
Holiday rentals 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.

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.

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.

Kona Sunsets & Ocean Views at Hillside Home
Watch Kona’s world-famous sunsets from two private balconies at this spectacular tropical retreat. Perched on a Hualalai hillside among sleepy palms, this luxury getaway boasts unmatched ocean views. This modern home features a full kitchen, indoor & outdoor dining, 2bd/1.5 bath, office, parking, and free laundry. When the breeze isn’t enough, air-conditioned bedrooms keep you cool. We are proud to be top-rated Airbnb Superhosts and provide you with an award-winning level of service. Aloha!

Romantic Cabin Treehouse in Hawaii Cloud Forest
Stay in a unique cloud forest at a 2500 foot elevation, yet minutes to airport, beaches, restaurants, bars and shops. Extraordinary lodging, perfect for a honeymoon, writers retreat or meditation vacation. Surrounded by native forest, with tree fern and Hawaiian song birds. Afternoon rains end in grand sunsets. Nights are cool for sleeping with windows open. State forest hiking trails are at your doorstep. Great bird watching, including a local flock of cockatoos that visit in the morning!

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

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.

Bungalow Bliss Ocean & Pool View
Your home away from home after exploring the island’s many beaches, coffee farms, snorkeling/diving spots, & downtown Kailua-Kona! Sun-kissed ocean & pool views await you in this cozy, stylish space. A perfect budget-friendly, clean, cool place to rest between your island adventures! Located near downtown Kailua-Kona and 500 ft above sea level, this property offers cooler temperatures and breezes that delight guests. This suite best fits solo travelers or couples who like to be cozy!

Tiny House in Kona - 5 Minute Walk to the Beach!
Mahalo nui for your Interest! After a short break, I am happy to be back hosting this wonderful space ~ Click my profile to check my 1400+ 5-Star Reviews and book with Confidence! This is a real Tiny House on Wheels with an additional connected open air and fully screened kitchen for dining and relaxing. You'll love this "rustic" and private experience in an upscale neighborhood just 4 miles south of downtown Kona! And, you are only a 5 Minute Walk to Magic Sands - the best beach in town!

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.

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.

Love Kona farm life *Superstar Truss Cabin!
If you like nature and animals, come and enjoy our hobby farm! It's glamping in a tiny house with the incredible view. (It is a farm, not a hotel) The loft bed with ladder as picture shown. Screened/no windows so you can enjoy breeze and view. Cute living room and big shower/restroom down stairs. Patio with outdoor grill and sink. Beautiful sunset and infinity sea/sky line from the bedroom. Galaxy and shooting stars at the night. About 20mins from many beaches, and downtown.

Space for Couples w/ garden view near airport
Enjoy cool breezes in a garden-like setting at 860 foot elevation on our large property. Only a 5 minute drive to the Kona airport and a 15 minute drive to town. An ideal spot for couples, this updated one bedroom, one bath condo includes a king bed, large closet, free parking, Roku TV, mini-fridge, BBQ grill, beach gear and much more. A perfect place for couples to relax on the lanai w/ a cup of Kona coffee after a fun day of exploring the island.
Popular amenities for Kailua-Kona holiday rentals
Other great holiday rentals in Kailua-Kona

Kona Condo:AC, Near Beach &Shops

Cloud Forest Retreat with Treehouse Vibes

Tranquil Tropical Retreat

1BR, 1Bath, Full Kitchen, Guest Suite

Private guest house in the Hawaii Island tropics.

NEW! ADORABLEbungalow in Kona

Brand new Luxury Oceanfront Living in Kona with AC

Oceanfront Chic • Just Renovated
When is the best time to visit Kailua-Kona?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $312 SGD | $325 SGD | $296 SGD | $281 SGD | $264 SGD | $260 SGD | $283 SGD | $273 SGD | $263 SGD | $293 SGD | $274 SGD | $298 SGD |
| Avg. temp | 6°C | 6°C | 6°C | 7°C | 9°C | 10°C | 9°C | 9°C | 9°C | 9°C | 7°C | 6°C |
Quick stats about holiday rentals in Kailua-Kona

Total holiday rentals
Explore 2,350 holiday rentals in Kailua-Kona

Verified guest reviews
Over 106,870 verified reviews to help you choose

Family-friendly holiday rentals
1,160 properties offer extra space & child-friendly amenities

Pet-friendly holiday rentals
Find 100 rentals that welcome pets

Holiday rentals with a pool
1,940 properties feature pools

Rentals with dedicated workspaces
1,250 properties have a dedicated workspace

Wifi availability
2,320 of Kailua-Kona holiday rentals include wifi 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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- Hapuna Beach
- Pahoa Beach
- Kaunaoa Beach
- Mauna Kea Golf Course
- Kohanaiki Private Club Community
- Ke‘EI Beach
- Waikōloa Beach
- Mauna Lani Golf
- Volcano Golf and Country Club
- 49 Black Sand Beach
- Waikoloa Beach Golf Course
- Kona Dog Beach
- Kuki’o Golf & Beach Club
- Hapuna Golf Course
- Kona Country Club
- Makalawena Beach
- Nanea Golf Club
- Kealakekua Bay State Historical Park
- Mauumae Beach
- ʻAlula Beach
- Honokohau Beach
- Pololū Beach
- Mahaiʻula Beach
- Wawaloli Beach
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