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
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
Stunning Views & Tropical Tranquility 429 LS

Stunning Views & Tropical Tranquility 429 LS

Lahaina HI
With a stay at this vacation home, you'll be centrally located in Lahaina, within a 10-minute drive of Kaanapali Beach and Whalers Village.
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
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
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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
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!
Puamana Ocean Front Tropical Paradise 226-1

Puamana Ocean Front Tropical Paradise 226-1

Lahaina HI
With a stay at this vacation home in Lahaina, you'll be on the beach, within a 15-minute drive of Whalers Village and Launiupoko Beach Park.
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
With a stay at this vacation home in Maunaloa, you'll be on the beach, just a 2-minute walk from Pohakumauliuli Beach and 9 minutes by foot from Kepuhi ...
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
When you stay at this vacation home in Lahaina, you'll be by the sea, within a 15-minute drive of Kaanapali Beach and Whalers Village.
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
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
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
When you stay at this vacation home in Kaanapali, you'll be near the beach, within a 5-minute drive of Kaanapali Beach and Whalers Village.
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
163 Holiday Homes
Lowest Price
AU$420
Highest Price
AU$947
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
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
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
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 AU$947 per night from 4 Jan to 5 Jan
AU$947
4 Jan - 5 Jan 2026
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 ...
Opens in a new windowThe Westin Maui Resort & Spa, Ka'anapali
Save an average of 15% on thousands of hotels when you're signed in
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 AU$420 per night from 16 Dec to 17 Dec
AU$420
16 Dec - 17 Dec
includes taxes & fees
With a stay at Royal Lahaina Resort & Bungalows in Kaanapali, you'll be on the beach, within a 15-minute walk of Kaanapali Beach and Black Rock.
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.

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^Subject to availability and chosen travel dates.