Holiday houses in Kailua-Kona

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, 168 reviews

Ocean-View Retreat in Kona Countryside

Escape to a private, 2BR retreat on 3 lush acres in Holualoa—where hotel-style efficiency meets island charm.Step onto the lanai for sweeping ocean views, stunning sunsets, and cool mountain breezes.Just 10 minutes to Kona town, beaches, and the airport.With a full kitchen, BBQ, fire pit table, and modern comforts, it’s perfect for couples seeking a peaceful and private escape with scenic veiws. Grill dinner, unwind by the fire pit, or roll out a yoga mat and greet the day in serene surroundings

LocationFamilyHospitality

4.98 out of 5 average rating, 204 reviews

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.

Home in Holualoa

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

Experience true island living! This 2k sq ft home features indoor/outdoor living, Thai/Balinese architecture, hand-carved wood, and ample windows/skylights that showcase the island's beauty. The kitchen/living rooms connect to the owner's retreat via covered dining lanai stretching 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 without being too far. ***WE'RE OK! The hurricanes didn't affect us.***

FamilyLocationCheck-in

4.99 out of 5 average rating, 285 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.

FamilyLocationGetting around

4.92 out of 5 average rating, 132 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

A private oasis across from the desirable Kahaluʻu Beach Park. This two bedroom luxury suite is bright & airy with a private lanai & your own KOI pond. A private guest only pool deck includes a barbecue and dining area for outside entertainment. The living room is a great place to relax with ocean views and the sounds of ocean waves. The chef of the family will appreciate a fully stocked modern kitchen. The whole group will enjoy everything Kona has to offer from this centrally located Oasis.

LocationValueCleanliness

5.0 out of 5 average rating, 301 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.

FamilyValueLong stay

Farm stay in Captain Cook

The custom glass house is surrounded by lush greenery, featuring large windows that provide views of the forest. The structure is elevated with a small deck, blending into its natural surroundings. Soft lighting highlights the exterior, creating a serene evening ambiance.

Glass House near Capt. Cook Trail

Hinu Hale is a beautiful unique glass house. It is located on a gorgeous horse ranch with private access to the Ka'awaloa Trail (Captain Cook Trail). The hale (home) is newly built, custom small home. Surrounded by 360 degrees of nature, it's nestled in Kukui nut and Hau tree forest. Stunning, it is a piece of art. Lava tile floors and bathroom, all interior is wrapped wood, this place is a perfect space to enjoy a one-of-a-kind experience in the heart of Hawaii. 4WD/AWD vehicle recommended.

FamilyValueDecor

4.97 out of 5 average rating, 236 reviews

4.94 out of 5 average rating, 209 reviews

Condo in Kailua-Kona

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

Get away from it all right in the heart of Kona! Feel the ocean spray as you watch for turtles on the lanai, or gaze at the tropical paradise through your bedroom window. While only steps away from the active downtown, this top-floor unit is on the ocean side of a boutique complex, meaning no noise from the street or guests above. After a busy day at the beach and a night on the town, you'll appreciate the peace and quiet of your own space with only the sound of the ocean to lull you to sleep.

FamilyValueWalkability

4.98 out of 5 average rating, 126 reviews

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.

Home in Keauhou

The Mango Cottage on Keauhou Bay

Cottage on private, gated, 1 acre waterfront estate. Swim, surf, kayak, and snorkel from yard. Watch dolphins and boats in the bay. Walk to manta ray, snorkeling, kayaking, whale and dolphin tours, golf, restaurants, movie theater, and outdoor market. Two room suite. King bed. Full kitchen. Large shower. Covered deck with partial ocean views. Use of kayaks and stand-up paddle boards. Book alone or with Ocean Cottage. Couples and single travellers only. 100% non-smoking property inside and out.

ValueLocationBeach

4.96 out of 5 average rating, 190 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.

LocationFamilyCleanliness

4.94 out of 5 average rating, 199 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

Incredible views of the bay and surfers! Modern house(built 2014) with A/C all rooms. It’s across the street from Kahalu’u Beach. This is the BEST snorkeling and surfing spot in Kona. Surfboards,The Kona Trolley stop, and food trucks are steps away. The house has a hot tub, 4 brms, one upstairs, 3 downstrs, There’s one full bath en-suite upstairs with toilet, tub and shower. There is a toilet downstairs with very private outdoor shower. Plus one bdrm has a sink/vanity & 2nd outdoor shower.

LocationValueCheck-in

4.94 out of 5 average rating, 287 reviews

Home in Holualoa

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.

LocationFamilySleep quality

4.98 out of 5 average rating, 121 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|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

ValueLocationBathroom

Popular amenities for Kailua-Kona holiday rentals

Kitchen

Wi-Fi

Pool

Free parking on premises

Air conditioning

Other great holiday rentals in Kailua-Kona

4.84 out of 5 average rating, 174 reviews

A spacious wrap-around lanai offers a panoramic view of the ocean and lush greenery. Palm trees frame the scene, while a small seating area invites relaxation. The deck features wood flooring and a metal railing, blending harmoniously with the surrounding tropical landscape.

Home in Captain Cook

KEALAKEKUA HOME STUNNING VIEW SPACIOUS ELEGANCE

LocationFamilyWalkability

4.91 out of 5 average rating, 221 reviews

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.

Home in Holualoa

Mini Plantation with a View

ValueFamilyHospitality

A sunset view is captured over the ocean, with vibrant shades of orange, pink, and purple filling the sky. Silhouetted palm trees line the horizon, adding a tropical touch to the scenic landscape. The tranquil atmosphere invites relaxation.

4.97 out of 5 average rating, 277 reviews

Knox Dojo – 2b/2b House

LocationValueAir conditioning

4.98 out of 5 average rating, 54 reviews

Kona Cloud • Treehouse Inspired Jungle Escape

FamilyLocationHot tub

4.98 out of 5 average rating, 63 reviews

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

FamilyLocationParking

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.

4.99 out of 5 average rating, 70 reviews

Panoramic Ocean View in Cloud Forest

ValueLocationKitchen

Apartment in Kahaluu-Keauhou

Central AC 2B/2B Ocean View unit@Magic Sands Beach

LocationViewNearby

5.0 out of 5 average rating, 10 reviews