Book Holiday Homes in Hawaii Island

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Featured Holiday Homes in Hawaii Island

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
Spacious 4-bedroom house plus bunk room with WiFi and AC in charming Kailua-Kona

Spacious 4-bedroom house plus bunk room with WiFi and AC in charming Kailua-Kona

Kailua-Kona HI
Stay at this beach holiday home in Kailua-Kona. Enjoy free Wi-Fi, private pools and a beach locale. Popular attractions Magic Sands Beach and Old Kona Airport ...
Opens in a new windowSpacious 4-bedroom house plus bunk room with WiFi and AC in charming Kailua-Kona
Experience Tranquility in a Spacious 3-Bedroom Surrounded by Hawaiian Forest

Experience Tranquility in a Spacious 3-Bedroom Surrounded by Hawaiian Forest

Mountain View HI
Stay at this holiday home in Volcano. Enjoy free Wi-Fi, laundry facilities and an in-room coffee maker. Popular attractions Volcano Garden Arts and Aloha Candy ...
Opens in a new windowExperience Tranquility in a Spacious 3-Bedroom Surrounded by Hawaiian Forest
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Lovely home with hot tub near Volcano National Park

Lovely home with hot tub near Volcano National Park

Volcano HI
Stay at this holiday home in Volcano. Enjoy a garden, laundry facilities and patios. Popular attractions Aloha Candy Company and Volcano Garden Arts are located ...
Opens in a new windowLovely home with hot tub near Volcano National Park
'My Favorite Place on Earth'

'My Favorite Place on Earth'

Kamuela HI
Stay at this beach holiday home in Kamuela. Enjoy free Wi-Fi, a beach locale and a garden. Popular attractions Hāpuna Beach State Recreation Area and Mauna Lani ...
Opens in a new window'My Favorite Place on Earth'
Hale Mauka Volcano Village Hawaii Volcanoes National Park

Hale Mauka Volcano Village Hawaii Volcanoes National Park

Volcano HI
Stay at this holiday home in Volcano. Enjoy free Wi-Fi, a garden and laundry facilities. Popular attractions Volcano Garden Arts and Aloha Candy Company are ...
Opens in a new windowHale Mauka Volcano Village Hawaii Volcanoes National Park
Gorgeous 3bd/2ba villa with covered patio, ping pong table, BBQ & playground

Gorgeous 3bd/2ba villa with covered patio, ping pong table, BBQ & playground

Volcano HI
Stay at this holiday home in Volcano. Enjoy free Wi-Fi, a garden and patios. Popular attractions Volcano Garden Arts and Aloha Candy Company are located ...
Opens in a new windowGorgeous 3bd/2ba villa with covered patio, ping pong table, BBQ & playground
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
Family Friendly Home, with a Man Cave!

Family Friendly Home, with a Man Cave!

Keaau HI
Stay at this holiday home in Keaau. Enjoy laundry facilities, a pool table and patios. Our guests praise the property condition in their reviews. Popular attractions ...
Opens in a new windowFamily Friendly Home, with a Man Cave!
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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.

Hawaii Island 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 Hawaii Island vacation homes are the perfect way for you to wing it.

Holiday houses in Hawaii Island 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 Hawaii Island 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 Hawaii Island adventures, obvs.

If your adventure buddy happens to have fur and four legs, you just might find a pet-friendly holiday house in Hawaii Island 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 Hawaii Island 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.

Hawaii Island Holiday Homes essential information

Accommodation
661 Holiday Homes
Lowest Price
NZ$403
Highest Price
NZ$562
Popular accommodation
Walk to White Sands Beach or Relax by Your Private Pool, Spacious 4-bedroom house plus bunk room with WiFi and AC in charming Kailua-Kona, Experience Tranquility in a Spacious 3-Bedroom Surrounded by Hawaiian Forest, Lovely home with hot tub near Volcano National Park, 'My Favorite Place on Earth', Hale Mauka Volcano Village Hawaii Volcanoes National Park, Gorgeous 3bd/2ba villa with covered patio, ping pong table, BBQ & playground, Stunning Ocean Views + Designer Designed Kona Home, Family Friendly Home, with a Man Cave!

Top trending hotels in Hawaii Island

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$403 per night from 12 May to 13 May
NZ$403
12 May - 13 May
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
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$437 per night from 12 May to 13 May
NZ$437
12 May - 13 May
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
OUTRIGGER Kona Resort & Spa

OUTRIGGER Kona Resort & Spa

4 out of 5
78-128 Ehukai Street Kailua-Kona HI
Fully refundableReserve now, pay when you stay
The price is NZ$562 per night from 9 June to 10 June
NZ$562
9 June - 10 June
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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Hilton Grand Vacations Club Ocean Tower Waikoloa Village

Hilton Grand Vacations Club Ocean Tower Waikoloa Village

4 out of 5
69-425 Waikoloa Beach Drive Waikoloa HI
The price is NZ$487 per night from 10 May to 11 May
NZ$487
10 May - 11 May
includes taxes & fees
Stay at this spa resort in Waikoloa. Enjoy 3 outdoor pools, a full-service spa and 6 restaurants. Our guests praise the pool and the helpful staff in their reviews. ...
Opens in a new windowHilton Grand Vacations Club Ocean Tower Waikoloa Village
Don't see what you're looking for?
See all available properties in Hawaii Island
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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.