Montego Bay Vacation Rentals

131 Rentals

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Montego Bay Jamaica Vacation Rentals - Cottage

2BR / 1BA - Sleeps 4 - Montego Bay Cottage

Explore beyond the stereotypical tourist traps such as the hotel star systems and Sandals resort experience....

$78 / nt

2 Reviews
Montego Bay Jamaica Vacation Rentals - Villa

6BR / 5BA - Sleeps 12 - Montego Bay Villa

"Soon Come" Villa has 6 air- conditioned bedrooms with Cable TV, private bathrooms and ceiling fan,...

$118 - $141 / nt

Montego Bay Jamaica Vacation Rentals - Apartment

1BR / 1BA - Sleeps 2 - Montego Bay Apartment

Beautiful , quiet and very close to the water front , studio- apartment which is located about just...

$78 / nt

Montego Bay Jamaica Vacation Rentals - Guesthouse

2BR / 1BA - Sleeps 4 - Montego Bay Guesthouse

2 bed room, full bath, living, dinning and kitchen with front Patio Air condition and Hot water very...

$70 / nt

Montego Bay Jamaica Vacation Rentals - Townhouse

2BR / 1.5BA - Sleeps 4 - Montego Bay Townhouse

Brand new furnished two bedroom townhouse with central air/cable internet, hot water available for weekly...

$140 - $150 / nt

9 Reviews
Montego Bay Jamaica Vacation Rentals - Villa

3BR / 3BA - Sleeps 8 - Montego Bay Villa

Villa Swarm is a very comfortable one story villa with a tranquil feel to it. This is a sea view property...

$181 - $202 / nt

2 Reviews
A welcome walkway to Summerland

4BR / 4BA - Sleeps 8 - Montego Bay Villa

Summerland is a beautiful private home situated on 2 acres within the luxurious Round Hill Hotel compound....

$700 - $1,150 / nt

Montego Bay Jamaica Vacation Rentals - Condo

1BR / 1BA - Sleeps 5 - Montego Bay Condo

See Photos - This Is A Front Facing Beach View One Bedroom Suite ( Not A Studio Or Side View And Perfectly...

$145 - $170 / nt

1 Review
Montego Bay Jamaica Vacation Rentals - Villa

5BR / 7BA - Sleeps 16 - Montego Bay Villa

TEK TIME is Jamaican patois for advice that almost all of us need: TAKE TIME to slow down and take in...

$1,015 - $2,500 / nt

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4BR / 4BA - Sleeps 8 - Montego Bay Home

Clive House - Built in true Jamaican “Great House” fashion, Clive House is a beautiful combination...

$708 - $1,737 / nt

Photo not available

4BR / 4BA - Sleeps 8 - Montego Bay Home

Destiny Villa is the perfect union of dramatic architecture and spectacular setting. Located in the prestigious...

$1,215 - $2,400 / nt

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3BR / 0BA - Sleeps 6 - Montego Bay Home

Seagrape is a magnificent three- bedroom villa facing the edge of the blue waters of the Caribbean Sea....

$629 - $1,533 / nt

Montego Bay Jamaica Vacation Rentals - Home

-1BR / 6BA - Sleeps 2 - Montego Bay Home

Bambu Villa is our newest Montego Bay luxury property and is located at Tamarind Hill on the lush west...

$1,179 - $2,715 / nt

Montego Bay Jamaica Vacation Rentals - Home

5BR / 5BA - Sleeps 1 - Montego Bay Home

Drambuie Estate is a spectacular 35 acre hilltop villa with extraordinary views of the sea and Montego...

$643 - $1,858 / nt

Montego Bay Jamaica Vacation Rentals - Home

5BR / 5BA - Sleeps 1 - Montego Bay Home

Nutmeg Villa , is a beautiful, fully renovated 5- bedroom, 4, 600 sq ft. villa in the Spring Farm...

$929 - $2,500 / nt

Montego Bay Jamaica Vacation Rentals - Home

3BR / 3BA - Sleeps 1 - Montego Bay Home

Pinnacle is a charming three- bedroom villa with a superb location overlooking Tryall Club and the Caribbean...

$629 - $1,686 / nt

Montego Bay Jamaica Vacation Rentals - Home

9BR / 9BA - Sleeps 1 - Montego Bay Home

Summerhill Villa , one of the newest villas in the Spring Farm area, is a 10, 000 sq. ft, 3 story...

$1,000 - $2,572 / nt

Montego Bay Jamaica Vacation Rentals - Home

5BR / 5BA - Sleeps 1 - Montego Bay Home

Infinity is a spectacular new 5- bedroom addition to the Tryall Club family of villas. Completed in 2009,...

$1,715 - $3,572 / nt

Montego Bay Jamaica Vacation Rentals - Home

10BR / 8BA - Sleeps 20 - Montego Bay Home

Silent Waters is one of the most glamorous private homes in the Caribbean. It is distinguished by world-...

$2,072 - $6,072 / nt

Montego Bay Jamaica Vacation Rentals - Home

7BR / 7BA - Sleeps 14 - Montego Bay Home

Harmony Hill is one of the newest members to the exclusive North Coast Tryall Club. This villa is a private...

$1,786 - $5,072 / nt

Montego Bay Jamaica Vacation Rentals - Home

7BR / 7BA - Sleeps 14 - Montego Bay Home

Round House is a seven- bedroom villa and is one of the largest and most spacious villas at The Tryall...

$1,715 - $3,572 / nt

Montego Bay Jamaica Vacation Rentals - Home

7BR / 7BA - Sleeps 14 - Montego Bay Home

Sugar Hill is an elegant new island home perched atop a manicured 3- acre property overlooking the breathtaking...

$1,715 - $5,000 / nt

Montego Bay Jamaica Vacation Rentals - Home

6BR / 6BA - Sleeps 12 - Montego Bay Home

Anticipation is privately nestled on the hillside of the world renowned Tryall Club with an uninterrupted...

$1,429 - $4,286 / nt

Montego Bay Jamaica Vacation Rentals - Home

6BR / 6BA - Sleeps 12 - Montego Bay Home

Karma Bay is a unique fusion of Asia- Caribbean styles on a spectacular water front location in the historic...

$1,429 - $4,286 / nt

Montego Bay Jamaica Vacation Rentals - Home

6BR / 7BA - Sleeps 12 - Montego Bay Home

Rose Cottage, is a six- bedroom new villa to Tryall, sits quietly yet dramatically on a plateau affording...

$1,715 - $4,286 / nt

Montego Bay Jamaica Vacation Rentals - Home

5BR / 5BA - Sleeps 10 - Montego Bay Home

Overlook - is built on one of the prime sites at Tryall and conveniently located in easy walking distance...

$1,715 - $3,572 / nt

Montego Bay Jamaica Vacation Rentals - Home

5BR / 5BA - Sleeps 10 - Montego Bay Home

Villa Lolita is one of Tryall's newest and most fabulously equipped Premier luxury villas! It is 14,...

$1,429 - $3,572 / nt

Montego Bay Jamaica Vacation Rentals - Home

5BR / 6BA - Sleeps 10 - Montego Bay Home

Point of View is located on the highest point at Tryall Club 400 feet above sea level. With its breathtaking...

$1,429 - $3,572 / nt

Montego Bay Jamaica Vacation Rentals - Home

4BR / 4BA - Sleeps 8 - Montego Bay Home

Reef House is a delightful 4- bedroom seaside villa located in the prestigious Tryall Club. You approach...

$708 - $1,737 / nt

Montego Bay Jamaica Vacation Rentals - Home

4BR / 4BA - Sleeps 8 - Montego Bay Home

Sunrise is a lovely four bedroom, comfortably furnished, villa located beach front in Tryall Club....

$708 - $1,737 / nt

Montego Bay Jamaica Vacation Rentals - Home

3BR / 3BA - Sleeps 6 - Montego Bay Home

Bumper’ s Nest is an elegantly designed 13, 000 sq foot, deluxe three bedroom villa sitting...

$786 - $2,279 / nt

Montego Bay Jamaica Vacation Rentals - Home

-1BR / 5BA - Sleeps 2 - Montego Bay Home

Allamanda Villa completed in 2012, is an elegant five bedroom Caribbean vacation home. All on one level,...

$858 - $2,643 / nt

Montego Bay Jamaica Vacation Rentals - Home

4BR / 4BA - Sleeps 1 - Montego Bay Home

Tradewinds Villa sits on two acres at the famous Tryall Club directly on the Caribbean Sea. There are...

$865 - $1,737 / nt

Montego Bay Jamaica Vacation Rentals - Home

4BR / 4BA - Sleeps 8 - Montego Bay Home

When Round Hill was only an undeveloped knob of lush green hillside rising over the sea, one man had...

$857 - $2,000 / nt

Montego Bay Jamaica Vacation Rentals - Home

4BR / 0BA - Sleeps 4 - Montego Bay Home

Casa Bella villa in Jamaica is a 4 bedroom villa - Nestled in the foothills of exotic Montego Bay, Jamaica...

$680 - $1,050 / nt

Montego Bay Jamaica Vacation Rentals - Home

6BR / 6BA - Sleeps 1 - Montego Bay Home

Serendipity Villa is located in the prestigious Spring Farm neighborhood above and overlooking Half Moon...

$500 - $1,715 / nt

Montego Bay Jamaica Vacation Rentals - Home

4BR / 4BA - Sleeps 8 - Montego Bay Home

Bluebird is a four- bedroom villa overlooking a magnificent tropical garden and the glittering panorama...

$865 - $1,737 / nt

Montego Bay Jamaica Vacation Rentals - Home

6BR / 0BA - Sleeps 6 - Montego Bay Home

Following Seas at the Tryall Club is a fabulous private villa in Montego Bay, with premier rating among...

$1,429 - $3,572 / nt

Montego Bay Jamaica Vacation Rentals - Home

5BR / 0BA - Sleeps 5 - Montego Bay Home

Over 8, 000 sq ft of new luxury villa! Absolute luxury! One of our newest villas in our villa collections...

$911 - $1,815 / nt

Montego Bay Jamaica Vacation Rentals - Home

7BR / 0BA - Sleeps 7 - Montego Bay Home

Limited time offer! Stay for 7 nights, pay for 6 nights. Get ONE NIGHT FREE! (Applies to certain dates...

$550 - $1,500 / nt

Montego Bay Jamaica Vacation Rentals - Home

6BR / 6BA - Sleeps 12 - Montego Bay Home

Hammerstein Highland House Villa sits high in the hillswith breathtaking views of Montego Bay. This six-...

$858 - $2,286 / nt

Montego Bay Jamaica Vacation Rentals - Home

5BR / 6BA - Sleeps 12 - Montego Bay Home

Coconut Cottage is a very private 5- bedroom cottage nestled into an acre on a gentle hillside that was...

$571 - $5,000 / nt

Montego Bay Jamaica Vacation Rentals - Home

7BR / 0BA - Sleeps 7 - Montego Bay Home

Greatview is one of Jamaica's most luxurious villas, set high above the Half Moon golf course to the...

$1,272 - $2,500 / nt

Montego Bay Jamaica Vacation Rentals - Home

4BR / 0BA - Sleeps 4 - Montego Bay Home

Fairwinds is a lovely four- bedroom private villa with a fantastic view of the glittering Caribbean Sea...

$708 - $1,336 / nt

Montego Bay Jamaica Vacation Rentals - Home

4BR / 4BA - Sleeps 8 - Montego Bay Home

Little Hill - was built in 1959 by an architect Robert Hartley. It was the first villa to be built at...

$1,429 - $2,858 / nt

Montego Bay Jamaica Vacation Rentals - Home

9BR / 13BA - Sleeps 18 - Montego Bay Home

L'Dor V'Dor - Overlooking the majestic Tryall Club and providing 360 degree panoramic views of Montego...

$1,429 - $7,858 / nt

Montego Bay Jamaica Vacation Rentals - Home

7BR / 0BA - Sleeps 7 - Montego Bay Home

BRAND NEW RENOVATIONS! ! ! - Come and view all our top quality finishes in the bedrooms and our new...

$940 - $1,810 / nt

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