Search Holiday Homes in Kailua-Kona

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Browse Select Kailua-Kona Holiday Homes

Stunning Ocean Views + Designer Designed Kona Home
9.8 out of 10, Exceptional, (70)
"What a beautiful, well maintained place. Was a wonderful experience! "
Stunning Ocean Views + Designer Designed Kona Home
Panoramic view of ocean. Excellent location. Quiet neighborhood. Sleep 10
10.0 out of 10, Exceptional, (19)
"We had an amazing experience at this VRBO! The house was clean, comfortable, and well-stocked with everything we needed. The owner was responsive and helpful with the check-in/out process. He even provided an extensive list of recommendations before our trip. The view from the lanai is unparalleled. I would highly recommend this VRBO for anyone visiting Kona!"
Panoramic view of ocean. Excellent location. Quiet neighborhood. Sleep 10
Kimo's Getaway
10.0 out of 10, Exceptional, (54)
"All good!!!!"
The price is £301
includes taxes & fees
25 Sept - 26 Sept
Kimo's Getaway
Beautiful Pool with Stunning Ocean and Sunset Views
9.4 out of 10, Exceptional, (48)
"Stayed at the property for 3 nights. Large kitchen and living room area. Outside cookout area was relaxing next to the pool. Neighbors were quiet. "
Beautiful Pool with Stunning Ocean and Sunset Views
Kona Ocean View Home - Downtown, Fruit Trees, Sunset views
10.0 out of 10, Exceptional, (110)
"Property is well maintained and very comfortable. Would suggest the owner provide a book/binder including information on TV operation, a map indicating parking and posting of checkout time (maybe a tasteful small sign on the refrigerator or other obvious location.). (Master bedroom window would not close completely.)"
The price is £310
includes taxes & fees
15 Oct - 16 Oct
Kona Ocean View Home - Downtown, Fruit Trees, Sunset views
Afforable & quaint upstairs 2Bedroom 1Bath apartment with lanai and Ocean views
9.8 out of 10, Exceptional, (16)
"It was great. Five star experience."
Afforable & quaint upstairs 2Bedroom 1Bath apartment with lanai and Ocean views
Direct Oceanfront Condo on Private Beach Resort *Central AC *
9.6 out of 10, Exceptional, (152)
"We found the property everything we needed. Clean and quiet with all the amenities we needed. We will be back!"
Direct Oceanfront Condo on Private Beach Resort *Central AC *
Hale Nene | Private Pool
10.0 out of 10, Exceptional, (5)
"A Family trip to Kona planned a year ago went beautifully! 10 of us flew from California and ended up at this amazing home! We were all so pleased, especially the kiddos as they were in the pool from 8am to 8pm with so many pool toys to keep them occupied!! All the rooms were perfect, the kitchen was made for a large group and was equipped with all you needed. But the best was the doors to the back with the view and pool. We all enjoyed ourselves immensely! Thank you, Kona and to this beautiful...
Hale Nene | Private Pool
Exotic Kona Bay Hawaii Beachfront Tropical Paradise Stunning Home.
10.0 out of 10, Exceptional, (141)
"This home is dreamy. It is open-air so you always have the feeling of being in synch with the Hawaiian air. It is uniquely divided into rooms that provide privacy. The Master suite is amazing. There is no air conditioning, so if you are coming in the middle of summer, be prepared to use fans in the evening as it can be warm and stuffy. The infinity pool was as advertised, and the views of the ocean were surreal. A short 5-minute walk gets you down the beach to a swimmable cove that was never...
Exotic Kona Bay Hawaii Beachfront Tropical Paradise Stunning Home.
Walk to Beach! HUGE 5 bedroom, 5 bath with Pool!!
9.2 out of 10, Wonderful, (85)
"Lovely spacious cool accommodations We walked to hiking beach restaurants from this fabulous location Water views Short drive to wonderful hiking and historic sites Perfect location for IRONMAN TRIATHLON EACH ROOM VERY PROVATE FOR COUPLES TO ENJOY"
Walk to Beach! HUGE 5 bedroom, 5 bath with Pool!!
🏖️Stunning Ocean Front Views - AC | Rate Special, 9/1 - 10/16/24, $689/n++. | vrKCV
9.8 out of 10, Exceptional, (48)
"We loved staying at this property. Concierge service was fantastic. Property is located within walking distance to restaurants and shopping. The home is very spacious and well maintained. Caution to summer renters: there is no air conditioning in the main living area and kitchen so it is quite warm in the daytime. At night, there is a ocean breeze to help but still warm. The bedrooms do have air conditioning so sleeping is fine. "
🏖️Stunning Ocean Front Views - AC | Rate Special, 9/1 - 10/16/24, $689/n++. | vrKCV
Panoramic Ocean Front Views! Private Corner Townhouse. AC included! Pickleball!
9.8 out of 10, Exceptional, (176)
"Clean fully stocked with everyrhing you need. Beach within 2 min walk. Quiet at night. Very nice place to stay. Close to downtown, parking on site right outside your door. We would stay here again!"
Panoramic Ocean Front Views! Private Corner Townhouse. AC included! Pickleball!
Private ocean view oasis with dream pool, rooftop deck, vaulted ceilings
9.2 out of 10, Wonderful, (17)
"Ended up having to find another place half way through the trip. VRBO has not refunded our fee to them."
Private ocean view oasis with dream pool, rooftop deck, vaulted ceilings
Kahalu’u Surf and Snorkel Beachfront Paradise, with Hot Tub
10.0 out of 10, Exceptional, (16)
"Loved the location of this home! It was a great home to stay in with our family, the only thing is that the bedrooms didn’t have a twin bed like I thought. It was a pull out bed from the queen bed, wet l which was fine but distant l different than what was advertised. It would also have been great to gave a better umbrella for the beach. I would definitelyStay here again!"
Kahalu’u Surf and Snorkel Beachfront Paradise, with Hot Tub
Charming townhome with WiFi in Kailua-Kona
2.0 star property
The price is £414
includes taxes & fees
22 Sept - 23 Sept
Charming townhome with WiFi in Kailua-Kona
Dolphin Manor: Stunning Oceanfront Home w/Pool, Spa, A/C, Private Lanai
9.8 out of 10, Exceptional, (14)
"This property was perfect for our family of 11. Most in Hawaii for the first time. It was worth every penny to stay in beautiful Dolphin Manor. We loved being all together enjoying the shared spaces, especially the lanai which was very safe for our youngest grandson of 19 months. Plenty of bedrooms, most with a view of the ocean and very nice spacious bathrooms. We made wonderful memories on this trip of a lifetime!"
Dolphin Manor: Stunning Oceanfront Home w/Pool, Spa, A/C, Private Lanai
Awesome View, Best Snorkel Beach, Big Lanais, Private Home
9.4 out of 10, Exceptional, (78)
"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
Hale Pua: Private Oceanfront Luxury Home w/Pool, Spa, AC & Lanai - Relax & Enjoy
9.6 out of 10, Exceptional, (80)
"Fabulous property! It was beyond our expectations and the home was perfect for our family! 10 out of 10! We will definitely book again!"
Hale Pua: Private Oceanfront Luxury Home w/Pool, Spa, AC & Lanai - Relax & Enjoy
🏖️Ocean View Home with Pool Walking Distance to Ocean and Beach | vrKCV
9.6 out of 10, Exceptional, (75)
"Wow - this house is amazing. It was perfect for our group of 6. Super clean and well stocked. The pool was fantastic and location could not be beat. We could walk everywhere and it was safe with good sidewalks. The bonus keiki beach across the street was also awesome. The AC units were really nice to have. Will definitely be back! "
🏖️Ocean View Home with Pool Walking Distance to Ocean and Beach | vrKCV
Direct Oceanfront 2BR/2BA Townhouse with Pool and Pickleball & Tennis Courts
9.4 out of 10, Exceptional, (130)
"First, the direct ocean front access was completely incredible. It was so soothing to watch the sunset on the back porch and hear the waves all night long. The house was clean, in a great location, and it was helpful to have parking directly in front of the entry door. There was plenty of space in both bedrooms as well as the bathrooms. We didn't have time to use any of the beach equipment because of other things we had planned, but there was a ton of it under the staircase storage room. There...
The price is £417
includes taxes & fees
22 Sept - 23 Sept
Direct Oceanfront 2BR/2BA Townhouse with Pool and Pickleball & Tennis Courts
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Other property types in Kailua-Kona

Sea Village
2.5 star property
8.6 out of 10, Excellent, (44)
"Room was super hot and no AC. Portable AC was locked so couldn't use."
The price is £146
includes taxes & fees
26 Sept - 27 Sept
Sea Village
Aston Kona by the Sea
4.0 star property
8.8 out of 10, Excellent, (1017)
"Third time we have stayed here. Overall very nice. This was the worst condo of the three we stayed in. Grounds are well taken care of. Staff are very friendly and helpful. Beautiful ocean views from lanai and condo. Very clean and safe place to stay. Very close to all activities so very convenient. I had to fix both toilets on the condo as they were not flushing correctly. One toilet in second bathroom was leaking and continued to run periodically. The ceiling fan in the living room...
The price is £385
includes taxes & fees
29 Sept - 30 Sept
Aston Kona by the Sea
Castle Kanaloa at Kona
3.0 star property
7.6 out of 10, Good, (409)
"I really love the Stay Amazing. I would definitely book here all the time. Trust me when I say you’ll never regret it."
Castle Kanaloa at Kona
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.