Book Holiday Homes in Waimanalo

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Featured Holiday Homes in Waimanalo

Just steps from the sand—enjoy a pool, hot tub, bikes, beach gear & more!

Just steps from the sand—enjoy a pool, hot tub, bikes, beach gear & more!

Kailua HI
With a stay at this vacation home in Kailua (Beachside), you'll be a 4-minute walk from Kailua Beach and within a 5-minute drive of Lanikai Beach.
Opens in a new windowJust steps from the sand—enjoy a pool, hot tub, bikes, beach gear & more!
Perfect Kailua Vacation at Ka Hale Lai-House of Serenity-pool and spa.

Perfect Kailua Vacation at Ka Hale Lai-House of Serenity-pool and spa.

Kailua HI
When you stay at this vacation home in Kailua, you'll be near the beach, within a 15-minute drive of Kailua Beach and Lanikai Beach.
Opens in a new windowPerfect Kailua Vacation at Ka Hale Lai-House of Serenity-pool and spa.
BEACH FRONT KAILUA ESTATE, OCEAN VIEWS, HUGE LUSH PRIVATE HISTORIC PROPERTY

BEACH FRONT KAILUA ESTATE, OCEAN VIEWS, HUGE LUSH PRIVATE HISTORIC PROPERTY

Kailua HI
With a stay at this vacation home in Kailua (Kalama Tract), you'll be within a 15-minute drive of Kailua Beach and Lanikai Beach.
Opens in a new windowBEACH FRONT KAILUA ESTATE, OCEAN VIEWS, HUGE LUSH PRIVATE HISTORIC PROPERTY
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Hale Oahu Estate Lic. #1990/NUC-1777 CHRISTMAS CANCELLATION!

Hale Oahu Estate Lic. #1990/NUC-1777 CHRISTMAS CANCELLATION!

Kailua HI
With a stay at this vacation home in Kailua (Beachside), you'll be a 1-minute drive from Kailua Beach and 7 minutes from Lanikai Beach.
Opens in a new windowHale Oahu Estate Lic. #1990/NUC-1777 CHRISTMAS CANCELLATION!
Gigi's Retreat-Kailua Beach Front + Pool - Lic.1990/NUC-1783

Gigi's Retreat-Kailua Beach Front + Pool - Lic.1990/NUC-1783

Kailua HI
With a stay at this vacation home in Kailua (Kalama Tract), you'll be a 3-minute drive from Kailua Beach and 9 minutes from Lanikai Beach.
Opens in a new windowGigi's Retreat-Kailua Beach Front + Pool - Lic.1990/NUC-1783
2BR/2BA Close to Waikiki Beach with Free Parking!

2BR/2BA Close to Waikiki Beach with Free Parking!

Honolulu HI
The price is AU$1,327 per night from 11 Jan to 12 Jan
AU$1,327
11 Jan - 12 Jan 2026
includes taxes & fees
With a stay at this vacation home in Honolulu (Waikiki), you'll be a 3-minute walk from Waikiki Beach and 6 minutes by foot from International Market Place.
Opens in a new window2BR/2BA Close to Waikiki Beach with Free Parking!
Manoa Valley Duplex with ocean and mountain views

Manoa Valley Duplex with ocean and mountain views

Honolulu HI
With a stay at this vacation home in Honolulu (Manoa), you'll be within a 10-minute drive of Ala Moana Center and Waikiki Beach Walk.
Opens in a new windowManoa Valley Duplex with ocean and mountain views
Waterfront Bliss at Tropical Townhouse

Waterfront Bliss at Tropical Townhouse

2 out of 5
Honolulu Hawaii
With a stay at this vacation home in Honolulu (Hawaii Kai), you'll be a 4-minute drive from Hanauma Bay Nature Preserve and 6 minutes from Hanauma Bay.
Opens in a new windowWaterfront Bliss at Tropical Townhouse
★ Amazing ★ Kailua Bliss Beach House ★ Pool! Game Room! 1 House from the Beach

★ Amazing ★ Kailua Bliss Beach House ★ Pool! Game Room! 1 House from the Beach

Kailua HI
When you stay at this vacation home in Kailua, you'll be by the sea, a 5-minute drive from Kailua Beach and 8 minutes from Lanikai Beach.
Opens in a new window★ Amazing ★ Kailua Bliss Beach House ★ Pool! Game Room! 1 House from the 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.

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

Holiday houses in Waimanalo 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 Waimanalo 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 Waimanalo adventures, obvs.

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

Waimanalo Holiday Homes essential information

Accommodation
298 Holiday Homes
Lowest Price
AU$425
Highest Price
AU$1,327
Popular accommodation
Just steps from the sand—enjoy a pool, hot tub, bikes, beach gear & more!, Perfect Kailua Vacation at Ka Hale Lai-House of Serenity-pool and spa., BEACH FRONT KAILUA ESTATE, OCEAN VIEWS, HUGE LUSH PRIVATE HISTORIC PROPERTY, Hale Oahu Estate Lic. #1990/NUC-1777 CHRISTMAS CANCELLATION!, Gigi's Retreat-Kailua Beach Front + Pool - Lic.1990/NUC-1783, 2BR/2BA Close to Waikiki Beach with Free Parking!, Manoa Valley Duplex with ocean and mountain views, Waterfront Bliss at Tropical Townhouse, ★ Amazing ★ Kailua Bliss Beach House ★ Pool! Game Room! 1 House from the Beach

Top trending hotels in Waimanalo

Sheraton Waikiki Beach Resort

Sheraton Waikiki Beach Resort

4.5 out of 5
2255 Kalakaua Ave Honolulu HI
The price is AU$964 per night from 22 Jan to 23 Jan
AU$964
22 Jan - 23 Jan 2026
includes taxes & fees
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 ...
Opens in a new windowSheraton Waikiki Beach Resort
Waikiki Beach Marriott Resort & Spa

Waikiki Beach Marriott Resort & Spa

4 out of 5
2552 Kalakaua Ave Honolulu HI
The price is AU$478 per night from 4 Jan to 5 Jan
AU$478
4 Jan - 5 Jan 2026
includes taxes & fees
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.
Opens in a new windowWaikiki Beach Marriott Resort & Spa
Waikiki Resort Hotel

Waikiki Resort Hotel

3.5 out of 5
2460 Koa Avenue Honolulu HI
The price is AU$425 per night from 9 Jan to 10 Jan
AU$425
9 Jan - 10 Jan 2026
includes taxes & fees
With a stay at Waikiki Resort Hotel, you'll be centrally located in Honolulu, within a 10-minute walk of International Market Place and Honolulu Zoo.
Opens in a new windowWaikiki Resort Hotel
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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$640 per night from 16 Jan to 17 Jan
AU$640
16 Jan - 17 Jan 2026
includes taxes & fees
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 ...
Opens in a new windowHilton Hawaiian Village Waikiki Beach Resort
Don't see what you're looking for?
See all available properties in Waimanalo
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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.