Short-Term Rentals in Kaupulehu, HI: Compare 10+ Sites & Save

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104 Best Short-Term Rentals in Kaupulehu (Starting from $145)

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
Check Availability
Laueki 8 – Stunning Ocean View | Onsite Staff & Daily Housekeeping
Laueki 8 – Stunning Ocean View | Onsite Staff & Daily Housekeeping
House
Kailua Kona, HI, 96740, United States
0.1k from Kaupulehu center

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

4 Bedrooms8 Guests
New to Booking
$8527
Average price / night
Check Availability
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
Check Availability
Laueki 5 – Ocean View Estate | Onsite Staff & Daily Housekeeping
Laueki 5 – Ocean View Estate | Onsite Staff & Daily Housekeeping
House
Kailua Kona, HI, 96740, United States
0.1k from Kaupulehu center

AC, Barbecue, Dryer, Kitchen, Laundry, Living Area, Microwave, No Smoking, Patio

5 Bedrooms10 Guests
New to Booking
$9330
Average price / night
Check Availability
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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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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Bears' Place Guest House
Bears' Place Guest House
House
Kailua-Kona, HI, USA
8.5k from Kaupulehu center

B&bs, Accommodations, Parking, Guest houses, Homestays, Lodgings, Vacation rentals, Places to stay, Self-catering

5 Bedrooms17 Guests
8.1

Very Good

101 reviews

$160
Average price / night
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Luxury Estate at Hualalai Resort -Sweeping Ocean and Golf Course Views
Luxury Estate at Hualalai Resort -Sweeping Ocean and Golf Course Views
House
Kailua Kona, HI, 96740, United States
0.2k from Kaupulehu center

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

5 Bedrooms10 Guests
New to Booking
$7355
Average price / night
Check Availability
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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Hualalai Ocean View Easter Special 900.00
Hualalai Ocean View Easter Special 900.00
Apartment
Holualoa, HI, 96725, United States
0.2k from Kaupulehu center

AC, Barbecue, Crib, Dryer, Free Parking, Internet, Laundry, Microwave, No Smoking

2 Bedrooms4 Guests
10.0

Exceptional

2 reviews

$1301
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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Hualalai Hainoa Estate | private residence | pool | panoramic ocean views
Hualalai Hainoa Estate | private residence | pool | panoramic ocean views
House
Kailua-Kona, HI, 96740, United States
0.2k from Kaupulehu center

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

4 Bedrooms8 Guests
9.4

Superb

3 reviews

$3737
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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Designer Oceanview Estate w/Pool & Spa, at Hualalai Resort: 122 Hainoa
Designer Oceanview Estate w/Pool & Spa, at Hualalai Resort: 122 Hainoa
House
Kailua Kona, HI, 96740, United States
0.2k from Kaupulehu center

AC, Balcony, Barbecue, Crib, Dryer, Extra Bed, Fireplace, Fitness Equipment, Free Parking

4 Bedrooms8 Guests
10.0

Exceptional

7 reviews

$3316
Average price / night
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Hainoa 10 – Commanding Ocean Views | Onsite Staff & Daily Housekeeping
Hainoa 10 – Commanding Ocean Views | Onsite Staff & Daily Housekeeping
House
Kailua Kona, HI, 96740, United States
0.3k from Kaupulehu center

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

3 Bedrooms6 Guests
New to Booking
$7125
Average price / night
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Hainoa Villa 2903B
Hainoa Villa 2903B
House
Kailua Kona, HI, 96740, United States
0.3k from Kaupulehu center

AC, Balcony, Barbecue, Dryer, Free Parking, Kitchen, Laundry, Microwave, No Smoking

2 Bedrooms4 Guests
10.0

Exceptional

1 reviews

$2026
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
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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Ultra Luxe Oceanview Estate at Hualalai, Private Pool & Spa: 102 Hainoa
Ultra Luxe Oceanview Estate at Hualalai, Private Pool & Spa: 102 Hainoa
House
Kailua Kona, HI, 96740, United States
0.3k from Kaupulehu center

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

4 Bedrooms8 Guests
10.0

Exceptional

1 reviews

$4224
Average price / night
Check Availability
Ke Alaula Villa 232B – Vibrant Ocean Views
Ke Alaula Villa 232B – Vibrant Ocean Views
House
Kailua Kona, HI, 96740.0, United States
0.4k from Kaupulehu center

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

3 Bedrooms6 Guests
New to Booking
$3005
Average price / night
Check Availability
Ke Alaula Villa 228A – Prime Ocean View | Onsite Staff & Daily Housekeeping
Ke Alaula Villa 228A – Prime Ocean View | Onsite Staff & Daily Housekeeping
House
Kailua Kona, HI, 96740, United States
0.4k from Kaupulehu center

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

3 Bedrooms6 Guests
New to Booking
$3005
Average price / night
Check Availability
Ke Alaula Estate: Hualalai Luxury w/Lanai, Heated Pool & Golf Views
Ke Alaula Estate: Hualalai Luxury w/Lanai, Heated Pool & Golf Views
House
Kailua Kona, HI, 96740, United States
0.5k from Kaupulehu center

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

4 Bedrooms8 Guests
10.0

Exceptional

1 reviews

$3526
Average price / night
Check Availability
Ultra Luxurious New Home in Four Seasons Hualalai
Ultra Luxurious New Home in Four Seasons Hualalai
House
Kailua-Kona, HI, 96740, United States
0.6k from Kaupulehu center

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

6 Bedrooms14 Guests
10.0

Exceptional

6 reviews

$8730
Average price / night
Check Availability
Ke Alaula Hale 7 – Private & Secluded | Onsite Staff & Daily Housekeeping
Ke Alaula Hale 7 – Private & Secluded | Onsite Staff & Daily Housekeeping
House
Kailua Kona, HI, 96740, United States
0.6k from Kaupulehu center

AC, Dryer, Free Parking, Kitchen, Laundry, Microwave, No Smoking, Outdoor Space, Pool

3 Bedrooms6 Guests
New to Booking
$5138
Average price / night
Check Availability
Premier 5BR Hualalai Estate—Infinity Pool, 2 Golf Carts, Ocean Vistas
Premier 5BR Hualalai Estate—Infinity Pool, 2 Golf Carts, Ocean Vistas
House
Kailua Kona, HI, 96740, United States
0.6k from Kaupulehu center

AC, Balcony, Barbecue, Crib, Dryer, Free Parking, Hot Tub, Kitchen, Microwave

5 Bedrooms10 Guests
New to Booking
$4203
Average price / night
Check Availability
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
Check Availability
Luxurious & Serene Home w/ Private Pool & Spa
Luxurious & Serene Home w/ Private Pool & Spa
House
Kailua-Kona, HI, 96740, United States
0.6k from Kaupulehu center

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

4 Bedrooms10 Guests
10.0

Exceptional

7 reviews

$5188
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 Short-Term Rentals in Kaupulehu.

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Kaupulehu Short-Term Rentals on the Map

Frequently Asked Questions

You can explore 104 verified short-term rentals in Kaupulehu, including apartments, houses, and furnished stays suitable for both travel and temporary living.

Short-term rental prices in Kaupulehu vary depending on location, property size, and travel dates. Rates typically start from around $145 per night, with higher prices for premium properties or peak seasons.

Many short-term rentals in Kaupulehu include Wi-Fi, making them suitable for remote work. Some listings also provide dedicated workspaces, but it is recommended to check property details for specific features.

Booking 30 to 45 days in advance is generally recommended for the best availability. For peak travel periods or major events in Kaupulehu, booking earlier can help secure better options.

In many cases, utilities such as electricity, water, and internet are included in the rental price. However, this can vary by property, so it is important to review the listing details before booking.

Short-term rentals in Kaupulehu often include amenities such as Internet, Guest Services, and Kitchen, providing a comfortable and convenient stay.

Short-term rentals in Kaupulehu are often used for flexible stays, including work trips or temporary housing, while vacation rentals are typically geared toward leisure stays in tourist areas. Both offer furnished, home-like accommodations.