New Round House With Pool 180 Degree Ocean View 13% discount for 7 nightsFrom $282/night · Sleeps 6
South Kona Rentals Above the Bay
Captain Cook Vacation Rentals
Escape to Captain Cook - A Hidden Gem in South Kona
Escape to the scenic beauty of South Kona with our exclusive collection of Captain Cook vacation rentals. This peaceful area of the Big Island offers an authentic Hawaiian experience, with lush coffee farms, panoramic ocean views, and a relaxed, local vibe. Choose from charming cottages, oceanfront homes, and tropical hideaways right for exploring famous spots like Kealakekua Bay and Pu'uhonua o Honaunau National Historical Park. Our rentals provide a private stay while keeping you close to popular beaches like Two Step Beach, ideal for snorkeling and swimming with dolphins.
Key Features of Captain Cook Vacation Rentals
- Oceanfront cottages and homes with stunning views
- Access to Honaunau Bay, Kealakekua Bay, and Two Step Beach
- Located near historic landmarks such as Pu'uhonua o Honaunau National Historical Park
- Private retreats amidst tropical foliage and coffee farms
- Ideal for both adventure and relaxation with hiking, snorkeling, and stargazing opportunities
Find the Charm of Captain Cook
Whether you're seeking adventure or tranquility, Captain Cook is the right base for discovering the Big Island's wonders. Spend your mornings touring nearby coffee farms, your afternoons at Honaunau Bay, and your evenings stargazing from your private lanai. Browse our full selection of Captain Cook vacation rentals and find your dream Hawaiian escape today. With easy access to Kailua-Kona vacation rentals as well, you'll have the flexibility to explore even more of the island's breathtaking beauty!
Rental Listings
Captain Cook Vacation Rentals Listings
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Captain Cook Vacation Rentals Map
New Round House With Pool 180 Degree Ocean View 13% discount for 7 nightsFrom $282/night · Sleeps 6
Hale Hanai - near Kealakekua Bay - Proximity to ocean without oceanfront priceFrom $334/night · Sleeps 10
At Awapuhi Views, you can check out the surf conditions, and enjoy the breezesFrom $169/night · Sleeps 4
Aloha Awaits at the Southern Belle of Miloli'iFrom $266/night · Sleeps 4
Exceptional Historic Home in South KonaFrom $425/night · Sleeps 6
Walk to Beach! Big Island Bungalow w/ Ocean ViewFrom $434/night · Sleeps 8
Kona Cliff House at Pebble Beach - a romantic getaway!From $189/night · Sleeps 2
Papa Belle 3.5 Acre Estate w/Pool, Spa, Epic Ocean Views, and OrchardFrom $446/night · Sleeps 4
Oceanfront - Dolphin Retreat - KAYAKS INCLUDEDFrom $662/night · Sleeps 10
Oceanview, luxury pool, 7 acres of avocados! Gorgeous coffee district jewel!From $1,258/night · Sleeps 12
Dragonfly Healing FarmFrom $150/night · Sleeps 6
Spectacular Oceanfront! 20' from the SeaFrom $395/night · Sleeps 6
Kealakekua Bay, Steps to the Ocean, at Manini Beach ParkFrom $212/night · Sleeps 4
Romantic Tropical Retreat, 150 yds from the Ocean!From $289/night · Sleeps 4
Stunning ocean views guest house in Kona Paradise, quiet & safe neighborhood.From $121/night · Sleeps 2
Hawaii Spinner dolphins visit Kealakekua BayFrom $241/night · Sleeps 4
South Kona Ocean View Luxury 4+ Br Pool, Sleeps 10From $550/night · Sleeps 10
South Kona House with Spectacular Ocean ViewFrom $225/night · Sleeps 4
Cottage-like Duplex in South Kona on the Big Island.Sleeps two adult guestsFrom $147/night · Sleeps 4
Kona Paradise - Stunning Ocean Views from Lanai - Captain Cook, HawaiiFrom $150/night · Sleeps 4
Captain Cook Home on Quiet 3 Acres w/ Fruit TreesFrom $99/night · Sleeps 3
New Oceanfront Captain Cook Home Near Kealakekua BayFrom $688/night · Sleeps 8
*NEW* Kealakekua Bay Oceanfront Home with Views from Every RoomFrom $554/night · Sleeps 6
Bay View Farms - Incredible Oceanfront Estate - Private Infinity Pool/Hot TubFrom $2,865/night · Sleeps 20
Stylized Captain's HouseFrom $206/night · Sleeps 7
South Kona Coastal ViewsFrom $244/night · Sleeps 4
Private Island Basecamp • Lanai, BBQ & Beach GearFrom $283/night · Sleeps 8
Kona Ocean Paradise with Pool and Hot TubFrom $307/night · Sleeps 6
One bedroom cabin with fridge,kitchen and shower close to the clean toilets.From $120/night · Sleeps 10
Two Bedroom Bungalow with Hot TubFrom $199/night · Sleeps 6
The Surf Shack 2 Bdrm house w Loft in Ocean ViewFrom $216/night · Sleeps 8
Luxurious Hosted Oceanview Coffee Farm StayFrom $220/night · Sleeps 6
Idyllic Getaway with Ocean Views in Captain Cook, HawaiiFrom $303/night · Sleeps 4
From $282/night
New Round House With Pool 180 Degree Ocean View 13% discount for 7 nights
Captain Cook, Hawaii
★★★★★ 9.8/10 · 74 reviews
Make this home your base camp for all of your Big Island adventures. This unique round house with spectacular ocean views is located one hour from...
From $334/night
Hale Hanai - near Kealakekua Bay - Proximity to ocean without oceanfront price
Captain Cook, Hawaii
★★★★★ 9.8/10 · 73 reviews
PLEASE NOTE: DURING THE HOLIDAYS, FROM DECEMBER 15 TO JANUARY 1, WE REQUIRE AT LEAST A TWO-WEEK BOOKING. "Pathway of the Gods" is the meaning of the...
From $169/night
At Awapuhi Views, you can check out the surf conditions, and enjoy the breezes
Captain Cook, Hawaii
★★★★★ 9.8/10 · 69 reviews
Our home is located halfway down the Miloli'i Rd. We have a very large master bedroom with a King bed, the Master has bow- windows and its own door...
From $266/night
Aloha Awaits at the Southern Belle of Miloli'i
Captain Cook, Hawaii
★★★★★ 9.8/10 · 58 reviews
Create your own private paradise away from the hustle and bustle! Enjoy 180 degree ocean views and the comforts of a luxurious home all to yourself!...
From $425/night
Exceptional Historic Home in South Kona
Captain Cook, Hawaii
★★★★★ 9.8/10 · 53 reviews
The very best place to gather as a family where social distancing is easy with your own gourmet kitchen and private pool! We have adopted expanded...
From $434/night
Walk to Beach! Big Island Bungalow w/ Ocean View
Captain Cook, Hawaii
★★★★★ 9.8/10 · 43 reviews
On-Site Whale Watching | 4 Snorkeling Sets | Boogie Boards & Beach ChairsYour next dreamy island getaway awaits at 'Anji's Beach House,' a serene...
From $189/night
Kona Cliff House at Pebble Beach - a romantic getaway!
Captain Cook, Hawaii
★★★★★ 9.8/10 · 35 reviews
Kona Cliff House at Pebble Beach is a romantic getaway & perfect for all things ocean! Spectacular coastal views from every room in this remodeled...
From $446/night
Papa Belle 3.5 Acre Estate w/Pool, Spa, Epic Ocean Views, and Orchard
Captain Cook, Hawaii
★★★★★ 9.8/10 · 20 reviews
The moment you enter the Royal Palm lined driveway of this gorgeous estate, you'll know you have arrived at your new sanctuary! Papa Belle Estate is...
From $662/night
Oceanfront - Dolphin Retreat - KAYAKS INCLUDED
Captain Cook, Hawaii
★★★★★ 9.6/10 · 48 reviews
On the shores of Kealakekua Bay, a Protected Marine Conservation area, is an enchanting, 4 bedroom/3 bath, water front house called the Dolphin...
From $1,258/night
Oceanview, luxury pool, 7 acres of avocados! Gorgeous coffee district jewel!
Captain Cook, Hawaii
★★★★★ 9.6/10 · 47 reviews
Pu'u Mahana Plantation is the perfect destination for vacations and celebrations. Our hosted property lies in the heart of the coffee district, a...
From $150/night
Dragonfly Healing Farm
Captain Cook, Hawaii
★★★★★ 9.6/10 · 41 reviews
Cozy Ohana, located on a beautiful 5 acre working avocado farm. Picture perfect ocean views away from the hustle and bustle of Kona, but close enough...
From $395/night
Spectacular Oceanfront! 20' from the Sea
Captain Cook, Hawaii
★★★★★ 9.4/10 · 182 reviews
Hale Kai means 'Home by the Sea' and sits only 20' from the ocean. Step outside this home onto your own private white sand under the shade of your...
From $212/night
Kealakekua Bay, Steps to the Ocean, at Manini Beach Park
Captain Cook, Hawaii
★★★★★ 9.4/10 · 116 reviews
Kealakekua Bay (which means Pathway to the Gods) has one of the Big Island's most spectacular coral reefs. Because it is a Marine Life Sanctuary, the...
From $289/night
Romantic Tropical Retreat, 150 yds from the Ocean!
Captain Cook, Hawaii
★★★★★ 9.4/10 · 78 reviews
Kona Dreams sleeps 4 adults. Walk 150 yards to the ocean. 2 bed/2 bath tropical home in a quiet neighborhood. Chef’s kitchen, laundry, beach gear,...
From $121/night
Stunning ocean views guest house in Kona Paradise, quiet & safe neighborhood.
Captain Cook, Hawaii
★★★★★ 9.4/10 · 44 reviews
Kona Paradise is located towards the south part of the island, 45 mins from Kona, offering stunning views to the ocean, and a quiet neighborhood.The...
From $241/night
Hawaii Spinner dolphins visit Kealakekua Bay
Captain Cook, Hawaii
★★★★★ 9.4/10 · 29 reviews
A rare find at the beach! Just painted April 2026. Dolphins come in often and swim me while I am out playing in the Bay. The "Ohana"-guest apartment...
From $550/night
South Kona Ocean View Luxury 4+ Br Pool, Sleeps 10
Captain Cook, Hawaii
★★★★★ 9.4/10 · 24 reviews
Puhala Hale is a lovely coastal hillside home boasting stunning panoramic ocean views of the South Kona Coast, offering a pool to lounge, and a...
From $225/night
South Kona House with Spectacular Ocean View
Captain Cook, Hawaii
★★★★★ 9.4/10 · 10 reviews
Exceptional vacation house with ocean view. 33 miles south of Kailua-Kona on the Big Island of Hawaii. Located near the village of Milolii. From...
From $147/night
Cottage-like Duplex in South Kona on the Big Island.Sleeps two adult guests
Captain Cook, Hawaii
★★★★★ 9.0/10 · 31 reviews
This Wonderful Spacious house-like One Bedroom apt/flat is on a side-by-side duplex building has peaceful cottage setting on a working farm in South...
From $150/night
Kona Paradise - Stunning Ocean Views from Lanai - Captain Cook, Hawaii
Captain Cook, Hawaii
★★★★★ 8.8/10 · 65 reviews
Escape the lights and traffic of downtown Kona and unwind in this peaceful oceanside retreat. This 2-bedroom, 2-bath home offers breathtaking ocean...
From $99/night
Captain Cook Home on Quiet 3 Acres w/ Fruit Trees
Captain Cook, Hawaii
★★★★★ 8.8/10 · 12 reviews
Escape to paradise in this 1-bedroom, 1-bath vacation rental house in Captain Cook. Located near top attractions, like Kealakekua Bay and Puʻuhonua o...
From $688/night
New Oceanfront Captain Cook Home Near Kealakekua Bay
Captain Cook, Hawaii
★★★★★ 46 reviews
Summary:Wake to the sound of water and step onto the lanai while the Kona Coast comes alive around you. This oceanfront Captain Cook home gives up to...
From $554/night
*NEW* Kealakekua Bay Oceanfront Home with Views from Every Room
Captain Cook, Hawaii
★★★★★ 44 reviews
Summary:Wake with Kealakekua Bay in view from every bedroom, then step outside to one of the Big Island's most remarkable ocean settings. This...
From $2,865/night
Bay View Farms - Incredible Oceanfront Estate - Private Infinity Pool/Hot Tub
Captain Cook, Hawaii
★★★★★ 35 reviews
Summary:Gather the whole family above the Kona Coast, where 18 acres of working coffee farmland give you privacy, ocean air, and room to make a trip...
From $206/night
Stylized Captain's House
Captain Cook, Hawaii
★★★★★ 2 reviews
This Stylized Captain's House is located minutes away from family friendly scenic Kealakekua Bay beaches, the national park Pu'uhonua O Honaunau, &...
From $244/night
South Kona Coastal Views
Captain cook, Hawaii
★★★★★ 2 reviews
Sitting about 350 feet above sea level, this stunning property provides unparalleled views of the ocean and over 30 plus miles of unbroken coastline....
From $283/night
Private Island Basecamp • Lanai, BBQ & Beach Gear
Captain Cook, Hawaii
★★★★★ 1 reviews
This beautiful 3BR/2BA home sits on a quiet, gated, one-acre property in Ocean View and is ideal for guests seeking space, privacy, and a central...
From $307/night
Kona Ocean Paradise with Pool and Hot Tub
Captain Cook, Hawaii
★★★★★ 1 reviews
Nestled in the serene and picturesque locale of Captain Cook on the beautiful Kona Coast, our brand-new, easily accessible vacation rental offers an...
From $120/night
One bedroom cabin with fridge,kitchen and shower close to the clean toilets.
Captain Cook, Hawaii
Nice cabin for a couple with a cozy full size bed,private deck for stargazing and sunrise/sunsets/ocean viewwith coffe in the morning....
From $199/night
Two Bedroom Bungalow with Hot Tub
Captain Cook, Hawaii
Nestled in the more wooded area of Capitan Cook / Ocean View, you have the most beautiful breezes and relaxing sounds of nature all around you.The...
From $216/night
The Surf Shack 2 Bdrm house w Loft in Ocean View
Captain Cook, Hawaii
Beautifully renovated Hawaiian home designed for comfort and relaxed indoor-outdoor living—ideal for couples, families, or small groups. Features two...
From $220/night
Luxurious Hosted Oceanview Coffee Farm Stay
Captain Cook, Hawaii
Come relax in this calm, stylish coffee shack, revamped to host our avid South Kona visitors. The Ohana or family home, is located in the heart of...
From $303/night
Idyllic Getaway with Ocean Views in Captain Cook, Hawaii
Captain Cook, Hawaii
This self-catering idyllic getaway is located in Captain Cook, Hawaii, and can accommodate up to four guests. There are two bedrooms and two full...