
Holiday houses in Kailua
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Top-rated holiday rentals in Kailua
Guests agree: these stays are highly rated for location, cleanliness and more.

Kailua Beach Park - 2 BR Cottage
Kailua Beach is once again been rated as the best beach in the USA for 2019, by Dr. Beach. "The cottage is directly across the street from Kailua Beach Park and less than two minutes walk to step into the ocean at the beach. This a legal vacation rental, license1990/NUC-1758. The property is tucked away one house back from the road into Lanikai, and described by guests as "a little oasis of quiet and calm." The bathroom has been remodeled with a new shower, sink and plumbing fixtures April 2022!

32nd Floor Penthouse. 3min walk to Waikiki Beach
Welcome to HaleHinano Penthouse, Waikiki Beach. Enjoy this rarely find 1BR Penthouse on the 32nd floor with panoramic ocean views of the crisp Hawaiian waters. This condo is fully renovated with modern furnishings and decor. Just a few steps away, you’ll be at beach fronts of Waikiki beach. You’ll be surrounded with local favorite fine dining, shopping plazas. -In unit washer and dryer. -Top roof Pool, Jacuzzi, BBQ -3 min walk to the Waikiki beach. -$35/day parking attached to the building.

Beachfront Getaway - Hawaiian Princess Condo
Mesmerizing sunset views from this sandy beach front condo. Nothing separates you from sparkling turquoise waters but footprints in the sand. Balcony is ideal height for turtle watching. From Nov- April you may spot a whale. This vibrant land is full of surprises. Even dolphins spin by now and then. Escape the crowds of Waikiki to experience a real Hawaiian lifestyle. Snorkel, boogie board or surf right out your door. Awakening to the rhythm of the ocean can change your life forever.

Kailua - Ocean/Mtn Views - 60' Pool - 2 Decks
Kailua Absolutely Oceanfront Deluxe Vacation Rental One of the few Legal short-term rentals (Less than 30 days) The closest house to the Ocean in Kailua Located in an upscale Kailua neighborhood The quiet uncongested North side of Kailua Only 8 minutes to the center of Kailua Town 60ft salt-sanitized waterfall lap pool 16-foot vaulted skylight ceilings with a loft Two outside covered decks, one overlooking the pool and the mountains. The other has a partial ocean view between the houses

Free Parking/Ocean View/Steps to Beach & Mall 33F
Fully newly remodeled in April this year! Everything is brand NEW! Amazing sweeping ocean view! Located on 33rd floor of Waikiki city, just a few minutes’ walk to the famous Waikiki Kahanamoku Beach & Lagoon, Ala Moana Beach Park, Ala Moana Shopping Mall, many restaurants , Cafes and Bars - everything is within walking distance. FREE PARKING is a Big Plus with a designated parking spot in the garage. You’ll have a great time in this brand new home with a queen bed and a sofa to stay!

Nai’a Suite at La Bella’s-Walk to Beach-Licensed
La Bella’s B&B is a High End Luxury home filled with charm and a touch of farmhouse/beach elegance. Two Suites are available for booking. Owners live onsite. Starbucks, Safeway, Gas Stations and Eateries are right across the street. Nai’a (Dolphin) Suite Offers: -Kitchenette -Private Bathroom -Separate Entrance -AC and Powerful high end fan -King size bed w/luxury bedding If you want a beautiful garden, great host family and a short walk to the beach this is the place for you.

Waikiki Beachfront Home (Car & Parking Available)
* Aloha! Welcome to the happiest place in the world. * Featuring a direct ocean view from an entire wall of windows, where you can see the ocean, beach, lagoon, surfers, whales, sunsets, and more. This beachfront home is within minutes of walking distance to almost everything - beaches, restaurants, bars, surfing lessons, boat tours, grocery stores, shopping malls, and more. Every time I come to Hawaii, I am so happy. I hope our place can bring you some happiness too. :-)

Amazing Waikiki Beach Views!!
Perfect vacation getaway, with amazing views of Waikiki Beach and Lagoon!! Best location, walking distance to many points of interest, Ala Moana Mall/Designer stores and many restaurants! Enjoy visiting Oahu - there's sightseeing, swimming, hiking, surfing or shopping etc! Enjoy watching the fireworks every Friday nights from the patio, sponsored by Hilton Hawaiian Village! Hotel pool is also available for our guests. Also accepting long term stays at special rates.

Waikiki Beachfront Home with Ocean and Beach View
* Aloha! Welcome to our happy place in the heart of Waikiki! * If you are looking for stunning ocean views directly from your bed, this is it! You are within minutes of walking distance to almost everything - beaches, restaurants, bars, surfing lessons, boat tours, grocery stores, shopping malls, and more. Our spacious bedroom, full kitchen, and freshly updated bathroom will make you feel just like home. Welcome to our little paradise!

[Rare] Premier Ocean and Diamond Head Views 33 FL
The Honu Suite is a serene, design-forward retreat in the heart of Waikiki - just one block from the beach. Enjoy panoramic Diamond Head and ocean views from the 33rd floor, curated amenities, and five-star touches throughout. Rooted in Hawaiian heritage, it's perfect for discerning couples seeking comfort, style, and a sense of escape. Limited-time: Complimentary early check-in and late check-out, based on availability.

Kailua Rental for Med/Long Term ($1,500/month)
Escape to beautiful Kailua and enjoy our cozy guest suite! Located in a quiet cul-de-sac, this unit provides modern amenities, a new full-sized bed and direct access to your own private lanai. Mountain views, nearby attractions, shopping, dining, and world-class beaches ensure an ideal destination for your next retreat! We welcome minimum stays of 30 days or more. Please contact for inquiry details. * 30 night minimum

Kailua Palm Studio. Walk to Beach! PERMITTED
Licensed, legal (NUC short term rental #1990/NUC-1819, Tax map key: 43073024) *not impacted by Honolulu ordinances banning short term **RECENTLY RENOVATED BATHROOM AND KITCHENETTE (at end of June 2023)** Peaceful retreat in desirable Kailua! An easy 8-10 minute walk to Kailua Beach. Airbnb “Guest Favorite” awardee! Sister Unit: Kailua Pineapple Studio. Walk to Beach! PERMITTED. Property managed by Kupono Services.
Popular amenities for Kailua holiday rentals
Other great holiday rentals in Kailua

Beach Front, King Bed, the Princess - low level

Beautiful OceanView&Sunset @IlikaiResort w/Parking

North Shore Turtle Bay Hideout

Lanikai ocean view home

Best Kept Secret on Oahu! and WE ARE LICENSED!!!

Honu Hideout at Turtle Bay

Ocean View Sunset, Free Parking, Pool, 5m to Beach

Sunset Hale
When is the best time to visit Kailua?
Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
---|---|---|---|---|---|---|---|---|---|---|---|---|
Avg. price | $434 NZD | $436 NZD | $392 NZD | $392 NZD | $413 NZD | $413 NZD | $418 NZD | $391 NZD | $397 NZD | $397 NZD | $391 NZD | $403 NZD |
Avg. temp | 22°C | 22°C | 23°C | 24°C | 24°C | 26°C | 26°C | 27°C | 26°C | 26°C | 24°C | 23°C |
Quick stats about holiday rentals in Kailua
Total holiday rentals
Explore 340 holiday rentals in Kailua
Nightly prices starting at
Kailua holiday rentals start at $70 NZD per night before taxes and fees
Verified guest reviews
Over 10,940 verified reviews to help you choose
Family-friendly holiday rentals
200 properties offer extra space and kid-friendly amenities
Pet-friendly accommodation
Find 40 rentals that welcome pets
Holiday rentals with a pool
90 properties feature pools
Rentals with dedicated workspaces
160 properties have a dedicated workspace
Wi-Fi availability
340 of Kailua holiday rentals include Wi-Fi access
Popular amenities for guests
Guests love Beachfront, Self check-in and Gym across Kailua rentals
4.8 Average rating
Kailua stays are highly rated by guests—averaging 4.8 out of 5!
Destinations to explore
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- Kailua Beach
- Waimea Bay Beach
- Kualoa Ranch
- Kepuhi Beach
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- Honolulu Zoo
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- Bishop Museum
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- Wet 'n' Wild Hawaii
- Diamond Head Beach Park
- Pyramid Rock Beach
- Ke Iki Beach
- Kalani Beach
- Nimitz Beach
- Waimea Valley
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