Book Holiday Homes in Kailua

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

We keep it easy with the option to pay now or later on select accommodation

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

Featured Holiday Homes in Kailua

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
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
Located in Honolulu (Waikiki), this vacation home is within a 10-minute walk of Waikiki Beach and Honolulu Zoo.
Waikiki Sunset Hotel remodeled unit with a magnificent view of the Koʻolau Range
Hale Aina, walkable to beach, A/C

Hale Aina, walkable to beach, A/C

Laie
With a stay at this vacation home in Hauula, you'll be by the sea, within a 5-minute drive of Polynesian Cultural Center and Kokololio Beach Park.
Hale Aina, walkable to beach, A/C
Save an average of 15% on thousands of hotels when you're signed in
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
Located in Honolulu (Waikiki), this vacation home is within a 10-minute walk of Waikiki Beach and International Market Place.
Newly renovated Waikiki Sunset unit with STUNNING Diamond Head and ocean views
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 AU$1,633 per night from 19 Nov to 20 Nov
AU$1,633
includes taxes & fees
19 Nov - 20 Nov
With a stay at this vacation home in Honolulu (Waikiki), you'll be steps from Waikiki Beach and 7 minutes by foot from International Market Place.
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
With a stay at this vacation home in Waimanalo (Waimanalo Beach), you'll be within a 15-minute drive of Hanauma Bay Nature Preserve and Waimanalo Beach.
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
Located in Hauula, this vacation home is in a rural location, within a 15-minute walk of Hau'ula Forest Reserve and Hauʻula Beach Park.
Aloha Adventure Home - 2 min from beach
Sunrise Escape, AC, 2min drive to beach, in Kahuku

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

Laie
With a stay at this vacation home in Laie, you'll be by the sea, within a 5-minute drive of Polynesian Cultural Center and Hukilau Beach.
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 AU$1,427 per night from 6 Nov to 7 Nov
AU$1,427
includes taxes & fees
6 Nov - 7 Nov
With a stay at this vacation home in Honolulu (Waikiki), you'll be steps from Waikiki Beach and 6 minutes by foot from International Market Place.
Direct Oceanfront in the Heart of Waikiki! Spectacular New Custom Reno!!
Don't see what you're looking for?
See all available properties in Kailua
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.

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
417 Holiday Homes
Lowest Price
AU$444
Highest Price
AU$1,633
Popular accommodation
Oceanside Estate - Spacious home with Pool & AC, Waikiki Sunset Hotel remodeled unit with a magnificent view of the Koʻolau Range, Hale Aina, walkable to beach, A/C, 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, 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 AU$460 per night from 26 Nov to 27 Nov
AU$460
includes taxes & fees
26 Nov - 27 Nov
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
'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 AU$576 per night from 18 Nov to 19 Nov
AU$576
includes taxes & fees
18 Nov - 19 Nov
Located in Honolulu (Waikiki), 'Alohilani Resort Waikiki Beach is within a 5-minute walk of Kuhio Beach Park and Duke Kahanamoku Statue.
'Alohilani Resort Waikiki Beach
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 AU$514 per night from 24 Nov to 25 Nov
AU$514
includes taxes & fees
24 Nov - 25 Nov
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
Save an average of 15% on thousands of hotels when you're signed in
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 AU$444 per night from 25 Nov to 26 Nov
AU$444
includes taxes & fees
25 Nov - 26 Nov
Located in Honolulu (Waikiki), Hyatt Regency Waikiki Beach Resort & Spa is a 3-minute walk from Kuhio Beach Park and 6 minutes by foot from International Market ...
Hyatt Regency Waikiki Beach Resort & Spa
Don't see what you're looking for?
See all available properties in Kailua
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.