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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A private solar heated pool is surrounded by tropical landscaping, featuring a waterfall cascading over black rocks. Comfortable outdoor seating is arranged nearby, with vibrant plants adding color and lushness to the serene atmosphere.

4.96 out of 5 average rating, 158 reviews

Tropical Oasis: Heated Pool, Waterfall, Ocean View

Welcome to Nakukui Hale, your own private Hawaiian sanctuary — a beautifully designed estate for up to 8 guests in a gated community. A resort-style waterfall spills over lava rock into a deep blue-tiled heated pool. Wander the lush landscape, listen to colorful birds sing, and unwind in the elevated private gazebo as the sun sets over the Pacific. Just minutes from Ali'i Drive, Magic Sands Beach, Ironman Pier and the best restaurants in Kona town. This is Hawaii living at its absolute finest.

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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, 112 reviews

Exceptional Oceanview Home - Pool & Stunning View

Exceptional quality, unobstructed panoramic Oceanview, three-bedroom home with AC and a heated pool located in Kailua-Kona. As you walk through the door and see the deep blue ocean, you have arrived in Hawaiian paradise! The home features wide pocket doors that seamlessly expand the living space out to a large balcony (lanai). Relax in your own private oasis swimming pool, lounge in the shade under a poolside gazebo, unwind in your own hot tub! All just minutes from restaurants & shopping.

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4.97 out of 5 average rating, 186 reviews

Farm stay in Keauhou

Kona Coffee Estate Retreat | 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.

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4.86 out of 5 average rating, 209 reviews

Kona Landing | Ocean Views, BBQ, Pool, Beach Gear

Kona Landing ~ Walkable ✔ Resort amenities ✔ Beach access ✔ ★ "Alisha’s place is all you want! Cute, cozy, clean and conveniently located." ☞ Walk Score 76 (Walk to cafes, dining, shopping) ☞ Private lanai w/ outdoor dining + day bed ☞ Resort style shared pool + BBQ area ☞ 7th-floor sundeck w/ ocean view ☞ Fully equipped + stocked kitchen ☞ Designated parking → 1 car ☞ 55” TV smart TV w/ Netflix ☞ Onsite washer + dryer 2 mins → DT Kailua-Kona 15 mins → Ellison Onizuka Kona Airport (KOA) ✈

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4.94 out of 5 average rating, 280 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.

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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 spacesFamilyLayout

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, 217 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.

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4.94 out of 5 average rating, 126 reviews

Ocean View 2BR Condo in Kailua-Kona

Kona Reef A1 places you right on the Kona coastline, where ocean views, easy beach access, and the relaxed energy of Kailua-Kona set the tone for a memorable island stay. This inviting 2-bedroom, 2-bath condo offers 905 square feet of comfortable living space and is thoughtfully designed for up to 6 guests, making it a great fit for families, couples traveling together, or small groups seeking a scenic Big Island escape.

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4.91 out of 5 average rating, 233 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. 🌺

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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

Luxury ocean front property Kolea A'Bay ! Gated community and 24/7 security with high maintenance for everything in Kolea. peaceful and centrally-located place with private pool club house right by the ocean and private road to the ocean. You can walk to the LavaLava sunset lounge on A bay and walk to the King shopping center where upscale stores are located with restaurant and grocery store.

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4.92 out of 5 average rating, 626 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

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Popular amenities for Kailua-Kona family-friendly rentals

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Wifi

Pool

Free parking on premises

Air conditioning

Family-friendly home rentals with a hot tub

4.76 out of 5 average rating, 148 reviews

The image captures a serene view of palm trees swaying gently against a backdrop of the ocean. The blue waters reflect the sky's hues, and well-maintained greenery is visible amidst the condo buildings, highlighting the calm coastal atmosphere.

Condo in Kahaluu-Keauhou

Beachfront Condo in Kailua

KitchenFamilyCheck-in

4.94 out of 5 average rating, 195 reviews

A bright and airy living room is showcased, featuring a comfortable blue sofa and armchairs. Large glass doors open to the outdoor seating area, revealing views of the ocean. Decorative items are neatly arranged on the built-in shelves, enhancing the space.

Home in Keauhou

Kona Surf Snorkel Paradise, Beachfront, Hot Tub

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4.97 out of 5 average rating, 107 reviews

Apartment in Keauhou

High-End Ocean Sanctuary with Upgraded Interiors

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4.92 out of 5 average rating, 225 reviews

Downtown Kona Loft•Ocean View•Walk to Beach/Dining

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A sparkling pool is surrounded by lush tropical foliage, creating a serene environment. Several lounge chairs are positioned nearby for relaxation. A hot tub is situated next to the pool, inviting guests to unwind in a tranquil setting.

4.76 out of 5 average rating, 659 reviews

Kailua Bay Resort

KitchenFamilyNearby

4.94 out of 5 average rating, 165 reviews

The Ocean Club grounds are depicted, featuring lush tropical landscaping and a lagoon-style pool surrounded by seating areas. Palm trees sway gently in the breeze, with a sunset sky adding a warm glow. Private cabanas offer shaded relaxation spots near the tranquil waters.

Condo in Puako

Newer Luxury Townhouse - Exceptional Value

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Superhost

Condo in Holualoa

4.8 out of 5 average rating, 193 reviews

Ocean Front Family Condo across from Lyman's Cove

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4.99 out of 5 average rating, 111 reviews

A modern kitchen boasts sleek grey cabinetry and a large island with a light marble surface, featuring a decorative bowl of fruit. Pendant lighting hangs above, and expansive windows offer sweeping views of the ocean beyond, enhancing the bright and airy ambiance.

Home in Kahaluu-Keauhou

New Modern Interior|OceanView| HotTub|Forest Deck

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Family- and pet-friendly home rentals

4.83 out of 5 average rating, 629 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

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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, 538 reviews

Convenient Island Stay Near Airport and Beaches

Indoor spacesKitchenLong stay

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, 187 reviews

Hale Aka'ula, House of the Red Sunset

Indoor spacesKitchenWi-Fi

4.93 out of 5 average rating, 280 reviews

Apartment in Kailua-Kona

Great Location, In Town, Modern and Clean

Indoor spacesFamilyHot tub

A spacious home is depicted against a lush green backdrop, featuring a large deck with a hot tub. The structure showcases multiple solar panels on the roof, white railings, and an elegant staircase leading to the ground level, surrounded by vibrant tropical foliage.

4.93 out of 5 average rating, 149 reviews

Kona Mountain Home, 3/2, lanai, hot tub, sleeps 8

FamilyIndoor spacesValue

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

Indoor spacesFamilyShared spaces

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

KitchenFamilyCondition

4.94 out of 5 average rating, 204 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!

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Family-friendly home rentals with a pool

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.

4.97 out of 5 average rating, 199 reviews

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

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4.92 out of 5 average rating, 130 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 spacesKitchenBiking

4.99 out of 5 average rating, 279 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

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4.96 out of 5 average rating, 184 reviews

An oceanfront sandy beach area is framed by palm trees, with lounge chairs arranged for relaxation. The ocean is visible in the background, with calm waves lapping at the shore. A gated pool area is nearby, enhancing the serene coastal setting.

Condo in Holualoa

Updated condo with ocean views & air conditioning

FamilyIndoor spacesCondition

Guest suite in Kailua-Kona

A tranquil saltwater pool is surrounded by a well-maintained lawn and lush tropical landscaping. Sun loungers and umbrellas are arranged nearby, inviting relaxation. In the background, a two-story villa features solar panels and a charming balcony, set against a sunny blue sky.

4.97 out of 5 average rating, 317 reviews

Family-Friendly Retreat Guest Suite-Pool & Lanai!

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4.97 out of 5 average rating, 118 reviews

Kona Rose's Hideaway at Kona Plaza, center of town

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4.88 out of 5 average rating, 280 reviews

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.

Condo in Holualoa

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

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