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

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 laundry facilities. Our guests praise the helpful staff in our reviews. Popular attractions ...
Kona Ocean View Home - Downtown, Fruit Trees, Sunset views
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 laundry facilities. Our guests praise the pool in our reviews. ...
Walk to White Sands Beach or Relax by Your Private Pool
Oceanfront Kona Beach House

Oceanfront Kona Beach House

Kailua-Kona
Book a stay at this beach vacation home in Kailua-Kona. Enjoy a beach locale, a garden, and laundry facilities. Popular attractions Magic Sands Beach and Kailua ...
Oceanfront Kona Beach House
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Huge June 2025 discount! Rare BEACH FRONT Home at Kona Surf and Racquet Club

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

Kailua-Kona
Book a stay at this beach vacation home in Kailua-Kona. Enjoy free WiFi, a beach locale, and a garden. Popular attractions Magic Sands Beach and Kailua Pier ...
Huge June 2025 discount! Rare BEACH FRONT Home at Kona Surf and Racquet Club
🏖️Next to Keauhou Bay! | Concierge Included | Large Private Pool & Lanai

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

Kailua Kona
Stay at this vacation home in Kailua-Kona. Enjoy free WiFi, private pools, and laundry facilities. Popular attractions Magic Sands Beach and Kailua Pier are ...
🏖️Next to Keauhou Bay! | Concierge Included | Large Private Pool & Lanai
🏖️Ocean Front | Central AC | Private Pool & Grill | Concierge Included

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

Kailua Kona
Stay at this vacation home in Kailua-Kona. Enjoy free WiFi, private pools, and laundry facilities. Popular attractions Magic Sands Beach and Kailua Pier are ...
🏖️Ocean Front | Central AC | Private Pool & Grill | Concierge Included
Outrigger Paradise Hale Wa a Pale with Private Pool!

Outrigger Paradise Hale Wa a Pale with Private Pool!

Kailua Kona
Stay at this vacation home in Kailua-Kona. Enjoy private pools, a garden, and laundry facilities. Popular attractions Magic Sands Beach and Kailua Pier are located ...
Outrigger Paradise Hale Wa a Pale with Private Pool!
Panoramic view of ocean.  Excellent location. Quiet neighborhood. Sleep 10

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

Kailua-Kona
Book a stay at this family-friendly vacation home in Kailua-Kona. Enjoy free WiFi, a water park, and a garden. Popular attractions Magic Sands Beach and Kailua ...
Panoramic view of ocean. Excellent location. Quiet neighborhood. Sleep 10
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 laundry facilities. Popular attractions Four Seasons Resort Hualalai Golf ...
Stunning Ocean Views + Designer Designed Kona Home
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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
570 Holiday Homes
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

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
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
Kona Coast Resort

Kona Coast Resort

3.5 out of 5
78-6842 Alii Dr, Kailua-Kona, HI
Stay at this 3.5-star golf hotel in Kailua-Kona. Enjoy free WiFi, free parking, and 2 outdoor pools. Our guests praise the pool and the helpful staff in our ...
Kona Coast Resort
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
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
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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
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
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See all available properties in Kailua-Kona
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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.

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^Subject to availability and chosen travel dates.