Book Holiday Homes in Captain Cook

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Featured Holiday Homes in Captain Cook

Kona Ocean View Home - Downtown, Fruit Trees, Sunset views

Kona Ocean View Home - Downtown, Fruit Trees, Sunset views

Kailua-Kona
When you stay at this vacation home in Kailua-Kona, you'll be near the bay, a 5-minute drive from Kailua Pier and 10 minutes from Magic Sands Beach.
Kona Ocean View Home - Downtown, Fruit Trees, Sunset views
Private, ocean front home with private pool,  Amazing place!

Private, ocean front home with private pool, Amazing place!

Milolii
When you stay at this vacation home in Captain Cook, you'll be on the waterfront and 11 minutes by foot from Papa Bay.
Private, ocean front home with private pool, Amazing place!
Walk to White Sands Beach or Relax by Your Private Pool

Walk to White Sands Beach or Relax by Your Private Pool

Kailua-Kona
With a stay at this vacation home in Kailua-Kona (Kahaluu-Keauhou), you'll be within a 15-minute drive of Magic Sands Beach and Kailua Pier.
Walk to White Sands Beach or Relax by Your Private Pool
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Oceanfront Kona Beach House

Oceanfront Kona Beach House

Kailua-Kona
With a stay at this vacation home in Kailua-Kona (Holualoa Village), you'll be a 2-minute drive from Magic Sands Beach and 8 minutes from Kailua Pier.
Oceanfront Kona Beach House
Home with Swimming Pool | 3 Bed, 2 Bath

Home with Swimming Pool | 3 Bed, 2 Bath

Naalehu
With a stay at this vacation home in Naalehu (Discovery Harbour), you'll be within a 15-minute drive of Hawaii Volcanoes National Park and Paradise Meadows.
Home with Swimming Pool | 3 Bed, 2 Bath
Huge June 2025 discount! Rare BEACH FRONT Home at Kona Surf and Racquet Club

Huge June 2025 discount! Rare BEACH FRONT Home at Kona Surf and Racquet Club

Kailua-Kona
With a stay at this vacation home in Kailua-Kona (Kahaluu-Keauhou), you'll be within a 15-minute drive of Magic Sands Beach and Kailua Pier.
Huge June 2025 discount! Rare BEACH FRONT Home at Kona Surf and Racquet Club
🏖️Next to Keauhou Bay! | Concierge Included | Large Private Pool & Lanai

🏖️Next to Keauhou Bay! | Concierge Included | Large Private Pool & Lanai

Kailua Kona
With a stay at this vacation home in Kailua-Kona (Kahaluu-Keauhou), you'll be within a 10-minute drive of Magic Sands Beach and Keauhou Bay Beach.
🏖️Next to Keauhou Bay! | Concierge Included | Large Private Pool & Lanai
🏖️Ocean Front | Central AC | Private Pool & Grill | Concierge Included

🏖️Ocean Front | Central AC | Private Pool & Grill | Concierge Included

Kailua Kona
With a stay at this vacation home in Kailua-Kona (Kahaluu-Keauhou), you'll be within a 15-minute drive of Magic Sands Beach and Holua Tennis Center.
🏖️Ocean Front | Central AC | Private Pool & Grill | Concierge Included
Outrigger Paradise Hale Wa a Pale with Private Pool!

Outrigger Paradise Hale Wa a Pale with Private Pool!

Kailua Kona
With a stay at this vacation home, you'll be centrally located in Kailua-Kona, within a 10-minute drive of Magic Sands Beach and Kailua Pier.
Outrigger Paradise Hale Wa a Pale with Private Pool!
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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.

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

Holiday houses in Captain Cook 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 Captain Cook 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 Captain Cook adventures, obvs.

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

Captain Cook Holiday Homes essential information

Accommodation
633 Holiday Homes
Lowest Price
Highest Price
Popular accommodation
Kona Ocean View Home - Downtown, Fruit Trees, Sunset views, Private, ocean front home with private pool, Amazing place!, Walk to White Sands Beach or Relax by Your Private Pool, Oceanfront Kona Beach House, Home with Swimming Pool | 3 Bed, 2 Bath, Huge June 2025 discount! Rare BEACH FRONT Home at Kona Surf and Racquet Club, 🏖️Next to Keauhou Bay! | Concierge Included | Large Private Pool & Lanai, 🏖️Ocean Front | Central AC | Private Pool & Grill | Concierge Included, Outrigger Paradise Hale Wa a Pale with Private Pool!

Top trending hotels in Captain Cook

Dragonfly Ranch

Dragonfly Ranch

3 out of 5
84-5146 Keala O Keawe Road, Captain Cook, HI
Fully refundableReserve now, pay when you stay
Located in Captain Cook, Dragonfly Ranch is within a 5-minute drive of Painted Church and Bay View Farm.
Dragonfly Ranch
Ka'awaloa Plantation Bed & Breakfast

Ka'awaloa Plantation Bed & Breakfast

3.5 out of 5
82-5990 Napoopoo Road, Captain Cook, HI
When you stay at Ka'awaloa Plantation Bed & Breakfast in Captain Cook, you'll be near the beach, within a 5-minute drive of Amy B.H. Greenwell Ethnobotanical ...
Ka'awaloa Plantation Bed & Breakfast
Kona Palace in Captain Cook

Kona Palace in Captain Cook

3.5 out of 5
82-5815 Napoopoo Rd., Captain Cook, HI
Located in Captain Cook, Kona Palace in Captain Cook is in the historical district, within a 5-minute drive of Kona Pacific Farmers Cooperative and Big Island ...
Kona Palace in Captain Cook
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Makai Hideaway  600ft from  Ocean Giant Deck
 Gameroom/10 day special in Fall

Makai Hideaway 600ft from Ocean Giant Deck Gameroom/10 day special in Fall

Captain Cook
When you stay at this vacation home in Captain Cook, you'll be by the sea and 10 minutes by foot from Papa Bay.
Makai Hideaway 600ft from Ocean Giant Deck Gameroom/10 day special in Fall
Don't see what you're looking for?
See all available properties in Captain Cook
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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.