Book Holiday Homes in Kaunakakai

More Flash, Less Cash - Take advantage of our Price Pledge** (even on luxey stays)

We keep it easy with the option to pay now or later on select accommodation

Book up 'til the last second - millions of rooms to crash tonight^

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

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

Lanai HI
The price is NZ$1,353 per night from 2 Apr to 3 Apr
NZ$1,353
2 Apr - 3 Apr
includes taxes & fees
Stay at this holiday home in Lanai City. Enjoy free Wi-Fi, a garden and laundry facilities. Popular attractions Munro Trail and Lanaʻi Culture & Heritage Center ...
Opens in a new windowLana’i Oasis and Gem, The Artist's House
100-4 Island living at its best!!

100-4 Island living at its best!!

Lahaina HI
Stay at this holiday home in Lahaina. Enjoy free Wi-Fi, a garden and laundry facilities. Popular attractions Kaanapali Beach and Whalers Village are located ...
Opens in a new window100-4 Island living at its best!!
Save an average of 15% on thousands of hotels when you're signed in
Puamana 272-3 presents a unique opportunity to experience oceanfront.

Puamana 272-3 presents a unique opportunity to experience oceanfront.

Lahaina HI
Stay at this holiday home in Maui County. Enjoy free Wi-Fi, laundry facilities and tennis courts. Popular attractions Kaanapali Beach and Whalers Village are ...
Opens in a new windowPuamana 272-3 presents a unique opportunity to experience oceanfront.
Spectacular Oceanfront 4 bedroom 4 bath, AC, pool in tropical oasis.

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

Lahaina HI
Stay at this beach holiday home in Lahaina. Enjoy free Wi-Fi, a beach locale and laundry facilities. Popular attractions Kaanapali Beach and Whalers Village ...
Opens in a new windowSpectacular Oceanfront 4 bedroom 4 bath, AC, pool in tropical oasis.
Holomakani Retreat: Your Ohana's Hale (Home) by Kaanapali Beach

Holomakani Retreat: Your Ohana's Hale (Home) by Kaanapali Beach

Lahaina HI
Stay at this golf holiday home in Kaanapali. Enjoy free Wi-Fi, private pools and laundry facilities. Popular attractions Kaanapali Beach and Whalers Village ...
Opens in a new windowHolomakani Retreat: Your Ohana's Hale (Home) by Kaanapali Beach
Lovely 2 bdr 2 bath condo in prestigious Paniolo Hale, 4min walk to Kepuhi Beach

Lovely 2 bdr 2 bath condo in prestigious Paniolo Hale, 4min walk to Kepuhi Beach

Maunaloa HI
Stay at this holiday home in Maunaloa. Enjoy laundry facilities, patios and cable/satellite TV service. Popular attractions Pohakumauliuli Beach and Kepuhi Beach ...
Opens in a new windowLovely 2 bdr 2 bath condo in prestigious Paniolo Hale, 4min walk to Kepuhi Beach
Kapalua Golf Villas by KBM Resorts

Kapalua Golf Villas by KBM Resorts

4 out of 5
Lahaina HI
The price is NZ$3,408 per night from 16 Apr to 17 Apr
NZ$3,408
16 Apr - 17 Apr
includes taxes & fees
Stay at this holiday home in Kapalua. Enjoy free parking, a beach locale and free food shopping service. Popular attractions Kaanapali Beach and Napili Bay are ...
Opens in a new windowKapalua Golf Villas by KBM Resorts
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!
Don't see what you're looking for?
See all available properties in Kaunakakai
View all properties
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$658
Highest Price
NZ$3,408
Popular accommodation
The #1 Luxury OCEAN FRONT Mansion! Sleeps 32, Lana’i Oasis and Gem, The Artist's House, 100-4 Island living at its best!!, Puamana 272-3 presents a unique opportunity to experience oceanfront., Spectacular Oceanfront 4 bedroom 4 bath, AC, pool in tropical oasis., Holomakani Retreat: Your Ohana's Hale (Home) by Kaanapali Beach, Lovely 2 bdr 2 bath condo in prestigious Paniolo Hale, 4min walk to Kepuhi Beach, Kapalua Golf Villas by KBM Resorts, Legendary Estate 50 Steps to Maui’s Best Beach! New! 5 Bedroom, Pool With Slide!

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
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
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
Wavecrest

Wavecrest

3 out of 5
7142 Kamehameha V Hwy Kaunakakai HI
Stay at this condo in Kaunakakai. Enjoy free Wi-Fi, free parking and cable TV channels. Popular attractions Hokukano-Ualapue Complex and Smith-Bronte Landing ...
Opens in a new windowWavecrest
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 NZ$658 per night from 19 Apr to 20 Apr
NZ$658
19 Apr - 20 Apr
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
View all properties
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.