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Compare 420 Vacation Homes in Kailua with updated reviews, rates, and availability.

Stunning Kaikea 4Br/4Ba Estate: Luxurious and Private - 5 min from Lanikai Beach
10.0 out of 10, Exceptional, (1)
Stunning Kaikea 4Br/4Ba Estate: Luxurious and Private - 5 min from Lanikai Beach
Experience the Beauty of Paradise, Stunning Gardens, Steps from Kailua Beach
9.6 out of 10, Exceptional, (183)
"Great location, Zak was easy to communicate with and Susie and Steve were so helpful. We would stay here again."
Experience the Beauty of Paradise, Stunning Gardens, Steps from Kailua Beach
Bayside Haven- Pool and Hot Tub
10.0 out of 10, Exceptional, (12)
"We couldn't have imagined a more beautiful location and house for a special family gathering! Everything we needed to relax and enjoy our vacation "
Bayside Haven- Pool and Hot Tub
Direct Oceanfront in the Heart of Waikiki! Spectacular New Custom Reno!!
9.8 out of 10, Exceptional, (43)
"Absolutely as advertised! Perfect beach Condo for our group of 7. Very thoughtful layout and amenities. Responsive Host!"
The price is SAR 1,122
SAR 2,952 total
includes taxes & fees
29 Sep - 30 Sep
Direct Oceanfront in the Heart of Waikiki! Spectacular New Custom Reno!!
Aloha Adventure Home - 2 min from beach
9.2 out of 10, Wonderful, (17)
"It was nothing fancy but it was exactly what we needed this trip. The neighborhood is a little run down but the house was excellent."
Aloha Adventure Home - 2 min from beach
Newly renovated Waikiki Sunset unit with STUNNING Diamond Head and ocean views
10.0 out of 10, Exceptional, (42)
"My husband and I recently celebrated our 37th anniversary. Our daughter and son-in-law both turned 30 this year. To celebrate these special occasions, we decided to go to Hawaii. We saw this listing and fell in love with the photos, descriptions, and read all the very positive reviews about our host, Kameron. When we arrived at the condo, the checkin was very easy. I was in awe of how beautiful the unit is and the view is so spectacular. The condo is very clean, well stocked, and a stone’s...
Newly renovated Waikiki Sunset unit with STUNNING Diamond Head and ocean views
Waikiki Sunset Hotel remodeled unit with a magnificent view of the Koʻolau Range
10.0 out of 10, Exceptional, (30)
"Wonderful condo! Was within walking distance to the beach, restaurants and shops. Parking lot always had enough spots and getting in/out was easy. The kids loved the pool! The view was amazing and we saw several rainbows. Kameron was a wonderful host! He checked in with us several times to make sure we had everything we needed and had great recommendations. The check in/check out process was super easy. We highly recommend this condo and would stay here again in a heartbeat! "
Waikiki Sunset Hotel remodeled unit with a magnificent view of the Koʻolau Range
Oceanview Oasis - Ocean views, AC
8.0 out of 10, Very Good, (1)
Oceanview Oasis - Ocean views, AC
BEACH FRONT ESTATE, STEPS TO KAILUA BEACH, OCEAN VIEWS, HUGE LUSH PROPERTY
9.2 out of 10, Wonderful, (120)
"Absolutely loved this property! Very clean and spacious home that comfortably accommodated my family of 4. The backyard and both patios served as a great reprieve from sun on the beach. Ocean views from second floor balcony and just steps from the beach which was wasn’t crowded at all-it felt like our own private oasis! Can’t wait to return!"
BEACH FRONT ESTATE, STEPS TO KAILUA BEACH, OCEAN VIEWS, HUGE LUSH PROPERTY
Hale Aina, walkable to beach, A/C
10.0 out of 10, Exceptional, (16)
"The location is a minute walk away from the beach, and you can see and feel the ocean from the property. Nice quiet location where you can feel the nature of the island."
Hale Aina, walkable to beach, A/C
Studio within 7 minute walk of Waikiki Beach
9.4 out of 10, Exceptional, (8)
"Great place to stay! I had a wonderful time and all the accommodations are accurate. Parking is a pain but that’s the nature of Waikiki. 10/10."
The price is SAR 307
SAR 832 total
includes taxes & fees
2 Oct - 3 Oct
Studio within 7 minute walk of Waikiki Beach
Hawaii Palm B - Beachfront, Hot Tub
8.8 out of 10, Excellent, (10)
"House was absolutely perfect for our trip. Well maintained. Semi Private Beach is within feet from property made for wonderful beach time and amazing views. Sunrises were speechless. Listening to the sounds of the waves at night was so relaxing. Teens had a blast playing basketball and having the spacious backyard was great. Beds were comfortable. Big spacious kitchen, laundry on site. Beach towels, boogie boards, snorkels, beach toys and hot tub were perfect to complete our stay. Host and...
Hawaii Palm B - Beachfront, Hot Tub
Oceanside Estate - Spacious home with Pool & AC
10.0 out of 10, Exceptional, (2)
"This house was amazing. I couldn't ask for a better location. Near beaches PPC BYU Hawai, Big house with plenty of room for the whole family. We especially loved the pool. Host was so easy to work with the house is even better then the pictures"
Oceanside Estate - Spacious home with Pool & AC
Laie Family Escape - 2 min walk to beach
9.6 out of 10, Exceptional, (14)
"Property was ideal for a large group. Great location near lots of different beaches and a nice trail to walk on. "
Laie Family Escape - 2 min walk to beach
Oahu Paradise - AC, 1 block to beach!
8.4 out of 10, Very Good, (8)
"Check in was easy. Loved waking to the beach and the grocery store. Plenty to do on the north shore with pretty easy access - traffic is always a guess.. we loved that there were beach items for our use and a nice big patio AND lanai - I wish we had spent more time on that lanai!"
Oahu Paradise - AC, 1 block to beach!
Ocean View Escape - Gorgeous ocean views, AC
Ocean View Escape - Gorgeous ocean views, AC
Impeccable Penthouse - Ocean & Diamondhead Views
9.8 out of 10, Exceptional, (159)
"Our host - Jan - was absolutely amazing and has kitted the condo out perfectly. The room was perfect for our needs - super clean. The bed was VERY comfortable! A great studio suite. Highly recommend for proximity to ocean and Waikīkī. 👍"
Impeccable Penthouse - Ocean & Diamondhead Views
Sunrise Escape, AC, 2min drive to beach, in Kahuku
10.0 out of 10, Exceptional, (12)
"The property was clean, comfortable, & in a great location. The property managers were incredibly responsive when we reported the fire alarm battery beeping (the only issue we had & they fixed it immediately). The neighborhood was quiet & the house exactly as represented in the photos. We loved being around the corner from all the food trucks & 7 brothers & the local beaches were uncrowded & beautiful. Highly recommend this property & would stay there again. Thanks!"
Sunrise Escape, AC, 2min drive to beach, in Kahuku
White Hibiscus B -home on Laie Point, Beach access
10.0 out of 10, Exceptional, (1)
"We traveled as a group of 15, four families, for ten days in Laie point. The house was so great, room for kids to play, adults played cards, and room for large group meals. Each bedroom had a bathroom with shower for each family to retreat to during the day. The view is unbelievable and the semiprivate beach was so special. No one wanted to leave as it was such a special experience."
White Hibiscus B -home on Laie Point, Beach access
Family friendly home in Hauula; steps from beach
10.0 out of 10, Exceptional, (5)
"Our family really enjoyed our time together. From Tiffany keeping in contact with me made it easy to know what was expected. Our little one year old had a great yard to play in. She enjoyed the beach also. Beach toys were available for her to play with. The older kids enjoyed the beach. The shopping center directly across the road made it convenient for last minute items. The Polynesian Cultural Center was just ten minutes away. Thank you for a great family bonding time."
Family friendly home in Hauula; steps from beach
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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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Other property types in Kailua

BEACH FRONT ESTATE, STEPS TO KAILUA BEACH, OCEAN VIEWS, HUGE LUSH PROPERTY
9.2 out of 10, Wonderful, (120)
"Absolutely loved this property! Very clean and spacious home that comfortably accommodated my family of 4. The backyard and both patios served as a great reprieve from sun on the beach. Ocean views from second floor balcony and just steps from the beach which was wasn’t crowded at all-it felt like our own private oasis! Can’t wait to return!"
BEACH FRONT ESTATE, STEPS TO KAILUA BEACH, OCEAN VIEWS, HUGE LUSH PROPERTY
Kuhio Banyan Club
2.0 star property
6.8 out of 10, (1715)
"Nice easy check in and out."
The price is SAR 349
SAR 566 total
includes taxes & fees
29 Sep - 30 Sep
Kuhio Banyan Club
Aston Waikiki Sunset
4.0 star property
7.8 out of 10, Good, (2791)
"I like this hotel but this time I needed to change the room because it was dirty. "
The price is SAR 673
SAR 949 total
includes taxes & fees
29 Sep - 30 Sep
Aston Waikiki Sunset
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.