Book Holiday Homes in Kaunakakai

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Featured Holiday Homes in Kaunakakai

272-1 Large oceanfront home- fully air conditioned, 25 feet from the water

272-1 Large oceanfront home- fully air conditioned, 25 feet from the water

Lahaina
Book a stay at this beach vacation home in Lahaina. Enjoy free WiFi, a beach locale, and a garden. Popular attractions Kaanapali Beach and Puamana Beach Park ...
272-1 Large oceanfront home- fully air conditioned, 25 feet from the water
The #1 Luxury OCEAN FRONT Mansion!  Sleeps 32

The #1 Luxury OCEAN FRONT Mansion! Sleeps 32

lahina
Book a stay at this beach vacation home in Honokowai. Enjoy private pools, a beach locale, and a fitness center. Popular attractions Kaanapali Beach and Napili ...
The #1 Luxury OCEAN FRONT Mansion! Sleeps 32
Celebrity Home Across the Street From Beach! Pool With Slide, Pickleball, Gym!

Celebrity Home Across the Street From Beach! Pool With Slide, Pickleball, Gym!

Lahaina
Book a stay at this family-friendly vacation home in Napili. Enjoy free WiFi, private pools, and a garden. Popular attractions Kaanapali Beach and Napili Bay ...
Celebrity Home Across the Street From Beach! Pool With Slide, Pickleball, Gym!
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Spectacular, fully renovated 3-Bedroom Oceanfront Townhome in Kahana

Spectacular, fully renovated 3-Bedroom Oceanfront Townhome in Kahana

Lahaina
Book a stay at this beach vacation home in Kahana. Enjoy free WiFi, a beach locale, and a garden. Popular attractions Kaanapali Beach and Napili Bay are located ...
Spectacular, fully renovated 3-Bedroom Oceanfront Townhome in Kahana
#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 Kaanapali Beach and Napili ...
#1 Luxury BEACHFRONT! Pickleball, Sand Volleyball, 2 Gyms, Pool
The #1 Vacation Rental on Maui!!  Steps to Maui's Best Beach!

The #1 Vacation Rental on Maui!! Steps to Maui's Best Beach!

Lahaina
Book a stay at this family-friendly vacation home in Napili. Enjoy private pools, a garden, and patios. Popular attractions Kaanapali Beach and Napili Bay are ...
The #1 Vacation Rental on Maui!! Steps to Maui's Best Beach!
THE WHALE HOUSE - POOL & OCEAN VIEWS near BEAUTIFUL KAANAPALI BEACH

THE WHALE HOUSE - POOL & OCEAN VIEWS near BEAUTIFUL KAANAPALI BEACH

Lahaina
Book a stay at this golf vacation home in Kaanapali. Enjoy private pools, a garden, and patios. Popular attractions Kaanapali Beach and Napili Bay are located ...
THE WHALE HOUSE - POOL & OCEAN VIEWS near BEAUTIFUL KAANAPALI BEACH
Lana’i Oasis and Gem, The Artist's House

Lana’i Oasis and Gem, The Artist's House

Lanai
The price is NZ$1,417 per night from 22 Jan to 23 Jan
NZ$1,417
includes taxes & fees
22 Jan - 23 Jan
Stay at this vacation home in Lanai City. Enjoy free WiFi, a garden, and tennis courts. Popular attractions Munro Trail and Lanaʻi Culture & Heritage Center ...
Lana’i Oasis and Gem, The Artist's House
Secluded Ocean View Napili Home - Sleeps 14

Secluded Ocean View Napili Home - Sleeps 14

Lahaina
Stay at this vacation home in Napili. Enjoy free WiFi, a garden, and patios. Popular attractions Kaanapali Beach and Napili Bay are located nearby.
Secluded Ocean View Napili Home - Sleeps 14
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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.

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

Holiday houses in Kaunakakai 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 Kaunakakai 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 Kaunakakai adventures, obvs.

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

Kaunakakai Holiday Homes essential information

Accommodation
130 Holiday Homes
Lowest Price
NZ$660
Highest Price
NZ$1,417
Popular accommodation
272-1 Large oceanfront home- fully air conditioned, 25 feet from the water, The #1 Luxury OCEAN FRONT Mansion! Sleeps 32, Celebrity Home Across the Street From Beach! Pool With Slide, Pickleball, Gym!, Spectacular, fully renovated 3-Bedroom Oceanfront Townhome in Kahana, #1 Luxury BEACHFRONT! Pickleball, Sand Volleyball, 2 Gyms, Pool, The #1 Vacation Rental on Maui!! Steps to Maui's Best Beach!, THE WHALE HOUSE - POOL & OCEAN VIEWS near BEAUTIFUL KAANAPALI BEACH, Lana’i Oasis and Gem, The Artist's House, Secluded Ocean View Napili Home - Sleeps 14

Top trending hotels in Kaunakakai

Castle at Moloka'i Shores

Castle at Moloka'i Shores

3 out of 5
109 Ala Malama St, Building D, Unit A, Kaunakakai, HI
Stay at this 3-star beach condo in Kaunakakai. Enjoy free WiFi, a beach locale, and laundry facilities. Popular attractions St. Joseph's Catholic Church and ...
Castle at Moloka'i Shores
Hotel Moloka'i

Hotel Moloka'i

3 out of 5
1300 Kamehameha V Hwy, Kaunakakai, HI
Fully refundableReserve now, pay when you stay
The price is NZ$660 per night from 3 Feb to 4 Feb
NZ$660
includes taxes & fees
3 Feb - 4 Feb
Stay at this 3-star beach hotel in Kaunakakai. Enjoy free WiFi, free parking, and a business center. Our guests praise the helpful staff in our reviews. Popular ...
Hotel Moloka'i
MOLOKAI ISLAND   Two Bedroom Oceanfront Top End Unit!

MOLOKAI ISLAND Two Bedroom Oceanfront Top End Unit!

Kaunakakai
Book a stay at this beach condo in Kaunakakai. Enjoy a beach locale, a garden, and tennis courts. Our guests praise the helpful staff in our reviews. Popular ...
MOLOKAI ISLAND Two Bedroom Oceanfront Top End Unit!
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The Ultimate Oceanfront Penthouse - 'Hale No Ka Oi'

The Ultimate Oceanfront Penthouse - 'Hale No Ka Oi'

Kaunakakai,
Book a stay at this beach condo in Kaunakakai. Enjoy free WiFi, private pools, and a beach locale. Popular attractions St. Joseph's Catholic Church and Molokai ...
The Ultimate Oceanfront Penthouse - 'Hale No Ka Oi'
Don't see what you're looking for?
See all available properties in Kaunakakai
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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.