Book Holiday Homes in Kaunakakai

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Featured Holiday Homes in Kaunakakai

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
When you stay at this vacation home in Napili, you'll be by the sea, within a 15-minute drive of Napili Bay and Whalers Village.
Celebrity Home Across the Street From Beach! Pool With Slide, Pickleball, Gym!
Lana’i Oasis and Gem, The Artist's House

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

Lanai
With a stay at this vacation home in Lanai City, you'll be a 2-minute walk from Munro Trail and 10 minutes by foot from Lanaʻi Culture & Heritage Center.
Lana’i Oasis and Gem, The Artist's House
The #1 Luxury OCEAN FRONT Mansion!  Sleeps 32

The #1 Luxury OCEAN FRONT Mansion! Sleeps 32

lahina
When you stay at this vacation home in Honokowai, you'll be on the beach, within a 10-minute drive of Kaanapali Beach and Whalers Village.
The #1 Luxury OCEAN FRONT Mansion! Sleeps 32
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#1 Direct Beach Front Mansion!  Pickleball, Sand Volleyball, 2 Gyms, Pool

#1 Direct Beach Front Mansion! Pickleball, Sand Volleyball, 2 Gyms, Pool

2 out of 5
Lahaina
When you stay at this vacation home in Kaanapali, you'll be on the beach, a 4-minute drive from Whalers Village and 7 minutes from Kaanapali Beach.
#1 Direct Beach Front Mansion! Pickleball, Sand Volleyball, 2 Gyms, Pool
Spectacular Sunset and Ocean Views with Pool & Hotbub near Kaanapali Beach

Spectacular Sunset and Ocean Views with Pool & Hotbub near Kaanapali Beach

Lahaina
With a stay at this vacation home, you'll be centrally located in Kaanapali, a 4-minute drive from Whalers Village and 5 minutes from Kaanapali Beach.
Spectacular Sunset and Ocean Views with Pool & Hotbub near Kaanapali Beach
Molokai Oceanfront large beautiful home - Gorgeous secluded beaches out front!

Molokai Oceanfront large beautiful home - Gorgeous secluded beaches out front!

Maunaloa
With a stay at this vacation home in Maunaloa, you'll be on the beach, just a 2-minute walk from Pohakumauliuli Beach and 9 minutes by foot from Kepuhi ...
Molokai Oceanfront large beautiful home - Gorgeous secluded beaches out front!
Discounts Now for July & August! New Luxury Rental With Panoramic Ocean Views!

Discounts Now for July & August! New Luxury Rental With Panoramic Ocean Views!

Lahaina
When you stay at this vacation home in Kapalua, you'll be next to a golf course, within a 15-minute drive of Napili Bay and Whalers Village.
Discounts Now for July & August! New Luxury Rental With Panoramic Ocean Views!
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
When you stay at this vacation home in Napili, you'll be by the sea, within a 15-minute drive of Napili Bay and Whalers Village.
The #1 Vacation Rental on Maui!! Steps to Maui's Best Beach!
The Best of the Best JUST GOT BETTER with 3rd Remodel

The Best of the Best JUST GOT BETTER with 3rd Remodel

Lahaina
When you stay at this vacation home in Kaanapali, you'll be on the beach, within a 10-minute drive of Kaanapali Beach and Whalers Village.
The Best of the Best JUST GOT BETTER with 3rd Remodel
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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
101 Holiday Homes
Lowest Price
AU$312
Highest Price
AU$312
Popular accommodation
Celebrity Home Across the Street From Beach! Pool With Slide, Pickleball, Gym!, Lana’i Oasis and Gem, The Artist's House, The #1 Luxury OCEAN FRONT Mansion! Sleeps 32, #1 Direct Beach Front Mansion! Pickleball, Sand Volleyball, 2 Gyms, Pool, Spectacular Sunset and Ocean Views with Pool & Hotbub near Kaanapali Beach, Molokai Oceanfront large beautiful home - Gorgeous secluded beaches out front!, Discounts Now for July & August! New Luxury Rental With Panoramic Ocean Views!, The #1 Vacation Rental on Maui!! Steps to Maui's Best Beach!, The Best of the Best JUST GOT BETTER with 3rd Remodel

Top trending hotels in Kaunakakai

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 AU$312 per night from 30 Sep to 1 Oct
AU$312
per night
30 Sep - 1 Oct
When you stay at Hotel Moloka'i in Kaunakakai, you'll be on the waterfront, within a 5-minute drive of St. Joseph's Catholic Church and Kapuaiwa Coconut ...
Hotel Moloka'i
Castle at Moloka'i Shores

Castle at Moloka'i Shores

3 out of 5
109 Ala Malama St, Building D, Unit A, Kaunakakai, HI
Located in Kaunakakai, Castle at Moloka'i Shores is by the ocean, within a 5-minute drive of Molokai Harbor and St. Joseph's Catholic Church.
Castle at Moloka'i Shores
MOLOKAI ISLAND   Two Bedroom Oceanfront Top End Unit!

MOLOKAI ISLAND Two Bedroom Oceanfront Top End Unit!

Kaunakakai
With a stay at this condo in Kaunakakai, you'll be on the beach, just steps from Hokukano-Ualapue Complex and a 3-minute drive from Kaluaʻaha Church.
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,
When you stay at this condo in Kaunakakai, you'll be on the beach, within a 5-minute drive of Molokai Harbor and St. Joseph's Catholic Church.
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.