Captain Cook Vacation Rentals

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 perfect for exploring famous spots like Kealakekua Bay and Pu'uhonua o Hōnaunau National Historical Park. Our rentals provide a private retreat while keeping you close to popular beaches like Two Step Beach, ideal for snorkeling and swimming with dolphins.

Whether you're seeking adventure or tranquility, Captain Cook is the perfect 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!

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Miloli'i Beach Bungalow - Tranquil Big Island Retreat

Miloli'i Beach Bungalow - Tranquil Big Island Retreat

Escape to the serene Miloli'i Beach Bungalow, a charming 700 sq. foot two-story home nestled 33 miles south of Kona on the Big Island. This peaceful retreat offers a perfect blend of comfort and natural beauty, ideal for travelers seeking a quiet getaway in paradise.

3 bedroom
2 bathroom
Sleeps 6

from $295

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Makai Hideaway Ocean View Hawaii Vacation Home

Makai Hideaway Ocean View Hawaii Vacation Home

Experience tranquility at Makai Hideaway, a beautiful oceanview home nestled in the peaceful Milolii area of Hawaii. The house features two bedrooms, three baths, and multiple beds, comfortably accommodating families or groups. A large lanai extends along the house, providing breathtaking views of dolphins, whales, and stunning sunsets—ideal for whale watching, dining, or simply relaxing with coastal breezes.

3 bedroom
3 bathroom
Sleeps 10

from $302

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South Kona Hideaway: Cozy Suite Near Snorkeling

South Kona Hideaway: Cozy Suite Near Snorkeling

Experience the tranquility of South Kona Hideaway, a beautifully decorated suite situated between Honaunau and Kealakekua Bay at 900 ft elevation. The suite features a spacious living area with a queen sofa bed and a large flat-screen TV with cable, perfect for relaxing after a day of exploring.

2 bedroom
1 bathroom
Sleeps 4

from $175

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Oceanfront Hawaii Vacation Home with Privacy & Stunning Views

Oceanfront Hawaii Vacation Home with Privacy & Stunning Views

Welcome to this stunning oceanfront vacation home in Hawaii, a perfect retreat designed for privacy and comfort. This property has received the Hawaii Short Term Rental Seal of Approval, ensuring it meets all county regulations and safety standards.

3 bedroom
1 bathroom
Sleeps 5

from $259

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Unique Kona Beach Boys Estate with Pool & Ocean Views

Unique Kona Beach Boys Estate with Pool & Ocean Views

The Kona Beach Boys Estate offers a rare blend of history, luxury, and natural beauty. 5 gated acres, this unique property evokes the spirit of an endless summer with its expansive grounds and iconic past.
The centerpiece is a spacious plantation-style home designed by a California architect, capturing the essence of a Hawaiian exotic retreat.

5 bedroom
5 bathroom
Sleeps 12

from $1,846

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Luxury Cliffside Estate with Breathtaking Ocean Views in Hawaii

Luxury Cliffside Estate with Breathtaking Ocean Views in Hawaii

Aloha and welcome to Maka Nui! The name means Big View, which you'll truly experience upon entering this stunning estate. Nestled on a cliff overlooking the historic and undeveloped coastline, including Kealakekua Bay and Pu'uhonua o Honaunau National Historical Park, this property offers unmatched scenery and privacy.

6 bedroom
6 bathroom
Sleeps 10

from $1,145

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Hawaiian Island Cottage with Sunset Views & Gardens

Hawaiian Island Cottage with Sunset Views & Gardens

Escape to this beautiful island-style cottage offering breathtaking sunset views and a lush tropical garden. Designed for eco-conscious guests, this non-smoking retreat immerses you in authentic Hawaiian living. Relax in the soaking tub, pick fresh herbs, vegetables, and fruits from the garden, or take a peaceful stroll through the vibrant greenery.

2 bedroom
1 bathroom
Sleeps 4

from $204

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Luxury Kealakekua Bay Guest House with Ocean Views

Luxury Kealakekua Bay Guest House with Ocean Views

Your hosts Tammy and Joe are dedicated to providing a five-star experience in this meticulously maintained guest house, located in the beautiful Kealakekua Bay area. The property offers unmatched privacy with secure gated access and parking for up to two cars under a custom-built carport.

2 bedroom
2 bathroom
Sleeps 4

from $487

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Luxury Pu`uhonua House with Ocean Views near Kealakekua Bay

Luxury Pu`uhonua House with Ocean Views near Kealakekua Bay

Immerse yourself in the tropical beauty of Hawaii at Pu`uhonua, a distinctive pole house perched above Kealakekua Bay. Built in 1988 by a physicist and his wife, this home combines innovative design with natural surroundings. Supported by nine towering cedar poles imported from Washington state, the house features an open floor plan with extensive glass walls that seamlessly blend indoor comfort with outdoor vistas.

5 bedroom
3 bathroom
Sleeps 10

from $726

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Ocean Song: Secluded Waterfront Retreat in Kealakekua Bay

Ocean Song: Secluded Waterfront Retreat in Kealakekua Bay

Welcome to Ocean Song, a stunning vacation home nestled right on the edge of crystal-clear waters in Kealakekua Bay. Tucked away at the end of a charming plumeria-lined lane, this property offers unparalleled privacy and seclusion amid lush tropical surroundings, making it the perfect sanctuary to unwind, rejuvenate, and soak in Hawaii’s natural beauty.

3 bedroom
3 bathroom
Sleeps 6

from $935

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Okika Lani: Luxury Oceanview Home in Hawaii

Okika Lani: Luxury Oceanview Home in Hawaii

Okika Lani is a luxurious retreat located at the south end of Kealakekua Bay, accessible via a private road that offers breathtaking views of the Pacific Ocean, the iconic Captain Cook Monument, and the crescent-shaped Ke'ei Beach with its pristine white sands.

3 bedroom
3 bathroom
Sleeps 6

from $952

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Charming Mango Orchard Cottage in Hawaii

Charming Mango Orchard Cottage in Hawaii

The property offers a peaceful retreat on a one-acre lot featuring a small mango orchard with 30 trees, and an array of fruit trees including lime, lemon, orange, and avocado. The beautifully manicured landscape creates a serene environment, ideal for relaxation.

1 bedroom
1 bathroom
Sleeps 2

from $161

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Secluded Hawaiian Mountain Cabin Near Kealakekua Bay

Secluded Hawaiian Mountain Cabin Near Kealakekua Bay

5-acre farm next to a lush forest. ' - Teri). Just five miles from Kealakekua Bay, guests have easy access to kayaking, snorkeling, the Captain Cook Monument, and the Place of Refuge, making it a perfect spot for ocean adventures.
A short ten-minute drive takes you to a local shopping center featuring a supermarket, Chinese restaurant, sandwich and bagel shops, and pizza spots.

2 bedroom
1 bathroom
Sleeps 3

from $195

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Ocean View Hawaii Home Near Beach in Captain Cook

Ocean View Hawaii Home Near Beach in Captain Cook

Discover this beautifully crafted new home located just 200 feet from the ocean in the heart of Old Hawaii's Captain Cook area. The residence boasts expansive ocean views visible from every room, complemented by covered lanais and large open-air decks that invite relaxation and outdoor gatherings.

2 bedroom
3 bathroom
Sleeps 4

from $435

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Oceanfront Kona Coast Vacation Home with Pool & Spa

Oceanfront Kona Coast Vacation Home with Pool & Spa

Experience breathtaking front-row sunset views in our two-story oceanfront home on the Kona Coast. Every room offers stunning vistas, complemented by tropical breezes flowing through the rooftop cupola and large windows. The upper level features a spacious main living area, four bedrooms, and three bathrooms, including two luxurious master suites—one with a queen bed and another with a king.

4 bedroom
4 bathroom
Sleeps 9

from $489

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Sun Tracks Cross the Water - Scenic Hawaiian Retreat

Sun Tracks Cross the Water - Scenic Hawaiian Retreat

Discover Sun Tracks Cross the Water, a stunning Hawaiian vacation home offering breathtaking panoramic sunset views across the curvature of the earth. Nestled on a private one-acre lot at 600 feet elevation, this brand-new, custom-built two-story house provides an ideal escape from crowded tourist spots.

2 bedroom
1 bathroom
Sleeps 3

from $167

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Kealakekua Bay Cozy Vacation Studio with Ocean Access

Kealakekua Bay Cozy Vacation Studio with Ocean Access

Escape to this cozy studio nestled in the picturesque Manini Beach subdivision, just a two-minute walk from the renowned Kealakekua Bay. Perfect for both adventure seekers and those seeking relaxation, this private retreat offers everything needed for an unforgettable Hawaiian vacation.

1 bedroom
1 bathroom
Sleeps 2

from $255

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Charming Cottage with Stunning Kealakekua Bay Views

Charming Cottage with Stunning Kealakekua Bay Views

Discover this charming private cottage perched atop 49 tropical steps in Kealakekua Bay, Hawaii. Ideal for couples, it offers spectacular ocean views and easy access to world-renowned snorkeling and wildlife experiences. The cottage features a full-sized outdoor kitchen, a modern indoor/outdoor bathroom, and a cozy, inviting atmosphere.

1 bedroom
1 bathroom
Sleeps 2

from $288

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Luxury Oceanfront Cottage in Kailua Kona with Bay Views

Luxury Oceanfront Cottage in Kailua Kona with Bay Views

Come explore this unique and beautifully renovated oceanfront cottage in Kailua Kona, offering breathtaking views of Kealakekua Bay. The property features a expansive 153-foot deck facing the ocean, perfect for relaxing and enjoying the stunning sunsets.

3 bedroom
3 bathroom
Sleeps 6

from $496

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Charming Kona Mauna Kai Farm with Ocean Views

Charming Kona Mauna Kai Farm with Ocean Views

Kona Mauna Kai is a working farm nestled on the slopes of Mauna Loa on Hawaii's Big Island, offering breathtaking 180-degree views of the Kona coast. The farm cultivates a variety of fresh produce including avocados, macadamia nuts, Kona coffee, citrus fruits, bananas, guava, and more, with seasonal harvests providing a delicious farm-to-table experience.

1 bedroom
1 bathroom
Sleeps 2

from $175

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Ohia Cottage Secluded Kona Hawaii Getaway

Ohia Cottage Secluded Kona Hawaii Getaway

Ohia Cottage offers a charming, well-furnished guest house nestled on a private farm in the heart of Kona’s coffee belt. Wake up to the aroma of fresh coffee each morning and enjoy the serenity of this secluded tropical retreat.
This cozy 2-bedroom, 1-bath cottage comfortably accommodates up to three guests, making it ideal for honeymooners or small families looking for an intimate getaway.

2 bedroom
1 bathroom
Sleeps 3

from $321

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Charming Hawaiian Family Home Near Kealakekua Bay

Charming Hawaiian Family Home Near Kealakekua Bay

Experience authentic Hawaiian hospitality in this welcoming family home just a short stroll from the stunning waters of Kealakekua Bay. The property offers a peekaboo ocean view where you can see sparkling waters and enjoy the gentle trade breezes.

4 bedroom
3 bathroom
Sleeps 6

from $439

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Luxury Bay View Farms Estate House in Hawaii

Luxury Bay View Farms Estate House in Hawaii

Escape to the serene beauty of Bay View Farms Estate House, a luxurious 6,400 sq. ft. retreat nestled on a working coffee plantation on Hawaii's Big Island. This beautifully decorated estate offers a perfect blend of indoor comfort and outdoor paradise, making it ideal for families or groups seeking a memorable vacation.

4 bedroom
7 bathroom
Sleeps 20

from $2,902

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Kealakekua Bay Hawaiian Vacation Home with Marine Views

Kealakekua Bay Hawaiian Vacation Home with Marine Views

Discover the ultimate Hawaiian retreat at this charming, spacious home nestled near the pristine Kealakekua Bay, a protected marine sanctuary teeming with spinner dolphins, sea turtles, humpback whales in winter, manta rays, and vibrant coral reefs.

3 bedroom
2 bathroom
Sleeps 7

from $429

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Charming Guesthouse Near Kealakekua Bay, Hawaii

Charming Guesthouse Near Kealakekua Bay, Hawaii

Experience a cozy and stylish guesthouse nestled near the renowned Kealakekua Bay and Captain Cook Monument. This welcoming retreat features 2 bedrooms with comfortable queen beds, a fully equipped kitchen, spacious lanai, laundry facilities, and a BBQ area.

3 bedroom
1 bathroom
Sleeps 4

from $394

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Kealakekua Bay Coffee Cottage in Captain Cook, Hawaii

Kealakekua Bay Coffee Cottage in Captain Cook, Hawaii

Escape to the charming Coffee Cottage in Captain Cook, Hawaii, offering breathtaking views of Kealakekua Bay. Located at 1350 ft. elevation among lush coffee trees, this newly built retreat provides a perfect year-round temperature for relaxation and adventure.

1 bedroom
1 bathroom
Sleeps 2

from $339

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Hawaiian Ocean View Vacation Home in Captain Cook

Hawaiian Ocean View Vacation Home in Captain Cook

Escape to this beautiful 3-bedroom, 3-bathroom Hawaiian vacation home nestled on 3 serene acres dotted with mature fruit trees in Captain Cook. The spacious 2,800 sq ft property offers a perfect blend of indoor comfort and outdoor beauty, featuring a private ocean-view lanai ideal for morning coffees or breathtaking sunsets.

3 bedroom
3 bathroom
Sleeps 6

from $362

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Quiet Big Island Rental with Ocean Views and Gardens

Quiet Big Island Rental with Ocean Views and Gardens

Our charming home is nestled in a peaceful rural area of the Big Island, spanning one acre of beautifully landscaped grounds featuring orchids, palms, banana plants, a tranquil koi pond, and more. This is our personal residence, available when we're away, offering a perfect retreat for guests seeking solitude and natural beauty.

2 bedroom
2 bathroom
Sleeps 4

from $195

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Big Island Round House with Ocean Views and Pool

Big Island Round House with Ocean Views and Pool

Experience the unique charm of this round house on the Big Island, offering spectacular ocean vistas and a prime central location. Just an hour from Hawaii Volcano National Park and Kona, this home is an ideal base for exploring the island's sights and natural beauty.

2 bedroom
1 bathroom
Sleeps 6

from $282

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Luxury Kona Ocean View Top Floor with Hot Tub

Luxury Kona Ocean View Top Floor with Hot Tub

Experience ultimate comfort in this newly built luxury home atop Kona with breathtaking 180-degree ocean views and a relaxing 6-person hot tub on the lanai. The top-floor living space spans 2,300 sq. , including a spacious covered lanai of 1,150 sq.

2 bedroom
2 bathroom
Sleeps 5

from $613

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Romantic Oceanview Cottage in South Kona Hawaii

Romantic Oceanview Cottage in South Kona Hawaii

Makalani Oceanview Cottage offers a romantic and authentic Hawaiian escape set amidst lush tropical gardens with stunning panoramic views of the Pacific Ocean. Perched at 1200 ft. above sea level on the side of Mauna Loa Volcano, this charming cottage provides a peaceful retreat away from crowds and resorts, immersing you in the natural beauty of Hawaii's Big Island.

2 bedroom
1 bathroom
Sleeps 4

from $185

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Beach House with Whale Watching & Snorkeling in Kona

Beach House with Whale Watching & Snorkeling in Kona

On-Site Whale Watching | 4 Snorkeling Sets | Wraparound LanaiAn unforgettable Hawaiian escape begins and ends here at 'Anji's Beach House,' a charming 3-bedroom, 3-bath vacation rental nestled on the scenic Kona Coast. This tropical retreat is just steps from the beach, offering a perfect blend of relaxation and adventure.

4 bedroom
3 bathroom
Sleeps 8

from $329

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Kona Cliff House at Pebble Beach - Oceanfront Luxury

Kona Cliff House at Pebble Beach - Oceanfront Luxury

The Kona Cliff House at Pebble Beach offers an unmatched oceanfront experience on the Big Island. This fully renovated penthouse boasts spectacular 180-degree coastal views from every room, making it ideal for romantic getaways or adventure seekers.

1 bedroom
1 bathroom
Sleeps 2

from $305

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Charming Mango Farm Cottage in Kealakekua, Hawaii

Charming Mango Farm Cottage in Kealakekua, Hawaii

Welcome to Hotel Pa'amalu, a cozy, one-room cottage nestled on a sprawling three-acre mango farm in Kealakekua, Hawaii. Built by local friends and family, this charming retreat offers a warm, inviting atmosphere perfect for romantic escapes, retreats, or a peaceful island interlude.

2 bedroom
1 bathroom
Sleeps 3

from $202

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Charming Hawaii Studio with Ocean Views & Hot Tub

Charming Hawaii Studio with Ocean Views & Hot Tub

The Tropical Hideaway offers a cozy Hawaii-style downstairs studio nestled in a vibrant, lush garden setting. This charming retreat features stunning ocean and sunset vistas, providing an authentic island experience. The property includes a chemical-free swimming pool with a waterfall and a private hot tub perfect for relaxing after a day of adventure.

1 bedroom
1 bathroom
Sleeps 4

from $197

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Luxury Oceanfront Vacation Home in Milolii, Hawaii

Luxury Oceanfront Vacation Home in Milolii, Hawaii

Koni Kai, meaning Passionate Sea in Hawaiian, is a beautifully designed and exceptionally comfortable oceanfront home perched on an ancient lava flow in Milolii, the oldest fishing village in Hawaii. This property has been thoughtfully equipped with everything needed for a memorable vacation, from modern appliances to relaxing outdoor spaces.

2 bedroom
2 bathroom
Sleeps 4

from $442

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Charming Miloli'i Village Home with Ocean Views

Charming Miloli'i Village Home with Ocean Views

, offering stunning ocean views and easy access to local adventures.
This spacious home features a large master bedroom with a King bed, bow-windows, and a private door opening onto a wrap-around oceanfront deck, perfect for relaxing while taking in the scenery.

2 bedroom
2 bathroom
Sleeps 4

from $215

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Captain Cook Hawaii Ocean View Vacation Home

Captain Cook Hawaii Ocean View Vacation Home

Welcome to our stunning 3-bedroom vacation home in Captain Cook, located just a 2-minute walk from the tranquil Kealakekua Bay. This Hawaiian-style house offers the perfect blend of comfort, beauty, and convenience for your island escape.
The spacious property features two master bedrooms, each with a queen bed and attached full bath, along with a loft equipped with three twin beds, making it ideal for families or groups.

3 bedroom
4 bathroom
Sleeps 7

from $527

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Charming Kona Paradise Home with Ocean Views & Beach Access

Charming Kona Paradise Home with Ocean Views & Beach Access

Experience the charm of 'A Little Peace of Heaven,' a beautifully decorated Hawaiian home perfect for romantic escapes or family vacations. The living and dining areas overlook an expansive lanai with breathtaking ocean vistas, ideal for relaxing or dining al fresco while watching unforgettable sunsets.

2 bedroom
1 bathroom
Sleeps 6

from $343

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Kealakekua Bay Family Vacation Home Near Captain Cook

Kealakekua Bay Family Vacation Home Near Captain Cook

Pathway of the Gods, or Kealakekua Bay, holds deep historical significance for ancient Hawaiians. Just 500 feet from this iconic bay, Hale Hanai offers a cozy, family-friendly retreat surrounded by lush palm trees, fragrant plumeria blossoms, bananas, and coconuts.

3 bedroom
2 bathroom
Sleeps 10

from $466

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Charming Historic Kona Ranch Home with Pool

Charming Historic Kona Ranch Home with Pool

Escape to this charming historic Kona ranch house built in 1955, nestled among lush Kealia ranch lands. Designed by renowned architect Albert Ives, this property blends old Hawaii charm with modern comforts. The house features three bedrooms and three bathrooms, a spacious chef's kitchen, a lovely dining area, and a cozy living room perfect for family gatherings.

4 bedroom
3 bathroom
Sleeps 6

from $493

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Southern Belle Private Ocean View Vacation Home

Southern Belle Private Ocean View Vacation Home

Escape to your own private paradise on Hawaii's Big Island with the Southern Belle. This luxurious home offers breathtaking 180-degree ocean views and ultimate privacy. Relax in two spacious king bedroom suites, each with ensuite bathrooms, perfect for couples or families seeking comfort and seclusion.

2 bedroom
2 bathroom
Sleeps 4

from $344

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Elegant Kona Estate with Ocean Views and Luxurious Amenities

Elegant Kona Estate with Ocean Views and Luxurious Amenities

5-acre sanctuary on the South Kona coast. From the moment you arrive via the royal palm-lined driveway, you'll feel the magic of this exquisite property. The estate offers sweeping ocean views, mesmerizing sunsets over the Pacific, and vibrant lush foliage visible from expansive lanais and the inviting spa.

2 bedroom
3 bathroom
Sleeps 4

from $762

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Charming 1BR Apartment Near Kealakekua Bay with Ocean View

Charming 1BR Apartment Near Kealakekua Bay with Ocean View

Welcome to this charming 1-bedroom, 1-bath apartment nestled in a peaceful neighborhood just a mile from Kealakekua Bay. This cozy B&B-style unit has been recently remodeled, offering 800 sq. ft. of comfortable living space with a warm, homey atmosphere.

1 bedroom
1 bathroom
Sleeps 4

from $187

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Manini Beachfront Getaway in Hawaii - Ocean Views & Luxury

Manini Beachfront Getaway in Hawaii - Ocean Views & Luxury

Escape to the Manini Beachfront Getaway, a luxurious Hawaiian retreat offering breathtaking ocean views and direct beach access. This palm-lined property is your private oasis, perfect for relaxing under the sun or enjoying evening barbecues on the lanai.

4 bedroom
3 bathroom
Sleeps 8

from $678

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Beautiful Ocean View Home in Kona Paradise Hawaii

Beautiful Ocean View Home in Kona Paradise Hawaii

Aloha and welcome to your tranquil retreat in Kona Paradise, Big Island Hawaii. Located on the west side, our single-story, ocean-inspired home offers nearly 180-degree unobstructed views of the Pacific Ocean, creating a perfect setting for relaxation and adventure.

3 bedroom
2 bathroom
Sleeps 8

from $398

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Eco-Friendly Geodesic Cottage Near Miloliʻi Beach

Eco-Friendly Geodesic Cottage Near Miloliʻi Beach

Experience the charm of Hawaii in this eco-friendly, solar-powered geodesic studio cottage located in the tranquil Miloliʻi area. Just 35 miles south of Kailua-Kona, this unique home offers a peaceful retreat with stunning sunset views over the Pacific Ocean.

2 bedroom
1 bathroom
Sleeps 4

from $183

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Charming Kealakekua Bay Ohana Guest Apartment

Charming Kealakekua Bay Ohana Guest Apartment

Discover the perfect retreat at Kealakekua Bay with this charming ground-floor Ohana guest apartment. , it offers a peaceful, chemical-free environment with a spacious bedroom featuring a high-quality Queen bed and a versatile living area with a futon and optional Queen air bed, all dressed in 100% cotton bedding.

1 bedroom
1 bathroom
Sleeps 4

from $244

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Oceanfront Dolphin Retreat in Kealakekua Bay

Oceanfront Dolphin Retreat in Kealakekua Bay

Dolphin Retreat is a charming 4-bedroom, 3-bath oceanfront home nestled on the shores of Kealakekua Bay, a protected marine conservation area renowned for its crystal-clear waters and vibrant marine life. This airy, private residence offers all the comforts needed for a memorable tropical vacation, surrounded by fragrant Plumeria Trees and towering Coco Palms.

5 bedroom
3 bathroom
Sleeps 10

from $963

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Luxury Pu'u Mahana Plantation with Infinity Pool

Luxury Pu'u Mahana Plantation with Infinity Pool

Puu Mahana Plantation offers a luxurious tropical retreat nestled in Hawaii’s coffee district. Spanning 7 acres, this secluded estate features meticulously maintained avocado and citrus orchards, lush borders for privacy, and stunning natural surroundings.

5 bedroom
3 bathroom
Sleeps 12

from $1,673

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