Holiday houses in Kailua-Kona

4.94 out of 5 average rating, 195 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!

4.92 out of 5 average rating, 172 reviews

Downtown Kona! Ocean View<1/2mi to Beach!

Say ‘Aloha’ to the good life when you book one of the best located condos in downtown Kailua-Kona! Located in the heart of downtown, this modern loft style home is just a 5-10 minute walk to the beach, the famous Alii Drive, restaurants, and on-the-water fun. Equipped with a private lanai and community amenities, you’ll have everything you need to enjoy Kona to it's fullest. Walk to the best downtown Kona Beach for a fun family-friendly day of sun, white sand, turquoise waters, and snorkeling!

5 out of 5 average rating, 214 reviews

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.

4.93 out of 5 average rating, 148 reviews

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.

Farm stay in Captain Cook

4.99 out of 5 average rating, 174 reviews

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.

Guesthouse in Kailua-Kona

4.97 out of 5 average rating, 747 reviews

Private Kona Oceanview Retreat with parking

Escape to a private oceanview retreat in North Kona! This cozy guesthouse offers breathtaking views from your private deck, surrounded by lush tropical plants. Enjoy your morning coffee while soaking in the serene ocean scenery, and unwind in a tastefully decorated interior with all essentials, a well-equipped kitchen, modern bathroom with a luxurious shower, and convenient laundry facilities. Perfect for couples or solo travelers and easy access to Kona’s attractions! Tax ID W01822068-01

Guest suite in Kailua-Kona

4.9 out of 5 average rating, 297 reviews

Jasmine Studio; No Cleaning Fee. King Bed

Located conveniently 5 minutes from the airport and a short 15 min drive to downtown Kailua Kona. Vaulted ceilings, a cute lanai to enjoy your morning coffee, large bathroom with double vanity, and a kitchenette make this rental a real gem. The AC is powerful for when the tropical breeze isn't quite cool enough, The WIFI is reliable and there is a large screen TV with ROKU for when you just want to hang out. We offer automated check in, excellent room amenities and flexibility with booking.

5 out of 5 average rating, 118 reviews

Cabin in Kailua-Kona

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.

Guest suite in Kailua-Kona

5 out of 5 average rating, 331 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.

4.97 out of 5 average rating, 187 reviews

Downtown Kona Plaza Condo w/AC

Visit all the Big Island has to offer and lay your head to rest at this comfortable, renovated condo located in the heart of downtown Kona. Situated on historical Ali'i Drive, we are just steps from shops, restaurants, coffee houses, and beaches. Take in the breathtaking sunsets and hear the nightly luau from the enclosed lanai. Enjoy the newly refinished pool, and head up to the sunset deck for a bbq or cocktail. Catch charters, sunset cruises, and snorkel tours off of Kailua Pier.

4.97 out of 5 average rating, 171 reviews

Deluxe Oceanfront Studio Condo@The Kona Bali Kai

Very oceanfront studio (Unit #225) giving you the very Hawaiian experience in a luxury setting. Located in the Kona Bali Kai resort, this is a north end unit and is the closest condo to the ocean there! It has a beautiful full sized kitchen as well as a Cal king size pedestal bed, so although a studio, it has all the right amenities!!