Family-Friendly Vacation Rentals in Kaupulehu, HI: Compare 10+ Sites & Save

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33 Best Family Vacation Rentals in Kaupulehu (Starting from $145)

3BD Hainoa Villa (2907C) at Hualalai Resort
3BD Hainoa Villa (2907C) at Hualalai Resort
Villa
Kukio, HI, USA
0.3k from Kaupulehu center

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

3 Bedrooms6 Guests
New to Booking
$2044
Average price / night
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Golf lovers delight Lau'eki ~ Hualalai ~ Sweeping Views
Golf lovers delight Lau'eki ~ Hualalai ~ Sweeping Views
House
Kailua Kona, HI, 96740, United States
0.1k from Kaupulehu center

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

4 Bedrooms8 Guests
10.0

Exceptional

7 reviews

$5308
Average price / night
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4BD Ke Alaula Estate (124) at Hualalai Resort
4BD Ke Alaula Estate (124) at Hualalai Resort
Villa
Kukio, HI, USA
0.5k from Kaupulehu center

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

4 Bedrooms8 Guests
New to Booking
$4321
Average price / night
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Premier Hualalai Resort Estate | Special Pricing | Includes Chef Experience
Premier Hualalai Resort Estate | Special Pricing | Includes Chef Experience
House
Kailua-Kona, HI, 96740, United States
0.3k from Kaupulehu center

AC, Breakfast Available, Crib, Dryer, Free Parking, Heater, Hot Tub, Internet, Kitchen

5 Bedrooms10 Guests
New to Booking
$8054
Average price / night
Check Availability
3BD Ka'Ulu Villa (131C) at Hualalai Resort
3BD Ka'Ulu Villa (131C) at Hualalai Resort
Villa
Kukio, HI, USA
0.7k from Kaupulehu center

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

3 Bedrooms6 Guests
New to Booking
$1684
Average price / night
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Panoramic Ocean and Golf Course Views ! Luxury Townhouse at Hualalai Resort- includes 2 Golf Carts
Panoramic Ocean and Golf Course Views ! Luxury Townhouse at Hualalai Resort- includes 2 Golf Carts
House
Kailua-Kona, HI, 96740, United States
0.3k from Kaupulehu center

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

3 Bedrooms6 Guests
10.0

Exceptional

7 reviews

$2150
Average price / night
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Hualalai Fairway Villa
Hualalai Fairway Villa
Villa
Kukio, HI, USA
2.4k from Kaupulehu center

Parking, Internet, Air Conditioner, Pool, Child Friendly

3 Bedrooms8 Guests
New to Booking
$582
Average price / night
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Luxe Coastal View 2907C Villa at Hualalai w/ Resort Pool & AC
Luxe Coastal View 2907C Villa at Hualalai w/ Resort Pool & AC
Villa
Kailua Kona, HI, 96740, United States
0.3k from Kaupulehu center

AC, Balcony, Barbecue, Dryer, Free Parking, Internet, Kitchen, Laundry, Microwave

3 Bedrooms6 Guests
9.6

Exceptional

5 reviews

$1476
Average price / night
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Charming Pu'ukala Sunset - Near Hiking and Golf home
Charming Pu'ukala Sunset - Near Hiking and Golf home
House
Kailua-Kona, HI, USA
8.5k from Kaupulehu center

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

1 Bedroom2 Guests
New to Booking
$247
Average price / night
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FOUR SEASONS RESORT \"HUALALAI HALE” MODERN OCEANVIEW, 7 & 28- SPECIAL NIGHT RATE
FOUR SEASONS RESORT \"HUALALAI HALE” MODERN OCEANVIEW, 7 & 28- SPECIAL NIGHT RATE
House
Kailua Kona, HI, 96740, United States
0.6k from Kaupulehu center

AC, Barbecue, Dryer, Free Parking, Hot Tub, Internet, Kitchen, Laundry, Living Area

4 Bedrooms8 Guests
10.0

Exceptional

78 reviews

$3958
Average price / night
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Cozy Sunset Views with Lanai - Close to Beach home
Cozy Sunset Views with Lanai - Close to Beach home
House
Kailua-Kona, HI, USA
8.5k from Kaupulehu center

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

1 Bedroom2 Guests
New to Booking
$241
Average price / night
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Luxurious Oceanview Villa at Hualalai w/Resort Pool & AC - Ka'ulu 131C
Luxurious Oceanview Villa at Hualalai w/Resort Pool & AC - Ka'ulu 131C
Villa
Kailua Kona, HI, 96740, United States
0.7k from Kaupulehu center

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

3 Bedrooms6 Guests
10.0

Exceptional

9 reviews

$1441
Average price / night
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Pu'ukala Sunset Estate with Amazing Ocean Views! home
Pu'ukala Sunset Estate with Amazing Ocean Views! home
House
Kailua-Kona, HI, USA
8.5k from Kaupulehu center

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

3 Bedrooms6 Guests
New to Booking
$526
Average price / night
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Four Seasons Resort Hualalai at 4th Fairway, Ocean View with 2 Golf Carts
Four Seasons Resort Hualalai at 4th Fairway, Ocean View with 2 Golf Carts
Villa
Kailua-Kona, HI, 96740, United States
0.7k from Kaupulehu center

AC, Arcade, Balcony, Barbecue, Dryer, Fitness Equipment, Free Parking, Heater, Hot Tub

3 Bedrooms6 Guests
10.0

Exceptional

46 reviews

$2038
Average price / night
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Charming Kailua-Kona Apartment Near Hiking and Golf!
Charming Kailua-Kona Apartment Near Hiking and Golf!
House
Kailua-Kona, HI, USA
8.5k from Kaupulehu center

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

1 Bedroom2 Guests
9.0

Fabulous

2 reviews

$145
Average price / night
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Rare 4bd/4ba Hualalai Villa - Great Location near 4 Seasons, Ocean Views
Rare 4bd/4ba Hualalai Villa - Great Location near 4 Seasons, Ocean Views
Villa
Kailua-Kona, HI, 96740, United States
0.8k from Kaupulehu center

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

4 Bedrooms8 Guests
New to Booking
$2859
Average price / night
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Cozy Kona Coast Apt with Lanai about 8 Miles to Beach!
Cozy Kona Coast Apt with Lanai about 8 Miles to Beach!
House
Kailua-Kona, HI, USA
8.5k from Kaupulehu center

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

1 Bedroom2 Guests
6.5

Good

2 reviews

$145
Average price / night
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Stunning Kaimupulehu Grand Estate Hualalai
Stunning Kaimupulehu Grand Estate Hualalai
House
Kailua-Kona, HI, 96740, United States
0.9k from Kaupulehu center

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

5 Bedrooms10 Guests
10.0

Exceptional

12 reviews

$7631
Average price / night
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Kailua-Kona House with Balcony and Ocean Views!
Kailua-Kona House with Balcony and Ocean Views!
House
Kailua-Kona, HI, USA
8.5k from Kaupulehu center

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

3 Bedrooms6 Guests
8.0

Good

2 reviews

$555
Average price / night
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Premier Luxury 3 Bedroom Villa at Hualalai Resort with Golf Course Views!
Premier Luxury 3 Bedroom Villa at Hualalai Resort with Golf Course Views!
Condo
Kailua Kona, HI, 96740, United States
0.9k from Kaupulehu center

AC, Balcony, Barbecue, Dryer, Free Parking, Hot Tub, Internet, Kitchen, Laundry

4 Bedrooms6 Guests
9.6

Exceptional

38 reviews

$1502
Average price / night
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Serene Pakui Pua Estate ~ Hualalai ~ Secluded~Saltwater Pool~Personal Concierge
Serene Pakui Pua Estate ~ Hualalai ~ Secluded~Saltwater Pool~Personal Concierge
House
Kailua-Kona, HI, 96740, United States
1.0k from Kaupulehu center

AC, Barbecue, Breakfast Available, Crib, Dryer, Fitness Equipment, Free Parking, Heater, Hot Tub

3 Bedrooms6 Guests
10.0

Exceptional

11 reviews

$4599
Average price / night
Check Availability
Hualalai Palm Villa 126A - Perfect location along the15th Fairway!
Hualalai Palm Villa 126A - Perfect location along the15th Fairway!
House
Kailua-Kona, HI, 96740, United States
1.0k from Kaupulehu center

AC, Balcony, Barbecue, Dryer, Extra Bed, Free Parking, Internet, Kitchen, Laundry

3 Bedrooms6 Guests
10.0

Exceptional

10 reviews

$2163
Average price / night
Check Availability
Gorgeous Estate Home at Hualalai Resort -Ocean and Golf Course Views- Spring Special 10% off
Gorgeous Estate Home at Hualalai Resort -Ocean and Golf Course Views- Spring Special 10% off
House
Kailua Kona, HI, 96740, United States
1.1k from Kaupulehu center

AC, Barbecue, Dryer, Extra Bed, Free Parking, Hot Tub, Internet, Kitchen, Laundry

5 Bedrooms8 Guests
10.0

Exceptional

4 reviews

$6325
Average price / night
Check Availability
Discover Your Sanctuary ~ Hualalai ~ Infinity Pool ~ Concierge
Discover Your Sanctuary ~ Hualalai ~ Infinity Pool ~ Concierge
House
Kailua-Kona, HI, 96740, United States
1.1k from Kaupulehu center

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

4 Bedrooms8 Guests
10.0

Exceptional

3 reviews

$6778
Average price / night
Check Availability
Unmatched location Four Seasons Hualalai  5BR/5BA Ocean Estate 6500sqft 3/4 acre
Unmatched location Four Seasons Hualalai 5BR/5BA Ocean Estate 6500sqft 3/4 acre
House
Kailua-Kona, HI, 96740, United States
1.1k from Kaupulehu center

AC, Barbecue, Dryer, Fitness Equipment, Free Parking, Hot Tub, Internet, Kitchen, Laundry

5 Bedrooms14 Guests
10.0

Exceptional

1 reviews

$9251
Average price / night
Check Availability
Experience luxury near golf courses, 4 mins to Four Seasons Resort
Experience luxury near golf courses, 4 mins to Four Seasons Resort
House
Kailua-Kona, HI, 96740, United States
1.2k from Kaupulehu center

AC, Barbecue, Dryer, Fitness Equipment, Free Parking, Hot Tub, Internet, Kitchen, Laundry

4 Bedrooms8 Guests
10.0

Exceptional

71 reviews

$3988
Average price / night
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Hualalai Hillside Penthouse Oceanview Retreat
Hualalai Hillside Penthouse Oceanview Retreat
House
Kailua-Kona, HI, 96740, United States
1.2k from Kaupulehu center

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

3 Bedrooms6 Guests
10.0

Exceptional

30 reviews

$3086
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 Kaupulehu.

Stay Near Kaupulehu's Top Attractions

VacationByOwnerRentals can help you find hotels, resorts, and rentals near many of 's top attractions, neighborhoods, and points of interest.

Kaupulehu Family Vacation Rentals on the Map

Frequently Asked Questions

You can explore 33 verified family-friendly vacation rentals in Kaupulehu. These include spacious homes, villas, and condos designed to accommodate families of different sizes.

Prices for family-friendly rentals in Kaupulehu vary depending on the season, number of bedrooms, and included amenities. Rates typically start from around $145 per night, with larger homes and peak travel periods often costing more.

Many family-friendly rentals in Kaupulehu 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 Kaupulehu 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 Kaupulehu often include amenities such as Child Friendly, Internet, and Guest Services. 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.