Montego Bay Apartments & Villas with Swimming Pool - 178 Rentals Available.
178 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
$92.00
from $92.00 / night
Karma Bay - Tryall Club
Hopewell Villa
- 6 bedrooms 6
- 6 bathrooms
- sleeps 12 12
- min stay varies
- Swimming pool
- Air conditioning
$2,214.00
from $2,214.00 / night
Infinity - Tryall Club
Hopewell Villa
- 5 bedrooms 5
- 5 bathrooms
- sleeps 10 10
- min stay varies
- Swimming pool
- Child friendly
- Air conditioning
$2,091.00
from $2,091.00 / night
Sundance - Tryall Club
Hopewell Villa
- 5 bedrooms 5
- 5 bathrooms
- sleeps 10 10
- 7 nights min
- Swimming pool
$3,143.00
from $3,143.00 / night
Anticipation - Tryall Club
Hopewell Villa
- 6 bedrooms 6
- 4 bathrooms
- sleeps 12 12
- 7 nights min
- Swimming pool
- Child friendly
- Air conditioning
$2,241.00
from $2,241.00 / night
Twin Palms - Tryall Club
Hopewell Villa
- 7 bedrooms 7
- 5 bathrooms
- sleeps 14 14
- 7 nights min
- Swimming pool
- Child friendly
- Air conditioning
$3,507.00
from $3,507.00 / night
Overlook - Tryall Club
Hopewell Villa
- 5 bedrooms 5
- 5 bathrooms
- sleeps 10 10
- min stay varies
- Swimming pool
- Child friendly
- Air conditioning
$1,558.00
from $1,558.00 / night
Hummingbird House - Tryall Club
Hopewell Villa
- 7 bedrooms 7
- 7 bathrooms
- sleeps 14 14
- min stay varies
- Swimming pool
- Child friendly
- Air conditioning
$3,143.00
from $3,143.00 / 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
Summertime
Montego Bay Villa
- 6 bedrooms 6
- 6 bathrooms
- sleeps 14 14
- min stay varies
- Swimming pool
- Child friendly
- Air conditioning
$929.00
from $929.00 / 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
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
Reef House - Tryall Club
Hopewell Villa
- 4 bedrooms 4
- 4 bathrooms
- sleeps 8 8
- min stay varies
- Swimming pool
- Child friendly
- Air conditioning
$857.00
from $857.00 / 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
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
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
$900.00
from $900.00 / 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
Pineapple House - Tryall Club
Hopewell Villa
- 5 bedrooms 5
- 5 bathrooms
- sleeps 10 10
- min stay varies
- Swimming pool
- Child friendly
- Air conditioning
$2,054.00
from $2,054.00 / night
Little Hill - Tryall Club
Hopewell Villa
- 5 bedrooms 5
- 4 bathrooms
- sleeps 8 8
- min stay varies
- Swimming pool
- Air conditioning
$1,299.00
from $1,299.00 / night
Avalon - Tryall Club
Hopewell Villa
- 4 bedrooms 4
- 4 bathrooms
- sleeps 8 8
- 7 nights min
- Swimming pool
- Child friendly
- Air conditioning
$786.00
from $786.00 / 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
Linger Longer - Tryall Club
Hopewell Villa
- 3 bedrooms 3
- 3 bathrooms
- sleeps 6 6
- min stay varies
- Swimming pool
- Child friendly
- Air conditioning
$651.00
from $651.00 / night
GRAND ELEGANCE! CHEF! POOL! BUTLER SERVICE! SWIMMING POOL! FAMILY REUNIONS
Ironshore House
- 4 bedrooms 4
- 4 bathrooms
- sleeps 8 8
- min stay varies
- Swimming pool
- Child friendly
- Air conditioning
$1,286.00
from $1,286.00 / 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
Vista Del Mar - Tryall Club
Hopewell Villa
- 3 bedrooms 3
- 3 bathrooms
- sleeps 6 6
- min stay varies
- Swimming pool
- Child friendly
- Air conditioning
$1,039.00
from $1,039.00 / night
LARGE VILLA! LARGE SWIMMING POOL! BEACH MEMBERSHIP! FULLY STAFFED-Summerhill - 4
Rose Hall Villa
- 4 bedrooms 4
- 4 bathrooms
- sleeps 8 8
- min stay varies
- Swimming pool
- Child friendly
- Air conditioning
$1,143.00
from $1,143.00 / night
Haystack - Tryall Club
Hopewell Villa
- 8 bedrooms 8
- 9 bathrooms
- sleeps 16 16
- min stay varies
- Swimming pool
- Child friendly
- Air conditioning
$3,286.00
from $3,286.00 / 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
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
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
$586.00
from $586.00 / night
Endless Summer
Montego Bay Villa
- 6 bedrooms 6
- 7 bathrooms
- sleeps 16 16
- min stay varies
- Swimming pool
- Child friendly
- Air conditioning
$1,215.00
from $1,215.00 / 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 - 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
$1,000.00
from $1,000.00 / 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
GRAND ELEGANCE! CHEF! POOL! BUTLER SERVICE! SWIMMING POOL! FAMILY REUNIONS
Ironshore House
- 6 bedrooms 6
- 6 bathrooms
- sleeps 12 12
- min stay varies
- Swimming pool
- Child friendly
- Air conditioning
$1,714.00
from $1,714.00 / night
Yellowbird - Tryall Club
Hopewell Villa
- 4 bedrooms 4
- 4 bathrooms
- sleeps 8 8
- min stay varies
- Swimming pool
- Child friendly
- Air conditioning
$786.00
from $786.00 / 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
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