Montego Bay Apartments & Villas with Swimming Pool - 228 Rentals Available.
228 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
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
$1,948.00
from $1,948.00 / night
Summertime
Montego Bay Villa
- 6 bedrooms 6
- 6 bathrooms
- Sleeps 13 13
- Min stay varies
- Swimming pool
- Child friendly
- Air conditioning
$858.00
from $858.00 / night
Fairwinds at the Tryall Club - Ideal for Couples and Families, Beautiful Pool an
Hopewell Villa
- 4 bedrooms 4
- 4 bathrooms
- Sleeps 8 8
- Min stay varies
- Swimming pool
- Child friendly
- Air conditioning
$642.00
from $642.00 / night
Reef House - Tryall Club
Hopewell Villa
- 4 bedrooms 4
- 4 bathrooms
- Sleeps 8 8
- Min stay varies
- Swimming pool
- Air conditioning
$858.00
from $858.00 / night
Island House - Tryall Club
Hopewell Villa
- 3 bedrooms 3
- 3 bathrooms
- Sleeps 6 6
- Min stay varies
- Swimming pool
- Air conditioning
$643.00
from $643.00 / 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
Drambuie: Luxury Estate with Breathtaking Views
Montego Bay Villa
- 5 bedrooms 5
- 6 bathrooms
- Sleeps 10 10
- Min stay varies
- Swimming pool
- Child friendly
- Car not necessary
$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
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
Pavillion - Ideal for Couples and Families, Beautiful Pool and Beach
Montego Bay Villa
- 5 bedrooms 5
- 6 bathrooms
- Sleeps 14 14
- Min stay varies
- Swimming pool
- Child friendly
- Air conditioning
$1,128.00
from $1,128.00 / night
Jamaican Dream Golf Villa in Rose Hall - Ideal for Couples and Families, Beautif
Montego Bay Villa
- 4 bedrooms 4
- 1 bathroom
- Sleeps 8 8
- Min stay varies
- Swimming pool
- Child friendly
- Air conditioning
$858.00
from $858.00 / night
Villa Viviana - Tryall Club
Hopewell Villa
- 6 bedrooms 6
- 8 bathrooms
- Sleeps 12 12
- Min stay varies
- Swimming pool
- Air conditioning
$1,715.00
from $1,715.00 / 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
Summertime - Ideal for Couples and Families, Beautiful Pool and Beach
Montego Bay Villa
- 6 bedrooms 6
- 6 bathrooms
- Sleeps 12 12
- Min stay varies
- Swimming pool
- Child friendly
- Air conditioning
$858.00
from $858.00 / 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
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
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
$893.00
from $893.00 / night
Round House - Tryall Club
Hopewell Villa
- 8 bedrooms 8
- 10 bathrooms
- Sleeps 16 16
- Min stay varies
- Swimming pool
- Air conditioning
$2,143.00
from $2,143.00 / 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
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
Sundance - Tryall Club
Hopewell Villa
- 5 bedrooms 5
- 5 bathrooms
- Sleeps 10 10
- 7 nights min
- Swimming pool
$1,950.00
from $1,950.00 / night
Cliffside Cottage - 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
$928.00
from $928.00 / 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
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
Caribbean Jewel - Spring Farm, Montego Bay 4 Bdrms
Rose Hall Villa
- 4 bedrooms 4
- 4 bathrooms
- Sleeps 10 10
- Min stay varies
- Swimming pool
$858.00
from $858.00 / night
Goat Hill - Montego Bay 3 Bedrooms
Montego Bay House
- 3 bedrooms 3
- 3 bathrooms
- Sleeps 6 6
- Min stay varies
- Swimming pool
- Ask about children
- Air conditioning
$1,000.00
from $1,000.00 / 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! CHEF! BASKET BALL! TENNIS COURT! FAMILY FRIENDLY!
Montego Bay House
- 6 bedrooms 6
- 6 bathrooms
- Sleeps 14 14
- Min stay varies
- Swimming pool
- Child friendly
- Air conditioning
$855.00
from $855.00 / 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
Anticipation - Tryall Club
Hopewell Villa
- 6 bedrooms 6
- 4 bathrooms
- Sleeps 12 12
- 7 nights min
- Swimming pool
- Air conditioning
$2,241.00
from $2,241.00 / 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
$965.00
from $965.00 / night
Fairway Manor - 7 Bedrooms - Montego Bay
Montego Bay House
- 7 bedrooms 7
- 8 bathrooms
- Sleeps 14 14
- Min stay varies
- Swimming pool
- Ask about children
- Air conditioning
$1,760.00
from $1,760.00 / night
Almond Hill
Hopewell Villa
- 4 bedrooms 4
- 4 bathrooms
- Sleeps 8 8
- Min stay varies
- Swimming pool
- Child friendly
- Air conditioning
$965.00
from $965.00 / 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
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
$1,760.00
from $1,760.00 / night
Sunrise Villa - Tryall Club 4 Bedroom Oceanfront
Montego Bay House
- 4 bedrooms 4
- 4 bathrooms
- Sleeps 8 8
- 4 nights min
- Beach/lakeside relaxation
- Swimming pool
- Ask about children
$643.00
from $643.00 / 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
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
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