Book Holiday Homes in Hawaii

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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
Book a stay at this beach vacation home in Kaanapali. Enjoy private pools, a beach locale, and a fitness center. Popular attractions Whalers Village and Kaanapali ...
#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
Stay at this vacation home in Volcano. Enjoy free WiFi, a garden, and laundry facilities. Popular attractions Aloha Candy Company and Volcano Garden Arts are ...
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
Stay at this vacation home in Hana. Enjoy free WiFi, a garden, and laundry facilities. Our guests praise the helpful staff in our reviews. Popular attractions ...
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
Book a stay at this golf vacation home in Kahuku. Enjoy a garden, laundry facilities, and tennis courts. Popular attractions Turtle Bay Beach and Turtle Bay ...
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
Book a stay at this family-friendly vacation home in Koloa. Enjoy free WiFi, private pools, and a fitness center. Popular attractions Poipu Beach and Brennecke ...
Kauai Luxury home, Private Pool & Spa, walk to the beach, restaurants and shops
Nani Iki - Close to beach!

Nani Iki - Close to beach!

Hauula
Stay at this vacation home in Hauula. Enjoy free WiFi, laundry facilities, and an in-room coffeemaker. Popular attractions Polynesian Cultural Center and Hauula ...
Nani Iki - Close to beach!
Kaiholo Hale

Kaiholo Hale

3 out of 5
25 Kaiholo Place, Paia, HI
Stay at this 3-star vacation home in Paia. Enjoy free WiFi, laundry facilities, and concierge services. Our guests praise the property condition in our reviews. ...
Kaiholo Hale
Oceanside Estate - Spacious home with Pool & AC

Oceanside Estate - Spacious home with Pool & AC

Hauula
Stay at this vacation home in Hauula. Enjoy free WiFi, private pools, and a garden. Popular attractions Polynesian Cultural Center and Hauula Beaches are located ...
Oceanside Estate - Spacious home with Pool & AC
North Shore BEACHFRONT Bungalo Perfection @ Sunset Beach

North Shore BEACHFRONT Bungalo Perfection @ Sunset Beach

Haleiwa
Stay at this vacation home in Haleiwa. Enjoy a garden, laundry facilities, and patios. Popular attractions Turtle Bay Beach and Sunset Beach are located ...
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
4158 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
Stay at this 4.5-star luxury resort in Honolulu. Enjoy 5 outdoor pools, a full-service spa, and 9 restaurants. Our guests praise the pool and the helpful staff ...
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
Book a stay at this beach hotel in Honolulu. Enjoy free WiFi, 2 outdoor pools, and a full-service spa. Our guests praise the pool and the helpful staff in our ...
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
Stay at this hotel in Honolulu. Enjoy free WiFi, breakfast (surcharge), and a 24-hour fitness center. Our guests praise the pool and the restaurant in our reviews. ...
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
Book a stay at this beach resort in Honolulu. Enjoy free WiFi, 2 outdoor pools, and a full-service spa. Our guests praise the pool and the helpful staff in our ...
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.