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Featured Holiday Homes in Hawaii

#1 Luxury BEACHFRONT! Pickleball, Sand Volleyball, 2 Gyms, Pool

#1 Luxury BEACHFRONT! Pickleball, Sand Volleyball, 2 Gyms, Pool

2 out of 5
Lahaina
When you stay at this vacation home in Kaanapali, you'll be on the beach, a 4-minute drive from Whalers Village and 7 minutes from Kaanapali Beach.
#1 Luxury BEACHFRONT! Pickleball, Sand Volleyball, 2 Gyms, Pool
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
Fisher’s Hana Bay Hale - In Hana Town across from the Bay STHA-2017 0002

Fisher’s Hana Bay Hale - In Hana Town across from the Bay STHA-2017 0002

Hana
Located in Hana, this vacation home is in a rural location, within a 15-minute walk of Hana Bay Beach and Hana Cultural Center.
Fisher’s Hana Bay Hale - In Hana Town across from the Bay STHA-2017 0002
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Luxury townhouse on Turtle Bay golf course near the ocean

Luxury townhouse on Turtle Bay golf course near the ocean

Kahuku
When you stay at this vacation home in Kahuku, you'll be next to a golf course, a 4-minute drive from Turtle Bay and 5 minutes from Turtle Bay Beach.
Luxury townhouse on Turtle Bay golf course near the ocean
Kauai Luxury home, Private Pool & Spa, walk to the beach, restaurants and shops

Kauai Luxury home, Private Pool & Spa, walk to the beach, restaurants and shops

Koloa
With a stay at this vacation home in Koloa (Poipu), you'll be within a 15-minute walk of Poipu Beach and Brennecke Beach.
Kauai Luxury home, Private Pool & Spa, walk to the beach, restaurants and shops
Nani Iki - Close to beach!

Nani Iki - Close to beach!

Hauula
With a stay at this vacation home in Hauula, you'll be in the mountains, within a 10-minute drive of Polynesian Cultural Center and Hauula Beaches.
Nani Iki - Close to beach!
Kaiholo Hale

Kaiholo Hale

3 out of 5
25 Kaiholo Place, Paia, HI
With a stay at Kaiholo Hale in Paia, you'll be in the historical district, just a 4-minute walk from Kuau Bay Beach and 14 minutes by foot from Paia Bay.
Kaiholo Hale
Oceanside Estate - Spacious home with Pool & AC

Oceanside Estate - Spacious home with Pool & AC

Hauula
With a stay at this vacation home in Hauula, you'll be by the sea, within a 15-minute drive of Polynesian Cultural Center and Kaluanui Beach.
Oceanside Estate - Spacious home with Pool & AC
North Shore BEACHFRONT Bungalo Perfection @ Sunset Beach

North Shore BEACHFRONT Bungalo Perfection @ Sunset Beach

Haleiwa
With a stay at this vacation home in Haleiwa, you'll be a 3-minute drive from Sunset Beach and 9 minutes from Turtle Bay.
North Shore BEACHFRONT Bungalo Perfection @ Sunset Beach
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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 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 vacation homes are the perfect way for you to wing it.

Holiday houses in Hawaii 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 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 adventures, obvs.

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

Accommodation
4232 Holiday Homes
Lowest Price
Highest Price
Popular accommodation
#1 Luxury BEACHFRONT! Pickleball, Sand Volleyball, 2 Gyms, Pool, The Jungalow is a charming renovated bungalow minutes from Volcano National Park, Fisher’s Hana Bay Hale - In Hana Town across from the Bay STHA-2017 0002 , Luxury townhouse on Turtle Bay golf course near the ocean, Kauai Luxury home, Private Pool & Spa, walk to the beach, restaurants and shops, Nani Iki - Close to beach!, Kaiholo Hale, Oceanside Estate - Spacious home with Pool & AC, North Shore BEACHFRONT Bungalo Perfection @ Sunset Beach

Top trending hotels in Hawaii

Hilton Hawaiian Village Waikiki Beach Resort

Hilton Hawaiian Village Waikiki Beach Resort

4.5 out of 5
2005 Kalia Rd, Honolulu, HI
Fully refundableReserve now, pay when you stay
With a stay at Hilton Hawaiian Village Waikiki Beach Resort in Honolulu (Waikiki), you'll be a 2-minute drive from Ala Moana Center and 5 minutes from Honolulu ...
Hilton Hawaiian Village Waikiki Beach Resort
Sheraton Waikiki Beach Resort

Sheraton Waikiki Beach Resort

4 out of 5
2255 Kalakaua Ave, Honolulu, HI
Fully refundableReserve now, pay when you stay
With a stay at Sheraton Waikiki Beach Resort in Honolulu (Waikiki), you'll be steps from Royal Hawaiian Center and 4 minutes by foot from Waikiki Beach ...
Sheraton Waikiki Beach Resort
Wayfinder Waikiki

Wayfinder Waikiki

4 out of 5
2375 Ala Wai Blvd, Honolulu, HI
Fully refundableReserve now, pay when you stay
Wayfinder Waikiki is centrally located in Honolulu, a 4-minute walk from International Market Place and 7 minutes by foot from Waikiki Beach.
Wayfinder Waikiki
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Waikiki Beach Marriott Resort & Spa

Waikiki Beach Marriott Resort & Spa

4 out of 5
2552 Kalakaua Ave, Honolulu, HI
Fully refundableReserve now, pay when you stay
Located in Honolulu (Waikiki), Waikiki Beach Marriott Resort & Spa is a 4-minute walk from Honolulu Zoo and 6 minutes by foot from Waikiki Beach.
Waikiki Beach Marriott Resort & Spa
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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.