Search Holiday Homes in Kailua-Kona

    price find illustration

    Change your mind

    Book hotels with free cancellation
    deals illustration

    Treat yourself

    Save instantly and earn perks with One Key
    Learn about One Key
    bed illustration

    Be picky

    Search almost a million properties worldwide

Check prices for these dates

Next weekend
18 Jul - 20 Jul
In two weeks
25 Jul - 27 Jul
In one month
8 Aug - 10 Aug
In two months
5 Sept - 7 Sept

Browse Select Kailua-Kona Holiday Homes

Kona Ocean View Home - Downtown, Fruit Trees, Sunset views
Enjoy cooking in this well-lit kitchen with a large window view and modern appliances.

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

10.0 out of 10, Exceptional, (151)
"Great stay. Great amenities. Be aware it is 2nd floor with only stair access. "
The price is £286
includes taxes & fees
15 Jul - 16 Jul
Kona Ocean View Home - Downtown, Fruit Trees, Sunset views
Walk to White Sands Beach or Relax by Your Private Pool
Relax by the serene pool surrounded by lush greenery and palm trees.

Walk to White Sands Beach or Relax by Your Private Pool

9.6 out of 10, Exceptional, (237)
"We had a mix of family time while the younger set did snorkeling boogie boarding and hiking. Loved the pool "
Walk to White Sands Beach or Relax by Your Private Pool
Rare BEACH FRONT Home at Kona Surf and Racquet Club. Accessible beach 🏖️
Guests can enjoy a beachside setting with a palm tree and ocean views.

Rare BEACH FRONT Home at Kona Surf and Racquet Club. Accessible beach 🏖️

9.8 out of 10, Exceptional, (92)
"We loved our stay at this oceanfront property! The sunsets were second to none here!"
The price is £458
includes taxes & fees
29 Jul - 30 Jul
Rare BEACH FRONT Home at Kona Surf and Racquet Club. Accessible beach 🏖️
Elegant Giant Oceanfront Estate - steps to Magic Beach with pool, sub zero
Relax in this ocean-view space with a table and chairs, perfect for dining or unwinding.

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

10.0 out of 10, Exceptional, (44)
"We had a perfect getaway staying here. 6 nights, 12 people, grandparents, friends and our kids gathered for a birthday getaway!Our host Anne was wonderful and got us oriented. The house is amazing and private, with our own little walkway to the ocean for sunset drinks. We had easy walk to Magic Sands Beach, and nice drives to beaches and snorkeling spots. It was a two hour drive to see the volcano erupting, and 1.25 hours to the top of Mauna Kea for stargazing. House was fully accommodating...
Elegant Giant Oceanfront Estate - steps to Magic Beach with pool, sub zero
Spacious 4-bedroom house plus bunk room with WiFi and AC in charming Kailua-Kona
Relax by the ocean with a refreshing swim or sunbathe on the poolside lounge chairs.

Spacious 4-bedroom house plus bunk room with WiFi and AC in charming Kailua-Kona

10.0 out of 10, Exceptional, (3)
"We really enjoyed our stay at this house. The location was great for teens with an easy walk to town, parks and beaches. Open floor plan was great for relaxing by the pool and enjoying the ocean view. Ample private space for the adults and the home was well stocked. Would stay again for certain. "
Spacious 4-bedroom house plus bunk room with WiFi and AC in charming Kailua-Kona
Oceanfront Kona Beach House
Relax on the deck with a hot tub overlooking the ocean, surrounded by comfortable seating and a secure railing.

Oceanfront Kona Beach House

10.0 out of 10, Exceptional, (77)
"This home is just lovely-clean, very well equipped and right on the ocean. We certainly would stay here again. "
Oceanfront Kona Beach House
Don`t miss out on This Amazing Home for your vacation.
Relax by the serene pool surrounded by lush tropical plants and palm trees.

Don`t miss out on This Amazing Home for your vacation.

9.8 out of 10, Exceptional, (130)
"We are a group of 3 couples that came for a beach elopement and 3 of us had 50th birthdays to celebrate!The house and property are gorgeous! The house has absolutely everything we needed, and it is in a perfect location (we had a rental car)There is snorkeling, shopping and activities all within a 10 minute drive.The pool area was our favorite place to be every day and the beds are super comfy too! Annie, the host, was very responsive, helpful and went above and beyond. We truly enjoyed our stay...
Don`t miss out on This Amazing Home for your vacation.
Direct Oceanfront Condo on Private Beach Resort *Central AC *
Enjoy a scenic ocean view from this outdoor picnic table, situated on a platform surrounded by volcanic rocks and lush greenery.

Direct Oceanfront Condo on Private Beach Resort *Central AC *

9.6 out of 10, Exceptional, (169)
"************terrific"
Direct Oceanfront Condo on Private Beach Resort *Central AC *
UPPER UNIT -1500 sq/ ft - 30 + days !
Guests can enjoy a beachside retreat with access to the ocean.

UPPER UNIT -1500 sq/ ft - 30 + days !

9.8 out of 10, Exceptional, (13)
"We loved staying here. The home has a really nice layout. It was so clean and spacious. The host was very friendly and communicated great. I highly recommed. We really enjoyed the lanai and the host was reaa"
UPPER UNIT -1500 sq/ ft - 30 + days !
Remodeled Kona Home w/Panoramic Ocean Views & Vibrant Sunsets
Enjoy breathtaking views of the surrounding landscape from this balcony, featuring a hammock and a tree-lined view.

Remodeled Kona Home w/Panoramic Ocean Views & Vibrant Sunsets

10.0 out of 10, Exceptional, (3)
" Nice place, will visit again. "
Remodeled Kona Home w/Panoramic Ocean Views & Vibrant Sunsets
Outrigger Paradise Hale Wa a Pale with Private Pool!
Relax by the serene pool overlooking the ocean, surrounded by lush greenery and comfortable lounge chairs.

Outrigger Paradise Hale Wa a Pale with Private Pool!

9.4 out of 10, Exceptional, (43)
"The house is kind of a funky lay out, but it worked perfect for our group of three different house holds. Beautiful viewed, beautiful pool, and large, comfortable space."
Outrigger Paradise Hale Wa a Pale with Private Pool!
Waterfall House | 4 Bed, 3.5 Bath
Relax by the ocean-view pool, surrounded by a deck and shaded by a pergola.

Waterfall House | 4 Bed, 3.5 Bath

8.6 out of 10, Excellent, (26)
"Great place for taking it easy family and friends!! House had everything needed for cook outs and chilling"
The price is £1,288
includes taxes & fees
19 Jul - 20 Jul
Waterfall House | 4 Bed, 3.5 Bath
Magnificent! Private Pool & Hot Tub - 180 degree Ocean View; U pick Orchard
Relax by the pool surrounded by lush greenery and lounge chairs.

Magnificent! Private Pool & Hot Tub - 180 degree Ocean View; U pick Orchard

9.8 out of 10, Exceptional, (165)
"Absolutely lovely property! Loved the outdoor kitchen, pool, hot tub and great lawn for playing badminton and volleyball. "
Magnificent! Private Pool & Hot Tub - 180 degree Ocean View; U pick Orchard
Awesome View, Best Snorkel Beach, Big Lanais, Private Home
Enjoy ocean views from the balcony and dine with friends at the table for four.

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

9.4 out of 10, Exceptional, (84)
"The location was absolutely amazing. Views of the ocean, across the street from the beach, a short drive to downtown. Everything about this stay was absolutely perfect and we can’t wait to come back!!!!"
Awesome View, Best Snorkel Beach, Big Lanais, Private Home
Stunning Ocean Views + Designer Designed Kona Home
Relax on the deck with a swing chair, taking in the breathtaking ocean views.

Stunning Ocean Views + Designer Designed Kona Home

9.8 out of 10, Exceptional, (95)
"Beautiful accommodations and feels like home. Very clean and welcoming."
Stunning Ocean Views + Designer Designed Kona Home
Kimo's Getaway
Enjoy ocean views from this outdoor space with a deck, seating area, and potted plant.

Kimo's Getaway

10.0 out of 10, Exceptional, (70)
"Loved our stay! A little of everything to make our stay good."
The price is £295
includes taxes & fees
13 Jul - 14 Jul
Kimo's Getaway
🏖️Ocean Front | Central AC | Private Pool & Grill | Concierge Included
Relax in style with a bottle of wine and a view of the ocean.

🏖️Ocean Front | Central AC | Private Pool & Grill | Concierge Included

9.8 out of 10, Exceptional, (34)
"Couldn’t have been happier with the condo. It was clean, spacious and had everything we needed. The pool and hot tub were perfect and the location overlooking the golf course and the ocean was a dream. Would definitely book this condo again. "
🏖️Ocean Front | Central AC | Private Pool & Grill | Concierge Included
🏖️Next to Keauhou Bay! | Concierge Included | Large Private Pool & Lanai
Set amidst lush greenery, this two-story residence offers a peaceful retreat with a balcony and outdoor seating area.

🏖️Next to Keauhou Bay! | Concierge Included | Large Private Pool & Lanai

9.4 out of 10, Exceptional, (67)
"This was the best rental we've ever done. Place was great, fully accommodated six adults and four grandkids with beds and baths for all. Excellent indoor and outdoor dining. The pool area was beautifully landscaped and very private. All-in-all, couldn't have had a better stay. Very quit and peaceful."
🏖️Next to Keauhou Bay! | Concierge Included | Large Private Pool & Lanai
🏖️Great Location | Ocean Front Island Home | Pool | Gated
Enjoy stunning ocean views and beach access from this resort's hotel.

🏖️Great Location | Ocean Front Island Home | Pool | Gated

9.6 out of 10, Exceptional, (86)
"Our stay was fabulous - we were there to celebrate an anniversary and my husband's 82nd birthday. It was amazing!"
🏖️Great Location | Ocean Front Island Home | Pool | Gated
🏖️Ocean View | Private Pool, Patio, & Lanai | By Beachside Pier!
Relax by the pool surrounded by lounge chairs and a barbecue grill under a shaded pergola.

🏖️Ocean View | Private Pool, Patio, & Lanai | By Beachside Pier!

9.8 out of 10, Exceptional, (79)
"As expected. Everything was great."
🏖️Ocean View | Private Pool, Patio, & Lanai | By Beachside Pier!
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.
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free