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
The price is NZ$714 per night from 20 Jan to 21 Jan
NZ$714
includes taxes & fees
20 Jan - 21 Jan 2025
Stay at this vacation home in Kailua-Kona. Enjoy free WiFi, a garden, and patios. Our guests praise the helpful staff in our reviews. Popular attractions Kailua ...
Kona Ocean View Home - Downtown, Fruit Trees, Sunset views
Afforable & quaint upstairs 2Bedroom 1Bath apartment with lanai and Ocean views

Afforable & quaint upstairs 2Bedroom 1Bath apartment with lanai and Ocean views

Kailua-Kona
Stay at this vacation home in Kailua-Kona. Enjoy free WiFi, patios, and an in-room coffeemaker. Popular attractions Kailua Pier and Makalei Golf Club are located ...
Afforable & quaint upstairs 2Bedroom 1Bath apartment with lanai and Ocean views
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 Kailua Pier and Donkey Mill ...
Panoramic view of ocean. Excellent location. Quiet neighborhood. Sleep 10
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Direct Oceanfront Condo on Private Beach Resort *Central AC *

Direct Oceanfront Condo on Private Beach Resort *Central AC *

Kailua-Kona
Book a stay at this beach vacation home in Kailua-Kona. Enjoy free WiFi, private pools, and a beach locale. Our guests praise the helpful staff in our reviews. ...
Direct Oceanfront Condo on Private Beach Resort *Central AC *
Beautiful Pool with Stunning Ocean and Sunset Views

Beautiful Pool with Stunning Ocean and Sunset Views

Kailua-Kona
Stay at this vacation home in Kailua-Kona. Enjoy free WiFi, private pools, and a garden. Popular attractions Kailua Pier and Makalei Golf Club are located ...
Beautiful Pool with Stunning Ocean and Sunset Views
Oceanfront, 5 STAR, Home 3 BR/3 BA, wonderful lanai and  Jacuzzi -Sleeps 8

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

Kailua-Kona
Book a stay at this beach vacation home in Kailua-Kona. Enjoy free WiFi, a beach locale, and a garden. Popular attractions Kailua Pier and Kahalu'u Beach Park ...
Oceanfront, 5 STAR, Home 3 BR/3 BA, wonderful lanai and Jacuzzi -Sleeps 8
Three Palms

Three Palms

Kailua-Kona
Stay at this vacation home in Kailua-Kona. Enjoy free WiFi, a garden, and patios. Popular attractions Kailua Pier and UCC Hawaii Kona Coffee Estate are located ...
Three Palms
Dolphin Manor: Stunning Oceanfront Home w/Pool, Spa, A/C, Private Lanai

Dolphin Manor: Stunning Oceanfront Home w/Pool, Spa, A/C, Private Lanai

Kailua Kona
Book a stay at this beach vacation home in Kailua-Kona. Enjoy private pools, a beach locale, and a garden. Popular attractions Kailua Pier and Honl's Beach are ...
Dolphin Manor: Stunning Oceanfront Home w/Pool, Spa, A/C, Private Lanai
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 ...
Elegant Giant Oceanfront Estate - steps to Magic Beach with pool, sub zero
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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
453 Holiday Homes
Lowest Price
NZ$565
Highest Price
NZ$772
Popular accommodation
Kona Ocean View Home - Downtown, Fruit Trees, Sunset views, Afforable & quaint upstairs 2Bedroom 1Bath apartment with lanai and Ocean views, Panoramic view of ocean. Excellent location. Quiet neighborhood. Sleep 10, Direct Oceanfront Condo on Private Beach Resort *Central AC *, Beautiful Pool with Stunning Ocean and Sunset Views, Oceanfront, 5 STAR, Home 3 BR/3 BA, wonderful lanai and Jacuzzi -Sleeps 8, Three Palms, Dolphin Manor: Stunning Oceanfront Home w/Pool, Spa, A/C, Private Lanai, Elegant Giant Oceanfront Estate - steps to Magic Beach with pool, sub zero

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
The price is NZ$583 per night from 5 Jan to 6 Jan
NZ$583
includes taxes & fees
5 Jan - 6 Jan 2025
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
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$772 per night from 4 Jan to 5 Jan
NZ$772
includes taxes & fees
4 Jan - 5 Jan 2025
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 ...
OUTRIGGER 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$565 per night from 5 Jan to 6 Jan
NZ$565
includes taxes & fees
5 Jan - 6 Jan 2025
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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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
Don't see what you're looking for?
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.