Book Holiday Homes in Hawaii Island

More Flash, Less Cash - Take advantage of our Price Pledge** (even on luxey stays)

Book up 'til the last second - millions of rooms to crash tonight^

Featured Holiday Homes in Hawaii Island

Breezy Lanai with a Bedroom & Bath

Breezy Lanai with a Bedroom & Bath

Pahoa
The price is NZ$159 per night from 25 Feb to 26 Feb
NZ$159
includes taxes & fees
25 Feb - 26 Feb
Stay at this vacation home in Pahoa. Enjoy free WiFi. Popular attractions Lava Tree State Monument and Pahoa Museum are located nearby.
Breezy Lanai with a Bedroom & Bath
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
The price is NZ$772 per night from 4 Mar to 5 Mar
NZ$772
includes taxes & fees
4 Mar - 5 Mar
Stay at this vacation home in Volcano. Enjoy free WiFi, a garden, and patios. Popular attractions Aloha Candy Company and Volcano Garden Arts are located ...
The Jungalow is a charming renovated bungalow minutes from Volcano National Park
Awesome View, Best Snorkel Beach,  Big Lanais, Private Home

Awesome View, Best Snorkel Beach, Big Lanais, Private Home

Kailua Kona
Stay at this vacation home in Kailua-Kona. Enjoy free WiFi, patios, and cable/satellite TV service. Popular attractions Magic Sands Beach and Kailua Pier are ...
Awesome View, Best Snorkel Beach, Big Lanais, Private Home
Save an average of 15% on thousands of hotels when you're signed in
  Top Five Rated Vacation Rental In Pahoa ,Sale in March 79.00 per Night

Top Five Rated Vacation Rental In Pahoa ,Sale in March 79.00 per Night

Pahoa
Stay at this vacation home in Pahoa. Enjoy free WiFi, a garden, and patios. Popular attractions Lava Tree State Monument and Pahoa Museum are located ...
Top Five Rated Vacation Rental In Pahoa ,Sale in March 79.00 per Night
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
☀️🐋 Direct Ocean front ~The Views! Pool,AC in all rooms! November BIG DISCOUNTS!

☀️🐋 Direct Ocean front ~The Views! Pool,AC in all rooms! November BIG DISCOUNTS!

Keaau
Stay at this vacation home in Keaau. Enjoy private pools, a garden, and patios. Popular attractions Hobby Garden Hawaii and Ha'ena Beach are located nearby.
☀️🐋 Direct Ocean front ~The Views! Pool,AC in all rooms! November BIG DISCOUNTS!
Walk to White Sands Beach or Relax by Your Private Pool

Walk to White Sands Beach or Relax by Your Private Pool

Kailua-Kona
Book a stay at this family-friendly vacation home in Kailua-Kona. Enjoy private pools, a garden, and patios. Our guests praise the pool in our reviews. Popular ...
Walk to White Sands Beach or Relax by Your Private Pool
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
Winter Specials! Family Friendly, Close to Beaches!

Winter Specials! Family Friendly, Close to Beaches!

Waikoloa Village
Stay at this vacation home in Waikoloa. Enjoy private pools, a fitness center, and patios. Popular attractions Hāpuna Beach State Recreation Area and Mauna Kea ...
Winter Specials! Family Friendly, Close to Beaches!
Don't see what you're looking for?
See all available properties in Hawaii Island
View all properties
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
502 Holiday Homes
Lowest Price
NZ$159
Highest Price
NZ$772
Popular accommodation
Breezy Lanai with a Bedroom & Bath, The Jungalow is a charming renovated bungalow minutes from Volcano National Park, Awesome View, Best Snorkel Beach, Big Lanais, Private Home, Top Five Rated Vacation Rental In Pahoa ,Sale in March 79.00 per Night, Oceanfront, 5 STAR, Home 3 BR/3 BA, wonderful lanai and Jacuzzi -Sleeps 8, ☀️🐋 Direct Ocean front ~The Views! Pool,AC in all rooms! November BIG DISCOUNTS!, Walk to White Sands Beach or Relax by Your Private Pool, Afforable & quaint upstairs 2Bedroom 1Bath apartment with lanai and Ocean views, Winter Specials! Family Friendly, Close to Beaches!

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
The price is NZ$512 per night from 5 Mar to 6 Mar
NZ$512
includes taxes & fees
5 Mar - 6 Mar
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
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
The price is NZ$411 per night from 7 Mar to 8 Mar
NZ$411
includes taxes & fees
7 Mar - 8 Mar
Book a stay at this beach hotel in Hilo. Enjoy free WiFi, a beach locale, and a golf course. Our guests praise the bar and the helpful staff in our reviews. ...
Grand Naniloa Hotel Hilo - a Doubletree by Hilton
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$484 per night from 6 Mar to 7 Mar
NZ$484
includes taxes & fees
6 Mar - 7 Mar
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
Save an average of 15% on thousands of hotels when you're signed in
Castle Hilo Hawaiian Hotel

Castle Hilo Hawaiian Hotel

3.5 out of 5
71 Banyan Dr, Hilo, HI
Fully refundableReserve now, pay when you stay
The price is NZ$387 per night from 6 Mar to 7 Mar
NZ$387
includes taxes & fees
6 Mar - 7 Mar
Stay at this 3.5-star golf hotel in Hilo. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the breakfast and the helpful staff in ...
Castle Hilo Hawaiian Hotel
Don't see what you're looking for?
See all available properties in Hawaii Island
View all properties
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.

**Terms and Conditions apply.
^Subject to availability and chosen travel dates.