Vacation Rentals with Private Pool in Widowmaker's Cave, Montego Bay: Compare 10+ Sites & Save

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  3.  Jamaica
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  6.  Widowmaker's Cave

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124 Best Vacation Rentals with Private Pool in Widowmaker's Cave (Starting from $80)

Villa Chinnor-Kent Ave
Villa Chinnor-Kent Ave
Villa
Montego Bay, Jamaica
6.4k from Widowmaker's Cave center

Cheap, Accommodations, Pools, Parking, Villas, Vacation homes, Cottages, Lodgings, Vacation rentals

4 Bedrooms8 Guests
9.0

Fabulous

2 reviews

$389
Average price / night
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Ocean View King or 2 Twin beds - Located at Founders Cove
Ocean View King or 2 Twin beds - Located at Founders Cove
Condo
Montego Bay, 00000, Jamaica
0.1k from Widowmaker's Cave center

AC, Dryer, Fitness Equipment, Free Parking, Internet, Living Area, No Smoking, Patio, Pool

1 Bedroom3 Guests
New to Booking
$781
Average price / night
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Located at Eclipse Private Patio or Balcony King or double bds
Located at Eclipse Private Patio or Balcony King or double bds
Apartment
Montego Bay, 00000, Jamaica
0.1k from Widowmaker's Cave center

AC, Dryer, Fitness Equipment, Free Parking, Internet, Living Area, No Smoking, Pool, TV

1 Bedroom3 Guests
New to Booking
$1191
Average price / night
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Spacious Bedroom Located in Founders Cove Separate Living room
Spacious Bedroom Located in Founders Cove Separate Living room
Apartment
Montego Bay, 00000, Jamaica
0.1k from Widowmaker's Cave center

AC, Dryer, Fitness Equipment, Free Parking, Internet, Living Area, No Smoking, Pool, TV

1 Bedroom4 Guests
New to Booking
$1322
Average price / night
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Located at Founders Cove Spacious bedroom Separate living room
Located at Founders Cove Spacious bedroom Separate living room
Apartment
Montego Bay, 00000, Jamaica
0.1k from Widowmaker's Cave center

AC, Dryer, Fitness Equipment, Free Parking, Internet, Living Area, No Smoking, Pool, TV

1 Bedroom4 Guests
New to Booking
$1187
Average price / night
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Located in Founders Cove Spacious bathrooms King or double beds
Located in Founders Cove Spacious bathrooms King or double beds
Apartment
Montego Bay, 00000, Jamaica
0.1k from Widowmaker's Cave center

AC, Dryer, Fitness Equipment, Free Parking, Internet, Living Area, No Smoking, Pool, TV

1 Bedroom4 Guests
New to Booking
$1052
Average price / night
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Secluded 3BR Garden Villa | Pool & Ocean Views
Secluded 3BR Garden Villa | Pool & Ocean Views
Villa
Montego Bay, Jamaica
0.3k from Widowmaker's Cave center

AC, Arcade, Balcony, Free Parking, Internet, Kitchen, Microwave, No Smoking, Outdoor Space

3 Bedrooms8 Guests
New to Booking
$1127
Average price / night
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Luxury 6BR Hilltop Villa | Sweeping Sea Views & Private Pool
Luxury 6BR Hilltop Villa | Sweeping Sea Views & Private Pool
Villa
Montego Bay, Jamaica
0.5k from Widowmaker's Cave center

AC, Balcony, Barbecue, Fitness Equipment, Free Parking, Internet, Kitchen, Laundry, Microwave

6 Bedrooms16 Guests
New to Booking
$2230
Average price / night
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1br Guesthouse - King/WiFi/Pool/AC/Housekeeper
1br Guesthouse - King/WiFi/Pool/AC/Housekeeper
House
Reading, Montego Bay,, Jamaica
0.9k from Widowmaker's Cave center

Hot Tub, Pool

1 Bedroom2 Guests
New to Booking
$125
Average price / night
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Amazing One Bedroom Apartment! Pool & Bar! Food options available!
Amazing One Bedroom Apartment! Pool & Bar! Food options available!
Villa
Montego Bay, Jamaica
1.2k from Widowmaker's Cave center

AC, Internet, No Smoking, Pool, TV

1 Bedroom4 Guests
New to Booking
$140
Average price / night
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Montego Bay: Elegant Apt w/ Stunning Sunset Views
Montego Bay: Elegant Apt w/ Stunning Sunset Views
Apartment
Montego Bay, 00000, Jamaica
2.1k from Widowmaker's Cave center

AC, Balcony, Barbecue, Crib, Dryer, Elevator, Fitness Equipment, Free Parking, Internet

3 Bedrooms6 Guests
10.0

Exceptional

1 reviews

$611
Average price / night
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Tranquil 007 Getaway, With Chef, 20 mins to A/port
Tranquil 007 Getaway, With Chef, 20 mins to A/port
House
Montego Bay, JWI, Jamaica
2.1k from Widowmaker's Cave center

AC, Balcony, Barbecue, Dryer, Fitness Equipment, Free Parking, Internet, Kitchen, Laundry

3 Bedrooms6 Guests
New to Booking
$310
Average price / night
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PINES VACATION RENTALS- EXCELLENT LOCATION, MINUTES FROM EVERYTHING.
PINES VACATION RENTALS- EXCELLENT LOCATION, MINUTES FROM EVERYTHING.
Apartment
Montego Bay, Jamaica
2.2k from Widowmaker's Cave center

AC, Balcony, Barbecue, Breakfast Included, Crib, Dryer, Extra Bed, Free Parking, Hot Tub

3 Bedrooms10 Guests
9.8

Exceptional

24 reviews

$287
Average price / night
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5 bed villa, gated community, private pool, fully staffed, private chauffeur
5 bed villa, gated community, private pool, fully staffed, private chauffeur
House
Montego Bay, Jamaica
2.2k from Widowmaker's Cave center

AC, Balcony, Barbecue, Breakfast Available, Crib, Dryer, Extra Bed, Free Parking, Hot Tub

5 Bedrooms10 Guests
10.0

Exceptional

94 reviews

$850
Average price / night
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Tranquil Montego Bay City Getaway with Patio: The Perfect Stay!
Tranquil Montego Bay City Getaway with Patio: The Perfect Stay!
House
Montego Bay, Jamaica
2.4k from Widowmaker's Cave center

AC, Crib, Dryer, Free Parking, Internet, Kitchen, Laundry, Living Area, Microwave

2 Bedrooms4 Guests
New to Booking
$80
Average price / night
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 EXCLUSIVE 4BR DESIGNER WATERFRONT VILLA CHEF POOL BEACH ACCESS PICKLEBALL GYM
EXCLUSIVE 4BR DESIGNER WATERFRONT VILLA CHEF POOL BEACH ACCESS PICKLEBALL GYM
Villa
Montego Bay, 00000, Jamaica
2.4k from Widowmaker's Cave center

AC, Balcony, Barbecue, Breakfast Available, Crib, Dryer, Extra Bed, Free Parking, Internet

5 Bedrooms8 Guests
10.0

Exceptional

27 reviews

$1600
Average price / night
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1 Bedroom Ocean view Apartment, The Lagoons
1 Bedroom Ocean view Apartment, The Lagoons
Apartment
montego bay, 11702, Jamaica
2.5k from Widowmaker's Cave center

AC, Balcony, Dryer, Fitness Equipment, Free Parking, Internet, Kitchen, Laundry, Living Area

1 Bedroom2 Guests
7.6

Good

7 reviews

$185
Average price / night
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Sumptuous Luxury Unit w/pool, gym+more
Sumptuous Luxury Unit w/pool, gym+more
House
Montego Bay, 00000, Jamaica
2.5k from Widowmaker's Cave center

AC, Dryer, Fitness Equipment, Free Parking, Internet, Kitchen, Laundry, Microwave, No Smoking

4 Bedrooms8 Guests
New to Booking
$809
Average price / night
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Montego Bay Oasis: Luxe Retreat with Pool & Ocean Views!
Montego Bay Oasis: Luxe Retreat with Pool & Ocean Views!
Apartment
Montego Bay, 00000, Jamaica
2.5k from Widowmaker's Cave center

AC, Barbecue, Dryer, Elevator, Fitness Equipment, Free Parking, Internet, Kitchen, Laundry

3 Bedrooms6 Guests
New to Booking
$611
Average price / night
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Glory @ Montego Bay, St James
Glory @ Montego Bay, St James
Cottage
Montego Bay, Jamaica
2.6k from Widowmaker's Cave center

AC, Balcony, Barbecue, Breakfast Available, Dryer, Fitness Equipment, Free Parking, Internet, Kitchen

2 Bedrooms4 Guests
9.6

Exceptional

16 reviews

$236
Average price / night
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PERFECT FOR LARGE GROUPS-EXCELLENT LOCATION, MINUTES FROM EVERYTHING.
PERFECT FOR LARGE GROUPS-EXCELLENT LOCATION, MINUTES FROM EVERYTHING.
Apartment
Montego Bay, Jamaica
2.9k from Widowmaker's Cave center

AC, Balcony, Barbecue, Crib, Dryer, Extra Bed, Free Parking, Heater, Hot Tub

5 Bedrooms16 Guests
9.8

Exceptional

15 reviews

$957
Average price / night
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Wild Orchid 5 BR 5.5 Bth staff Private Paradise Spring Gardens Montego Bay<br>
Wild Orchid 5 BR 5.5 Bth staff Private Paradise Spring Gardens Montego Bay<br>
Villa
Montego Bay, Jamaica
2.9k from Widowmaker's Cave center

AC, Balcony, Barbecue, Breakfast Available, Dryer, Free Parking, Internet, Kitchen, Laundry

5 Bedrooms10 Guests
8.0

Good

1 reviews

$2520
Average price / night
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Waterfront Villa Private Pool comp Floating Breakfast \nFully Staffed Chef Avable
Waterfront Villa Private Pool comp Floating Breakfast \nFully Staffed Chef Avable
House
Montego Bay, 11702, Jamaica
2.9k from Widowmaker's Cave center

AC, Balcony, Barbecue, Breakfast Available, Crib, Dryer, Fitness Equipment, Free Parking, Internet

3 Bedrooms6 Guests
10.0

Exceptional

49 reviews

$761
Average price / night
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5 BDR LUX MODERN BEACHFRONT VILLA PRIVATE INFINITY POOL & OCEAN VIEWS STAFF
5 BDR LUX MODERN BEACHFRONT VILLA PRIVATE INFINITY POOL & OCEAN VIEWS STAFF
Villa
Montego Bay, Jamaica
3.0k from Widowmaker's Cave center

AC, Arcade, Balcony, Barbecue, Breakfast Available, Dryer, Extra Bed, Free Parking, Internet

5 Bedrooms14 Guests
10.0

Exceptional

91 reviews

$2108
Average price / night
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A luxurious beachfront villa with private beach on a calm lagoon. Montego Bay JA
A luxurious beachfront villa with private beach on a calm lagoon. Montego Bay JA
Villa
Montego Bay, JMCJS12, Jamaica
3.0k from Widowmaker's Cave center

AC, Balcony, Barbecue, Breakfast Available, Dryer, Fitness Equipment, Free Parking, Heater, Internet

4 Bedrooms8 Guests
9.8

Exceptional

13 reviews

$1170
Average price / night
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Sun Drenched Beachfront Villa Upscale Living, Private Pool, Breezy Ocean Breezes
Sun Drenched Beachfront Villa Upscale Living, Private Pool, Breezy Ocean Breezes
Villa
Montego Bay, 0000, Jamaica
3.0k from Widowmaker's Cave center

AC, Breakfast Included, Dryer, Free Parking, Internet, Kitchen, Laundry, Living Area, Microwave

5 Bedrooms10 Guests
New to Booking
$2677
Average price / night
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AMA VILLAS - Luxury Collection -  **BRAND NEW ****DISCOUNT AVAILABLE
AMA VILLAS - Luxury Collection - **BRAND NEW ****DISCOUNT AVAILABLE
Villa
Rose Hall, 1, Jamaica
3.1k from Widowmaker's Cave center

AC, Balcony, Barbecue, Crib, Dryer, Fireplace, Free Parking, Heater, Internet

5 Bedrooms12 Guests
New to Booking
$2634
Average price / night
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Pro Tip:
VacationByOwnerRentals aggregates the best inventory from leading travel sites, including Booking.com, Agoda.com, Expedia.com, Vrbo.com, and Airbnb.com. Use our Advanced Filters to compare verified homes, villas, cabins, condos, cottages, vacation rentals, hotels, and eco-friendly stays. Our goal is to help you find the absolute best Vacation Rentals with Private Pool in Widowmaker's Cave.

Where to stay in Widowmaker's Cave? Best neighborhoods & areas

Widowmaker's Cave Vacation Rentals with Private Pool on the Map

Frequently Asked Questions

You can explore 124 verified vacation rentals with a private pool in Widowmaker's Cave. These include standalone villas and private homes where the pool is reserved exclusively for your group.

Prices for rentals with a private pool in Widowmaker's Cave vary depending on the property size, location, and travel season. Rates typically start from around $80 per night, with higher prices for larger homes, prime locations, or peak travel periods.

Yes, properties listed with private pools are intended for the exclusive use of guests staying at that home. You can review listing photos and descriptions to better understand the layout and level of privacy offered.

Yes, some vacation rentals with private pools in Widowmaker's Cave also welcome pets. Currently, 2 listings allow pets, although policies may vary. It’s a good idea to review any rules related to pets and outdoor areas before booking.

Private pool properties are often in high demand, especially during holidays and warmer months, so booking 90 to 120 days in advance is recommended. During quieter periods, you may still find availability closer to your travel dates.

Vacation rentals with private pools in Widowmaker's Cave often include additional features such as Private Pool, Pool, and Wellness Facilities. These amenities enhance comfort and create a more relaxing, self-contained stay.

Some family-friendly vacation rentals in Widowmaker's Cave include safety features such as pool fences, covers, or screened enclosures. It’s recommended to check the property details to confirm whether a specific rental meets your safety preferences.