Family-Friendly Vacation Rentals in Cave Hill Estate, Hellshire: Compare 10+ Sites & Save

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  3.  Jamaica
  4.  Saint Catherine

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  6.  Cave Hill Estate

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141 Best Family Vacation Rentals in Cave Hill Estate (Starting from $83)

Seascape Beach House
Seascape Beach House
House
Drunkenmans Cay, Jamaica
1.7k from Cave Hill Estate center

Accommodations, Parking, Villas, Vacation homes, Cottages, Lodgings, Places to stay

1 Bedroom3 Guests
New to Booking
$85
Average price / night
Check Availability
Ac'ed 2 bedroom Beach House
Ac'ed 2 bedroom Beach House
House
Hellshire, Jamaica
0.5k from Cave Hill Estate center

AC, Balcony, Barbecue, Extra Bed, Fitness Equipment, Free Parking, Internet, Kitchen, Laundry

4 Bedrooms6 Guests
9.2

Superb

15 reviews

$140
Average price / night
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Luxurious 6 Bed Villa Wown Pool
Luxurious 6 Bed Villa Wown Pool
House
Goshen Pen, Jamaica
1.8k from Cave Hill Estate center

B&bs, Accommodations, Pools, Parking, Guest houses, Homestays, Lodgings, Places to stay, Accessible hotels

2 Bedrooms4 Guests
New to Booking
$316
Average price / night
Check Availability
Coastal Breeze Escape
Coastal Breeze Escape
House
Hellshire, Jamaica
0.6k from Cave Hill Estate center

AC, Free Parking, Internet, Kitchen, Laundry, Microwave, No Smoking, Outdoor Space, Patio

2 Bedrooms4 Guests
New to Booking
$115
Average price / night
Check Availability
Ocean Paradise Getaway Short Term Rental
Ocean Paradise Getaway Short Term Rental
House
Drunkenmans Cay, Jamaica
2.3k from Cave Hill Estate center

B&bs, Cheap, Accommodations, Parking, Guest houses, Homestays, Pet-friendly, Lodgings, Places to stay

1 Bedroom4 Guests
10.0

Exceptional

1 reviews

$330
Average price / night
Check Availability
The Hellshire Beach House
The Hellshire Beach House
Villa
64 Sandhills Vista, Hellshire, Jamaica
1.1k from Cave Hill Estate center

AC, Barbecue, Crib, Extra Bed, Free Parking, Internet, Kitchen, Laundry, Living Area

New to Booking
$241
Average price / night
Check Availability
Mountain Beach View, Apartments in Sandhills Hellshire
Mountain Beach View, Apartments in Sandhills Hellshire
Apartment
Cave Hill Estate, Hellshire, Saint Catherine, Jamaica
2.3k from Cave Hill Estate center

Apartments, Accommodations, Parking, Lodgings, Vacation rentals, Jacuzzis, Places to stay

10 Bedrooms12 Guests
New to Booking
$200
Average price / night
Check Availability
The Beach Estate Country Club Villa
The Beach Estate Country Club Villa
Villa
64 Sandhills Vista, Kingston, Hellshire, Jamaica
1.9k from Cave Hill Estate center

AC, Babysitting, Crib, Free Parking, Heater, Internet, Kitchen, Living Area, Microwave

10.0

Exceptional

1 reviews

$291
Average price / night
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Perfect vibez
Perfect vibez
House
Portmore, Jamaica
4.0k from Cave Hill Estate center

Cheap, Accommodations, Parking, Villas, Vacation homes, Cottages, Pet-friendly, Lodgings, Places to stay

1 Bedroom3 Guests
10.0

Exceptional

1 reviews

$95
Average price / night
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5-Bedroom Retreat Near Beach
5-Bedroom Retreat Near Beach
Villa
Hellshire, Jamaica
2.0k from Cave Hill Estate center

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

5 Bedrooms10 Guests
New to Booking
$371
Average price / night
Check Availability
Bayfront paradise villa
Bayfront paradise villa
Apartment
Cave Hill Estate, Hellshire, Saint Catherine, Jamaica
4.9k from Cave Hill Estate center

Parking, Pool, Internet, Air Conditioner, Pet Friendly, Breakfast, Child Friendly

3 Bedrooms6 Guests
New to Booking
$90
Average price / night
Check Availability
Seascape2Hellshire
Seascape2Hellshire
House
Hellshire, Jamaica
2.1k from Cave Hill Estate center

AC, Free Parking, Internet, Kitchen, Laundry, Living Area, Microwave, No Smoking, Outdoor Space

2 Bedrooms4 Guests
New to Booking
$87
Average price / night
Check Availability
Sunrise villa
Sunrise villa
Apartment
Cave Hill Estate, Hellshire, Saint Catherine, Jamaica
5.2k from Cave Hill Estate center

Parking, Air Conditioner, Pool, Pet Friendly, Balcony/Terrace, Internet, Child Friendly

3 Bedrooms6 Guests
New to Booking
$99
Average price / night
Check Availability
2-bedroom  Portmore home with WiFi, AC in a gated community. Close to Kingston.
2-bedroom Portmore home with WiFi, AC in a gated community. Close to Kingston.
House
Portmore, Jamaica
5.6k from Cave Hill Estate center

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

2 Bedrooms4 Guests
New to Booking
$120
Average price / night
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Phoenix park 2 bedroom gated community 1
Phoenix park 2 bedroom gated community 1
House
Cave Hill Estate, Hellshire, Saint Catherine, Jamaica
5.6k from Cave Hill Estate center

Child Friendly, Internet, Air Conditioner, Parking, View, Wheelchair Accessible, Ocean View

1 Bedroom5 Guests
New to Booking
$120
Average price / night
Check Availability
Relax by the pool with the sounds of waves and enjoy   ocean and mountains views
Relax by the pool with the sounds of waves and enjoy ocean and mountains views
Villa
Portmore, Jamaica
5.9k from Cave Hill Estate center

AC, Dryer, Free Parking, Internet, Kitchen, Laundry, Living Area, Microwave, No Smoking

2 Bedrooms5 Guests
10.0

Exceptional

2 reviews

$135
Average price / night
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Caribbean estate deluxe 2
Caribbean estate deluxe 2
Apartment
Portmore, Jamaica
6.0k from Cave Hill Estate center

Apartments, Accommodations, Parking, Pet-friendly, Lodgings, Vacation rentals, Places to stay, Family, Self-catering

2 Bedrooms5 Guests
8.0

Good

16 reviews

$110
Average price / night
Check Availability
Beachfront Bliss in Portmore 2BR with Ocean Views & Modern Comfort, pool access
Beachfront Bliss in Portmore 2BR with Ocean Views & Modern Comfort, pool access
Apartment
Portmore, Jamaica
6.0k from Cave Hill Estate center

AC, Free Parking, Internet, Kitchen, Microwave, No Smoking, Pool, Toys, TV

2 Bedrooms6 Guests
New to Booking
$126
Average price / night
Check Availability
Caymanas estate beautiful two bedroom suites
Caymanas estate beautiful two bedroom suites
House
Goshen Pen, Jamaica
6.1k from Cave Hill Estate center

Accommodations, Pools, Parking, Villas, Vacation homes, Cottages, Lodgings, Vacation rentals, Places to stay

2 Bedrooms4 Guests
New to Booking
$120
Average price / night
Check Availability
Beachfront Bliss in Portmore – Stylish 1BR with Ocean Views & Modern Comfort
Beachfront Bliss in Portmore – Stylish 1BR with Ocean Views & Modern Comfort
Condo
Portmore, Jamaica
6.1k from Cave Hill Estate center

AC, Free Parking, Internet, Kitchen, Microwave, No Smoking, Pool, TV

1 Bedroom2 Guests
New to Booking
$127
Average price / night
Check Availability
Bayfront Apartment & villa
Bayfront Apartment & villa
Apartment
Portmore, 11702, Jamaica
6.1k from Cave Hill Estate center

AC, Free Parking, Internet, Kitchen, Living Area, Microwave, No Smoking, Pool, TV

2 Bedrooms4 Guests
7.0

Good

2 reviews

$121
Average price / night
Check Availability
 Cozy Beachfront Apartment,\n
Cozy Beachfront Apartment,\n
Apartment
Portmore, Jamaica
6.1k from Cave Hill Estate center

AC, Extra Bed, Free Parking, Hot Tub, Internet, Kitchen, Microwave, No Smoking, Pool

2 Bedrooms6 Guests
2.0

Review score

1 reviews

$290
Average price / night
Check Availability
Island Oasis, Portmore
Island Oasis, Portmore
Apartment
Portmore, Jamaica
6.2k from Cave Hill Estate center

AC, Arcade, Dryer, Elevator, Free Parking, Internet, Kitchen, Laundry, Living Area

2 Bedrooms5 Guests
New to Booking
$172
Average price / night
Check Availability
Delightful, brand new, 1 bedroom apartment
Delightful, brand new, 1 bedroom apartment
Apartment
Portmore, Jamaica
6.2k from Cave Hill Estate center

AC, Dryer, Free Parking, Internet, Kitchen, Laundry, Living Area, Microwave, No Smoking

1 Bedroom3 Guests
10.0

Exceptional

1 reviews

$87
Average price / night
Check Availability
  ROPER'S PLACE...Bayfront apartment/Balcony view Close to Kingston/Airport\n
ROPER'S PLACE...Bayfront apartment/Balcony view Close to Kingston/Airport\n
Apartment
Portmore, Jamaica
6.3k from Cave Hill Estate center

AC, Balcony, Dryer, Elevator, Free Parking, Internet, Kitchen, Laundry, Living Area

1 Bedroom3 Guests
New to Booking
$83
Average price / night
Check Availability
Barefoot Bliss Apartment
Barefoot Bliss Apartment
Apartment
Portmore, Jamaica
6.3k from Cave Hill Estate center

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

1 Bedroom2 Guests
New to Booking
$135
Average price / night
Check Availability
Charming 1-bedroom apartment in wonderful Portmore with AC, WiFi
Charming 1-bedroom apartment in wonderful Portmore with AC, WiFi
Apartment
Portmore, Jamaica
6.3k from Cave Hill Estate center

AC, Dryer, Elevator, Free Parking, Internet, Kitchen, Laundry, Microwave, No Smoking

1 Bedroom2 Guests
10.0

Exceptional

3 reviews

$96
Average price / night
Check Availability

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 Family Vacation Rentals in Cave Hill Estate.

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Cave Hill Estate Family Vacation Rentals on the Map

Frequently Asked Questions

You can explore 141 verified family-friendly vacation rentals in Cave Hill Estate. These include spacious homes, villas, and condos designed to accommodate families of different sizes.

Prices for family-friendly rentals in Cave Hill Estate vary depending on the season, number of bedrooms, and included amenities. Rates typically start from around $83 per night, with larger homes and peak travel periods often costing more.

Many family-friendly rentals in Cave Hill Estate offer baby-friendly items such as high chairs, cribs, or pack-and-play options. Availability can vary, so it’s helpful to check the listing details before booking.

Yes, some rentals in Cave Hill Estate are well suited for multi-generational stays, offering multiple bedrooms, separate living areas, and enough space for larger groups to stay comfortably together.

For busy travel periods such as school holidays or summer breaks, booking 90 to 120 days in advance is recommended to secure the best options. Availability may be more flexible during quieter times of the year.

Family-friendly rentals in Cave Hill Estate often include amenities such as Child Friendly, View, and Internet. These features help make stays more convenient and enjoyable for both adults and children.

You can use search filters to find rentals that offer features like game rooms, playgrounds, or entertainment areas. Checking property descriptions can also help you identify homes that are well suited for families with children.