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Holiday Homes in Kailua

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Featured Holiday Homes in Kailua

Beachfront Hawaiian Private Villa Premium Location on Usno1 Beach
The price is AU$4,748 per night from 11 Aug. to 11 Aug.
Situated on the beach, this property is within a 5-minute walk of Kailua Bay Beach and Kailua Beach. Lanikai Beach is 1.3 mi (2.1 km) away.
5/5Exceptional! (1 review)
Greatest Beach House ever.
"Trust me!!! This is where you want to be. Words can’t describe how perfect it was for me and my family and team. Do yourself & your family a favor and book this place."

Reviewed on 4 Jul. 2021

Beachfront Hawaiian Private Villa Premium Location on Usno1 Beach
Kailua Absolutely Oceanfront Views-60' Waterfall Lap Pool
Nestled on the beach, this Kailua holiday home is within 3 mi (5 km) of Kailua Bay Beach, Kailua Beach and Kaneohe Bay. Kalama Beach Park and Kawainui Park are ...
4.6/5Wonderful! (75 reviews)
Amazing!
"We absolutely loved this house. We stayed in the ocean view unit and it really was an amazing view! The pool was amazing and the beds were comfortable…couldn’t ask for more :)"

Reviewed on 18 Jul. 2021

Kailua Absolutely Oceanfront Views-60' Waterfall Lap Pool
Legal Rental Just Steps to Kailua Beach, Pool, Jacuzzi, Bikes, A/C
This family-friendly Kailua holiday home is located by the sea, within a 15-minute walk of Kailua Beach and Lanikai Beach. Kailua Bay Beach and Lanikai Pillboxes ...
4.5/5Wonderful! (42 reviews)
wonderful location!
"great property in a wonderful location. very close to the beach (Kailua truly is the prettiest beach on the island). Our 2-bedroom condo was large enough for our family of four, although the bedrooms were on the smaller side. not an issue since we spent most of our time outside. We enjoyed sitting ..."

Reviewed on 8 Jul. 2021

Legal Rental Just Steps to Kailua Beach, Pool, Jacuzzi, Bikes, A/C
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An Oceanfront Location- Studio + 60 ft lap Pool w/ Waterfalls
Nestled on the beach, this Kailua holiday home is within 3 mi (5 km) of Kailua Bay Beach, Kailua Beach and Kaneohe Bay. Kalama Beach Park and Kawainui Park are ...
4.5/5Wonderful! (65 reviews)
Beautiful location, friendly host and a wonderful lap pool for swimmers.
"Well appointed and well kept unit. It had all the amenities you need and we were welcomed with a bottle of wine and macadamia nuts!"

Reviewed on 29 Jun. 2021

An Oceanfront Location- Studio + 60 ft lap Pool w/ Waterfalls
Brand new Beachside Kailua Breeze
154 Mokumanu Dr, Kailua, HI
Located in Lanikai, this holiday home is steps away from Lanikai Pillboxes Trailhead and Lanikai Beach. Kailua Beach is 0.5 mi (0.9 km) away.
4.9/5Exceptional! (16 reviews)
Amazing stay in Lanikai
"We had such an excellent time staying at Patrick’s rental. We had six adults and two toddlers and it was incredibly comfortable for all of us. Amazingly clean and outfitted with absolutely everything you’ll need and more. One block from the beach. We had an awesome stay and would definitely return. ..."

Reviewed on 3 Feb. 2020

Brand new Beachside Kailua Breeze
Kailua Beach Park Cottage - 1BR
27 Alala Road, Kailua, HI
Situated by the sea, this holiday home is steps away from Kailua Bay Beach and Kailua Beach. Lanikai Beach is 0.5 mi (0.9 km) away.
4.8/5Exceptional! (32 reviews)
Great little spot right near the beach
"We had a fantastic stay at the property. It’s directly across the street from the Kailua Beach Park, a short walk to a market and a few restaurants, and only 20 mins into town by foot. It was perfect for our visit. Bob was extremely friendly and easy to communicate with. We would definitely stay ..."

Reviewed on 26 Jul. 2021

Kailua Beach Park Cottage - 1BR
Gorgeous Renovated 1937 Plantation Style Beach House 50 Steps To The Center Of The Beach 5 Bedroom Home
Located in Kalama Tract, this holiday home is within 1 mi (2 km) of Kalama Beach Park and Kailua Beach. Lanikai Beach is 2.1 mi (3.3 km) away.
Gorgeous Renovated 1937 Plantation Style Beach House 50 Steps To The Center Of The Beach 5 Bedroom Home
Kehaulani - Lanikai~ Stunning Ocean Views~ Private Residence
Located in Lanikai, this holiday home is within 1 mi (2 km) of Lanikai Pillboxes Trailhead and Lanikai Beach. Kailua Beach is 1.5 mi (2.4 km) away.
5/5Exceptional! (1 review)
We loved our stay in this home. It was clean and well maintained. We would probably stay here again
"The Property was well located in a quiet cul de sac. The view was beautiful everyday and the house mangers were very attentive to our needs."

Reviewed on 21 Jan. 2020

Kehaulani - Lanikai~ Stunning Ocean Views~ Private Residence
Kailua Beach Vacation Cottage / Weekly Rates & Terms Available Upon Request
This family-friendly Kailua holiday home is located by the sea, within a 5-minute walk of Kailua Bay Beach and Kailua Beach. Lanikai Beach is 1.2 mi (2 km) ...
4.9/5Exceptional! (37 reviews)
Awesome Vacation
"It was perfectly located for easy beach access and exploring Oahu..,we loved it here, plenty of space, comfortable and perfectly clean...thank you Kelly and Patrick, we hope to be back!"

Reviewed on 26 Jul. 2021

Kailua Beach Vacation Cottage / Weekly Rates & Terms Available Upon Request
Kailua Beach Park Cottage - 2BR
27 Alala Road, Kailua, HI
This family-friendly Kailua holiday home is located by the sea, just steps away from Kailua Bay Beach and Kailua Beach. Lanikai Beach is 0.5 mi (0.9 km) ...
4.9/5Exceptional! (25 reviews)
Great location
"Great location next to Kailua beach park. 3 mins walk to arguably one of the best beaches on Oahu. Older, smaller home, needs a little bit of TLC (replace mattresses, beds etc) but otherwise very good and accurate representation from listing . Great communication by host."

Reviewed on 27 Jul. 2021

Kailua Beach Park Cottage - 2BR
Open-plan Lush Garden Home Near Kailua & Lanikai Beaches
This family-friendly Kailua holiday home is within 1 mi (2 km) of Kailua Bay Beach and Kawainui Park. Kailua Beach and Kaneohe Bay are also within 3 miles (5 ...
4.5/5Wonderful! (47 reviews)
We were 2 seniors traveling with our granddaughteres
"The home was spacious, kitchen had everything we needed, nice space to relax inside and out. This was in a residential area away from massive tourism giving you a better feel for the island. We would recommend."

Reviewed on 14 Jul. 2021

Open-plan Lush Garden Home Near Kailua & Lanikai Beaches
Lanikai Beach Front - Sunrise Over the "mokes"
Located in Lanikai, this holiday home is within 1 mile (2 km) of Kailua Bay Beach, Lanikai Beach and Kailua Beach. Kalama Beach Park is 2.6 mi (4.2 km) ...
Lanikai Beach Front - Sunrise Over the "mokes"
Close to the Beautiful Kailua Beach-a/c-full Kitchen-wifi-covered Patio-laundry
This family-friendly Kailua holiday home is located by the sea, within 1 mi (2 km) of Kailua Bay Beach and Kawainui Park. Kailua Beach and Kaneohe Bay are also ...
4.7/5Exceptional! (24 reviews)
Great place
"Easy communication with owner, beautiful location that was close to family on the island, interior well laid out, very well stocked kitchen, extra sheets, pillows etc, easy access with key pad (no keys to keep track of), very comfortable bed & futon, efficient AC in both bedroom & living room, ability ..."

Reviewed on 6 Jul. 2021

Close to the Beautiful Kailua Beach-a/c-full Kitchen-wifi-covered Patio-laundry
Entire, Spacious, Airy Family House - Minutes to Beach
This family-friendly Kailua holiday home is located by the sea, within 2 mi (3 km) of Kailua Bay Beach and Kaneohe Bay. Kailua Beach is 2.5 mi (4 km) away.
4.6/5Exceptional! (26 reviews)
great stay
"Carol was a great host. the property was clean and had a lot of things we did not have to go buy (tissues, spices, shampoo, soap, garbage bags ect). the stay was great. It was a lot quieter than on the waikii side of the island and we liked that. The only thing was that it did not have air conditioning ..."

Reviewed on 5 Jun. 2021

Entire, Spacious, Airy Family House - Minutes to Beach
Kimos Beach House Lovely Renovated Home and 10 min Walk to the Beach
This family-friendly Kailua holiday home is located near the beach, within 1 mi (2 km) of Kailua Bay Beach and Kailua Beach. Lanikai Beach is 1.8 mi (2.8 km) ...
4.8/5Exceptional! (48 reviews)
Dream stay
"Pua and Kimo are very responsive to all inquiries and requests. Place is clean, quiet, accessible to the beach, complete kitchen accessories, spices and a big place for 7 adults. Thank you for making my birthday extra special. We will definitely go back."

Reviewed on 16 Jul. 2021

Kimos Beach House Lovely Renovated Home and 10 min Walk to the Beach
Kailua Beach Front W/large Garden Lawn - Nightly Rental Available
Located in Kalama Tract, this holiday home is within a 15-minute walk of Kalama Beach Park and Kailua Beach. Lanikai Beach is 1.8 mi (2.8 km) away.
5/5Exceptional! (20 reviews)
Epic beach
"The location is unbeatable."

Reviewed on 21 Jul. 2021

Kailua Beach Front W/large Garden Lawn - Nightly Rental Available
Email FOR Monthly Rate. Legal Rental! Beach Front Estate, Steps TO Kailua Beach!
Nestled on the beach, this Kalama Tract holiday home is within 3 mi (5 km) of Kailua Bay Beach, Kailua Beach and Lanikai Beach. Kaneohe Bay is 2.7 mi (4.3 km) ...
4.3/5Excellent! (42 reviews)
Paradise Found!
"We had such a great week on Oahu! The location in Kailua offered us a quiet retreat away from the hustle and bustle of Honolulu. The proximity and easy access to Kailua Beach gave us a nice place to come relax after a busy day on the North Shore or a long day hiking. The house was beautiful and had ..."

Reviewed on 12 Jul. 2021

Email FOR Monthly Rate. Legal Rental! Beach Front Estate, Steps TO Kailua Beach!
Ocean Tree House W/ Lanai & Yard - Walk To Beach 3 Bedroom Home
Located in Lanikai, this holiday home is within 1 mile (2 km) of Lanikai Pillboxes Trailhead, Lanikai Beach and Kailua Beach. Kailua Bay Beach and Kalama Beach ...
Ocean Tree House W/ Lanai & Yard - Walk To Beach 3 Bedroom Home
Hawaii Life Rentals Presents Large Home With Pool Just Steps to Kailua Beach
Situated in Kailua, this holiday home is 1.2 mi (1.9 km) from Kawainui Park and within 3 miles (5 km) of Kailua Beach and Lanikai Beach. Kailua Bay Beach and ...
5/5Exceptional! (2 reviews)
Loved Kailua
"Staying on Oahu to check out University of Hawaii, absolutely loved the house! Easy walk to the beach, kids loved the pool and backyard. Can’t wait to come back!"

Reviewed on 30 Mar. 2021

Hawaii Life Rentals Presents Large Home With Pool Just Steps to Kailua Beach
Kolea Landing Modern Beach House w/ Double Master
This family-friendly Kailua property is located near the beach, within a 15-minute walk of Lanikai Beach and Kailua Beach. Kailua Bay Beach and Kalama Beach ...
5/5Exceptional! (3 reviews)
Beautiful property
"The property was better than expected. The location was perfect. About 1 min walk to an access spot on Lanikai Beach. Would love to return. Highly recommend!"

Reviewed on 26 Jul. 2021

Kolea Landing Modern Beach House w/ Double Master
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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.

Other property types in Kailua

Beachfront Hawaiian Private Villa Premium Location on Usno1 Beach

Beachfront Hawaiian Private Villa Premium Location on Usno1 Beach

Kailua, HI
The price is AU$4,748 per night from 11 Aug. to 11 Aug.
5/5Exceptional! (1 review)
Greatest Beach House ever.
"Trust me!!! This is where you want to be. Words can’t describe how perfect it was for me and my family and team. Do yourself & your family a favor and book this place."

Reviewed on 4 Jul. 2021

Beachfront Hawaiian Private Villa Premium Location on Usno1 Beach
Hawaii's Hidden Hideaway Bed & Breakfast

Hawaii's Hidden Hideaway Bed & Breakfast

3 out of 5
1369 Mokolea Drive, Kailua, HI
3.9/5Very Good! (18 reviews)
"Unique location, charm, owner friendliness, comforts"

Reviewed on 23 Mar. 2020

Hawaii's Hidden Hideaway Bed & Breakfast
Hawaii Luxury Beachfront Private Luxury Villa in Premium Location

Hawaii Luxury Beachfront Private Luxury Villa in Premium Location

Kailua, HI
The price is AU$7,944 per night from 1 Aug. to 1 Aug.
Hawaii Luxury Beachfront Private Luxury Villa in Premium Location
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.