Montego Bay Apartments & Villas with Swimming Pool - 170 Rentals Available.
170 Vacation rentals
Filters applied: Swimming pool
Sea View Villa Montego Bay
Montego Bay Villa
- 18 bedrooms 18
- 22 bathrooms
- Sleeps 36 36
- 1 night min
- Beach/lakeside relaxation
- Swimming pool
- Child friendly
$80.00
from $80.00 / night
Luxury Beach Resort! Gym! Tennis! Golf! Fully Staffed!Blue Bird
Hopewell Villa
- 4 bedrooms 4
- 4 bathrooms
- Sleeps 8 8
- Min stay varies
- Swimming pool
- Child friendly
- Air conditioning
$643.00
from $643.00 / night
GRAND ELEGANCE! CHEF! POOL! BUTLER SERVICE! SWIMMING POOL! FAMILY REUNIONS
Ironshore House
- 9 bedrooms 9
- 9 bathrooms
- Sleeps 22 22
- Min stay varies
- Swimming pool
- Child friendly
- Air conditioning
$2,143.00
from $2,143.00 / night
Calypso Shores, Montego Bay 4BR
Montego Bay Villa
- 4 bedrooms 4
- 4 bathrooms
- Sleeps 8 8
- Min stay varies
- Swimming pool
- Child friendly
- Air conditioning
$950.00
from $950.00 / night
Hummingbird at the Tryall Club - Ideal for Couples and Families, Beautiful Pool
Hopewell Villa
- 7 bedrooms 7
- 8 bathrooms
- Sleeps 14 14
- Min stay varies
- Swimming pool
- Child friendly
- Air conditioning
$3,142.00
from $3,142.00 / night
Endless Summer - 6 Bedrooms - Spring Farm
Montego Bay House
- 6 bedrooms 6
- 6 bathrooms
- Sleeps 12 12
- Min stay varies
- Swimming pool
- Ask about children
- Air conditioning
$1,357.00
from $1,357.00 / night
Greatview - Ideal for Couples and Families, Beautiful Pool and Beach
Montego Bay Villa
- 6 bedrooms 6
- 8 bathrooms
- Sleeps 12 12
- Min stay varies
- Swimming pool
- Child friendly
- Air conditioning
$2,085.00
from $2,085.00 / night
Sunset on the Beach at the Tryall Club
Montego Bay Villa
- 5 bedrooms 5
- 5 bathrooms
- Sleeps 10 10
- Min stay varies
- Swimming pool
- Child friendly
- Air conditioning
$1,629.00
from $1,629.00 / night
Endless Summer - Ideal for Couples and Families, Beautiful Pool and Beach
Ironshore Villa
- 6 bedrooms 6
- 7 bathrooms
- Sleeps 14 14
- Min stay varies
- Swimming pool
- Child friendly
- Air conditioning
$1,657.00
from $1,657.00 / night
Coconut Cottage - Ideal for Couples and Families, Beautiful Pool and Beach
Montego Bay Villa
- 5 bedrooms 5
- 6 bathrooms
- Sleeps 10 10
- Min stay varies
- Swimming pool
- Child friendly
- Air conditioning
$892.00
from $892.00 / night
MONTEGO BAY, FULLY STAFFED! PRIVATE POOL! 4 BEDROOMS! Sterling
Ironshore House
- 4 bedrooms 4
- 4 bathrooms
- Sleeps 8 8
- Min stay varies
- Swimming pool
- Child friendly
- Air conditioning
$643.00
from $643.00 / night
Sea Salt at the Tryall Club
Montego Bay Villa
- 5 bedrooms 5
- 6 bathrooms
- Sleeps 10 10
- Min stay varies
- Swimming pool
- Child friendly
- Air conditioning
$1,559.00
from $1,559.00 / night
Nutmeg - Ideal for Couples and Families, Beautiful Pool and Beach
Ironshore Villa
- 6 bedrooms 6
- 6 bathrooms
- Sleeps 12 12
- Min stay varies
- Swimming pool
- Child friendly
- Air conditioning
$1,214.00
from $1,214.00 / night
LUXURY! POOL! GATED COMMUMITY! STAFF!Georgian House, Montego Bay 7BR
Rose Hall Villa
- 7 bedrooms 7
- 6 bathrooms
- Sleeps 16 16
- Min stay varies
- Swimming pool
- Child friendly
- Air conditioning
$1,000.00
from $1,000.00 / night
Affordable! Cook! Housekeeper! Pool! Bogue Villa
Montego Bay Villa
- 5 bedrooms 5
- 4 bathrooms
- Sleeps 10 10
- Min stay varies
- Swimming pool
- Child friendly
- Air conditioning
$485.00
from $485.00 / night
Windsong - Ideal for Couples and Families, Beautiful Pool and Beach
Montego Bay Villa
- 4 bedrooms 4
- 4 bathrooms
- Sleeps 8 8
- Min stay varies
- Swimming pool
- Child friendly
- Air conditioning
$1,000.00
from $1,000.00 / night
gRAND LUXURY! STAFFED! POOL! CHEF! FAMILY FRIENDLY-Georgian House- 5BR
Rose Hall Villa
- 5 bedrooms 5
- 5 bathrooms
- Sleeps 12 12
- Min stay varies
- Swimming pool
- Child friendly
- Air conditioning
$950.00
from $950.00 / night
LARGE VILLA! LARGE SWIMMING POOL! BEACH MEMBERSHIP! FULLY STAFFED-Summerhill - 8
Rose Hall Villa
- 8 bedrooms 8
- 8 bathrooms
- Sleeps 16 16
- Min stay varies
- Swimming pool
- Child friendly
- Air conditioning
$1,600.00
from $1,600.00 / night
Great River House - Montego Bay 5 Bedrooms
Montego Bay House
- 5 bedrooms 5
- 6 bathrooms
- Sleeps 10 10
- Min stay varies
- Swimming pool
- Ask about children
- Air conditioning
$1,357.00
from $1,357.00 / night
PRIVATE POOL! STAFF! GATED COMMUNITY! DRIVER! Bienvenue
Montego Bay House
- 4 bedrooms 4
- 4 bathrooms
- Sleeps 8 8
- Min stay varies
- Swimming pool
- Child friendly
- Air conditioning
$743.00
from $743.00 / night
Karma Bay at the Tryall Club
Montego Bay Villa
- 6 bedrooms 6
- 7 bathrooms
- Sleeps 12 12
- Min stay varies
- Swimming pool
- Child friendly
- Air conditioning
$1,429.00
from $1,429.00 / night
Butler Service! Chef! Pool! Elegant! Caribbean Jewel
Rose Hall Villa
- 4 bedrooms 4
- 4 bathrooms
- Sleeps 10 10
- Min stay varies
- Swimming pool
- Child friendly
- Air conditioning
$857.00
from $857.00 / night
Kenyan Sunset Golf Villa in Rose Hall - Ideal for Couples and Families, Beautifu
Rose Hall Villa
- 5 bedrooms 5
- 7 bathrooms
- Sleeps 12 12
- Min stay varies
- Swimming pool
- Child friendly
- Air conditioning
$1,542.00
from $1,542.00 / night
GRAND LUXURY! STAFF! CHEF! VIEWS! POOL!Georgian House, Montego Bay 4BR
Rose Hall Villa
- 4 bedrooms 4
- 4 bathrooms
- Sleeps 8 8
- Min stay varies
- Swimming pool
- Child friendly
- Air conditioning
$901.00
from $901.00 / night
Bumper's Nest at the Tryall Club - Ideal for Couples and Families, Beautiful Poo
Hopewell Villa
- 6 bedrooms 6
- 7 bathrooms
- Sleeps 12 12
- Min stay varies
- Swimming pool
- Child friendly
- Air conditioning
$2,272.00
from $2,272.00 / night
Skylark - Spring Farm 4 Bedrooms
Montego Bay House
- 4 bedrooms 4
- 4 bathrooms
- Sleeps 1 1
- Min stay varies
- Swimming pool
- Ask about children
- Air conditioning
$571.00
from $571.00 / night
Drambuie Estate - Ideal for Couples and Families, Beautiful Pool and Beach
Montego Bay Villa
- 5 bedrooms 5
- 5 bathrooms
- Sleeps 10 10
- Min stay varies
- Swimming pool
- Child friendly
- Air conditioning
$1,000.00
from $1,000.00 / night
Almond Hill - Ideal for Couples and Families, Beautiful Pool and Beach
Montego Bay Villa
- 4 bedrooms 4
- 4 bathrooms
- Sleeps 8 8
- Min stay varies
- Swimming pool
- Child friendly
- Air conditioning
$964.00
from $964.00 / night
ULTIMATE LUXURY! STAFF! POOL! RESORT MEMBERSHIP!Endless Summer - Montego Bay 4BR
Rose Hall Villa
- 4 bedrooms 4
- 4 bathrooms
- Sleeps 8 8
- Min stay varies
- Swimming pool
- Child friendly
- Air conditioning
$1,215.00
from $1,215.00 / night
Pimento Hill - Ideal for Couples and Families, Beautiful Pool and Beach
Montego Bay Villa
- 6 bedrooms 6
- 6 bathrooms
- Sleeps 14 14
- Min stay varies
- Swimming pool
- Child friendly
- Air conditioning
$1,694.00
from $1,694.00 / night
Jus' Paradise Golf Villa in Rose Hall - Ideal for Couples and Families, Beautifu
Ironshore Villa
- 3 bedrooms 3
- 6 bathrooms
- Sleeps 6 6
- Min stay varies
- Swimming pool
- Child friendly
- Air conditioning
$1,100.00
from $1,100.00 / night
Knockando on Round Hill - Ideal for Couples and Families, Beautiful Pool and Bea
Hopewell Villa
- 5 bedrooms 5
- 6 bathrooms
- Sleeps 13 13
- Min stay varies
- Swimming pool
- Child friendly
- Air conditioning
$1,278.00
from $1,278.00 / night
PRIVATE POOL! STAFF! GATED COMMUNITY! DRIVER! Bienvenue
Rose Hall Villa
- 2 bedrooms 2
- 4 bathrooms
- Sleeps 4 4
- Min stay varies
- Swimming pool
- Child friendly
- Air conditioning
$543.00
from $543.00 / night
Fairway Manor
Montego Bay Villa
- 7 bedrooms 7
- 9 bathrooms
- Sleeps 16 16
- Min stay varies
- Swimming pool
- Child friendly
- Air conditioning
$1,470.00
from $1,470.00 / night
GRAND ELEGANCE! CHEF! POOL! BUTLER SERVICE! SWIMMING POOL! FAMILY REUNIONS
Ironshore House
- 7 bedrooms 7
- 7 bathrooms
- Sleeps 14 14
- Min stay varies
- Swimming pool
- Child friendly
- Air conditioning
$1,858.00
from $1,858.00 / night
Cliffside Cottage
Montego Bay Villa
- 5 bedrooms 5
- 5 bathrooms
- Sleeps 10 10
- Min stay varies
- Swimming pool
- Child friendly
- Air conditioning
$643.00
from $643.00 / night
Cielo at the Tryall Club - Ideal for Couples and Families, Beautiful Pool and Be
Hopewell Villa
- 5 bedrooms 5
- 5 bathrooms
- Sleeps 10 10
- Min stay varies
- Swimming pool
- Child friendly
- Air conditioning
$1,000.00
from $1,000.00 / night
Bambu - Montego Bay 6 Bedrooms
Montego Bay House
- 6 bathrooms
- Sleeps 12 12
- Min stay varies
- Beach/lakeside relaxation
- Swimming pool
- Ask about children
$1,801.00
from $1,801.00 / night
Own Chef! Housekeepers! Pool! Staff! AWESOME VIEWS! Family Friendly! Near Beach!
Hopewell Villa
- 3 bedrooms 3
- 2 bathrooms
- Sleeps 6 6
- Min stay varies
- Swimming pool
- Child friendly
- Air conditioning
$585.00
from $585.00 / night
Almond Hill
Montego Bay Villa
- 4 bedrooms 4
- 4 bathrooms
- Sleeps 8 8
- Min stay varies
- Swimming pool
- Child friendly
- Air conditioning
$823.00
from $823.00 / night
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