Book Holiday Homes in Kaunakakai

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Featured Holiday Homes in Kaunakakai

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

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

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.
Opens in a new windowThe #1 Vacation Rental on Maui!! Steps to Maui's Best Beach! Pickle Ball Ct!
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.
Opens in a new windowThe #1 Luxury OCEAN FRONT Mansion! Sleeps 32
Spectacular Oceanfront 4 bedroom 4 bath, AC, pool in tropical oasis.

Spectacular Oceanfront 4 bedroom 4 bath, AC, pool in tropical oasis.

Lahaina
With a stay at this vacation home in Lahaina, you'll be on the beach, within a 15-minute drive of Whalers Village and Lahaina Pali Trail.
Opens in a new windowSpectacular Oceanfront 4 bedroom 4 bath, AC, pool in tropical oasis.
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#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, a 4-minute drive from Whalers Village and 7 minutes from Kaanapali Beach.
Opens in a new window#1 Luxury BEACHFRONT! Pickleball, Sand Volleyball, 2 Gyms, Pool
Privacy In Paradise - Top Rated Vacation Home in West Maui

Privacy In Paradise - Top Rated Vacation Home in West Maui

Lahaina
With a stay at this vacation home in Launiupoko, you'll be near the beach, within a 15-minute drive of Kaanapali Beach and Launiupoko Beach Park.
Opens in a new windowPrivacy In Paradise - Top Rated Vacation Home in West Maui
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 Napili, you'll be on the beach, within a 15-minute drive of Napili Bay and Whalers Village.
Opens in a new windowLegendary Estate 50 Steps to Maui’s Best Beach! New! 5 Bedroom, Pool With Slide!
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.
Opens in a new windowSpectacular Sunset and Ocean Views with Pool & Hotbub near Kaanapali Beach
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, a 1-minute drive from Napili Bay and 10 minutes from Whalers Village.
Opens in a new windowMaui Vacation Home w/Dazzling Oceanfront Views Honu Hale (Turtle House)
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 on the beach, within a 15-minute drive of Napili Bay and Whalers Village.
Opens in a new windowCelebrity Home Across the Street From Beach! Pool With Slide, Pickleball, Gym!
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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
224 Holiday Homes
Lowest Price
AU$374
Highest Price
AU$374
Popular accommodation
The #1 Vacation Rental on Maui!! Steps to Maui's Best Beach! Pickle Ball Ct!, The #1 Luxury OCEAN FRONT Mansion! Sleeps 32, Spectacular Oceanfront 4 bedroom 4 bath, AC, pool in tropical oasis., #1 Luxury BEACHFRONT! Pickleball, Sand Volleyball, 2 Gyms, Pool, Privacy In Paradise - Top Rated Vacation Home in West Maui, Legendary Estate 50 Steps to Maui’s Best Beach! New! 5 Bedroom, Pool With Slide!, Spectacular Sunset and Ocean Views with Pool & Hotbub near Kaanapali Beach, Maui Vacation Home w/Dazzling Oceanfront Views Honu Hale (Turtle House), Celebrity Home Across the Street From Beach! Pool With Slide, Pickleball, Gym!

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
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 ...
Opens in a new windowHotel 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.
Opens in a new windowCastle 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.
Opens in a new windowMOLOKAI ISLAND Two Bedroom Oceanfront Top End Unit!
Save an average of 15% on thousands of hotels when you're signed in
Aston Kaanapali Shores

Aston Kaanapali Shores

3.5 out of 5
3445 Lower Honoapiilani Hwy, Lahaina, HI
Fully refundableReserve now, pay when you stay
The price is AU$374 per night from 23 Sept to 24 Sept
AU$374
23 Sept - 24 Sept
includes taxes & fees
When you stay at Aston Kaanapali Shores in Kaanapali, you'll be on the beach, within a 10-minute drive of Kaanapali Beach and Whalers Village.
Opens in a new windowAston Kaanapali Shores
Don't see what you're looking for?
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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.