Book Holiday Homes in Kailua-Kona
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Featured Holiday Homes in Kailua-Kona

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

Walk to White Sands Beach or Relax by Your Private Pool

Oceanfront Kona Beach House

Huge June 2025 discount! Rare BEACH FRONT Home at Kona Surf and Racquet Club

🏖️Next to Keauhou Bay! | Concierge Included | Large Private Pool & Lanai

🏖️Ocean Front | Central AC | Private Pool & Grill | Concierge Included

Outrigger Paradise Hale Wa a Pale with Private Pool!

Panoramic view of ocean. Excellent location. Quiet neighborhood. Sleep 10

Stunning Ocean Views + Designer Designed Kona Home
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 | 570 Holiday Homes |
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Lowest Price | |
Highest Price | |
Popular accommodation | Kona Ocean View Home - Downtown, Fruit Trees, Sunset views, Walk to White Sands Beach or Relax by Your Private Pool, Oceanfront Kona Beach House, Huge June 2025 discount! Rare BEACH FRONT Home at Kona Surf and Racquet Club, 🏖️Next to Keauhou Bay! | Concierge Included | Large Private Pool & Lanai, 🏖️Ocean Front | Central AC | Private Pool & Grill | Concierge Included, Outrigger Paradise Hale Wa a Pale with Private Pool!, Panoramic view of ocean. Excellent location. Quiet neighborhood. Sleep 10, Stunning Ocean Views + Designer Designed Kona Home |
More accommodations in Kailua-Kona
Top trending hotels in Kailua-Kona

Royal Kona Resort

Kona Coast Resort

PACIFIC 19 Kona

OUTRIGGER Kona Resort and Spa
More ways to explore Kailua-Kona
Top picks
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^Subject to availability and chosen travel dates.