Montego Bay Apartments & Villas with Swimming Pool - 169 Rentals Available.
169 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
Longview Manor on Round Hill - Ideal for Couples and Families, Beautiful Pool an
Hopewell Villa
- 7 bedrooms 7
- 7 bathrooms
- sleeps 14 14
- min stay varies
- Swimming pool
- Child friendly
- Air conditioning
$2,700.00
from $2,700.00 / 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
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
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
Fairwinds - Tryall Club, Montego Bay 4 Bedrooms
Montego Bay House
- 4 bedrooms 4
- 4 bathrooms
- sleeps 8 8
- 5 nights min
- Swimming pool
- Ask about children
- Air conditioning
$643.00
from $643.00 / night
Tradewinds - Tryall Club Montego Bay 4 Bedrooms
Montego Bay House
- 4 bedrooms 4
- 4 bathrooms
- sleeps 8 8
- 5 nights min
- Beach/lakeside relaxation
- Swimming pool
- Ask about children
$643.00
from $643.00 / night
Tranquility on the Beach - Ideal for Couples and Families, Beautiful Pool and Be
Montego Bay Villa
- 7 bedrooms 7
- 6 bathrooms
- sleeps 14 14
- min stay varies
- Swimming pool
- Child friendly
- Air conditioning
$1,651.00
from $1,651.00 / night
Sunset on the Beach at the Tryall Club - Ideal for Couples and Families, Beautif
Hopewell Villa
- 3 bedrooms 3
- 4 bathrooms
- sleeps 6 6
- min stay varies
- Swimming pool
- Child friendly
- Air conditioning
$2,143.00
from $2,143.00 / 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
LARGE VILLA! LARGE SWIMMING POOL! BEACH MEMBERSHIP! FULLY STAFFED-Summerhill - 6
Rose Hall Villa
- 6 bedrooms 6
- 6 bathrooms
- sleeps 12 12
- min stay varies
- Swimming pool
- Child friendly
- Air conditioning
$1,329.00
from $1,329.00 / 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
$1,800.00
from $1,800.00 / night
Round House at the Tryall Club - Ideal for Couples and Families, Beautiful Pool
Hopewell Villa
- 8 bedrooms 8
- 10 bathrooms
- sleeps 16 16
- min stay varies
- Swimming pool
- Child friendly
- Air conditioning
$2,357.00
from $2,357.00 / night
Noble House on the Beach
Montego Bay Villa
- 5 bedrooms 5
- 7 bathrooms
- sleeps 10 10
- 5 nights min
- Swimming pool
- Child friendly
- Air conditioning
$1,050.00
from $1,050.00 / 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
$3,457.00
from $3,457.00 / 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
$1,620.00
from $1,620.00 / night
Tranquillity on the Beach
Montego Bay Villa
- 7 bedrooms 7
- 6 bathrooms
- sleeps 14 14
- 5 nights min
- Swimming pool
- Child friendly
- Air conditioning
$1,143.00
from $1,143.00 / night
Own Chef! Housekeepers! Pool! Staff! Family Friendly! ELEGANT LUXURY! Bambu
Hopewell Villa
- 4 bedrooms 4
- 6 bathrooms
- sleeps 8 8
- min stay varies
- Swimming pool
- Child friendly
- Air conditioning
$1,179.00
from $1,179.00 / night
Vista Del Mar at the Tryall Club - Ideal for Couples and Families, Beautiful Poo
Hopewell Villa
- 3 bedrooms 3
- 3 bathrooms
- sleeps 6 6
- min stay varies
- Swimming pool
- Child friendly
- Air conditioning
$1,143.00
from $1,143.00 / night
Caribbean Jewel - Spring Farm, Montego Bay 4 Bdrms
Rose Hall Villa
- 4 bedrooms 4
- 4 bathrooms
- sleeps 10 10
- min stay varies
- Swimming pool
$857.00
from $857.00 / night
Serendipity - Spring Farm, Montego Bay 6 Bedrooms
Montego Bay House
- 6 bedrooms 6
- 6 bathrooms
- sleeps 1 1
- min stay varies
- Swimming pool
- Ask about children
$1,280.00
from $1,280.00 / night
Flower Hill - Spring Farm, Montego Bay 6 bedrooms
Montego Bay House
- 6 bedrooms 6
- 14 bathrooms
- sleeps 12 12
- min stay varies
- Swimming pool
- Ask about children
- Air conditioning
$3,000.00
from $3,000.00 / 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
$1,275.00
from $1,275.00 / 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
$1,740.00
from $1,740.00 / 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
Nutmeg - Spring Farm, Montego Bay 6 Bedrooms
Montego Bay House
- 5 bedrooms 5
- 6 bathrooms
- sleeps 12 12
- min stay varies
- Swimming pool
- Ask about children
- Air conditioning
$1,214.00
from $1,214.00 / night
Coconut Cottage - Montego Bay 5 Bedroom
Montego Bay House
- 5 bedrooms 5
- 5 bathrooms
- sleeps 10 10
- min stay varies
- Swimming pool
- Ask about children
- Air conditioning
$894.00
from $894.00 / night
Fairway Manor - Ideal for Couples and Families, Beautiful Pool and Beach
Rose Hall Villa
- 7 bedrooms 7
- 9 bathrooms
- sleeps 16 16
- min stay varies
- Swimming pool
- Child friendly
- Air conditioning
$1,848.00
from $1,848.00 / 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
$1,050.00
from $1,050.00 / 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
$1,100.00
from $1,100.00 / night
LARGE VILLA! LARGE SWIMMING POOL! BEACH MEMBERSHIP! FULLY STAFFED-Summerhill - 7
Rose Hall Villa
- 7 bedrooms 7
- 7 bathrooms
- sleeps 14 14
- min stay varies
- Swimming pool
- Child friendly
- Air conditioning
$1,529.00
from $1,529.00 / 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
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
$937.00
from $937.00 / 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
Yellowbird at the Tryall Club - Ideal for Couples and Families, Beautiful Pool a
Hopewell Villa
- 4 bedrooms 4
- 4 bathrooms
- sleeps 8 8
- min stay varies
- Swimming pool
- Child friendly
- Air conditioning
$864.00
from $864.00 / 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
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
$1,050.00
from $1,050.00 / night
Butler Service! Chef! Pool! Elegant! Caribbean Jewel
Rose Hall Condo
- 3 bedrooms 3
- 3 bathrooms
- sleeps 6 6
- min stay varies
- Swimming pool
- Child friendly
- Air conditioning
$715.00
from $715.00 / night
Round House at the Tryall Club
Montego Bay Villa
- 8 bedrooms 8
- 10 bathrooms
- sleeps 16 16
- min stay varies
- Swimming pool
- Child friendly
- Air conditioning
$1,340.00
from $1,340.00 / 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
$2,190.00
from $2,190.00 / night
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