Book Holiday Homes in Halena

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Featured Holiday Homes in Halena

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

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

Maunaloa
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 ...
Molokai Oceanfront large beautiful home - Gorgeous secluded beaches out front!
Remote Island Retreat: Ocean Views & Pool

Remote Island Retreat: Ocean Views & Pool

2 out of 5
Maunaloa
Located in Maunaloa, this vacation home is within a 15-minute walk of Pohakumauliuli Beach and Kepuhi Beach.
Remote Island Retreat: Ocean Views & Pool
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
Located in Maunaloa, this vacation home is within a 5-minute drive of Pohakumauliuli Beach and Kepuhi Beach.
Lovely 2 bdr 2 bath condo in prestigious Paniolo Hale, 4min walk to Kepuhi Beach
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Discounted for summer 2025! Laid back Molokai beach-hideaway

Discounted for summer 2025! Laid back Molokai beach-hideaway

Maunaloa
With a stay at this vacation home in Maunaloa, you'll be on the beach, just a 4-minute walk from Pohakumauliuli Beach and 10 minutes by foot from Kepuhi ...
Discounted for summer 2025! Laid back Molokai beach-hideaway
Beautiful oceanfront condo with lanai, pool, beach access, & washer/dryer

Beautiful oceanfront condo with lanai, pool, beach access, & washer/dryer

Maunaloa
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 ...
Beautiful oceanfront condo with lanai, pool, beach access, & washer/dryer
Walk to Beach: Paniolo Hale Townhome w/ Ocean View

Walk to Beach: Paniolo Hale Townhome w/ Ocean View

Maunaloa
When you stay at this vacation home in Maunaloa, you'll be on the beach, within a 5-minute drive of Pohakumauliuli Beach and Kepuhi Beach.
Walk to Beach: Paniolo Hale Townhome w/ Ocean View
Romantic Spanish villa w/hot tub — 5 min from the beach!

Romantic Spanish villa w/hot tub — 5 min from the beach!

Kaunakakai
With a stay at this vacation home in Kaunakakai, you'll be within a 5-minute walk of Molokai Harbor and Lanikaula's grave.
Romantic Spanish villa w/hot tub — 5 min from the beach!
Beach Front Luxury on 3 Mile White Sand Papohaku Beach

Beach Front Luxury on 3 Mile White Sand Papohaku Beach

Maunaloa
Located in Maunaloa, this vacation home is a 1-minute drive from Papohaku Beach and 6 minutes from Kapukahehu Beach.
Beach Front Luxury on 3 Mile White Sand Papohaku Beach
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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.

Halena 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 Halena vacation homes are the perfect way for you to wing it.

Holiday houses in Halena 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 Halena 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 Halena adventures, obvs.

If your adventure buddy happens to have fur and four legs, you just might find a pet-friendly holiday house in Halena 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 Halena 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.

Halena Holiday Homes essential information

Accommodation
8 Holiday Homes
Lowest Price
Highest Price
Popular accommodation
Molokai Oceanfront large beautiful home - Gorgeous secluded beaches out front!, Remote Island Retreat: Ocean Views & Pool, Lovely 2 bdr 2 bath condo in prestigious Paniolo Hale, 4min walk to Kepuhi Beach, Discounted for summer 2025! Laid back Molokai beach-hideaway, Beautiful oceanfront condo with lanai, pool, beach access, & washer/dryer, Walk to Beach: Paniolo Hale Townhome w/ Ocean View, Romantic Spanish villa w/hot tub — 5 min from the beach!, Beach Front Luxury on 3 Mile White Sand Papohaku Beach

Top trending hotels in Halena

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 ...
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
Exceptional Molokai vacation condo - Steps from Hawaii's longest beach

Exceptional Molokai vacation condo - Steps from Hawaii's longest beach

Molokai
With a stay at this condo in Maunaloa, you'll be near the beach, just a 5-minute walk from Pohakumauliuli Beach and 7 minutes by foot from Puʻu o Kaiaka.
Exceptional Molokai vacation condo - Steps from Hawaii's longest beach
Save an average of 15% on thousands of hotels when you're signed in
Ocean Front-Unobstructed Views- Beautiful Upgraded Condo

Ocean Front-Unobstructed Views- Beautiful Upgraded Condo

Maunaloa
With a stay at this apartment in Maunaloa, you'll be on the beach, just a 2-minute walk from Pohakumauliuli Beach and 5 minutes by foot from Kepuhi Beach.
Ocean Front-Unobstructed Views- Beautiful Upgraded Condo
Don't see what you're looking for?
See all available properties in Halena
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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.