Holiday Homes in Kailua-Kona

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Check prices for these dates

Next weekend
22 Aug - 24 Aug
In two weeks
29 Aug - 31 Aug
In one month
12 Sept - 14 Sept
In two months
10 Oct - 12 Oct

Featured Holiday Homes in Kailua-Kona

Kona Ocean View Home - Downtown, Fruit Trees, Sunset views
Fridge, microwave, oven, stovetop

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

10.0 out of 10, Exceptional, (154)
"Great stay. Great amenities. Be aware it is 2nd floor with only stair access. "
The price is NZ$733
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!
Exterior

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 NZ$478
includes taxes & fees
17 Aug - 18 Aug
Kona Rose's Hideaway is at Kona Plaza, a step from Alii Drive. No Cleaning Fee!
Stunning Ocean Views + Designer Designed Kona Home
Property grounds

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
Pool

🏖️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
Pool

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 🏖️
On the beach, sun-loungers, beach towels

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!
On the beach

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

9.4 out of 10, Exceptional, (99)
"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
On the beach, sun-loungers

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
Terrace/patio

Three Palms

9.8 out of 10, Exceptional, (48)
"We had a wonderful stay at the rental. "
Three Palms
Ocean Breeze Kona Home
On the beach, sun-loungers, beach towels

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
Outdoor dining

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
Outdoor dining

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
Terrace/patio

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
Beach nearby, sun-loungers, beach towels

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

9.4 out of 10, Exceptional, (151)
"Beautiful location and amenities "
The price is NZ$911
includes taxes & fees
27 Aug - 28 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
Outdoor dining

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.
Pool

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

9.8 out of 10, Exceptional, (132)
"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
Outdoor pool, a heated pool

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
Outdoor spa tub

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

8.8 out of 10, Excellent, (31)
"We enjoyed our stay this year at this beautiful home! The house had more than enough beds for everyone and it was clean and comfortable. We really enjoyed listening to the waves crash into the rocks 24/7, very relaxing! We had no idea about the show we got to watch every morning when all the surfers came out to Lyman’s Cove. It was a great treat being able to sit in the hot tub or on the deck and watch them all day long! We already miss this home and will definitely be back! "
Kona Spectacular Ocean Front 5BR, 4BA Pool,Spa,AC
Walk to Beach! HUGE 5 bedroom, 5 bath with Pool!!
Smart TV, books

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

9.4 out of 10, Exceptional, (91)
"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

Kona Coast Resort

Kona Coast Resort

10/10 Excellent
"Very nice area. "
DENNIS 6-night trip
Posted 12 hours ago
Kona Coast Resort