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
A stay at this vacation home places you in the heart of Lahaina, within a 5-minute drive of Lahaina Pali Trail 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
When you stay at this vacation home in Honokowai, you'll be on the beach, within a 10-minute drive of Kaanapali Beach and Napili Bay.
The #1 Luxury OCEAN FRONT Mansion! Sleeps 32
Maui Vacation Home w/Dazzling Oceanfront Views Honu Hale (Turtle House)

Maui Vacation Home w/Dazzling Oceanfront Views Honu Hale (Turtle House)

Lahiana
When you stay at this vacation home in Napili, you'll be on the beach, within a 15-minute drive of Kaanapali Beach and Napili Bay.
Maui Vacation Home w/Dazzling Oceanfront Views Honu Hale (Turtle House)
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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, just steps from Napili Bay and Napili Bay Beach.
Celebrity Home Across the Street From Beach! Pool With Slide, Pickleball, Gym!
#1 Luxury BEACHFRONT! Pickleball, Sand Volleyball, 2 Gyms, Pool

#1 Luxury BEACHFRONT! 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, within a 10-minute drive of Kaanapali Beach and Napili Bay.
#1 Luxury BEACHFRONT! Pickleball, Sand Volleyball, 2 Gyms, Pool
THE WHALE HOUSE - POOL & OCEAN VIEWS near BEAUTIFUL KAANAPALI BEACH

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

Lahaina
When you stay at this vacation home in Kaanapali, you'll be next to a golf course, within a 10-minute drive of Kaanapali Beach and Napili Bay.
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 AU$1,291 per night from 22 Jan to 23 Jan
AU$1,291
includes taxes & fees
22 Jan - 23 Jan
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
Secluded Ocean View Napili Home - Sleeps 14

Secluded Ocean View Napili Home - Sleeps 14

Lahaina
When you stay at this vacation home in Napili, you'll be near the beach, within a 15-minute drive of Kaanapali Beach and Napili Bay.
Secluded Ocean View Napili Home - Sleeps 14
105-1  Puamana Spacious Townhome Near Ocean.

105-1 Puamana Spacious Townhome Near Ocean.

Lahaina
A stay at this vacation home places you in the heart of Lahaina, within a 5-minute drive of Lahaina Pali Trail and West Maui Mountains.
105-1 Puamana Spacious Townhome Near Ocean.
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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
AU$595
Highest Price
AU$1,291
Popular accommodation
272-1 Large oceanfront home- fully air conditioned, 25 feet from the water, The #1 Luxury OCEAN FRONT Mansion! Sleeps 32, Maui Vacation Home w/Dazzling Oceanfront Views Honu Hale (Turtle House), Celebrity Home Across the Street From Beach! Pool With Slide, Pickleball, Gym!, #1 Luxury BEACHFRONT! Pickleball, Sand Volleyball, 2 Gyms, Pool, 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, 105-1 Puamana Spacious Townhome Near Ocean.

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
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
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$595 per night from 22 Jan to 23 Jan
AU$595
includes taxes & fees
22 Jan - 23 Jan
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
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.