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 AU$653 per night from 20 Jan to 21 Jan
AU$653
includes taxes & fees
20 Jan - 21 Jan 2025
With a stay at this vacation home in Kailua-Kona, you'll be near the bay, within a 5-minute drive of Kailua Pier and Mauka Meadows Coffee Farm.
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
With a stay at this vacation home in Kailua-Kona, you'll be within a 15-minute drive of Kailua Pier and Makalei Golf Club.
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
With a stay at this vacation home, you'll be centrally located in Kailua-Kona, within a 10-minute drive of Kailua Pier and Sadie Seymour Botanical Garden.
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
With a stay at this vacation home, you'll be centrally located in Kailua-Kona, within a 15-minute drive of Kailua Pier and Kailua-Kona Beaches.
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
With a stay at this vacation home in Kailua-Kona (Kona Palisades), you'll be within a 15-minute drive of Kailua Pier and The Vanillerie.
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
With a stay at this vacation home in Kailua-Kona (Kahaluu-Keauhou), you'll be within a 15-minute drive of Kailua Pier and Kailua-Kona Beaches.
Oceanfront, 5 STAR, Home 3 BR/3 BA, wonderful lanai and Jacuzzi -Sleeps 8
Three Palms

Three Palms

Kailua-Kona
With a stay at this vacation home, you'll be centrally located in Kailua-Kona, within a 5-minute drive of Kailua Pier and Mauka Meadows Coffee Farm.
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
With a stay at this vacation home in Kailua-Kona (Holualoa Village), you'll be within a 5-minute drive of Kailua Pier and Honl's Beach.
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
With a stay at this vacation home in Kailua-Kona (Holualoa Village), you'll be within a 10-minute drive of Kailua Pier and Magic Sands Beach.
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
AU$511
Highest Price
AU$698
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 AU$527 per night from 5 Jan to 6 Jan
AU$527
includes taxes & fees
5 Jan - 6 Jan 2025
With a stay at Royal Kona Resort in Kailua-Kona (Historic Kailua Village), you'll be a 1-minute drive from Hulihee Palace and 6 minutes from Magic Sands ...
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 AU$698 per night from 4 Jan to 5 Jan
AU$698
includes taxes & fees
4 Jan - 5 Jan 2025
Located in Kailua-Kona (Kahaluu-Keauhou), OUTRIGGER Kona Resort and Spa is within a 5-minute drive of Kona Country Club and Keauhou Bay Beach.
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 AU$511 per night from 5 Jan to 6 Jan
AU$511
includes taxes & fees
5 Jan - 6 Jan 2025
With a stay at PACIFIC 19 Kona in Kailua-Kona, you'll be 5.4 mi (8.8 km) from Kahalu'u Beach Park and 11.7 mi (18.9 km) from Mahai'ula Beach.
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
With a stay at Kona Coast Resort in Kailua-Kona (Kahaluu-Keauhou), you'll be within a 15-minute drive of Kailua Pier and Keauhou Shopping Center.
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.