Book Holiday Homes in Wailua

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Featured Holiday Homes in Wailua

Tropical breezes, ocean view and sunny white sand beaches.

Tropical breezes, ocean view and sunny white sand beaches.

Kapaa HI
With a stay at this vacation home in Kapaa (Waipouli), you'll be steps from Waipouli Beach and 6 minutes by foot from Fuji Beach.
Opens in a new windowTropical breezes, ocean view and sunny white sand beaches.
Exquisite Oceanfront Home, 4 Bedrooms, 2 Baths, Central A/C, Sleeps 8

Exquisite Oceanfront Home, 4 Bedrooms, 2 Baths, Central A/C, Sleeps 8

Kapaʻa HI
With a stay at this vacation home in Kapaa (Waipouli), you'll be steps from Waipouli Beach and 6 minutes by foot from Fuji Beach.
Opens in a new windowExquisite Oceanfront Home, 4 Bedrooms, 2 Baths, Central A/C, Sleeps 8
Wailua Bay View Condo w/ Private Washer/Dryer, Free WiFi, Shared Pool

Wailua Bay View Condo w/ Private Washer/Dryer, Free WiFi, Shared Pool

Kapaa HI
With a stay at this vacation home in Kapaa (Waipouli), you'll be within a 15-minute drive of Nawiliwili Harbor and Wailua Beach.
Opens in a new windowWailua Bay View Condo w/ Private Washer/Dryer, Free WiFi, Shared Pool
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Kapaa Shore Resort A207, Oceanfront, 2nd Floor, Cal King Bed, Wifi, AC

Kapaa Shore Resort A207, Oceanfront, 2nd Floor, Cal King Bed, Wifi, AC

Kapaa Hawaii
With a stay at this vacation home, you'll be centrally located in Kapaa, within a 15-minute drive of Nawiliwili Harbor and Waipouli Beach.
Opens in a new windowKapaa Shore Resort A207, Oceanfront, 2nd Floor, Cal King Bed, Wifi, AC
Wailua Bay View condo near surf & sand with pool, ocean views & W/D

Wailua Bay View condo near surf & sand with pool, ocean views & W/D

Kapaa HI
With a stay at this vacation home in Kapaa (Waipouli), you'll be within a 15-minute drive of Nawiliwili Harbor and Wailua Beach.
Opens in a new windowWailua Bay View condo near surf & sand with pool, ocean views & W/D
Fern Grotto Inn - Lonely Planet Recommends our Cottages! VRBO Bear Stayed Here!

Fern Grotto Inn - Lonely Planet Recommends our Cottages! VRBO Bear Stayed Here!

Kapaa HI
With a stay at this vacation home in Kapaa, you'll be by the sea, within a 15-minute drive of Nawiliwili Harbor and Holoholoku Heiau.
Opens in a new windowFern Grotto Inn - Lonely Planet Recommends our Cottages! VRBO Bear Stayed Here!
Kauai Hale Melemele Cottage 1 Block to the Beach!

Kauai Hale Melemele Cottage 1 Block to the Beach!

KAPAA HI
With a stay at this vacation home in Kapaa (Waipouli), you'll be within a 15-minute drive of Nawiliwili Harbor and Lae Nani Beach.
Opens in a new windowKauai Hale Melemele Cottage 1 Block to the Beach!
New Listing! Charming Kapa'a Garden Cottage

New Listing! Charming Kapa'a Garden Cottage

KAPAA HI
With a stay at this vacation home in Kapaa (Waipouli), you'll be within a 15-minute drive of Nawiliwili Harbor and Lae Nani Beach.
Opens in a new windowNew Listing! Charming Kapa'a Garden Cottage
New Modern Hawaiian  2-bedroom house in Kapaʻa with amazing ocean/mountain views

New Modern Hawaiian 2-bedroom house in Kapaʻa with amazing ocean/mountain views

2 out of 5
Kapaʻa HI
With a stay at this vacation home in Kapaa (Waipouli), you'll be within a 15-minute drive of Nawiliwili Harbor and Coconut Marketplace.
Opens in a new windowNew Modern Hawaiian 2-bedroom house in Kapaʻa with amazing ocean/mountain views
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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.

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

Holiday houses in Wailua 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 Wailua 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 Wailua adventures, obvs.

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

Wailua Holiday Homes essential information

Accommodation
12 Holiday Homes
Lowest Price
AU$368
Highest Price
AU$607
Popular accommodation
Tropical breezes, ocean view and sunny white sand beaches., Exquisite Oceanfront Home, 4 Bedrooms, 2 Baths, Central A/C, Sleeps 8, Wailua Bay View Condo w/ Private Washer/Dryer, Free WiFi, Shared Pool, Kapaa Shore Resort A207, Oceanfront, 2nd Floor, Cal King Bed, Wifi, AC, Wailua Bay View condo near surf & sand with pool, ocean views & W/D, Fern Grotto Inn - Lonely Planet Recommends our Cottages! VRBO Bear Stayed Here!, Kauai Hale Melemele Cottage 1 Block to the Beach!, New Listing! Charming Kapa'a Garden Cottage, New Modern Hawaiian 2-bedroom house in Kapaʻa with amazing ocean/mountain views

Top trending hotels in Wailua

Sheraton Kauai Coconut Beach Resort

Sheraton Kauai Coconut Beach Resort

4 out of 5
650 Aleka Loop Kapaa HI
Fully refundableReserve now, pay when you stay
The price is AU$607 per night from 4 Jan to 5 Jan
AU$607
4 Jan - 5 Jan 2026
includes taxes & fees
With a stay at Sheraton Kauai Coconut Beach Resort in Kapaa (Waipouli), you'll be within a 15-minute drive of Nawiliwili Harbor and Coconut Marketplace.
Opens in a new windowSheraton Kauai Coconut Beach Resort
Kauai Shores Hotel

Kauai Shores Hotel

3.5 out of 5
420 Papaloa Rd Kapaa HI
The price is AU$446 per night from 21 Jan to 22 Jan
AU$446
21 Jan - 22 Jan 2026
includes taxes & fees
With a stay at Kauai Shores Hotel in Kapaa (Waipouli), you'll be a 1-minute drive from Lae Nani Beach and 7 minutes from Lydgate Beach.
Opens in a new windowKauai Shores Hotel
Aston Islander on the Beach

Aston Islander on the Beach

3 out of 5
440 Aleka Place Kapaa HI
The price is AU$368 per night from 3 Jan to 4 Jan
AU$368
3 Jan - 4 Jan 2026
includes taxes & fees
With a stay at Aston Islander on the Beach in Kapaa (Waipouli), you'll be within a 15-minute drive of Nawiliwili Harbor and Coconut Marketplace.
Opens in a new windowAston Islander on the Beach
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The ISO by Castle

The ISO by Castle

3.5 out of 5
4-796 Kuhio Hwy Kapaa HI
Fully refundable
The price is AU$426 per night from 23 Dec to 24 Dec
AU$426
23 Dec - 24 Dec
includes taxes & fees
Located in Kapaa (Waipouli), The ISO by Castle is within a 5-minute drive of Waipouli Beach and Coconut Marketplace.
Opens in a new windowThe ISO by Castle
Don't see what you're looking for?
See all available properties in Wailua
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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.

**Terms and Conditions apply.
^Subject to availability and chosen travel dates.