Holiday Homes in Kailua-Kona

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Check prices for these dates

Next weekend
15 Aug - 17 Aug
In two weeks
22 Aug - 24 Aug
In one month
5 Sept - 7 Sept
In two months
3 Oct - 5 Oct

Featured Holiday Homes in Kailua-Kona and around

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, (153)
"Great stay. Great amenities. Be aware it is 2nd floor with only stair access. "
The price is €391
includes taxes & fees
20 Aug - 21 Aug
Kona Ocean View Home - Downtown, Fruit Trees, Sunset views
Kona Rose's Hideaway is at Kona Plaza, a step from Alii Drive. No Cleaning Fee!
Guests can enjoy stunning ocean views from this coastal property, surrounded by palm trees and a rooftop with solar panels.

Kona Rose's Hideaway is at Kona Plaza, a step from Alii Drive. No Cleaning Fee!

10.0 out of 10, Exceptional, (5)
"Great location to experience a beach town experience walking to a variety of food, bars and local places. Enjoyed each evening walking to a different place for a cocktail and either back to the condo for dinner or dinner overlooking the water at a local place Not a White Lotus area and some buildings are a little tired. But well worth the stay "
The price is €225
includes taxes & fees
15 Aug - 16 Aug
Kona Rose's Hideaway is at Kona Plaza, a step from Alii Drive. No Cleaning Fee!
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, (96)
"Beautiful accommodations and feels like home. Very clean and welcoming."
Stunning Ocean Views + Designer Designed Kona Home
🏖️Gorgeous Ocean Front Estate | Gated Community | Walk to Town
Relax by the serene pool surrounded by palm trees and a stone deck.

🏖️Gorgeous Ocean Front Estate | Gated Community | Walk to Town

9.8 out of 10, Exceptional, (46)
"This property was just right for our family of 10 ranging in age of 3-68! Pool/hot tub was a highlight for us all. Keiki beach a short walk away. House was just the right size for all to have privacy and togetherness."
🏖️Gorgeous Ocean Front Estate | Gated Community | Walk to Town
Oceanfront - Private- Family Friendly He'eia Bay-House and Cottage-
Outdoor pool

Oceanfront - Private- Family Friendly He'eia Bay-House and Cottage-

10.0 out of 10, Exceptional, (99)
"The property was beautiful. Our family enjoyed our stay there. "
Oceanfront - Private- Family Friendly He'eia Bay-House and Cottage-
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, (239)
"This was an excellent place to stay. The location and view was as advertised. Communication with owner very good. "
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, (94)
"We loved our stay at this oceanfront property! The sunsets were second to none here!"
Rare BEACH FRONT Home at Kona Surf and Racquet Club. Accessible beach 🏖️
Delightful Ocean/Beach Front - Budget Friendly with AC in Both Bedrooms!
Guests can enjoy breathtaking ocean views from this beachfront accommodation.

Delightful Ocean/Beach Front - Budget Friendly with AC in Both Bedrooms!

9.4 out of 10, Exceptional, (98)
"Right when you open the door, you’re hit with a view of the ocean that can’t be beat. Yes, the unit is a little rough around the edges. But it had everything we needed to feel right at home and thoroughly enjoy our stay. It’s close to groceries and great activities, and the neighborhood is peaceful and well maintained. "
Delightful Ocean/Beach Front - Budget Friendly with AC in Both Bedrooms!
WEST SUITE EXCEPTIONAL 195.00 +10% SUMMER SPECIAL on this beautiful property
Enjoy breathtaking ocean views with waves gently breaking onto the rocky shoreline.

WEST SUITE EXCEPTIONAL 195.00 +10% SUMMER SPECIAL on this beautiful property

10.0 out of 10, Exceptional, (175)
"Great place. I would definitely stay here again."
WEST SUITE EXCEPTIONAL 195.00 +10% SUMMER SPECIAL on this beautiful property
Three Palms
Enjoy ocean views from this balcony with a table and chairs, shaded by a large umbrella amidst lush greenery and palm trees.

Three Palms

9.8 out of 10, Exceptional, (48)
"We had a wonderful stay at the rental. "
Three Palms
Ocean Breeze Kona Home
Enjoy a serene beach experience with calm waters and lush surroundings.

Ocean Breeze Kona Home

9.6 out of 10, Exceptional, (202)
"We have been all over big island and this place is absolutely my fav! Absolutely wonderful "
Ocean Breeze Kona Home
Panoramic view of ocean. Excellent location. Quiet neighborhood. Sleep 10
Enjoy the breathtaking ocean views from this balcony, featuring a round table and comfortable seating.

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

10.0 out of 10, Exceptional, (40)
"Super clean and full of useful stuffGorgeous view and close to family staying on same street"
Panoramic view of ocean. Excellent location. Quiet neighborhood. Sleep 10
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, (46)
"Our group of 10 loved our stay at the Ke-Alohi Kai house. It was walkable to Magic Sands beach, immaculately cleaned, and well-stocked. All elements appeared to be well cared for, and everything including the A/C worked well. Hosts had thought of everything - beach chairs, ample linens, and even some boogie boards. Plenty of space for both relaxing and eating, but also plenty of separate spaces for everyone to feel like they could retreat when they didn’t want to socialize. Gated community made...
Elegant Giant Oceanfront Estate - steps to Magic Beach with pool, sub zero
Private | Oceanview | Spacious | Bright 3BR House
Relax in this serene outdoor space, complete with a green chair and small table, surrounded by lush plants and a white railing.

Private | Oceanview | Spacious | Bright 3BR House

9.6 out of 10, Exceptional, (64)
"We enjoyed our visit in Kona with our family. The couple of small issues were handled by the owners immediately, and we were very grateful for their speedy response. They went above and beyond by sending us a gift for NYE during our stay, which was lovely! Mahalo!"
Private | Oceanview | Spacious | Bright 3BR House
Direct Oceanfront 2BR/2BA Townhouse with Pool and Pickleball & Tennis Courts
Enjoy breathtaking ocean views from this coastal property, featuring a pathway to a building with a flat roof.

Direct Oceanfront 2BR/2BA Townhouse with Pool and Pickleball & Tennis Courts

9.4 out of 10, Exceptional, (150)
"Beautiful location and amenities "
The price is €478
includes taxes & fees
17 Aug - 18 Aug
Direct Oceanfront 2BR/2BA Townhouse with Pool and Pickleball & Tennis Courts
Charming Surfer's dream Hawaiian Home near Lyman Beach on Ali'i Drive
Relax in a serene outdoor seating area with a round table and four comfortable chairs, surrounded by lush greenery and a tranquil body of water.

Charming Surfer's dream Hawaiian Home near Lyman Beach on Ali'i Drive

9.6 out of 10, Exceptional, (14)
"Very convenient and ideal location. Watched people surfing every morning of our stay. Had everything you would need for a stay. "
Charming Surfer's dream Hawaiian Home near Lyman Beach on Ali'i Drive
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, (131)
"As local Hawai’i residents we were stoked with Annie’s house in Kailua-Kona! It was close to stores and restaurants and the pool was a huge plus! We cannot wait to return for our next girls trip 😍"
Don`t miss out on This Amazing Home for your vacation.
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, (4)
"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
Kona Spectacular Ocean Front 5BR, 4BA Pool,Spa,AC
Relax in a hot tub surrounded by palm trees and enjoy unobstructed ocean views.

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

8.8 out of 10, Excellent, (30)
"Outstanding location, right on the water, with great views and a real feeling of being at a private resort. Wonderful features and lay out. Property managers were very responsive and solved a small problem immediately. "
Kona Spectacular Ocean Front 5BR, 4BA Pool,Spa,AC
Walk to Beach! HUGE 5 bedroom, 5 bath with Pool!!
Relax in this airy living room with a high ceiling, comfortable sofa, and large windows.

Walk to Beach! HUGE 5 bedroom, 5 bath with Pool!!

9.4 out of 10, Exceptional, (90)
"Annual family vacation to the Islands and this was by far the best property we’ve stayed at. Entire experience was very good. We had a group of 10 (8 adults and 2kids). The pool was used extensively."
Walk to Beach! HUGE 5 bedroom, 5 bath with Pool!!
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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Top Kailua-Kona Hotel Reviews

PACIFIC 19 Kona

PACIFIC 19 Kona

10/10 Excellent
"Good place. Nice and clean "
Raghuveer 3-night trip
Posted 1 day ago
PACIFIC 19 Kona