Holiday houses in Kailua-Kona

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Popular amenities for Kailua-Kona holiday rentals

Stay near Kailua-Kona's top sights

Kona Brewing Company226 locals recommend
Island Lava Java163 locals recommend
Huggo's162 locals recommend
KTA Super Stores156 locals recommend
Umekes Fish Market Bar & Grill153 locals recommend
Costco Wholesale153 locals recommend

Other great holiday rentals in Kailua-Kona

Top Guest favourite
Condo in Kailua-Kona
4.95 out of 5 average rating, 40 reviews

Coastal Paradise with a fabulous ocean view.

SonjaRating, 5 stars4 weeks ago
The view is unbelievably beautiful! Located right on the ocean’s edge. Fell asleep nightly to the sounds of the ocean! Spent every morning enjoying coffee on the lanai taking in the beauty. The condo was beautifully maintained! Betsy was a great host. When we return to the Big Island we will absolutely stay here again! Loved it!!!
Guest favourite
Condo in Keauhou
4.9 out of 5 average rating, 51 reviews

Ocean Front | Sleeps 6 | Poolside Penthouse

MeganRating, 5 stars1 week ago
We had a lovely stay. The complex is slightly older but matches the pictures well. The primary bedroom is actually a loft so if you have others in your party that wake up earlier, just keep this in mind. But we loved it here. We wanted to stay outside of Kona’s downtown, but we were just two minutes though from a shopping center and many restaurants. Downtown Kona is about 15-20 minutes. The views are amazing and this condo gives you more of a condo complex feel rather than resort, which means the pool was never crowded and it’s not loud. You can sit and enjoy the pool and ocean. I’d definitely stay again!
Superhost
Apartment in Waikoloa Village
4.71 out of 5 average rating, 7 reviews

NEW! Big Island Stay w Golf, Pickleball, Views!

KathyRating, 5 stars4 months ago
This condo is very quiet, overlooking the golf course and ocean. Nice sunsets. We really enjoyed the golfing (reasonable rate with the member's pass), and pickleball/tennis is very close ...beside the pool. Close by is a gym - which had a big workout area and daily cardo classes. Also - a very good grocery store nearby. The condo was well set-up for the two of us. particularly helpful were the beach chairs, umbrellas, etc. We spent many afternoons visiting different beaches along the Waikoloa coast. Some were a few miles away, others about 15 min drive. The guidebook in the condo was very helpful.
Superhost
Home in Kealakekua
5 out of 5 average rating, 9 reviews

Mountain Oasis: Modern Plantation Home

SreenivasRating, 5 stars8 months ago
Chris is an amazing host and is very clear in his communication. House was exactly as described. Very clean and well maintained. Kitchen was stuffed with a lot of condiments and a lot of attention to details. Yard had many fruit bearing trees. A quick drive to nice beaches, restaurants, grocery stores etc. All in all we were very satisfied.
Top Guest favourite
Condo in Waikoloa Village
4.95 out of 5 average rating, 82 reviews

Fabulous Waikoloa Beach Resort 3BR Colony Villas

AustinRating, 5 stars2 months ago
Great communication, very comfortable accommodations and in a great spot for all the things you would want to do on the big island.
Top Guest favourite
Condo in Waimea
4.98 out of 5 average rating, 56 reviews

Exquisite Sunsets and Beaches at Mauna Lani Resort

Marie And AlecRating, 5 stars1 month ago
Allyson is efficient, provided us with great info on what activities, resturants, shopping, and as I briefly mentioned, was remarkably supportive and kind during a medical emergency we were facing. Thank you Allyson.
Guest favourite
Apartment in Kailua-Kona
4.93 out of 5 average rating, 61 reviews

The Great Kona Escape - Private Ohana

DiishanRating, 5 stars3 months ago
Sandra’s place was really really nice. It felt very much like home. It was super clean, cozy, decorated nicely, and had everything I needed. Sandra was also super kind, responded very quickly to any of my messages, and was very accommodating. I’ll def book her place again when in Kona.
Guest favourite
Condo in Kailua-Kona
4.95 out of 5 average rating, 83 reviews

Oceanfront 2 bed, 2 bath, kitchen with full AC!

KooroshRating, 5 stars1 week ago
This place was neat and clean. The kitchen was stocked with many of the things we needed. The host was very helpful and responsive. We really loved sitting on the lanai having our morning coffee as the sun came up. This place is on the west side of the island so we were able to catch a couple of beautiful sunsets as well. There were a lot of places to see and do in the town nearby. It is within walking distance but there is no sidewalk so at times it felt safer to drive there. We stayed here for 3 nights and wished we could have stayed longer. We recommend this place to anyone looking for a quiet place to enjoy Hawaii.

Quick stats about holiday rentals in Kailua-Kona

  • Total rentals

    2.3K properties

  • Total number of reviews

    101K reviews

  • Family-friendly rentals

    1.1K properties are a good fit for families

  • Pet-friendly rentals

    80 properties allow pets

  • Rentals with a pool

    1.9K properties have a pool

  • Rentals with dedicated workspaces

    1.2K properties have a dedicated workspace

Destinations to explore

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