Book Holiday Homes in Kailua-Kona

More Flash, Less Cash - Take advantage of our Price Pledge** (even on luxey stays)

We keep it easy with the option to pay now or later on select accommodation

Book up 'til the last second - millions of rooms to crash tonight^

Featured Holiday Homes in Kailua-Kona

Kona Ocean View Home - Downtown, Fruit Trees, Sunset views

Kona Ocean View Home - Downtown, Fruit Trees, Sunset views

Kailua-Kona
Stay at this vacation home in Kailua-Kona. Enjoy free WiFi, a garden, and patios. Our guests praise the helpful staff in our reviews. Popular attractions Kailua ...
Kona Ocean View Home - Downtown, Fruit Trees, Sunset views
Kona Spectacular Ocean Front 5BR, 4BA Pool,Spa,AC

Kona Spectacular Ocean Front 5BR, 4BA Pool,Spa,AC

Kailua Kona
Stay at this vacation home in Kailua-Kona. Enjoy free WiFi, private pools, and patios. Popular attractions Magic Sands Beach and Kailua Pier are located ...
Kona Spectacular Ocean Front 5BR, 4BA Pool,Spa,AC
Afforable & quaint upstairs 2Bedroom 1Bath apartment with lanai and Ocean views

Afforable & quaint upstairs 2Bedroom 1Bath apartment with lanai and Ocean views

Kailua-Kona
Stay at this vacation home in Kailua-Kona. Enjoy free WiFi, patios, and an in-room coffeemaker. Popular attractions Kailua Pier and Makalei Golf Club are located ...
Afforable & quaint upstairs 2Bedroom 1Bath apartment with lanai and Ocean views
Save an average of 15% on thousands of hotels when you're signed in
Stunning Ocean Views + Designer Designed Kona Home

Stunning Ocean Views + Designer Designed Kona Home

Kailua-Kona
Book a stay at this golf vacation home in Kailua-Kona. Enjoy free WiFi, a garden, and patios. Popular attractions Four Seasons Resort Hualalai Golf Course and ...
Stunning Ocean Views + Designer Designed Kona Home
Walk to White Sands Beach or Relax by Your Private Pool

Walk to White Sands Beach or Relax by Your Private Pool

Kailua-Kona
Book a stay at this family-friendly vacation home in Kailua-Kona. Enjoy private pools, a garden, and patios. Our guests praise the pool in our reviews. Popular ...
Walk to White Sands Beach or Relax by Your Private Pool
Beautiful Pool with Stunning Ocean and Sunset Views

Beautiful Pool with Stunning Ocean and Sunset Views

Kailua-Kona
Stay at this vacation home in Kailua-Kona. Enjoy free WiFi, private pools, and a garden. Popular attractions Kailua Pier and Makalei Golf Club are located ...
Beautiful Pool with Stunning Ocean and Sunset Views
Direct Oceanfront 2BR/2BA Townhouse with Pool and Pickleball & Tennis Courts

Direct Oceanfront 2BR/2BA Townhouse with Pool and Pickleball & Tennis Courts

Kailua-Kona
Book a stay at this golf vacation home in Kailua-Kona. Enjoy free WiFi, tennis courts, and patios. Popular attractions Magic Sands Beach and Kailua Pier are ...
Direct Oceanfront 2BR/2BA Townhouse with Pool and Pickleball & Tennis Courts
4-Bedroom Retreat Near Magic Sands Beach with Outdoor Living & Beach Gear

4-Bedroom Retreat Near Magic Sands Beach with Outdoor Living & Beach Gear

Kailua-Kona
Stay at this vacation home in Kailua-Kona. Enjoy free WiFi, a garden, and patios. Popular attractions Magic Sands Beach and Kailua Pier are located nearby.
4-Bedroom Retreat Near Magic Sands Beach with Outdoor Living & Beach Gear
Kona's Shangri La: Private Oceanfront Home w/ Pool, Spa & Elevator

Kona's Shangri La: Private Oceanfront Home w/ Pool, Spa & Elevator

Kailua Kona
Book a stay at this beach vacation home in Kailua-Kona. Enjoy private pools, a beach locale, and tennis courts. Popular attractions Magic Sands Beach and Kailua ...
Kona's Shangri La: Private Oceanfront Home w/ Pool, Spa & Elevator
Don't see what you're looking for?
See all available properties in Kailua-Kona
View all properties
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Kailua-Kona Holiday Houses

Do you love last minute road trips and late-night food runs and sunrises on the beach? Do words like “schedule” and “calendar” make you shout, “Don’t box me in!”? You might be a little bit of a rebel. But you’re a rebel with a cause: having a smashing holiday. Itinerary? What’s that? Our Kailua-Kona vacation homes are the perfect way for you to wing it.

Holiday houses in Kailua-Kona let you live life on your own terms. You’ll have so much space, you’ll wish you had more friends and family—but you can always invite over the neighbours. You can often have luxury amenities, but with all the attractions of Kailua-Kona in your backyard, budget holiday homes will do just fine, too. That will just leave you more dough to spend on the important things: cocktails, brunch, and local Kailua-Kona adventures, obvs.

If your adventure buddy happens to have fur and four legs, you just might find a pet-friendly holiday house in Kailua-Kona with your name on it.

No need to spend big bickies for a holiday beach house the size of Buckingham Palace—unless you’re really in trouble with bae. We’ve got a great selection of Kailua-Kona vacation homes with everything you need for a seriously amazing getaway. Throw out that daily planner and hit “reject” on all those meeting invites. You’re off to a place where there are no rules.

Kailua-Kona Holiday Homes essential information

Accommodation
574 Holiday Homes
Lowest Price
NZ$443
Highest Price
NZ$589
Popular accommodation
Kona Ocean View Home - Downtown, Fruit Trees, Sunset views, Kona Spectacular Ocean Front 5BR, 4BA Pool,Spa,AC, Afforable & quaint upstairs 2Bedroom 1Bath apartment with lanai and Ocean views, Stunning Ocean Views + Designer Designed Kona Home, Walk to White Sands Beach or Relax by Your Private Pool, Beautiful Pool with Stunning Ocean and Sunset Views, Direct Oceanfront 2BR/2BA Townhouse with Pool and Pickleball & Tennis Courts, 4-Bedroom Retreat Near Magic Sands Beach with Outdoor Living & Beach Gear, Kona's Shangri La: Private Oceanfront Home w/ Pool, Spa & Elevator

Top trending hotels in Kailua-Kona

Royal Kona Resort

Royal Kona Resort

3.5 out of 5
75-5852 Alii Dr, Kailua-Kona, HI
Fully refundableReserve now, pay when you stay
The price is NZ$452 per night from 30 Mar to 31 Mar
NZ$452
includes taxes & fees
30 Mar - 31 Mar
Stay at this 3.5-star beach hotel in Kailua-Kona. Enjoy a full-service spa, breakfast (surcharge), and a fitness center. Our guests praise the pool and the restaurant ...
Royal Kona Resort
OUTRIGGER Kona Resort and Spa

OUTRIGGER Kona Resort and Spa

4 out of 5
78-128 Ehukai Street, Kailua-Kona, HI
Fully refundableReserve now, pay when you stay
The price is NZ$589 per night from 19 Apr to 20 Apr
NZ$589
includes taxes & fees
19 Apr - 20 Apr
Stay at this 4-star golf hotel in Kailua-Kona. Enjoy free WiFi, 2 outdoor pools, and 2 restaurants. Our guests praise the pool and the helpful staff in our reviews. ...
OUTRIGGER Kona Resort and Spa
PACIFIC 19 Kona

PACIFIC 19 Kona

3.5 out of 5
75-5646 Palani Rd, Kailua-Kona, HI
Fully refundableReserve now, pay when you stay
The price is NZ$443 per night from 30 Mar to 31 Mar
NZ$443
includes taxes & fees
30 Mar - 31 Mar
Stay at this 3.5-star hotel in Kailua-Kona. Enjoy free WiFi, parking (surcharge), and a 24-hour front desk. Our guests praise the pool and the helpful staff ...
PACIFIC 19 Kona
Save an average of 15% on thousands of hotels when you're signed in
Courtyard by Marriott King Kamehameha's Kona Beach Hotel

Courtyard by Marriott King Kamehameha's Kona Beach Hotel

3.5 out of 5
75-5660 Palani Road, Kailua-Kona, HI
Fully refundableReserve now, pay when you stay
The price is NZ$580 per night from 15 Apr to 16 Apr
NZ$580
includes taxes & fees
15 Apr - 16 Apr
Stay at this 3.5-star beach hotel in Kailua-Kona. Enjoy free WiFi, a full-service spa, and 2 restaurants. Our guests praise the helpful staff and the clean rooms ...
Courtyard by Marriott King Kamehameha's Kona Beach Hotel
Don't see what you're looking for?
See all available properties in Kailua-Kona
View all properties
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

**Terms and Conditions apply.
^Subject to availability and chosen travel dates.