Book Holiday Homes in Kailua-Kona

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Featured Holiday Homes in Kailua-Kona

Elegant Giant Oceanfront Estate - steps to Magic Beach with pool, sub zero

Elegant Giant Oceanfront Estate - steps to Magic Beach with pool, sub zero

Kailua-Kona
Book a stay at this family-friendly vacation home in Kailua-Kona. Enjoy free WiFi, private pools, and a garden. Popular attractions Magic Sands Beach and Kailua ...
Opens in a new windowElegant Giant Oceanfront Estate - steps to Magic Beach with pool, sub zero
Kona Ocean View Home - Downtown, Fruit Trees, Sunset views

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

Kailua-Kona
The price is NZ$725 per night from 3 Nov to 4 Nov
NZ$725
3 Nov - 4 Nov
includes taxes & fees
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 ...
Opens in a new windowKona Ocean View Home - Downtown, Fruit Trees, Sunset views
Panoramic view of ocean.  Excellent location. Quiet neighborhood. Sleep 10

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

Kailua-Kona
Stay at this vacation home in Kailua-Kona. Enjoy free WiFi, a garden, and laundry facilities. Popular attractions Magic Sands Beach and Kailua Pier are located ...
Opens in a new windowPanoramic view of ocean. Excellent location. Quiet neighborhood. Sleep 10
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WEST SUITE  195.00 SPECIAL TIL NOV +10% 7nt STAY on this beautiful property

WEST SUITE 195.00 SPECIAL TIL NOV +10% 7nt STAY on this beautiful property

Kailua-Kona
Book a stay at this beach vacation home in Kailua-Kona. Enjoy free WiFi, private pools, and a beach locale. Popular attractions Magic Sands Beach and Kailua ...
Opens in a new windowWEST SUITE 195.00 SPECIAL TIL NOV +10% 7nt STAY on this beautiful property
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 laundry facilities. Popular attractions Magic Sands Beach and Kailua Pier are ...
Opens in a new windowKona Spectacular Ocean Front 5BR, 4BA Pool,Spa,AC
Hale Pua: Private Oceanfront Luxury Home w/Pool, Spa, AC & Lanai - Relax & Enjoy

Hale Pua: Private Oceanfront Luxury Home w/Pool, Spa, AC & Lanai - Relax & Enjoy

Kailua Kona
Book a stay at this beach vacation home in Kailua-Kona. Enjoy private pools, a beach locale, and a garden. Popular attractions Magic Sands Beach and Kailua Pier ...
Opens in a new windowHale Pua: Private Oceanfront Luxury Home w/Pool, Spa, AC & Lanai - Relax & Enjoy
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 ...
Opens in a new windowStunning Ocean Views + Designer Designed Kona Home
🏖️Beautiful | Private | Fabulous Ocean Views! | Private Pool

🏖️Beautiful | Private | Fabulous Ocean Views! | Private Pool

Kailua Kona
Stay at this vacation home in Kailua-Kona. Enjoy free WiFi, private pools, and laundry facilities. Popular attractions Kailua Pier and Magic Sands Beach are ...
Opens in a new window🏖️Beautiful | Private | Fabulous Ocean Views! | Private Pool
Kona Keauhou Newly Remodeled Home, Quiet private home on Golf course with
Pool.

Kona Keauhou Newly Remodeled Home, Quiet private home on Golf course with Pool.

Kailua-Kona
Book a stay at this golf vacation home in Kailua-Kona. Enjoy free WiFi, private pools, and a garden. Popular attractions Magic Sands Beach and Kailua Pier are ...
Opens in a new windowKona Keauhou Newly Remodeled Home, Quiet private home on Golf course with Pool.
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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
588 Holiday Homes
Lowest Price
NZ$389
Highest Price
NZ$725
Popular accommodation
Elegant Giant Oceanfront Estate - steps to Magic Beach with pool, sub zero, Kona Ocean View Home - Downtown, Fruit Trees, Sunset views, Panoramic view of ocean. Excellent location. Quiet neighborhood. Sleep 10, WEST SUITE 195.00 SPECIAL TIL NOV +10% 7nt STAY on this beautiful property, Kona Spectacular Ocean Front 5BR, 4BA Pool,Spa,AC, Hale Pua: Private Oceanfront Luxury Home w/Pool, Spa, AC & Lanai - Relax & Enjoy, Stunning Ocean Views + Designer Designed Kona Home, 🏖️Beautiful | Private | Fabulous Ocean Views! | Private Pool, Kona Keauhou Newly Remodeled Home, Quiet private home on Golf course with Pool.

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$450 per night from 2 Nov to 3 Nov
NZ$450
2 Nov - 3 Nov
includes taxes & fees
Stay at this 4-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 ...
Opens in a new windowRoyal 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$560 per night from 14 Nov to 15 Nov
NZ$560
14 Nov - 15 Nov
includes taxes & fees
Stay at this 4-star golf resort in Kailua-Kona. Enjoy free WiFi, 2 outdoor pools, and 2 restaurants. Our guests praise the pool and the helpful staff in our ...
Opens in a new windowOUTRIGGER 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$389 per night from 2 Nov to 3 Nov
NZ$389
2 Nov - 3 Nov
includes taxes & fees
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 ...
Opens in a new windowPACIFIC 19 Kona
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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$558 per night from 16 Nov to 17 Nov
NZ$558
16 Nov - 17 Nov
includes taxes & fees
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 ...
Opens in a new windowCourtyard by Marriott King Kamehameha's Kona Beach Hotel
Don't see what you're looking for?
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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.