Book Holiday Homes in Kailua

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Featured Holiday Homes in Kailua

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
Waikiki Sunset Hotel remodeled unit with a magnificent view of the Koʻolau Range

Waikiki Sunset Hotel remodeled unit with a magnificent view of the Koʻolau Range

Honolulu
Stay at this vacation home in Honolulu. Enjoy free WiFi, a fitness center, and balconies. Popular attractions Waikiki Beach and International Market Place are ...
Waikiki Sunset Hotel remodeled unit with a magnificent view of the Koʻolau Range
Newly renovated Waikiki Sunset unit with STUNNING Diamond Head and ocean views

Newly renovated Waikiki Sunset unit with STUNNING Diamond Head and ocean views

Honolulu
Stay at this vacation home in Honolulu. Enjoy free WiFi, a fitness center, and cable/satellite TV service. Our guests praise the helpful staff in our reviews. ...
Newly renovated Waikiki Sunset unit with STUNNING Diamond Head and ocean views
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Direct Oceanfront in the Heart of Waikiki! Spectacular New Custom Reno!

Direct Oceanfront in the Heart of Waikiki! Spectacular New Custom Reno!

Honolulu
The price is NZ$1,802 per night from 13 Dec to 14 Dec
NZ$1,802
includes taxes & fees
13 Dec - 14 Dec
Book a stay at this beach vacation home in Honolulu. Enjoy free WiFi, a beach locale, and a fitness center. Popular attractions Waikiki Beach and International ...
Direct Oceanfront in the Heart of Waikiki! Spectacular New Custom Reno!
House that has it all, Hot Tub, Kayaks, Surf Boards, Snorkeling gear & more

House that has it all, Hot Tub, Kayaks, Surf Boards, Snorkeling gear & more

Waimanalo
Stay at this vacation home in Waimanalo. Enjoy free WiFi, a garden, and patios. Popular attractions Lanikai Beach and Kailua Beach are located nearby.
House that has it all, Hot Tub, Kayaks, Surf Boards, Snorkeling gear & more
Aloha Adventure Home - 2 min from beach

Aloha Adventure Home - 2 min from beach

Hauula
Stay at this vacation home in Hauula. Enjoy an in-room coffeemaker. Popular attractions Polynesian Cultural Center and Hauʻula Beach Park are located ...
Aloha Adventure Home - 2 min from beach
Oceanfront Romantic Couple's Getaway with Private Beach w/ Full Living Amenities

Oceanfront Romantic Couple's Getaway with Private Beach w/ Full Living Amenities

Hauula
Book a stay at this beach vacation home in Hauula. Enjoy free WiFi, a beach locale, and a garden. Popular attractions Polynesian Cultural Center and Hauula Beaches ...
Oceanfront Romantic Couple's Getaway with Private Beach w/ Full Living Amenities
Sunrise Escape, AC, 2min drive to beach, in Kahuku

Sunrise Escape, AC, 2min drive to beach, in Kahuku

Laie
Stay at this vacation home in Laie. Enjoy a garden, an in-room coffeemaker, and air conditioning. Popular attractions Polynesian Cultural Center and Turtle Bay ...
Sunrise Escape, AC, 2min drive to beach, in Kahuku
Direct Oceanfront in the Heart of Waikiki! Spectacular New Custom Reno!!

Direct Oceanfront in the Heart of Waikiki! Spectacular New Custom Reno!!

Honolulu
The price is NZ$1,802 per night from 7 Dec to 8 Dec
NZ$1,802
includes taxes & fees
7 Dec - 8 Dec
Book a stay at this beach vacation home in Honolulu. Enjoy free WiFi, a beach locale, and a fitness center. Popular attractions Waikiki Beach and International ...
Direct Oceanfront in the Heart of Waikiki! Spectacular New Custom Reno!!
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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.

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

Holiday houses in Kailua 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 Kailua 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 Kailua adventures, obvs.

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

Kailua Holiday Homes essential information

Accommodation
422 Holiday Homes
Lowest Price
NZ$544
Highest Price
NZ$1,802
Popular accommodation
Oceanside Estate - Spacious home with Pool & AC, Waikiki Sunset Hotel remodeled unit with a magnificent view of the Koʻolau Range, Newly renovated Waikiki Sunset unit with STUNNING Diamond Head and ocean views, Direct Oceanfront in the Heart of Waikiki! Spectacular New Custom Reno!, House that has it all, Hot Tub, Kayaks, Surf Boards, Snorkeling gear & more, Aloha Adventure Home - 2 min from beach, Oceanfront Romantic Couple's Getaway with Private Beach w/ Full Living Amenities, Sunrise Escape, AC, 2min drive to beach, in Kahuku, Direct Oceanfront in the Heart of Waikiki! Spectacular New Custom Reno!!

Top trending hotels in Kailua

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
The price is NZ$560 per night from 24 Nov to 25 Nov
NZ$560
includes taxes & fees
24 Nov - 25 Nov
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
'Alohilani Resort Waikiki Beach

'Alohilani Resort Waikiki Beach

5 out of 5
2490 Kalakaua Avenue, Honolulu, HI
Fully refundableReserve now, pay when you stay
The price is NZ$661 per night from 23 Nov to 24 Nov
NZ$661
includes taxes & fees
23 Nov - 24 Nov
Book a stay at this beach resort in Honolulu. Enjoy free WiFi, 5 restaurants, and a rooftop terrace. Our guests praise the pool and the helpful staff in our ...
'Alohilani Resort Waikiki Beach
Hyatt Regency Waikiki Beach Resort & Spa

Hyatt Regency Waikiki Beach Resort & Spa

4 out of 5
2424 Kalakaua Ave, Honolulu, HI
Fully refundableReserve now, pay when you stay
The price is NZ$544 per night from 23 Nov to 24 Nov
NZ$544
includes taxes & fees
23 Nov - 24 Nov
Book a stay at this beach resort in Honolulu. Enjoy free WiFi, a full-service spa, and 4 restaurants. Our guests praise the helpful staff and the clean rooms ...
Hyatt Regency Waikiki Beach Resort & Spa
Save an average of 15% on thousands of hotels when you're signed in
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
The price is NZ$576 per night from 9 Dec to 10 Dec
NZ$576
includes taxes & fees
9 Dec - 10 Dec
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
Don't see what you're looking for?
See all available properties in Kailua
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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.