Book Holiday Homes in Kailua-Kona

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Featured Holiday Homes in Kailua-Kona

Walk to White Sands Beach or Relax by Your Private Pool

Walk to White Sands Beach or Relax by Your Private Pool

Kailua-Kona HI
Stay at this family-friendly holiday home in Kailua-Kona. Enjoy private pools, a garden and laundry facilities. Our guests praise the pool in their reviews. ...
Opens in a new windowWalk to White Sands Beach or Relax by Your Private Pool
Don`t miss out on this amazing home for your Kona vacation!

Don`t miss out on this amazing home for your Kona vacation!

Kailua-Kona HI
Stay at this family-friendly holiday home in Kailua-Kona. Enjoy free Wi-Fi, private pools and a garden. Popular attractions Magic Sands Beach and Sadie Seymour ...
Opens in a new windowDon`t miss out on this amazing home for your Kona vacation!
Stunning Ocean Views + Designer Designed Kona Home

Stunning Ocean Views + Designer Designed Kona Home

Kailua-Kona HI
Stay at this golf holiday home in Kailua-Kona. Enjoy free Wi-Fi, a garden and laundry facilities. Popular attractions Four Seasons Resort Hualalai Golf Course ...
Opens in a new windowStunning Ocean Views + Designer Designed Kona Home
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Beautiful Pool with Stunning Ocean and Sunset Views

Beautiful Pool with Stunning Ocean and Sunset Views

Kailua-Kona HI
Stay at this holiday home in Kailua-Kona. Enjoy free Wi-Fi, private pools and a garden. Popular attractions Lyman Kona Coffee Farms and Makalei Golf Club are ...
Opens in a new windowBeautiful Pool with Stunning Ocean and Sunset Views
Kona Ocean View Home - Downtown, Fruit Trees, Sunset views

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

Kailua-Kona HI
The price is NZ$717 per night from 29 Mar to 30 Mar
NZ$717
29 Mar - 30 Mar
includes taxes & fees
Stay at this holiday home in Kailua-Kona. Enjoy free Wi-Fi, a garden and laundry facilities. Our guests praise the helpful staff in their reviews. Popular attractions ...
Opens in a new windowKona Ocean View Home - Downtown, Fruit Trees, Sunset views
Rare BEACH FRONT Home at Kona Surf and Racquet Club. Accessible beach 🏖️

Rare BEACH FRONT Home at Kona Surf and Racquet Club. Accessible beach 🏖️

Kailua-Kona HI
Stay at this beach holiday home in Kailua-Kona. Enjoy free Wi-Fi, a beach locale and a garden. Popular attractions Magic Sands Beach and Regal Keauhou are located ...
Opens in a new windowRare BEACH FRONT Home at Kona Surf and Racquet Club. Accessible beach 🏖️
Direct Oceanfront Condo on Private Beach Resort *Central AC *

Direct Oceanfront Condo on Private Beach Resort *Central AC *

Kailua-Kona HI
Stay at this beach holiday home in Kailua-Kona. Enjoy free Wi-Fi, private pools and a beach locale. Our guests praise the helpful staff in their reviews. Popular ...
Opens in a new windowDirect Oceanfront Condo on Private Beach Resort *Central AC *
5★Resort like paradise, heated pool, ocean views, AC, peaceful gated community.

5★Resort like paradise, heated pool, ocean views, AC, peaceful gated community.

Kailua-Kona HI
Stay at this holiday home in Kailua-Kona. Enjoy free Wi-Fi, private pools and a garden. Popular attractions Magic Sands Beach and Sadie Seymour Botanical Garden ...
Opens in a new window5★Resort like paradise, heated pool, ocean views, AC, peaceful gated community.
Panoramic view of ocean.  Excellent location. Quiet neighborhood. Sleep 10

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

Kailua-Kona HI
Stay at this holiday home in Kailua-Kona. Enjoy free Wi-Fi, a garden and laundry facilities. Popular attractions Magic Sands Beach and Donkey Mill Art Center ...
Opens in a new windowPanoramic view of ocean. Excellent location. Quiet neighborhood. Sleep 10
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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
577 Holiday Homes
Lowest Price
NZ$385
Highest Price
NZ$717
Popular accommodation
Walk to White Sands Beach or Relax by Your Private Pool, Don`t miss out on this amazing home for your Kona vacation!, Stunning Ocean Views + Designer Designed Kona Home, Beautiful Pool with Stunning Ocean and Sunset Views, Kona Ocean View Home - Downtown, Fruit Trees, Sunset views, Rare BEACH FRONT Home at Kona Surf and Racquet Club. Accessible beach 🏖️, Direct Oceanfront Condo on Private Beach Resort *Central AC *, 5★Resort like paradise, heated pool, ocean views, AC, peaceful gated community., Panoramic view of ocean. Excellent location. Quiet neighborhood. Sleep 10

Top trending hotels in Kailua-Kona

Royal Kona Resort

Royal Kona Resort

4 out of 5
75-5852 Alii Dr Kailua-Kona HI
Fully refundableReserve now, pay when you stay
The price is NZ$454 per night from 22 Mar to 23 Mar
NZ$454
22 Mar - 23 Mar
includes taxes & fees
Stay at this beach hotel in Kailua-Kona. Enjoy a full-service spa, breakfast (surcharge) and a fitness centre. Our guests praise the pool and the restaurant ...
Opens in a new windowRoyal Kona 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
The price is NZ$385 per night from 25 Mar to 26 Mar
NZ$385
25 Mar - 26 Mar
includes taxes & fees
Stay at this hotel in Kailua-Kona. Enjoy free Wi-Fi, parking (surcharge) and a 24-hour front desk. Our guests praise the pool and the helpful staff in their ...
Opens in a new windowPACIFIC 19 Kona
OUTRIGGER Kona Resort & Spa

OUTRIGGER Kona Resort & Spa

4 out of 5
78-128 Ehukai Street Kailua-Kona HI
The price is NZ$599 per night from 31 Mar to 1 Apr
NZ$599
31 Mar - 1 Apr
includes taxes & fees
Stay at this golf resort in Kailua-Kona. Enjoy free Wi-Fi, 2 outdoor pools and 2 restaurants. Our guests praise the pool and the helpful staff in their reviews. ...
Opens in a new windowOUTRIGGER Kona Resort & Spa
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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$632 per night from 29 Mar to 30 Mar
NZ$632
29 Mar - 30 Mar
includes taxes & fees
Stay at this beach hotel in Kailua-Kona. Enjoy free Wi-Fi, a full-service spa and 2 restaurants. Our guests praise the helpful staff and the clean rooms in their ...
Opens in a new windowCourtyard by Marriott King Kamehameha's Kona Beach Hotel
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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.

Top Picks

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^Subject to availability and chosen travel dates.