Montego Bay Apartments & Villas with Swimming Pool - 177 Rentals Available.
177 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
Karma Bay - Tryall Club
Hopewell Villa
- 6 bedrooms 6
- 6 bathrooms
- sleeps 12 12
- min stay varies
- Swimming pool
- Air conditioning
$2,143.00
from $2,143.00 / night
Sundance - Tryall Club
Hopewell Villa
- 5 bedrooms 5
- 5 bathrooms
- sleeps 10 10
- 7 nights min
- Swimming pool
$1,949.00
from $1,949.00 / night
GRAND ELEGANCE! CHEF! POOL! BUTLER SERVICE! SWIMMING POOL! FAMILY REUNIONS
Ironshore House
- 5 bedrooms 5
- 5 bathrooms
- sleeps 10 10
- min stay varies
- Swimming pool
- Child friendly
- Air conditioning
$1,429.00
from $1,429.00 / night
Avalon - Tryall Club
Hopewell Villa
- 4 bedrooms 4
- 4 bathrooms
- sleeps 8 8
- 7 nights min
- Swimming pool
- Child friendly
- Air conditioning
$714.00
from $714.00 / 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
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
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
$1,001.00
from $1,001.00 / 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
Overlook - Tryall Club
Hopewell Villa
- 5 bedrooms 5
- 5 bathrooms
- sleeps 10 10
- min stay varies
- Swimming pool
- Child friendly
- Air conditioning
$1,559.00
from $1,559.00 / night
Tradewinds - Tryall Club
Hopewell Villa
- 4 bedrooms 4
- 4 bathrooms
- sleeps 8 8
- 7 nights min
- Swimming pool
- Air conditioning
$1,637.00
from $1,637.00 / night
Linger Longer - Tryall Club
Hopewell Villa
- 3 bedrooms 3
- 3 bathrooms
- sleeps 6 6
- min stay varies
- Swimming pool
- Child friendly
- Air conditioning
$650.00
from $650.00 / 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
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
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
Island House - Tryall Club
Hopewell Villa
- 3 bedrooms 3
- 3 bathrooms
- sleeps 6 6
- min stay varies
- Swimming pool
- Child friendly
- Air conditioning
$643.00
from $643.00 / 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
GRAND ELEGANCE! CHEF! POOL! BUTLER SERVICE! SWIMMING POOL! FAMILY REUNIONS
Ironshore House
- 8 bedrooms 8
- 8 bathrooms
- sleeps 16 16
- min stay varies
- Swimming pool
- Child friendly
- Air conditioning
$2,001.00
from $2,001.00 / night
Almond Hill
Hopewell Villa
- 4 bedrooms 4
- 4 bathrooms
- sleeps 8 8
- min stay varies
- Swimming pool
- Child friendly
- Air conditioning
$964.00
from $964.00 / night
Round House - Tryall Club
Hopewell Villa
- 8 bedrooms 8
- 10 bathrooms
- sleeps 16 16
- min stay varies
- Swimming pool
- Child friendly
- Air conditioning
$2,143.00
from $2,143.00 / night
Annabella - Tryall Club
Hopewell Villa
- 6 bedrooms 6
- 8 bathrooms
- sleeps 12 12
- min stay varies
- Swimming pool
- Child friendly
- Air conditioning
$1,714.00
from $1,714.00 / 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
$893.00
from $893.00 / 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
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
Reveille - Tryall Club
Hopewell Villa
- 3 bedrooms 3
- 3 bathrooms
- sleeps 6 6
- min stay varies
- Swimming pool
- Child friendly
- Air conditioning
$714.00
from $714.00 / 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
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
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
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
Wheel House - Tryall Club
Hopewell Villa
- 6 bedrooms 6
- 6 bathrooms
- sleeps 12 12
- 7 nights min
- Swimming pool
- Air conditioning
$1,043.00
from $1,043.00 / 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
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
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
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
No Problem - Tryall Club
Hopewell Villa
- 3 bedrooms 3
- 3 bathrooms
- sleeps 6 6
- min stay varies
- Swimming pool
- Child friendly
- Air conditioning
$643.00
from $643.00 / night
Little Palm - Tryall Club
Hopewell Villa
- 2 bedrooms 2
- 2 bathrooms
- sleeps 4 4
- min stay varies
- Swimming pool
- Air conditioning
$585.00
from $585.00 / 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
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
What is Certificate of Excellence?
TripAdvisor gives a Certificate of Excellence to accommodations, attractions and restaurants that consistently earn great reviews from travelers.