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
Book a stay at this beach vacation home in Kaanapali. Enjoy private pools, a beach locale, and a fitness center. Popular attractions Whalers Village and Kaanapali ...
#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
Book a stay at this family-friendly vacation home in Launiupoko. Enjoy private pools, a fitness center, and a garden. Popular attractions Kaanapali Beach and ...
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
Book a stay at this family-friendly vacation home in Kaanapali. Enjoy free WiFi, private pools, and a garden. Popular attractions Whalers Village and Kaanapali ...
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
Book a stay at this beach vacation home in Kaanapali. Enjoy a beach locale, laundry facilities, and patios. Popular attractions Whalers Village and Kaanapali ...
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
Book a stay at this beach vacation home in Napili. Enjoy free WiFi, private pools, and a beach locale. Popular attractions Whalers Village and Kaanapali Beach ...
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
Book a stay at this beach vacation home in Lahaina. Enjoy free WiFi, a beach locale, and a fitness center. Popular attractions 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
Book a stay at this beach vacation home in Napili. Enjoy free WiFi, a beach locale, and a garden. Popular attractions Whalers Village and Kaanapali Beach are ...
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
Stay at this vacation home in Maui County. Enjoy free WiFi, a beach locale, and a garden. Popular attractions Kaanapali Beach and Whalers Village are located ...
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 NZ$1,321 per night from 4 Aug to 5 Aug
NZ$1,321
4 Aug - 5 Aug
includes taxes & fees
Stay at this vacation home in Lanai City. Enjoy free WiFi, a garden, and laundry facilities. Popular attractions Munro Trail and Lanaʻi Culture & Heritage Center ...
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
NZ$1,017
Highest Price
NZ$1,321
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
Stay at this 3-star beach hotel in Kaunakakai. Enjoy free WiFi, free parking, and a business center. Our guests praise the helpful staff in our reviews. Popular ...
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
Stay at this 3-star beach condo in Kaunakakai. Enjoy free WiFi, a beach locale, and laundry facilities. Popular attractions St. Joseph's Catholic Church and ...
Castle at Moloka'i Shores
MOLOKAI ISLAND   Two Bedroom Oceanfront Top End Unit!

MOLOKAI ISLAND Two Bedroom Oceanfront Top End Unit!

Kaunakakai
Book a stay at this beach condo in Kaunakakai. Enjoy a beach locale, a garden, and laundry facilities. Our guests praise the helpful staff in our reviews. Popular ...
MOLOKAI ISLAND Two Bedroom Oceanfront Top End Unit!
Save an average of 15% on thousands of hotels when you're signed in
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 NZ$1,017 per night from 23 Aug to 24 Aug
NZ$1,017
23 Aug - 24 Aug
includes taxes & fees
Stay at this 4.5-star luxury hotel in Kaanapali. Enjoy 3 outdoor pools, a full-service spa, and 2 restaurants. Our guests praise the helpful staff and the property ...
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.

**Terms and Conditions apply.
^Subject to availability and chosen travel dates.