Holiday Homes in Kailua-Kona

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Featured Holiday Homes in Kailua-Kona

Afforable & quaint upstairs 2Bedroom 1Bath apartment with lanai and Ocean views

9.8 out of 10, Exceptional, (20)
"Clean and stylish (not quaint at all). Relaxing, with a terrific porch overlooking the ocean. Surprisingly cool, temperature-wise. No air conditioning, but did not need it. Luxurious beds, like sinking into a pan of marshmallow foam. Stay here. "
Afforable & quaint upstairs 2Bedroom 1Bath apartment with lanai and Ocean views

Kona Ocean View Home - Downtown, Fruit Trees, Sunset views

10.0 out of 10, Exceptional, (117)
"A gorgeous get away, great vibe and the softest turkish towels! Sarah is very responsive and super helpful with suggestions for things to do. "
The price is AU$666
includes taxes & fees
10 Dec - 11 Dec
Kona Ocean View Home - Downtown, Fruit Trees, Sunset views

Kona Oceanfront-Gorgeous, Quiet, Sleeps 6

9.8 out of 10, Exceptional, (127)
"The home was clean and well appointed. Unfortunately we saw issues with the maintenance staff. They persisted in parking in our assigned shaded spot leaning us to park in the sun everyday. They painted all the parking spots while we were here blocking us out and they parked in our spot even before and after painting. The pool maintenance people had not checked the hot tub water level for at least 2 days and it gurggled and sputtered for those first 2 days. We are leaving today and is is low on...
Kona Oceanfront-Gorgeous, Quiet, Sleeps 6

Panoramic view of ocean. Excellent location. Quiet neighborhood. Sleep 10

10.0 out of 10, Exceptional, (23)
"The house is truly stunning with a breathtaking view from the lanai, and is equipped with everything you need for a stay. Given the altitude the air is much cooler than at sea level. The owner Radu is very kind and helpful, and also gave us valuable tips for visiting the island. I absolutely recommend a stay here."
Panoramic view of ocean. Excellent location. Quiet neighborhood. Sleep 10

Beautiful Pool with Stunning Ocean and Sunset Views

9.6 out of 10, Exceptional, (51)
"Great location good house the host was a good communicator "
Beautiful Pool with Stunning Ocean and Sunset Views

Elegant Giant Oceanfront Estate - steps to Magic Beach with pool, sub zero

10.0 out of 10, Exceptional, (35)
"Excellent communication by/with property manager."
Elegant Giant Oceanfront Estate - steps to Magic Beach with pool, sub zero

Awesome View, Best Snorkel Beach, Big Lanais, Private Home

9.4 out of 10, Exceptional, (79)
"House was in excellent repair. Everthing was clean and working properly. Host communication was quick and welcoming. Thanks for letting us use your home, we had a great visit!"
Awesome View, Best Snorkel Beach, Big Lanais, Private Home

Paradise palm Studio

9.6 out of 10, Exceptional, (10)
"Bathroom has a sliding door with no lock, but otherwise excellent, extremely clean and great hosts"
Paradise palm Studio

KONA 3 MASTER 3 BATH-CLOSE 2 BEACH- OCEAN VIEWS-UPGRADES-QUIET central AC

9.6 out of 10, Exceptional, (141)
"This house was perfect for the 5 of us. There was everything we could’ve needed plus more. It made our week here for our daughter’s wedding comfortable and stress free. "
KONA 3 MASTER 3 BATH-CLOSE 2 BEACH- OCEAN VIEWS-UPGRADES-QUIET central AC

Dolphin House | 3 Bed, 3.5 Bath

10.0 out of 10, Exceptional, (1)
"We had a great stay at the dolphin house while enjoying pool, view and home. The home was very well stocked with everything we needed. I would highly recommend this home!"
The price is AU$2,418
includes taxes & fees
10 Dec - 11 Dec
Dolphin House | 3 Bed, 3.5 Bath

🏖️Spectacular Ocean Views | Beautiful Landscaping | Private | vrKCV

10.0 out of 10, Exceptional, (33)
"We were thrilled with our stay at this location. It was so peaceful. We felt relaxed and felt at home immediately walking in the door. They even left an anniversary card for us and snacks. The view was amazing! We had everything we needed to make our meals at the house and we utilize the grill. We enjoyed the pool, as well. David, the concierge, was very helpful throughout our planning process! We are already thinking about our next trip there and will book this house again."
🏖️Spectacular Ocean Views | Beautiful Landscaping | Private | vrKCV

Beautiful conveniently located 2-bedroom ocean view home in Kailua-Kona.

Beautiful conveniently located 2-bedroom ocean view home in Kailua-Kona.

VERY PRIVATE, expansive ocean VIEWS, close to BEST BEACH

10.0 out of 10, Exceptional, (79)
"This was a lovely home, the host was very fast to respond to any questions that came up. Highly recommend! You won’t be disappointed! "
VERY PRIVATE, expansive ocean VIEWS, close to BEST BEACH

Direct Oceanfront Condo on Private Beach Resort *Central AC *

9.6 out of 10, Exceptional, (158)
"We loved the location of this condo. Close to the shops but far enough away from the busyness of the bars and restaurants if you want quiet. The condo is well stocked in the kitchen, lots of bath and beach towels, and plenty of bedding and pillows too. The light switches on the first floor take some time to figure out. Also, the condo is very close to the pool and tennis courts. Can’t say enough good things about this place! "
Direct Oceanfront Condo on Private Beach Resort *Central AC *

Kona Spectacular Ocean Front 5BR, 4BA Pool,Spa,AC

9.0 out of 10, Wonderful, (23)
"The house had plenty of room to accommodate our party of 15 adults. The views off the back lanais are indescribable. Dolphins were a giving us some morning entertainment on one of our mornings there. We drove a little way down to Hapuna Beach and saw sea turtles. Magic Sands Beach was just a mile down the road and a great little spot. It was never crowded when we went or drove by on our way to our next adventure. This stay has actually gotten my family and me Looking into moving there. The...
Kona Spectacular Ocean Front 5BR, 4BA Pool,Spa,AC

The Mai Tai Manor with unobstructed views of the ocean!

9.8 out of 10, Exceptional, (7)
"So blessed to stay in such a beautiful home! Everything was perfect! Sunsets on the patio we’re breathtaking. "
The Mai Tai Manor with unobstructed views of the ocean!

Walk to White Sands Beach or Relax by Your Private Pool

9.6 out of 10, Exceptional, (215)
"Great property, especially for families with kids. The pool comes in handy when the ocean is not cooperating. Great amenities was surprised to find a rice cooker in the kitchen score!"
Walk to White Sands Beach or Relax by Your Private Pool

🏖️Enjoy Breathtaking Sunsets over Keauhou Bay | Concierge Included | vrKCV

9.4 out of 10, Exceptional, (63)
"Our family of 8 had plenty of bedrooms, bathrooms and open space to spread out. We enjoyed the pool every day and outdoor space was easily accessed and provided plenty of seating for our group. The mango tree provided fruit for every breakfast and was delicious! Even though there was no ac and we were staying in late July the many windows and ceiling fans and pool kept us cool. Just a suggestion...beach chairs were sparse and more would have been appreciated. We would recommend this great family...
🏖️Enjoy Breathtaking Sunsets over Keauhou Bay | Concierge Included | vrKCV

🌴This beautiful, one of a kind 3-story home is located directly on the shoreline in Kona🌴

9.6 out of 10, Exceptional, (24)
"Excellent location,service.Highly recommended."
🌴This beautiful, one of a kind 3-story home is located directly on the shoreline in Kona🌴

Breathtaking Kona Home - Heated Pool / Air conditioning and Beautiful Sunsets

10.0 out of 10, Exceptional, (149)
"Wonderful place- good space for family to spread out. The grill was fantastic. If I had to complaint about something, we would’ve liked the pool to be a tad warmer on a few days, but the kids still enjoyed it often after days spent touring the island. Grateful for a private retreat to allow for memorable family vacation!"
Breathtaking Kona Home - Heated Pool / Air conditioning and Beautiful Sunsets
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Other property types in Kailua-Kona

Sea Village

2.5 star property
8.6 out of 10, Excellent, (55)
"It would have been nice to know that the a/c was an additional charge. But over all it was nice"
The price is AU$505
includes taxes & fees
5 Dec - 6 Dec
Sea Village

Aston Kona by the Sea

4.0 star property
8.8 out of 10, Excellent, (1032)
"Feels like a family owned & operated business. Amenities are not new/ updated but my family traveling appreciates the location & value. "
The price is AU$696
includes taxes & fees
5 Dec - 6 Dec
Aston Kona by the Sea

Kona Reef, A Raintree Vacation Club Resort

3.0 star property
8.6 out of 10, Excellent, (383)
"Great Customer Service!! 👍"
Kona Reef, A Raintree Vacation Club Resort
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
Beautiful view of the beach with palm trees

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Members save 30%+ on selected hotels until 4 Dec (property time) with our Black Friday deals. Stay by 15 Dec 2025.