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

Oceanfront, 5 STAR, Home 3 BR/3 BA, wonderful lanai and Jacuzzi -Sleeps 8

Three Palms

Awesome View, Best Snorkel Beach, Big Lanais, Private Home

Experience luxury at Hale Ola

🏖️Gorgeous Ocean Front Estate | Gated Community | Walk to Town

Resort-Style Home on Keauhou Bay: Great for Groups

🏖️Private Pool | Central AC | Concierge Included

Elegant Giant Oceanfront Estate - steps to Magic Beach with pool, sub zero
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 | 599 Holiday Homes |
---|---|
Lowest Price | AU$342 |
Highest Price | AU$667 |
Popular accommodation | Kona Ocean View Home - Downtown, Fruit Trees, Sunset views, Oceanfront, 5 STAR, Home 3 BR/3 BA, wonderful lanai and Jacuzzi -Sleeps 8, Three Palms, Awesome View, Best Snorkel Beach, Big Lanais, Private Home, Experience luxury at Hale Ola, 🏖️Gorgeous Ocean Front Estate | Gated Community | Walk to Town, Resort-Style Home on Keauhou Bay: Great for Groups, 🏖️Private Pool | Central AC | Concierge Included, Elegant Giant Oceanfront Estate - steps to Magic Beach with pool, sub zero |
Top trending hotels in Kailua-Kona

Royal Kona Resort

PACIFIC 19 Kona

OUTRIGGER Kona Resort and Spa

Courtyard by Marriott King Kamehameha's Kona Beach Hotel
More ways to explore Kailua-Kona
Top picks
- Kapaa Accommodation
- Apartment Hotels in Honolulu
- Boutique Hotels in Kihei
- Hilo Accommodation
- Casino Hotels in Honolulu
- Haleiwa Accommodation
- Captain Cook Accommodation
- Apartment Hotels in Hilo
- Kihei Accommodation
- Honolulu Accommodation
- Hana Accommodation
- Family Hotels in Honolulu
- Hanalei Accommodation
- Lahaina Accommodation
- Princeville Accommodation
- All Inclusive Hotels in Honolulu
**Terms and Conditions apply.
^Subject to availability and chosen travel dates.