Book Holiday Homes in Kaunakakai

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Featured Holiday Homes in Kaunakakai

#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.
#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.
Privacy In Paradise - Top Rated Vacation Home in West Maui
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
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Remodeled, Ground floor studio; Inquire about specials from 4/21 - 6/25

Remodeled, Ground floor studio; Inquire about specials from 4/21 - 6/25

Lahaina
When you stay at this vacation home in Kaanapali, you'll be on the beach, within a 10-minute drive of Whalers Village and Kaanapali Beach.
Remodeled, Ground floor studio; Inquire about specials from 4/21 - 6/25
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 Whalers Village and Napili Bay.
Celebrity Home Across the Street From Beach! Pool With Slide, Pickleball, Gym!
Spectacular Maui Family vacation home - 4 bedroom + den, 4 bath, AC, pool.

Spectacular Maui Family vacation home - 4 bedroom + den, 4 bath, AC, pool.

Lahaina
When you stay at this vacation home in Lahaina, you'll be on the beach, within a 15-minute drive of Kaanapali Beach and Whalers Village.
Spectacular Maui Family vacation home - 4 bedroom + den, 4 bath, AC, pool.
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.
Maui Vacation Home w/Dazzling Oceanfront Views Honu Hale (Turtle House)
272-6  Puamana 2 Bedroom Oceanfront  Remodeled!!

272-6 Puamana 2 Bedroom Oceanfront Remodeled!!

Lahaina
This beach vacation home is 5.3 mi (8.6 km) from Kaanapali Beach and 5.4 mi (8.8 km) from Whalers Village.
272-6 Puamana 2 Bedroom Oceanfront Remodeled!!
Lana’i Oasis and Gem, The Artist's House

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

Lanai
The price is AU$1,219 per night from 4 Aug to 5 Aug
AU$1,219
4 Aug - 5 Aug
includes taxes & fees
With a stay at this vacation home in Lanai City, you'll be near the beach, just a 2-minute walk from Munro Trail and 10 minutes by foot from Lanaʻi Culture & ...
Lana’i Oasis and Gem, The Artist's House
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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
199 Holiday Homes
Lowest Price
AU$929
Highest Price
AU$1,219
Popular accommodation
#1 Luxury BEACHFRONT! Pickleball, Sand Volleyball, 2 Gyms, Pool, Privacy In Paradise - Top Rated Vacation Home in West Maui, Spectacular Sunset and Ocean Views with Pool & Hotbub near Kaanapali Beach, Remodeled, Ground floor studio; Inquire about specials from 4/21 - 6/25, Celebrity Home Across the Street From Beach! Pool With Slide, Pickleball, Gym!, Spectacular Maui Family vacation home - 4 bedroom + den, 4 bath, AC, pool., Maui Vacation Home w/Dazzling Oceanfront Views Honu Hale (Turtle House), 272-6 Puamana 2 Bedroom Oceanfront Remodeled!!, Lana’i Oasis and Gem, The Artist's House

Top trending hotels in Kaunakakai

Hotel Moloka'i

Hotel Moloka'i

3 out of 5
1300 Kamehameha V Hwy, Kaunakakai, HI
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 Westin Maui Resort & Spa, Ka'anapali

The Westin Maui Resort & Spa, Ka'anapali

4.5 out of 5
2365 Kaanapali Pkwy, Lahaina, HI
Fully refundableReserve now, pay when you stay
The price is AU$929 per night from 23 Aug to 24 Aug
AU$929
23 Aug - 24 Aug
includes taxes & fees
When you stay at The Westin Maui Resort & Spa, Ka'anapali in Kaanapali, you'll be on the beach, just steps from Kaanapali Beach and 5 minutes by foot from Whalers ...
The Westin Maui Resort & Spa, Ka'anapali
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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.