Book Holiday Homes in Hawaii Island

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Featured Holiday Homes in Hawaii Island

The Jungalow is a charming renovated bungalow minutes from Volcano National Park

The Jungalow is a charming renovated bungalow minutes from Volcano National Park

Volcano
With a stay at this vacation home in Volcano, you'll be within a 10-minute drive of Hawaii Volcanoes National Park and Aloha Candy Company.
The Jungalow is a charming renovated bungalow minutes from Volcano National Park
 3-Level OCEANFRONT HOME

3-Level OCEANFRONT HOME

Pahoa
With a stay at this vacation home in Pahoa, you'll be on the beach, and 5.7 mi (9.2 km) from Kapoho Beach and 7 mi (11.3 km) from Pahoa Museum.
3-Level OCEANFRONT HOME
Kona Ocean View Home - Downtown, Fruit Trees, Sunset views

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

Kailua-Kona
When you stay at this vacation home in Kailua-Kona, you'll be near the bay, a 5-minute drive from Kailua Pier and 10 minutes from Magic Sands Beach.
Kona Ocean View Home - Downtown, Fruit Trees, Sunset views
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Private, ocean front home with private pool,  Amazing place!

Private, ocean front home with private pool, Amazing place!

Milolii
When you stay at this vacation home in Captain Cook, you'll be on the waterfront and 11 minutes by foot from Papa Bay.
Private, ocean front home with private pool, Amazing place!
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 Magic Sands Beach and Kailua Pier.
Panoramic view of ocean. Excellent location. Quiet neighborhood. Sleep 10
Walk to White Sands Beach or Relax by Your Private Pool

Walk to White Sands Beach or Relax by Your Private Pool

Kailua-Kona
With a stay at this vacation home in Kailua-Kona (Kahaluu-Keauhou), you'll be within a 15-minute drive of Magic Sands Beach and Kailua Pier.
Walk to White Sands Beach or Relax by Your Private Pool
BBQ, New Air Conditioning and upgrades!

BBQ, New Air Conditioning and upgrades!

Waikoloa Village
With a stay at this vacation home in Waikoloa, you'll be next to a golf course, within a 15-minute drive of Mauna Lani Resort Golf Course and Queens' ...
BBQ, New Air Conditioning and upgrades!
Oceanfront Kona Beach House

Oceanfront Kona Beach House

Kailua-Kona
With a stay at this vacation home in Kailua-Kona (Holualoa Village), you'll be a 2-minute drive from Magic Sands Beach and 8 minutes from Kailua Pier.
Oceanfront Kona Beach House
Home with Swimming Pool | 3 Bed, 2 Bath

Home with Swimming Pool | 3 Bed, 2 Bath

Naalehu
With a stay at this vacation home in Naalehu (Discovery Harbour), you'll be within a 15-minute drive of Hawaii Volcanoes National Park and Paradise Meadows.
Home with Swimming Pool | 3 Bed, 2 Bath
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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
634 Holiday Homes
Lowest Price
Highest Price
Popular accommodation
The Jungalow is a charming renovated bungalow minutes from Volcano National Park, 3-Level OCEANFRONT HOME, Kona Ocean View Home - Downtown, Fruit Trees, Sunset views, Private, ocean front home with private pool, Amazing place!, Panoramic view of ocean. Excellent location. Quiet neighborhood. Sleep 10, Walk to White Sands Beach or Relax by Your Private Pool, BBQ, New Air Conditioning and upgrades! , Oceanfront Kona Beach House, Home with Swimming Pool | 3 Bed, 2 Bath

Top trending hotels in Hawaii Island

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
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
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 Magic Sands Beach and Kailua Pier.
Kona Coast Resort
Hilton Grand Vacations Club Kings’ Land Waikoloa

Hilton Grand Vacations Club Kings’ Land Waikoloa

4 out of 5
69-699 Waikoloa Beach Dr, Waikoloa, HI
With a stay at Hilton Grand Vacations Club Kings’ Land Waikoloa in Waikoloa, you'll be next to a golf course, just steps from Waikoloa Kings Golf Course and ...
Hilton Grand Vacations Club Kings’ Land Waikoloa
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Grand Naniloa Hotel Hilo - a Doubletree by Hilton

Grand Naniloa Hotel Hilo - a Doubletree by Hilton

4 out of 5
93 Banyan Dr, Hilo, HI
Fully refundableReserve now, pay when you stay
In the heart of Hilo, Grand Naniloa Hotel Hilo - a Doubletree by Hilton is within a 5-minute drive of Coconut Island Park and Port of Hilo.
Grand Naniloa Hotel Hilo - a Doubletree by Hilton
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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.