House holiday rentals in Kailua-Kona

4.99 out of 5 average rating, 280 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

🌴 Guest Favorite - Top 10% on the Big Island Enjoy stunning ocean, mountain, sunset, and starry views from nearly every room in this cozy, family-friendly three-bedroom, two-bathroom Waikoloa Village, Hawaii home. The house includes everything you'll need on your paradise escape including a fully equipped kitchen, beach gear such as boogie boards, snorkels, coolers, umbrellas, towels and Wi-Fi. We also provide bath towels, bed linens, soaps/shampoos, coffee, children's toys, and a BBQ grill.

ValueLocationParks

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: Pool, Spa, 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 blue-tiled heated pool. Wander the lush landscape, listen to colorful birds sing, and unwind in the spa or relax in the 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. This is Hawaii living at its absolute finest.

FamilyLocationDecor

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.

LocationFamilyWi-Fi

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, 180 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

LocationFamilyAccuracy

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, 200 reviews

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

Experience true island living! This 2,000 sq ft home features indoor/outdoor living, Thai/Balinese architecture, hand-carved wood everywhere, and ample windows/skylights that showcase the beauty of the Big Island. The kitchen/living rooms connect to the owner's retreat via covered dining lanai stretching back to the private pool. Perched on a hill with 180º ocean views, this secluded retreat enjoys a quiet atmosphere and cooler temps than busy downtown while not being far from the action.

LocationValueWi-Fi

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.

4.99 out of 5 average rating, 114 reviews

New Modern Interior|OceanView| HotTub|AC|Forest V

180° ocean view from front door to bedroom Fully renovated in 2024 with modern design and furnishings 1700+ sq. ft. on a 12,000+ sq. ft. lot, ocean-facing with forest backdrop 5 mins to beach, including popular snorkeling at Kahaluu 9 mins to Kona downtown for dining and shopping Sunset Hot Tub – brand new for relaxation Four outdoor sitting areas; large deck in forest setting All rooms has brand new AC Dual Dishwasher 85-inch luxury TV Extremely safe neighborhood with private gate

FamilyValueLaundry

The exterior of the house showcases a wooden structure with multiple levels, surrounded by lush greenery. A wide porch wraps around the upper level, providing expansive outdoor space. Stairs lead up to the entrance, flanked by tropical plants and a stone pathway.

4.89 out of 5 average rating, 159 reviews

Beautiful, Spacious Home w/Expansive Ocean Views

This is a HOSTED RENTAL and we are fully HB 108 COMPLIANT, but you won't see us unless you need us-on site or by text 7 days a week. This is not a party house. We rent to fun-loving folks who seek tranquility in paradise. Bookings made after 6/28/21 include all taxes and fees. Guests walk in and we see wow on their faces: gourmet kitchen, huge bedrooms.. "perfect for a family reunion" "cool at night, was just right" "close to the best beach in Hawaii" "amazing sunset views"

ValueLocationCondition

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.

ValueFamilyBeach

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, 218 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.

LocationValueNearby

4.91 out of 5 average rating, 234 reviews

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. 🌺

ValueLocationTV

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.

5.0 out of 5 average rating, 136 reviews

Mollie’s Paradise Resort Home & Private Pool

Welcome to Mollie's Paradise! This gated resort vacation home features a beautifully crafted outdoor paradise with a private pool and spa. Your host, Mollie, has curated a vacation home experience that will exceed your expectations. Her attention to detail, quality amenities and extra clean home is loved by guests.

FamilyLocationPool

4.92 out of 5 average rating, 110 reviews

Kona retreat with Hot Tub, Tiki Bar & Pickleball

Your Kona reset starts here 🌊✨ Relax in the NEW hot tub, grill dinner at sunset, and enjoy breezy island living with room for the whole crew. Private hot tub • Ocean-view lanais • Pickleball Court • Pool table/game room • BBQ • Multiple king bedrooms • Second refrigerator • Family-friendly amenities

ValueLocationWalkability

Popular amenities for Kailua-Kona house rentals

Kitchen

Wi-Fi

Pool

Free parking on premises

Air conditioning

House rentals with a pool

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

LocationValueCheckout

A cozy seating area is highlighted with a white mattress and colorful throw pillows featuring pineapple designs. The space is sheltered and overlooks a well-maintained pool surrounded by tropical greenery, with warm light and blue skies enhancing the inviting ambiance.

4.96 out of 5 average rating, 102 reviews

Fully Equipped Lush Kona Home • AC • Pool • Lanai

LocationFamilyParking

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.

4.92 out of 5 average rating, 179 reviews

Tropical Oasis Home with Pool and Walk to Beach

ValueLocationWi-Fi

4.88 out of 5 average rating, 155 reviews

Home in Waikoloa Village

Big Family Home, Pool, Views, Yard, Lanai, Clean!

ValueFamilyLong stay

4.94 out of 5 average rating, 134 reviews

HAVEN: Poolside Sanctuary with Heavenly Views

FamilyLocationAmenities

4.98 out of 5 average rating, 174 reviews

Paradise + Aloha + Expansive Ocean View

FamilyValueBeach

4.96 out of 5 average rating, 105 reviews

Romantic Keauhou Retreat | Pool + Tropical Lanai!

ValueLocationHospitality

5.0 out of 5 average rating, 107 reviews

Tranquil Hawaiian Pineapple Poolhouse with A/C

LocationValueNearby

Weekly house rentals

The exterior of the Wailima Beach House is framed by lush greenery, featuring a vibrant green façade and a mix of colored siding. Sunlight bathes the garden area, highlighting the manicured lawn and tropical plants that create a serene retreat.

4.8 out of 5 average rating, 123 reviews

Wailima Beach House, Kona, Magic Sands Beach

ValueLocationCheck-in

Superhost

A spacious living area is showcased with a light-colored sofa positioned adjacent to a wooden coffee table. A television is mounted on the wall, and natural light enters through the windows, framed by light curtains. The plush carpet adds comfort to the space.

4.86 out of 5 average rating, 286 reviews

Clean spacious in Kailua Kona.

LocationValueQuiet

A lush green yard is framed by palm trees, with vibrant blue water visible beyond. A pathway of stepping stones leads through the manicured grass towards the ocean, highlighted by a clear sky dotted with scattered clouds.

4.98 out of 5 average rating, 120 reviews

The Mango Cottage on Keauhou Bay

ValueLocationShared spaces

A spacious family room features a large gray sectional sofa with colorful decorative pillows. A gallery wall adorned with various framed photographs enhances the vibrant atmosphere. In the background, a kitchen area is visible, equipped with wooden cabinetry and dark appliances, creating a cozy yet functional living space.

4.97 out of 5 average rating, 519 reviews

2 Bedroom in the Kona Hills on a Coffee Farm

FamilyLocationAir conditioning

The kitchen showcases wooden cabinetry and a central island with seating. Natural light enters through the large window, illuminating the space. A dining table with chairs is visible, along with various kitchen appliances and decor, creating a functional and inviting cooking area.

4.98 out of 5 average rating, 146 reviews

Magic Sands Beach Bungalow

LocationValueComfort

A dining set on a covered patio includes a round table with two cushioned chairs. The table is elegantly set with wine glasses and plates, with panoramic views of lush greenery and the ocean in the distance, framed by hanging decorative lights.

4.99 out of 5 average rating, 103 reviews

Kona Sunset Hale

LocationFamilyCleanliness

A spacious lanai features a patio table with six chairs, ideal for outdoor dining. Lush greenery surrounds the area, while a view of the ocean is visible in the distance under a bright blue sky dotted with clouds.

4.93 out of 5 average rating, 108 reviews

Spacious Open-Concept Home w/ Stunning Ocean View

FamilyLocationHospitality

4.96 out of 5 average rating, 449 reviews

A master suite features a spacious king bed adorned with neutral linens and a red floral accent. Floor-to-ceiling windows offer panoramic views of the lush landscape, while a cozy daybed is visible in the background, enhancing the serene atmosphere of the open space.

Home in Captain Cook

Oceanview Oasis: Jacuzzi Tub & Wraparound Decks

LocationValueCondition

Private house rentals

A spacious outdoor dining area features a table set beneath a canopy, with comfortable seating surrounded by tropical plants and palms. A view of the ocean is visible in the distance, complemented by a vibrant green lawn and an inviting in-ground spa nearby.

4.98 out of 5 average rating, 108 reviews

Kona Coffee Estate w/ Hot Tub & Ocean View

ValueLocationLaundry

A spacious lanai is presented with modern furnishings, including a sofa and a dining area. Large sliding glass doors offer views of the surrounding nature and ocean. The wooden deck is complemented by potted plants, allowing for an inviting outdoor space.

4.9 out of 5 average rating, 167 reviews

Ocean-View Retreat in Kona Countryside

ValueFamilyWalkability

A spacious lanai is shown, with a large table set for six, surrounded by comfortable chairs. The ocean view stretches across the horizon, framed by large sliding glass doors. A ceiling fan can be seen above, adding to the relaxed atmosphere.

4.84 out of 5 average rating, 271 reviews

OCEAN VIEW! Art Home 'IPU HALE'

LocationFamilyBathroom

A vibrant sunset is seen over the horizon, with clouds reflecting warm oranges and pinks. Silhouettes of palm trees and distant greenery frame the scene, creating a serene backdrop as day transitions to night.

4.97 out of 5 average rating, 325 reviews

Entire rental unit Kona Ohana

FamilyLocationCleanliness

4.98 out of 5 average rating, 53 reviews

Kona Cloud • Treehouse Inspired Jungle Escape

FamilyLocationAccess

5.0 out of 5 average rating, 30 reviews

Cloud 9 Luxury Oasis | Hike | Yoga| Fast Wi-Fi

LocationFamilyBathroom

4.98 out of 5 average rating, 58 reviews

Ocean View, Spacious, & Peaceful 3 BR home in Kona

FamilyLocationCondition

The house is situated on a grassy hillside, showcasing a spacious deck with panoramic ocean views. Solar panels are positioned on the ground beneath the deck. Surrounding trees and lush greenery contribute to the serene environment, complementing the natural beauty of the landscape.