Family-friendly holiday rentals in Kailua-Kona

A serene outdoor space features a sparkling turquoise pool and a hot tub, with a stunning sunset in the background. Comfortable seating under an umbrella is arranged nearby, surrounded by lush greenery and palm trees, enhancing the tranquil atmosphere.

4.96 out of 5 average rating, 174 reviews

Private Pool - 180° Ocean View - Minutes to Beach

WOW! That’s what guests always say when they arrive at Kona Heavens Hideaway — Surrounded by lush tropical gardens, exotic fruit trees, and vibrant birds, this 1-acre property offers total privacy, stunning 180° ocean views, and comfortable breezes at 900 ft elevation. Just 4 miles from Kona town and close to beaches, it's the perfect blend of quiet country living and convenient access to everything you need. Spacious, serene, truly special — with reallyFast WiFi Hawaii Tax ID: W01435344-01

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5.0 out of 5 average rating, 295 reviews

A spacious wooden deck surrounds a geodesic dome, offering a serene outdoor setting. Two hanging egg chairs are positioned for relaxation, while a portable heater is located nearby. The dome features a transparent facade that reflects sunlight, surrounded by lush greenery.

Dome in Holualoa

The Dome at Ulu Inn: Luxury Couples Retreat, Kona

Overlooking the beautiful Kona Coast...The Dome at Ulu Inn says: "Aloha...let's Disconnect, to Reconnect" Nestled within a gated 5 acre estate, Settle into our exclusive Geodesic Dome suite...experience elevated glamping, designed for ultimate relaxation and ensured seclusion from the outside world. THE DOME & neighboring unit THE CUBE, are an ample distance apart, providing privacy from each other. You may get up close and personal with our Goats, Pigs, Geckos & wild birds that roam freely.

Indoor spacesKitchenTV

4.96 out of 5 average rating, 188 reviews

Farm stay in Keauhou

Kona Coffee Farm Retreat with Ocean & Sunset Views

Escape to our family-friendly 3.5-acre Kona Coffee Farm, nestled in the mountains minutes from beaches, 15 min to Kailua-Kona, and 5 min to Captain Cook. Kids can feed our friendly chickens, spot geckos, and explore the lush grounds filled with coffee trees, fruit, and flowers. The 3BR, 2BA modern farmhouse includes a spacious lanai, perfect for family meals, morning coffee, and stargazing. Enjoy cool mountain breezes, a refreshing escape from the coastal heat, and the magic of Kona Coffee.

Indoor spacesFamilyCondition

Guesthouse 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.

4.93 out of 5 average rating, 203 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.

FamilyKitchenParking

4.83 out of 5 average rating, 635 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.

Apartment in Kailua

Amazing Kona Sunset View - Sleeps 4

Two Bedroom + One bath with an amazing sunset view! Sleeps 4! Take advantage of our September 5-day discounts. We’re off on Holiday family members will be managing the apartment. Kona has the best beaches, best food, and nicest people!! We’re close to Saddle Road to Hilo and both upper and lower roads circling the Big Island. Book NOW. Read our reviews. Check out the photos. You will love how quiet the place is and private. We will also work with you on pricing for longer term rentals.

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An outdoor dining area features a glass-topped table surrounded by six cushioned chairs. Lush greenery and colorful tropical plants frame the view, while a stone floor adds an elegant touch to this inviting space.

4.98 out of 5 average rating, 181 reviews

Private & Beautiful home on 1 acre

A beautiful & private home on 1 acre in Kona Palisades! Our home is in an ideal location at nearly 1,400 ft. elevation to take advantage of cooler temperatures, while being just minutes from the airport, beaches, and Kailua-Kona town. Enjoy a vaulted living room ceiling, 2 covered lanais, and thoughtful finishes throughout our home. Set on a single level, the home features 3 bedrooms, 2 1/2 bathrooms, with a spacious roundabout driveway and green grassy lawns Caretaker lives on property

Indoor spacesKitchenAccess

4.94 out of 5 average rating, 284 reviews

Huge Kona Home • Ocean View • Pool • 4 bdrms • AC

Bringing the whole crew—or two families? This breezy 4BR, 3BA Kona home is built for fun and flexibility. Two stories mean plenty of space to gather—or sneak off for quiet time. With two kitchens, two living rooms, A/C, smart TVs, and indoor laundry, everyone gets room to relax. Take in an almost 180° ocean view of Kona bay, lounge on breezy lanais, fire up the BBQ, or float in the pool. Pick fresh mangoes and starfruit on-site. Just 5 mins to Kona town—your perfect island escape awaits.

Indoor spacesKitchenHospitality

A large lap pool is surrounded by a wooden deck and tropical landscaping. Poolside loungers are positioned for relaxation, with views of the ocean and distant trees. The area is bathed in natural light, creating a serene outdoor atmosphere.

4.97 out of 5 average rating, 219 reviews

Halia Hale

Escape to your own private Kona retreat, perfect for couples or friends. This gated and fully fenced home sits among 500+ mature Kona coffee trees and seasonal fruit like mango, papaya, banana, tangerine, orange, and avocado. Relax by the lap pool, detox in the commercial-grade sauna, or sip fresh coffee on the lanai. Just minutes from Kona’s beaches, shops, and dining, yet peaceful and secluded—an ideal spot to recharge and enjoy the spirit of Hawai‘i.

Indoor spacesKitchenGetting around

The horizon is adorned with a vibrant sunset, where warm hues of orange and yellow transition into soft clouds against a backdrop of the ocean. Silhouettes of palm trees frame the scene, enhancing the tropical ambiance.

4.91 out of 5 average rating, 219 reviews

Mini Plantation with a View

2300 sq.ft home on over an acre is perfect for time with family & friends. 10 minutes from downtown Kona, in Holualoa, with organic coffee, fruit trees, and flowers. There is a roof-top games with ping-pong room overlooking the garden. Paddle boards, snorkeling gear, basketball, and lots of games are also provided. Entertaining is easy on the huge lanai with bbq and a kitchen equipped with cooking staples and equipment. Home is on-property hosted.

KitchenFamilyOutdoor spaces

4.91 out of 5 average rating, 237 reviews

Home in Kahaluu-Keauhou

Family-Friendly 4BR Oasis by Magic Sands

Escape to this spacious island retreat featuring an open-concept living area, gourmet kitchen, and beautifully designed coastal interiors. Relax on the covered lanai with outdoor dining, lounge seating, BBQ, and a lush tropical backyard. The home offers luxurious king suites, a spa-inspired primary bath with a Jacuzzi tub, and is just minutes from Kona's best beaches, snorkeling, shopping, and dining. 🌺

KitchenFamilyNearby

4.92 out of 5 average rating, 629 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

Indoor spacesKitchenLong stay

Superhost

A stone staircase winds through lush tropical foliage, leading to a wooden structure nestled among vibrant greenery. The entrance features a railing and is framed by ferns and palm leaves, creating a serene and secluded atmosphere.

Cottage in Captain Cook

4.85 out of 5 average rating, 247 reviews

NANAINA COTTAGE. JUNGLE LOVERS DREAM

NANAINA COTTAGE. JUNGLE LOVERS DREAM AWAY FROM THE REST OF THE WORLD This is the ultimate romantic getaway for two with a million-dollar-view of the South Kona coast. It is perched on a rock cropping surrounded by mango trees. A one-minute walk along a jungle path leads you to this secluded setting.

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Popular amenities for Kailua-Kona family-friendly rentals

Kitchen

Wi-Fi

Pool

Free parking on premises

Air conditioning

Family-friendly home rentals with a hot tub

5.0 out of 5 average rating, 136 reviews

An inviting outdoor space features a private pool surrounded by lush tropical plants. The soft glow of pool lighting highlights the stone patio, while lounge chairs are positioned for relaxation. Tall palm trees are visible against a colorful evening sky.

Home in Keauhou

Mollie’s Paradise Resort Home & Private Pool

KitchenFamilyLayout

Condo in Waikoloa Village

Lounge chairs are positioned under a large umbrella, offering shade and comfort. Vibrant pink flowers bloom in a pot nearby, complemented by lush green foliage. The ocean glimmers in the background under a partially cloudy sky, creating a serene outdoor environment.

4.95 out of 5 average rating, 112 reviews

Tax all included! Luxury Kolea at Waikoloa Resort

KitchenIndoor spacesCleanliness

4.88 out of 5 average rating, 157 reviews

A serene oceanfront view is framed by swaying palm trees and vibrant greenery. The blue ocean stretches to the horizon, meeting frothy white waves that break against dark volcanic rock along the shore. The lush grass adds to the inviting landscape.

Condo in Keauhou

OCEANFRONt 3+2.5 FREE AC BeachGear

Indoor spacesKitchenBarbecue

A tranquil pool area features a heated pool with a small waterfall and tropical landscaping. Two lounge chairs sit beside the pool, adorned with rolled towels and a refreshing drink. The vibrant greenery enhances the serene atmosphere.

4.99 out of 5 average rating, 156 reviews

Tropical villa: Heated pool, hot tub & ocean views

FamilyKitchenCheckout

4.95 out of 5 average rating, 156 reviews

Lush green lawn stretches out under clear blue skies, framed by swaying palm trees. In the background, manicured homes line a serene body of water, with hints of distant mountains adding depth to the landscape.

Condo in Puako

Casa Chilin-Waikoloa Beach Resort

KitchenIndoor spacesDecor

4.97 out of 5 average rating, 107 reviews

Apartment in Keauhou

High-End Ocean Sanctuary with Upgraded Interiors

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Guesthouse in Kailua-Kona

A covered outdoor patio area is shown, featuring casual seating and potted plants. A view of the ocean and surrounding palm trees is visible through the open space. The tiled flooring adds a functional element to the area, enhancing the outdoor experience.

4.91 out of 5 average rating, 315 reviews

Kimo’s Getaway

Indoor spacesFamilyBreakfast

The image captures a panoramic view of a private heated swimming pool surrounded by lush greenery. Lounge chairs are positioned around the pool, and a shaded gazebo adds to the outdoor space. In the background, the vibrant blue ocean stretches under a clear sky.

4.99 out of 5 average rating, 113 reviews

Exceptional Oceanview Home - Pool & Stunning View

KitchenIndoor spacesView

Family- and pet-friendly home rentals

Guest suite in Kailua-Kona

A living area is shown, featuring a futon sofa, a wooden coffee table, and a light blue armchair. A flat-screen TV is mounted on the wall. Natural light enters through several windows. A small dining table with chairs is visible in the background.

4.87 out of 5 average rating, 542 reviews

Convenient Island Stay Near Airport and Beaches

Indoor spacesKitchenBiking

4.93 out of 5 average rating, 229 reviews

Apartment in Kailua-Kona

Gated Tropical Retreat near Kailua Kona and Ocean.

Indoor spacesKitchenAccess

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.

4.97 out of 5 average rating, 188 reviews

Hale Aka'ula, House of the Red Sunset

FamilyIndoor spacesGetting around

The open-plan living area features a spacious kitchen with modern appliances and a large island. A comfortable sofa faces a mounted television, and large windows allow natural light. The wooden ceiling beams add character, enhancing the cozy atmosphere of the room.

4.92 out of 5 average rating, 187 reviews

Spacious Kona Home • Sleeps 8 • Lanai + BBQ

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4.9 out of 5 average rating, 126 reviews

A private lanai offers a round table set with fresh fruit and drinks, surrounded by wooden chairs. The expansive view showcases lush greenery and distant mountains beneath a clear blue sky, creating a serene outdoor space for relaxation.

Home in Waimea

Mauna Loa Suites

KitchenFamilyBarbecue

4.93 out of 5 average rating, 282 reviews

Apartment in Kailua-Kona

Great Location, In Town, Modern and Clean

KitchenIndoor spacesHot tub

Guesthouse in Waikoloa Village

A vibrant sunset casts a warm glow over the horizon, surrounded by lush greenery and colorful flowers. The scene is framed by tropical plants, showcasing a blend of deep pinks, oranges, and purples in the sky.

4.95 out of 5 average rating, 465 reviews

Synergy Near Golf & Beach

FamilyKitchenBeach

4.94 out of 5 average rating, 205 reviews

A clear pool reflects the blue sky and surrounding palm trees, featuring a gently sloping entry. Covered seating areas are visible nearby, with lounge chairs arranged for relaxation. The scene conveys a serene atmosphere ideal for enjoying the outdoors.

Townhouse in Puako

Spacious Fairways 2BD townhome. Pool/Beach Club!

KitchenFamilyBeach

Family-friendly home rentals with a pool

4.94 out of 5 average rating, 207 reviews

Condo in Kailua-Kona

True Oceanfront, Top-Floor, Downtown, A/C, Parking

FamilyKitchenCheckout

4.92 out of 5 average rating, 131 reviews

A spacious living area is shown with a light-colored rug and comfortable seating, complemented by ceiling fans. Large glass doors open to an outdoor space, revealing views of the adjacent garden and ocean. Natural light brightens the room, enhancing its airy feel.

Townhouse in Keauhou

Seahorse Luxury Suite at Seaspray Ocean View

Indoor spacesFamilyCheckout

4.94 out of 5 average rating, 101 reviews

Apartment in Kailua-Kona

Kona Condo: Walk to Ocean, Restaurants, Nightlife

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The spacious home features natural wood accents, a wide balcony, and large windows that reflect the tropical landscape. Surrounding gardens with lush greenery create a serene atmosphere, while a small pond with a waterfall adds a soothing element to the exterior.

4.98 out of 5 average rating, 201 reviews

Stunning Serene Bali Retreat [Pool/AC/Ocean View]

FamilyKitchenCheckout

5.0 out of 5 average rating, 107 reviews

Tranquil Hawaiian Pineapple Poolhouse with A/C

KitchenFamilyValue

4.99 out of 5 average rating, 282 reviews

A panoramic view of the ocean stretches across the horizon, framed by scattered clouds in a clear blue sky. Lush greenery and rooftops are visible in the foreground, with tall trees adding height to the landscape, creating a serene scene.

Home in Waikoloa Village

Ocean, Sunset, Mountain & Celestial Views

KitchenFamilyLayout

4.9 out of 5 average rating, 202 reviews

Condo in Kailua-Kona

The ❤️ of Kona Town! Walk to Beach Shops & Food!

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