Book Holiday Homes in Kaunakakai

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Featured Holiday Homes in Kaunakakai

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

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

Lanai
The price is AU$1,145 per night from 22 Nov to 23 Nov
AU$1,145
includes taxes & fees
22 Nov - 23 Nov
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
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!
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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!
#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
Private gated home with 300 Foot private beach front, beach toys and much more!

Private gated home with 300 Foot private beach front, beach toys and much more!

Lahaina
When you stay at this vacation home in Kahana, you'll be on the beach, a 4-minute drive from Napili Bay and 10 minutes from Kaanapali Beach.
Private gated home with 300 Foot private beach front, beach toys and much more!
Beautiful oceanfront condo with lanai, pool, beach access, & washer/dryer

Beautiful oceanfront condo with lanai, pool, beach access, & washer/dryer

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 ...
Beautiful oceanfront condo with lanai, pool, beach access, & washer/dryer
Legendary Estate 50 Steps to Maui’s Best Beach! New! 5 Bedroom, Pool With Slide!

Legendary Estate 50 Steps to Maui’s Best Beach! New! 5 Bedroom, Pool With Slide!

Lahaina
When you stay at this vacation home in Kapalua, you'll be by the sea, within a 15-minute drive of Napili Bay and Whalers Village.
Legendary Estate 50 Steps to Maui’s Best Beach! New! 5 Bedroom, Pool With Slide!
Kapalua Golf Villas by KBM Resorts

Kapalua Golf Villas by KBM Resorts

3.5 out of 5
Lahaina
The price is AU$1,170 per night from 9 Dec to 10 Dec
AU$1,170
includes taxes & fees
9 Dec - 10 Dec
When you stay at this vacation home in Kapalua, you'll be on the waterfront, within a 15-minute drive of Napili Bay and Whalers Village.
Kapalua Golf Villas by KBM Resorts
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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
108 Holiday Homes
Lowest Price
AU$462
Highest Price
AU$1,170
Popular accommodation
Lana’i Oasis and Gem, The Artist's House, The #1 Luxury OCEAN FRONT Mansion! Sleeps 32, Molokai Oceanfront large beautiful home - Gorgeous secluded beaches out front!, Celebrity Home Across the Street From Beach! Pool With Slide, Pickleball, Gym!, #1 Direct Beach Front Mansion! Pickleball, Sand Volleyball, 2 Gyms, Pool, Private gated home with 300 Foot private beach front, beach toys and much more!, Beautiful oceanfront condo with lanai, pool, beach access, & washer/dryer, Legendary Estate 50 Steps to Maui’s Best Beach! New! 5 Bedroom, Pool With Slide!, Kapalua Golf Villas by KBM Resorts

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$462 per night from 25 Nov to 26 Nov
AU$462
includes taxes & fees
25 Nov - 26 Nov
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'
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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.