Caribbean Sea. The villa has been totally remodeled with style and for comfort in 2008. Serendipity will delight you. The quiet entrance through a flowering...

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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....

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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

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Fantastic Sunsets
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 ...

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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

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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 ...

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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,...

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Street & Ocean View from Pvt Blcony
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...

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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

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A welcome walkway to Summerland
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...

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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 airport, entertainment, beach, and shopping/ business area. Gated community, 24hour security with pool on site. Housekeeper, chauffeur,...

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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

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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

$198

/ night

Email Owner
Bedrooms:3
Bathrooms:3
Sleeps:8
Type:Villa
Per night:$198 - $209
Per week:$1,382 - $1,459
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...

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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

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Montego Bay Jamaica Vacation Rentals - Apartment
1 / 12

Montego Bay Apartment
1 Bedroom / 1 Bathroom / Sleeps 2
Apartment / 1 Bedroom / Sleeps 2

(1)“ Excellent ”1 Review

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

Beautiful , quiet and very close to the water front , studio- apartment which is located about just 4 miles to Inter- National Airport . Luxurious apartment offers refrigerator, new micro- wave, iron with board, cooking utensils and facilities , well appointed bath with full...

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Je recommande

“ Excellent ”
February 9, 2015
5 minutes de l'aéroport.Face à la plage... mais il faut déboursé 6$.Près de toutes commodités. Propre. Vaisselle et accessoires inclus... y'avait même un extracteur à jus.Climatisation un peu bruyante, mais Un bel hôtel... je recommande !
Caro Côté, Québec, Canada

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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 ...

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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...

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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...

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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...

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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...

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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...

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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 ...

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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 ...

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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...

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Montego Bay Jamaica Vacation Rentals - Home
1 / 12

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

from

$929

/ night

Email Owner
Bedrooms:5
Bathrooms:6
Sleeps:10
Type:Home
Per night:$929 - $2,072
Per week:$6,500 - $14,500
Pets allowed:No
Internet:Yes

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...

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

from

$786

/ night

Email Owner
Bedrooms:4
Bathrooms:4
Sleeps:8
Type:Home
Per night:$786
Per week:$5,500
Pets allowed:No
Internet:Yes

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...

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Montego Bay Jamaica Vacation Rentals - Villa
1 / 48

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

(4)“ Excellent ”4 Reviews

from

$975

/ night

Email Owner
Bedrooms:4
Bathrooms:4
Sleeps:8
Type:Villa
Per night:$975 - $2,286
Per week:$6,825 - $16,000
Pets allowed:No
Internet:Yes

SERENITY 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. Additional amenities include: poolside shower, snorkel gear, connecting bedroom(s), golf on site or nearby, golf...

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1 / 9

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

(1)“ Excellent ”1 Review

from

$643

/ night

Email Owner
Bedrooms:4
Bathrooms:4
Sleeps:8
Type:Home
Per night:$643
Per week:$4,500
Pets allowed:No
Internet:Yes

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 ...

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Montego Bay Jamaica Vacation Rentals - Villa
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Montego Bay Villa
7 Bedrooms / 6 Bathrooms / Sleeps 14
Villa / 7 Bedrooms / Sleeps 14

(2)“ Excellent ”2 Reviews

Bedrooms:7
Bathrooms:6
Sleeps:14
Type:Villa
Per night:$1,143 - $3,429
Per week:$8,000 - $24,000
Pets allowed:No
Internet:Yes

True to its name, Tranquillity on the Beach is a place for relaxing into the calm ambiance of an exquisite home on a beautiful beachfront site ~ while being gently pampered by a competent staff. Additional amenities include: available for large groups, connecting bedroom(s), golf...

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Montego Bay Jamaica Vacation Rentals - Villa
1 / 35

Montego Bay Villa
5 Bedrooms / 7 Bathrooms / Sleeps 10
Villa / 5 Bedrooms / Sleeps 10

(2)“ Excellent ”2 Reviews

Bedrooms:5
Bathrooms:7
Sleeps:10
Type:Villa
Per night:$1,050 - $2,843
Per week:$7,350 - $19,900
Pets allowed:No
Internet:Yes

A paradigm of elegance and style, Noble House on the Beach is an architectural gem, unique in the Caribbean. Its design is a series of airy pavilions with peaked roofs, its living spaces separated by water gardens and bridges. Indoor spaces flow into outdoor with Oriental grace....

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1 / 26

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

Bedrooms:6
Bathrooms:8
Sleeps:12
Type:Home
Per night:$1,624 - $1,949
Per week:$11,365 - $13,640
Pets allowed:No
Internet:Yes

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...

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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...

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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...

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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...

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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...

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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...

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1 / 8

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

from

$565

/ night

Email Owner
Bedrooms:4
Bathrooms:4
Sleeps:8
Type:Home
Per night:$565 - $850
Per week:$3,950 - $5,950
Pets allowed:No
Internet:Yes

Designed by Prince Kasimir Korybut in 1993, Almond Hill is a lovely private home located on a former coconut plantation just 20 minutes from Montego Bay and one minute from posh Round Hill where guests enjoy complimentary resort membership. The villa is tastefully decorated with ...

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

Bedrooms:8
Bathrooms:8
Sleeps:16
Type:Home
Per night:$1,559 - $2,598
Per week:$10,909 - $18,182
Pets allowed:No
Internet:Yes

Haystack is the only eight- bedroom villa at the posh Tryall Club. Among the newest, its architecture defines spacious bedroom suites, a long furnished verandah perfect for dining outdoors, a striking red inside dining room and large family play room - all enhanced by overviews...

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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:...

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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...

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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...

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

Bedrooms:6
Bathrooms:7
Sleeps:12
Type:Villa
Per night:$1,299 - $1,948
Per week:$9,091 - $13,636
Pets allowed:No
Internet:Yes

A sprawling double lot directly on the Caribbean Sea is among the most stunning waterfront locations in all Jamaica. This is the rarefied site of the private villa named Karma Bay. Additional amenities include: poolside shower, snorkel gear, golf available, beach club, bathrobes,...

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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 - $1,559
Per week:$9,091 - $10,909
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 ...

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Montego Bay Jamaica Vacation Rentals - Home
1 / 21

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

from

$929

/ night

Email Owner
Bedrooms:5
Bathrooms:5
Sleeps:10
Type:Home
Per night:$929 - $1,143
Per week:$6,500 - $8,000
Pets allowed:No
Internet:Yes

A massive whole- house renovation has created this lovely vacation villa in the upscale residential neighborhood of Spring Farm just five minutes from three world- class golf courses, designer shops, bars, restaurants and beaches. Through carved entrance doors with antique brass...

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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 ...

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Montego Bay Jamaica Vacation Rentals - Villa
1 / 12

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....

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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 ...

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1 / 30

Montego Bay Villa
7 Bedrooms / 9 Bathrooms / Sleeps 16
Villa / 7 Bedrooms / Sleeps 16

Bedrooms:7
Bathrooms:9
Sleeps:16
Type:Villa
Per night:$1,010 - $2,915
Per week:$7,070 - $20,400
Pets allowed:No
Internet:Yes

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 ...

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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...

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Montego Bay Villa
6 Bedrooms / 6 Bathrooms / Sleeps 17
Villa / 6 Bedrooms / Sleeps 17

Bedrooms:6
Bathrooms:6
Sleeps:17
Type:Villa
Per night:$1,284 - $3,621
Per week:$8,988 - $25,347
Pets allowed:No
Internet:Yes

On floors of cool Jamaican marble in hues of gray, pink, cream and salmon; rich mahogany; high ceilings and lovely antiques. Knockando evokes a sense of old Jamaica updated with contemporary comforts and amenities. The living room opens wide to the heart of the house. A 1 300...

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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,...

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