Holiday houses in Kailua-Kona

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Top-rated holiday rentals in Kailua-Kona

Guests agree: these stays are highly rated for location, cleanliness and more.

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Top Guest favourite
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.
Condo in Kailua-Kona
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!

Top Guest favourite
A charming cottage with a red exterior features large windows and a welcoming porch. Surrounded by lush greenery and native plants, a well-maintained yard is visible. A paved driveway leads up to the cottage, complemented by a stone wall in the background.
Cottage in Kailua-Kona
4.95 out of 5 average rating, 442 reviews

Radiant Ocean View Cottage on a Coffee Farm. Very Private.

Centrally located between South Kohala's beaches, and the dining and entertainment scene of Kailua-Kona, the Kaloko Coffee Cottage is at a cool elevation making naps after adventures a...well a dream! Far from any roads, the dominant sounds are the many birds who make their homes in the surrounding trees. This is a thoughtfully furnished home with an open layout, on a coffee farm, just bring your food and clothes for which ever adventure you intend; leave the accommodations and ambiance to us.

Top Guest favourite
Lush greenery surrounds a well-maintained lawn that leads to a vibrant blue ocean. Palm trees and tropical plants enhance the natural setting, with gentle waves seen in the distance. The scene captures the essence of a serene waterfront environment.
Guesthouse in Keauhou
4.97 out of 5 average rating, 115 reviews

Kona Ocean Front Cottage on Keauhou Bay

Waterfront cottage on private, gated 1 acre estate. Close as you can get to an over the water bungalow in Hawaii with direct ocean access to swim, surf, kayak, snorkel and watch dolphins. Walking distance to manta ray, snorkeling, kayak, whale and dolphin tours, golf, restaurants, movie theater, and outdoor art market. Two room suite. Queen bed. Living room with 50 in TV. Bathroom with large shower. Large covered deck with seating area, kitchenette, dining table, lounge chairs. Outdoor shower.

Top Guest favourite
A modern wooden cabin is positioned on a gently sloping lawn, surrounded by native trees. A concrete path leads to the entrance, which features wooden accents. The sky is filled with colorful hues, suggesting a vibrant sunset behind the structure.
Cabin in Kailua-Kona
5 out of 5 average rating, 163 reviews

Romantic Kona Hideaway | Modern + Private Hot Tub

Tucked away in a peaceful native Hawaiian forest, this modern hideaway offers the perfect romantic escape just 10 miles from Kona’s beaches, airport, and town. Thoughtfully designed for couples, honeymooners, and those craving serenity, this stand-alone retreat blends minimalist style with beauty. Unwind in the private hot tub surrounded by nature, watch sunsets from the lanai, or grill under the stars. Inside, enjoy 384 sq. ft. of creative space that captures luxury, nature and seclusion.

Top Guest favourite
A colorful quilt covers a spacious bed, complementing the serene atmosphere of the room. A wall-mounted television displays a scenic image. Large glass doors provide access to a private lanai with ocean views, creating a bright and inviting space.
Guest suite in Kailua-Kona
4.99 out of 5 average rating, 375 reviews

Your Big Island Escape - King Bed & A/C

Kona sweet spot with private lanai, amazing ocean view, ideal temperatures & personal parking spot. Devoted Super-hosts on-site to maximize your accommodations & experience. Very safe neighborhood. Lots of amenities / beach gear. Only 6 minutes to beaches & great snorkeling, 10 minutes to downtown for diverse food options, shopping & historic sites. Exquisite Kohala beaches 30 minutes north. Popular Walua Trail just 2 blocks away to stroll or jog. * Please no 3rd party bookings. Mahalo.

Guest favourite
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.
Guest suite in Kailua-Kona
4.88 out of 5 average rating, 414 reviews

3 blocks to Turtle beach and Ali'i Dr

A small space with a big punch and a Hawaiian vibe. This cozy, “bungalow” is perfect for a couple or the solo traveler. Enjoy the handcarved mahogany doors and the newly tiled shower with a killer shower bar. This space is just three blocks to the ocean and a 10 minute car ride to old town Kona. Your space includes: Queen size bed, A/C. Hi speed Wi-Fi, Cable/Smart TV. Check out our other listings! airbnb.com/h/treetop-kona airbnb.com/h/guestwing-kona airbnb.com/h/hawaiianretreat-kona

Guest favourite
Condo in Kailua-Kona
4.95 out of 5 average rating, 242 reviews

Oceanfront Gem, Walk to Beach/Town, AC, Elevator

Right-on-the-ocean, newly renovated, spacious, upscale condo in a gated boutique complex. Unbelievable views from the lanai, living room and bedroom. Close to everything! 1-2 blocks to Honl's beach, farmers market, restaurants, bars, and shops in Kailua Village. New king bed and queen sleeper sofa with memory foam mattress for up to 4 guests. Heated, ocean-front salt water pool with outdoor shower and community BBQ. Quiet; no noise from Ali'i Drive. Reserved parking spot. A/C. Elevator.

Guest favourite
A vibrant tropical garden surrounds a modern villa, nestled within lush greenery and mature palm trees. A serene pool glimmers in the sunlight, creating a peaceful focal point amidst the rich landscaping. The sky above is bright with scattered clouds, enhancing the tranquil atmosphere.
Apartment in Kailua-Kona
4.96 out of 5 average rating, 118 reviews

Suite Magic Sands Beach

Save money & time! Ho'omalu located just off of Alii drive "Ironman Route" is only an 11 minute walk to magic sands beach and many more hot spots. In a private and tranquil gated community this modern day Villa awaits where sophistication meets relaxed Hawaiian living. The inviting pool enveloped with mature tropical landscaping is the centerpiece to this compound and features upscale finishes and flooring. The apartment is on the second level. Ask about our car rental fleet discounts.

Top Guest favourite
The bedroom features a queen bed with a light green quilt, positioned against a vibrant wall mural depicting bamboo foliage. Two nightstands flank the bed, each with a lamp. A large mirrored closet reflects the room's natural decor.
Guest suite in Kailua-Kona
4.99 out of 5 average rating, 471 reviews

Inna’s Cottage - Modern, Tropical Getaway

Located conveniently in Kailua-Kona, just minutes from downtown in upscale neighborhood! This 360 sf (34 sq m) studio with private patio, private entrance, air conditioning, private laundry facilities, high speed Wi-Fi, spa-inspired bathroom, queen bed, and a full size kitchen with dishwasher, ice maker, and filtered cold water. Relax in two recliners and enjoy a 65” (165 cm) OLED TV with Internet streaming, Netflix! Enjoy the sounds of tropical birds and singing frogs! Aloha!

Top Guest favourite
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.
Condo in Kailua-Kona
4.9 out of 5 average rating, 472 reviews

Plantation Hale

Step back in time to old Hawai'i at our Plantation Hale, located just steps from the beautiful beaches and shoreline of Ali’i drive where you'll discover all the best restaurants and shopping in Kona. Ever wonder what it might have been like to live back in the days when sugarcane was king, and everybody had a ukulele? Not only will you be delighted inside, but the atmosphere at Kona Islander, with all of its beautiful landscaping and meandering pathways, is just as enchanting.

Guest favourite
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.
Condo in Kailua-Kona
4.92 out of 5 average rating, 246 reviews

Blissful paradise with epic view- Hale Mahana

Serenity in Kona- with epic ocean views! Wake up with the ocean waves crashing below. Hang out on the lanai with some Kona coffee from the Green Flash cafe next door. You have a front row seat for whale watching during whale season. Or, hang out and enjoy the sunsets- at times with our local manta ray! We have a queen sofa bed, and AC. Close to town- an 18 minute walk. Quiet, very little road noise here. You can rent bikes too across the street.

Top Guest favourite
The exterior features a wooden deck, offering easy access to the entrance. A gentle overhang provides shelter, and string lights are visible, suggesting a cozy ambiance. The white facade of the tiny house is complemented by surrounding greenery and a pebbled walkway.
Tiny home in Kailua-Kona
4.93 out of 5 average rating, 155 reviews

Lilikoi Loft

Introducing a private oasis of comfort and charm, our newly renovated tiny house. This simple retreat is a testament to minimalist luxury and offers a convenient escape near Kona International Airport and downtown Kailua Kona. The exterior of the tiny house is a harmonious blend of rustic charm and simple design, featuring a quaint porch, perfect for sipping your morning coffee or working on the computer while gazing at the pacific ocean.

Popular amenities for Kailua-Kona holiday rentals

When is the best time to visit Kailua-Kona?

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Avg. price$402 NZD$418 NZD$381 NZD$361 NZD$340 NZD$335 NZD$335 NZD$311 NZD$320 NZD$353 NZD$338 NZD$386 NZD
Avg. temp6°C6°C6°C7°C9°C10°C9°C9°C9°C9°C7°C6°C

Frequently Asked Questions

  • What are the best places to stay in Kailua-Kona?

    Kailua-Kona has inviting neighborhoods along the coast and near its lively downtown, making both popular choices for visitors seeking local culture and access to restaurants. Many stays are found close to the water or nestled in quieter residential areas.

  • What are the best things to do in Kailua-Kona with kids?

    Families in Kailua-Kona often explore sandy beaches, visit marine centers, or try casual snorkeling around protected coves. Local parks and guided boat tours are frequently suggested for hands-on experiences and wildlife sightings.

  • What are some of the best things to do in Kailua-Kona?

    Explore historic sites like Hulihe‘e Palace, wander through local markets, or join a coffee farm tour to learn about regional flavors. Kailua-Kona also has ocean activities such as kayaking, snorkeling, and guided manta ray nights.

  • How is the weather in Kailua-Kona?

    Kailua-Kona typically has warm days with temperatures held near 70–85°F (21–29°C), and mild evenings. The region experiences low rainfall throughout the year and gentle ocean breezes are common.

  • What are the best places to visit in Kailua-Kona?

    Visit Hulihe‘e Palace for a glimpse into local history, stroll vibrant Kailua Pier, and explore nearby coffee farms. Many people also stop by local art galleries or tranquil beaches to relax and experience island life.

  • What are some hiking trails in Kailua-Kona?

    Kailua-Kona has trails through ancient lava fields, forested paths, and scenic coastal walks. Guided hikes around Kaloko-Honokōhau National Historical Park are frequently suggested for nature and Hawaiian heritage.

  • What are some family activities we can do in Kailua-Kona?

    Try gentle snorkeling or join a family-friendly boat tour, explore interactive displays at marine centers, and stroll through farmers markets together. Parks and walking trails make it easy for everyone to experience the outdoors.

  • What are some of the best day trip ideas from Kailua-Kona?

    Many travelers join guided excursions to volcanic landscapes, visit local coffee farms, or explore waterfalls and botanical gardens around the island. Culturally significant villages and historical sites are also often suggested.

  • Are there any pet friendly accommodations available in Kailua-Kona?

    Kailua-Kona has pet-friendly stays in coastal and residential neighborhoods, with easy access to outdoor paths. Some rentals welcome pets and share recommendations for local walks or nearby dog-friendly beaches.

  • What are some local tips for visiting Kailua-Kona?

    Locals suggest packing reef-safe sunscreen, supporting neighborhood coffee shops, and respecting culturally important sites. Early mornings are often quieter for exploring markets and beaches.

  • What is Kailua-Kona known for?

    Kailua-Kona is known for its role in Hawaiian royal history, distinctive coffee farms, and vibrant oceanfront. The town’s mix of heritage sites and relaxed beach culture draws visitors throughout the year.

  • What are the best hidden gems to explore in Kailua-Kona?

    Look for tucked-away art galleries, historic churches, and quiet tide pools along the shoreline. Small local cafes and lesser-known hiking paths reveal Kailua-Kona’s slower rhythms and creative spirit.

  • What are the best foods to try in Kailua-Kona?

    Try locally grown Kona coffee, fresh poke bowls, and dishes featuring sweet bread or tropical fruits. Island-style plate lunches are frequently suggested, highlighting the area’s diverse culinary influences.

  • What should I bring for a trip to Kailua-Kona?

    Pack lightweight clothing, swimwear, and sturdy footwear for outdoor exploring. Reef-safe sunscreen, a hat, and reusable water bottles are recommended staples for the warm climate.

  • What is the nightlife in Kailua-Kona like?

    Kailua-Kona has relaxed nightlife with beachfront bars, live music venues, and casual eateries around the downtown area. Many visitors enjoy evening walks or gatherings at open-air restaurants with ocean views.

  • What are the most popular events or festivals in Kailua-Kona?

    Kailua-Kona hosts events such as the Ironman World Championship and seasonal coffee festivals, which draw crowds and celebrate local culture. Community gatherings often feature artisans, food vendors, and music in public spaces.

  • Are there family friendly vacation rentals in Kailua-Kona?

    Family-friendly rentals are available across Kailua-Kona’s coastal and residential neighborhoods, with easy access to parks and beaches. Some listings include amenities suited for children and group stays.

  • When is the best time to visit Kailua-Kona?

    Late spring to early fall is often recommended for Kailua-Kona, when skies are typically sunnier and festivals bring energy to the area. Cooler months can be quieter and are popular with those looking for peaceful surroundings.

Quick stats about holiday rentals in Kailua-Kona

  • Total holiday rentals

    Explore 2,370 holiday rentals in Kailua-Kona

  • Nightly prices starting at

    Kailua-Kona holiday rentals start at $84 NZD per night before taxes and fees

  • Verified guest reviews

    Over 107,450 verified reviews to help you choose

  • Family-friendly holiday rentals

    1,180 properties offer extra space and kid-friendly amenities

  • Pet-friendly accommodation

    Find 100 rentals that welcome pets

  • Holiday rentals with a pool

    1,970 properties feature pools

  • Rentals with dedicated workspaces

    1,260 properties have a dedicated workspace

  • Wi-Fi availability

    2,350 of Kailua-Kona holiday rentals include Wi-Fi access

  • Popular amenities for guests

    Guests love Self check-in, Free parking on premises and Gym across Kailua-Kona rentals

  • 4.8 Average rating

    Kailua-Kona stays are highly rated by guests—averaging 4.8 out of 5!

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