Book Holiday Homes in Kaunakakai

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Featured Holiday Homes in Kaunakakai

The #1 Luxury OCEAN FRONT Mansion!  Sleeps 32

The #1 Luxury OCEAN FRONT Mansion! Sleeps 32

lahina HI
Stay at this beach holiday home in Honokowai. Enjoy private pools, a beach locale and a fitness centre. Popular attractions Kaanapali Beach and Whalers Village ...
Opens in a new windowThe #1 Luxury OCEAN FRONT Mansion! Sleeps 32
Stunning Views & Tropical Tranquility 429 LS

Stunning Views & Tropical Tranquility 429 LS

Lahaina HI
Stay at this beach holiday home in Lahaina. Enjoy free Wi-Fi, a beach locale and a garden. Popular attractions Kaanapali Beach and Whalers Village are located ...
Opens in a new windowStunning Views & Tropical Tranquility 429 LS
Spectacular Sunset and Ocean Views with Pool & Hotbub near Kaanapali Beach

Spectacular Sunset and Ocean Views with Pool & Hotbub near Kaanapali Beach

Lahaina HI
Stay at this family-friendly holiday home in Kaanapali. Enjoy free Wi-Fi, private pools and a garden. Popular attractions Kaanapali Beach and Black Rock are ...
Opens in a new windowSpectacular Sunset and Ocean Views with Pool & Hotbub near Kaanapali Beach
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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 HI
Stay at this beach holiday home in Napili. Enjoy free Wi-Fi, private pools and a beach locale. Popular attractions Kaanapali Beach and Napili Bay are located ...
Opens in a new windowLegendary Estate 50 Steps to Maui’s Best Beach! New! 5 Bedroom, Pool With Slide!
Puamana Ocean Front Tropical Paradise 226-1

Puamana Ocean Front Tropical Paradise 226-1

Lahaina HI
Stay at this beach holiday home in Lahaina. Enjoy a beach locale, a fitness centre and a garden. Popular attractions Kaanapali Beach and Whalers Village are ...
Opens in a new windowPuamana Ocean Front Tropical Paradise 226-1
Molokai Oceanfront large beautiful home - Gorgeous secluded beaches out front!

Molokai Oceanfront large beautiful home - Gorgeous secluded beaches out front!

Maunaloa HI
Stay at this beach holiday home in Maunaloa. Enjoy free Wi-Fi, private pools and a beach locale. Popular attractions Pohakumauliuli Beach and Kepuhi Beach are ...
Opens in a new windowMolokai Oceanfront large beautiful home - Gorgeous secluded beaches out front!
Beachside townhome with AC, 3 pools, & pickleball - Walk to ocean

Beachside townhome with AC, 3 pools, & pickleball - Walk to ocean

Lahaina HI
Stay at this holiday home in Lahaina. Enjoy a fitness centre, laundry facilities and tennis courts. Popular attractions Kaanapali Beach and Whalers Village are ...
Opens in a new windowBeachside townhome with AC, 3 pools, & pickleball - Walk to ocean
Privacy In Paradise - Top Rated Vacation Home in West Maui

Privacy In Paradise - Top Rated Vacation Home in West Maui

Lahaina HI
Stay at this family-friendly holiday home in Launiupoko. Enjoy private pools, a fitness centre and a garden. Popular attractions Kaanapali Beach and Launiupoko ...
Opens in a new windowPrivacy In Paradise - Top Rated Vacation Home in West Maui
Fantastic Ka'anapali home with pool! Great for families! Last minute specials!

Fantastic Ka'anapali home with pool! Great for families! Last minute specials!

Lahaina HI
Stay at this holiday home in Kaanapali. Enjoy a garden, laundry facilities and a pool table. Popular attractions Kaanapali Beach and Whalers Village are located ...
Opens in a new windowFantastic Ka'anapali home with pool! Great for families! Last minute specials!
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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
174 Holiday Homes
Lowest Price
NZ$501
Highest Price
NZ$1,090
Popular accommodation
The #1 Luxury OCEAN FRONT Mansion! Sleeps 32, Stunning Views & Tropical Tranquility 429 LS, Spectacular Sunset and Ocean Views with Pool & Hotbub near Kaanapali Beach, Legendary Estate 50 Steps to Maui’s Best Beach! New! 5 Bedroom, Pool With Slide!, Puamana Ocean Front Tropical Paradise 226-1, Molokai Oceanfront large beautiful home - Gorgeous secluded beaches out front!, Beachside townhome with AC, 3 pools, & pickleball - Walk to ocean, Privacy In Paradise - Top Rated Vacation Home in West Maui, Fantastic Ka'anapali home with pool! Great for families! Last minute specials!

Top trending hotels in Kaunakakai

Castle at Moloka'i Shores

Castle at Moloka'i Shores

3 out of 5
109 Ala Malama St Kaunakakai HI
Stay at this beach condo in Kaunakakai. Enjoy free Wi-Fi, a beach locale and laundry facilities. Popular attractions Molokai Harbor and Molokai War Memorial ...
Opens in a new windowCastle 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
Stay at this beach hotel in Kaunakakai. Enjoy free Wi-Fi, free parking and a business centre. Our guests praise the helpful staff in their reviews. Popular attractions ...
Opens in a new windowHotel Moloka'i
The Westin Maui Resort & Spa, Ka'anapali

The Westin Maui Resort & Spa, Ka'anapali

4.5 out of 5
2365 Kaanapali Pkwy Lahaina HI
The price is NZ$1,090 per night from 4 Jan to 5 Jan
NZ$1,090
4 Jan - 5 Jan 2026
includes taxes & fees
Stay at this luxury hotel in Kaanapali. Enjoy 3 outdoor pools, a full-service spa and 2 restaurants. Our guests praise the helpful staff and the property condition ...
Opens in a new windowThe Westin Maui Resort & Spa, Ka'anapali
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Royal Lahaina Resort & Bungalows

Royal Lahaina Resort & Bungalows

4 out of 5
2780 Kekaa Dr Lahaina HI
Fully refundableReserve now, pay when you stay
The price is NZ$501 per night from 21 Dec to 22 Dec
NZ$501
21 Dec - 22 Dec
includes taxes & fees
Stay at this beach hotel in Kaanapali. Enjoy free Wi-Fi, 2 outdoor pools and a full-service spa. Our guests praise the helpful staff and the clean rooms in their ...
Opens in a new windowRoyal Lahaina Resort & Bungalows
Don't see what you're looking for?
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.

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