Family-friendly holiday rentals in Captain Cook

A panoramic view of a lush outdoor space features a vibrant rainbow arching over the landscape. Tropical plants surround a solar heated pool, with lounge chairs positioned nearby. The tranquil setting offers glimpses of the ocean in the background, enhancing the serene atmosphere.

4.98 out of 5 average rating, 202 reviews

Tiny House Hawaii

The Tiny House is ready to welcome you to a drop of heaven on the Big Island!🌴 Please be my guest for an exquisite experience in beauty, peace, and tranquility! The Tiny House is a separate guest quarters attached to the main house by only a breezeway. It has its own private entrance, covered lanai, and private yard. Everything you need for an amazing stay is included--- all cooking amenities, beach towels and chairs. The main house has a solar heated pool which is available for Tiny House guests, and a large deck with magnificant ocean and sunset views. Contact us at hitinyhouse@gmail.com for more information or to inquire about booking a stay.

A vibrant sunset casts rich orange and purple hues across the sky, reflecting on the ocean's surface. Palm trees frame the view, while soft outdoor lighting accentuates the lush landscaping below. The tranquil scene invites relaxation and contemplation.

4.95 out of 5 average rating, 224 reviews

Aloha Paradise! Remodeled with A/C & Ocean View!

Best unit at Kailua-Kona’s popular Sea Village and one of the only with A/C! Captivating ocean views, breezes, tropical sights and sounds greet you in this easily accessible ground floor unit. Start your day on the private lanai watching the spinner dolphins and end it with a glass of wine watching sunset over the ocean. This fully updated, turn-key condo boasts open concept living and is 5 minutes to downtown. An ideal base for an individual, couple or small families to explore the Big Island!

4.81 out of 5 average rating, 194 reviews

An open living space features bamboo flooring and elegant wood beams. A cozy seating area is highlighted by a low coffee table, with a decorative rug beneath. Near the window, a king-size bed is positioned above a small dining table and chairs, blending comfort with functionality.

Cottage in Captain Cook

Honaunau Farm Retreat- Teahouse Cottage

Honaunau Farm is more than just a place to stay; it’s an experience of living sustainably amongst a rich botanical paradise. The farm sits on 7 lush acres with sweeping views of historical Kealakekua Bay and Honaunau National Park. Revel in the ocean views and the delicious fruit. The Teahouse provides a cozy setting for a variety of visitors, whether youʻre looking for some R&R or a spot to launch from to visit island destinations. Great for singles or couples looking for peace & adventure.

Treehouse in Captain Cook

A bright and spacious studio apartment features wooden beams overhead, with large windows dressed in light blue curtains allowing natural light to flow in. A comfortable seating area is arranged with a dark sofa, a wooden coffee table, and a mounted TV for entertainment.

4.93 out of 5 average rating, 136 reviews

Io’s Nest- studio on a coffee farm with ocean view

Retreat to Io's Nest (named after the Hawaiian hawk residing near by), a studio apartment tucked away on a vibrant and lush coffee farm in Captain Cook! You've a private bath, Kitchenette and king size bed. Fruits, vegetables, coffee, and herbs galore. A wonderful sweetheart escape for the adventurous, set just 2 miles from Kealakekua Bay a marine preserve with spectacular snorkeling and hiking. And 2.5 miles from the City of refuge. The perfect headquarters for your Big Island explorations.

Guest house in Captain Cook

A vibrant green cottage is surrounded by lush tropical vegetation. Steps lead up to a covered porch with white railings, offering access to the main entrance. The exterior reflects a charming, rustic style, set within a serene garden brimming with diverse plants.

4.92 out of 5 average rating, 182 reviews

Garden Cottage Ohana

Welcome to your small slice of paradise! Newly redone kitchen, LR, and bathroom! The garden cottage is surrounded on three sides by dense forest. Enjoy coffee and sunsets on your private porch overlooking our tropical fruit farm, the ocean, and stargazing skies. Birds singing, a chorus of frogs, and a wild rooster’s crow are just some of the “sounds of the jungle” that will surround you. The cottage sits between two beautiful bays that host some of the best snorkeling of the Hawaiian Islands.

4.99 out of 5 average rating, 120 reviews

A vibrant rainbow arches over the green landscape, accentuating the charming Coffee Cottage with its mint-green roof. Lush foliage surrounds the cottage while the serene ocean is visible in the background under a partly cloudy sky.

Cottage in Captain Cook

Romantic cottage Big Island coffee farm retreat

ENJOY SPECTACULAR VIEWS OF KEALAKEKUA BAY!! The Coffee Cottage is nestled on our small coffee farm, a very romantic vacation spot! Big lanai and outdoor kitchenette for open air living with gorgeous sunsets over the ocean. Stretch out in the California king bed and check out that view! Black out curtains add to your sleeping comfort. Nearby are many attractions, amazing snorkeling and hiking, a grocery & hardware store. We look forward to sharing our slice of paradise!!

Guest house in Captain Cook

A charming cottage constructed with intricate antique Bali panels is surrounded by lush greenery. The outdoor living area features seating arrangements under a partially covered roof, with soft lighting highlighting the unique decor and inviting atmosphere.

4.81 out of 5 average rating, 835 reviews

Kealakekua Bay Bali Cottage -steps from Bay

This hidden jewel is at Kealakekua Bay. Private setting in our lower backyard. Walk to nearby Manini Beach. We are located 4 miles down at the bottom of Napoopoo Rd Fully equipped outdoor kitchen. Gas stove, refrigerator/freezer. Living/Dining area and bedroom/vanity area enclosed with open area at roofline where a large ficus tree limb goes through. Outdoor shower/ wc area. Very Private. Daily pricing includes Hawaili State taxes, 11% TAT and 4.5% GE .

4.91 out of 5 average rating, 340 reviews

A charming cottage is nestled among palm and coffee trees, featuring a bright red metal roof and green wooden walls. The cottage includes a covered front porch with wooden railings, allowing for relaxed outdoor seating. Gentle sunlight bathes the structure, enhancing its welcoming appearance.

Cottage in Kealakekua

Private Cottage on coffee farm, Ocean-Sunset View

Ocean-sunset views from private cottage in coffee field. Cottage is next to our plant nursery on our private country road. Located above world-famous Kealakekua Bay, the cottage is surrounded by coffee, macadamia nut, palm and avocado trees..this is our Hog Wild Homestead. Studio Cottage is used as pickers quarters during harvest season. Brand new queen mattress, full fridge, microwave, toaster oven, skillet, sink, private semi-outdoor shower, dimmable lighting

4.93 out of 5 average rating, 471 reviews

A captivating sunset is visible over the ocean, with the sun's reflection creating a shimmering pathway on the water. Soft clouds are scattered in the sky, and silhouettes of palm trees contrast against the vibrant hues of orange and pink.

Flat in Kealakekua

Hale's Hale

This one-bedroom apartment with an ocean view is the perfect space for you to relax and unwind after a day of fun! It has it’s own private entry and includes a queen bed, a sofa bed, a fridge, a microwave, a cooktop, A shared washer/dryer and BBQ grill! Our home sits at a cool 1300' elevation with stunning sunsets. For our fellow adventurers, It’s only 10 minutes from Keauhou Bay, 15 minutes from Kona town to the North or 2 Step snorkeling to the South.

4.94 out of 5 average rating, 322 reviews

A traditional palapa equipped with a thatched roof is illuminated by string lights, creating a cozy atmosphere. A hammock hangs between the support beams, surrounded by lush tropical plants and an outdoor seating area on a concrete surface.

Flat in Captain Cook

BLUE BLISS: Hip Hideaway w/Hawaiian Gardens

Laid-back and retro-inspired yet ultra-comfy, this unique space offers a stylish, authentic Hawaiian escape. Just 20 minutes from Kona, South Kona’s relaxed pace provides the perfect retreat. Warm breezes flow through your screened living area and lanai, while vinyl records spin and a classic cruiser awaits. The calming blue hues reflect the nearby ocean, giving you all the beach vibes you crave. Long-term discounts available—stay and soak it all in!

Guest suite in Captain Cook

A private lanai offers a clear view of the ocean, framed by lush greenery. A patio table with chairs is visible, complemented by a large blue umbrella providing shade. The spacious lawn extends below, with hints of nearby tropical plants creating a serene outdoor atmosphere.

4.98 out of 5 average rating, 159 reviews

Ancient Trail Ohana

Newly renovated 1 bedroom apartment with beautiful ocean view off private lanai. Located in South Kona on 2 lush acres including many tropical fruit trees. Rural setting but 10 minutes to restaurants, farmers market and shopping. Short drive to amazing Kealakekua Bay and Two Step perfect for snorkeling, kayaking and stand up paddling. Easy day trip to Kilauea volcano. Our spacious unit has a king sized bed, large bathroom and full kitchen.

4.91 out of 5 average rating, 592 reviews

An open-air living space features a cozy seating area with a day-bed and wicker chairs, illuminated by soft lighting. Tropical plants are arranged throughout, while a decorative 'LOVE' sign adds a welcoming touch. The layout encourages relaxation and connection to nature.

Cottage in Captain Cook

Enchanting Eco-Hideaway: Bohemian Retreat

~ Open-Air Living on a lush mango farm ~ 1 mile from best snorkeling in Kealakekua Bay ~ King bed, hammock, fully-equipped kitchen, BBQ ~ Unique Balinese Bohemian Treehouse style ~ Indoor-Outdoor, Open-Air, Nature-Based Experience ~ 180° views from the Master Bedroom (screened in) ~ Private outdoor shower surrounded by Plumerias

Popular amenities for Captain Cook family-friendly rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Family-friendly home rentals with a hot tub

4.96 out of 5 average rating, 291 reviews

An infinity-edged hot tub sits perched on a hillside, offering expansive views of the ocean and Kona below. The clear water reflects the sky, while the surrounding lush foliage adds a serene natural setting.

Home in Holualoa

Piece of Paradise Coffee Farm

A well-appointed studio features a spacious bed covered in bright yellow linens, a cozy sofa adorned with tropical-patterned pillows, and a kitchenette visible in the background. A large piece of wall art displays a beach scene, while a flat-screen TV is mounted above a dresser.

4.86 out of 5 average rating, 123 reviews

Lovely studio condo with kitchenette and pool

An expansive covered lanai offers comfortable seating with plush blue cushions, overlooking the ocean and lush landscape. A large dining table and barbecue grill add to the outdoor space, enhancing the inviting atmosphere of relaxation and scenic views.

4.88 out of 5 average rating, 175 reviews

Luxury Magic Oceanview Home – Huge Lanai & Hot Tub

4.96 out of 5 average rating, 137 reviews

A cozy living area features a large window with views of a sunset, showcasing silhouetted palm trees. Two chairs are positioned on a private lanai outside the window, with a minimalist white cabinet and a decorative surfboard accenting the room's decor.

Flat in Kailua-Kona

Ocean view with central location tropical paradise

A modern living area is presented with a comfortable sofa and armchair, complemented by a light wooden coffee table. A large television is positioned opposite the seating. Floor-to-ceiling windows provide views of the ocean, allowing natural light to fill the space.

4.92 out of 5 average rating, 246 reviews

Blissful paradise with epic view- Hale Mahana

4.99 out of 5 average rating, 161 reviews

Updated Kona Condo • Central • <1 Mile to Ocean

A tranquil pool area is surrounded by lush tropical landscaping, featuring palm trees and vibrant foliage. Lounge chairs are placed around the pool, where guests are seen enjoying the water and the sunny environment. The two-story building with balconies is visible in the background.

4.9 out of 5 average rating, 472 reviews

Plantation Hale

Guest suite in Kailua-Kona

A colorful floral-patterned couch is positioned in the corner of the studio, complemented by a nearby decorative table. A wall-mounted television and framed artwork are visible, along with a shelf holding towels and clothing. Natural light enters through a mirror reflecting the compact kitchenette area.

4.95 out of 5 average rating, 268 reviews

Private and Quiet Studio Near Magic Sands Beach

Family- and pet-friendly home rentals

A coastal view is presented, featuring rolling hills and a rocky shoreline. Lush coconut palm trees frame the image, while gentle waves lap against the shore. The horizon showcases the deep blue ocean under a clear sky, punctuated by distant landforms.

4.94 out of 5 average rating, 199 reviews

Kona Paradise Home, Hawaii

4.95 out of 5 average rating, 476 reviews

A spacious outdoor living area is surrounded by lush greenery, showcasing a comfortable seating arrangement with a round table. A hammock hangs nearby, and peeking ocean views can be seen in the background, complemented by a partly cloudy sky.

Apartment in Kealakekua

Aka'ula House

4.92 out of 5 average rating, 104 reviews

A living area is furnished with a dark sectional sofa and a coffee table. Light wood flooring extends throughout the space. A dining area featuring a table and four chairs is visible in the background, illuminated by natural light from two windows.

Townhouse in Kailua-Kona

7 min walk to the Ocean & Ali'i

Guest suite in Kailua-Kona

A cozy sleeping area featuring a queen size bed adorned with a patterned blanket. Handcrafted wood accents complement the space, with natural light filtering in through a sliding glass door. The ceiling showcases a woven design, enhancing the room's warm aesthetic.

4.88 out of 5 average rating, 414 reviews

3 blocks to Turtle beach and Ali'i Dr

4.97 out of 5 average rating, 161 reviews

An open-concept living area features a kitchen island with a blue base and white countertop. Large windows provide views of the ocean, while a dining table is surrounded by black chairs. Tropical plants add greenery to the space, enhancing the bright and airy atmosphere.

Home in Kailua-Kona

Hale Aka'ula, House of the Red Sunset

4.86 out of 5 average rating, 210 reviews

Large windows frame sweeping ocean views, allowing natural light to fill the open space. The gentle landscape includes greenery visible through the glass, enhancing the serene atmosphere. A simple chair is positioned nearby, complementing the inviting setting.

Home in Naalehu

Large Ocean View Home “Aloha Friday”

4.82 out of 5 average rating, 563 reviews

A vibrant sunset sky stretches across the horizon, featuring shades of orange and pink amidst scattered clouds. Silhouetted trees frame the scene, enhancing the peaceful ambiance of this natural view.

Flat in Kailua

Amazing Kona Sunset View - Sleeps 4

A two-story wooden house is set against a clear blue sky, showcasing a large front porch with stairs leading up to it. The lush landscaping features vibrant tropical plants, and an unobstructed view of the ocean is visible in the background.

4.97 out of 5 average rating, 178 reviews

Milolii Whale House With Ocean Views and Pool!

Family-friendly home rentals with a pool

A private lanai is featured with a wooden table and two chairs, overlooking the vibrant blue ocean. Palm trees frame the scene against a clear sky, enhancing the peaceful outdoor setting. Colorful plants in pots add a pop of red to the coastal view.

4.94 out of 5 average rating, 230 reviews

Longboard Studio at Kona Magic Sands Beach

A spacious living area is shown, featuring a large sectional sofa and a wooden coffee table. A flat-screen television is positioned on a stand, with a sliding glass door leading to a patio. Warm wood paneling and neutral tones create a comfortable ambiance.

4.85 out of 5 average rating, 124 reviews

Hale Kapena (Captain's House)

Guest suite in Kailua-Kona

A spacious bedroom features a wooden bed with a neatly made light-colored quilt, accented by colorful pillows. A decorative rug covers the floor, and a ceiling fan is visible above. A small table and a shelving unit filled with essentials are present, creating a functional space.

4.96 out of 5 average rating, 169 reviews

1-Bedroom Suite with Private Pool and Garden Lanai

4.91 out of 5 average rating, 165 reviews

The exterior of a modern split-level home is showcased, featuring a spacious pool in the foreground. Tropical palm trees surround the property, while a shaded seating area with an umbrella is visible beside the pool. The expansive deck offers steps leading to the entrance of the home.

Home in Keauhou

Tropical Oasis Home with Pool and Steps to Beach

Superhost

A serene lanai is displayed with a view of a vibrant sunset. Lush greenery frames the scene, with palm trees and blooming flowers visible. Soft lighting is strung along the railing, adding a warm touch to the outdoor space designed for relaxation.

4.87 out of 5 average rating, 127 reviews

Keauhou Garden - Ocean view - Walk to Harbor

A contemporary living space features a sectional sofa adorned with orange accent pillows and a light rug. A wooden coffee table is centered, while a mounted TV sits above a wooden cabinet. Natural light flows in through large sliding doors opening to an outdoor view.

4.93 out of 5 average rating, 108 reviews

The Olena at Keauhou Bay

An expansive view of the ocean at sunset captures vibrant oranges and yellows illuminating the sky. A community pool is visible in the foreground, surrounded by lounge chairs. Lush palm trees frame the scene, enhancing the tropical ambiance.

4.89 out of 5 average rating, 242 reviews

Ali'i Dr w/ Ocean Sunsets next to Farmer's Market