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Holiday rentals in Kailua

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Top-rated holiday rentals in Kailua

Guests agree: these stays are highly rated for location, cleanliness and more.

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Home in Kailua

4.85 out of 5 average rating, 359 reviews

Kailua Beach Park - 1 BR Cottage

Kailua Beach was 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 a 2-minute walk to step into the ocean. It is a legal vacation rental, license number 1990/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 showers, sinks and plumbing fixtures April 2022!

Guest favourite

Apartment in Kahuku

5 out of 5 average rating, 145 reviews

HawaiianaLuxe_Townhouse at Turtle Bay_Hale LuLu

Come to escape to this newly renovated 1,150SF 2 bedrooms/2.5 bathroom townhouse for a soul comforting Northshore stay! Away from hustling downtown, Hale Lulu sits peacefully a few minutes away from iconic Turtle Bay Hotel and the most beautiful secluded beaches and trails! This unit is the biggest model in Kulima West. We offer 2 king size beds and 1 queen bed in three different bedrooms for your restful stay. The best cleaning crew was hired for your luxurious staying experience in Hawaii.

Guest favourite

Apartment in Kahuku

4.92 out of 5 average rating, 168 reviews

SEArider TWO at Turtle Bay (1 bedroom / 1 bath)

Our number one priority at SEArider is to provide our guests with a luxury Hawaiian experience. This unit has been completely renovated with our main focus being quality and comfort. Nestled in the condominiums that surround Turtle Bay, TWO has a luxurious but minimal feel with a mauka (mountain) inspired theme. Key features include locally made and dyed linens and waffle print towels. TWO sits directly below our other property, SEArider ONE (please search us on Air BnB for photos and reviews.)

Guest favourite

Apartment in Waianae

4.97 out of 5 average rating, 234 reviews

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.

Guest favourite

Home in Hauula

4.99 out of 5 average rating, 160 reviews

Moeʻuhane Kai Beach Front Home

Amazing beach front property on the East Shore of Oahu. 30-day minimum rental. Hear the waves from every room in the house. Very comfortable home, window units available, but you might rather open the five sets of French Doors & sliding glass door to enjoy the trade winds and ocean sounds. Great fishing right outside the back of the house. Ten minutes from the Polynesian Culture center and great food options. Great Thai food, malasadas, and Dole ice cream. Short drive to North Shore.

Guest favourite

Guest house in Kailua

4.86 out of 5 average rating, 141 reviews

Kailua's Premier Private Luxury Beach Bungalow

Kailua's Original Beach Bungalow premier private luxury bungalow getaway ~ Modern design mingles with traditional elegance in this newly renovated bungalow. Beautifully furnished with comfort and ease-open floor plan that features large floor to ceiling windows. Very private - with a large gated spacious patio - hot and cold running outdoor shower, outdoor private dining and just steps from your bungalow down the path to the most beautiful beach in the world.

Guest favourite

Apartment in Waikiki

4.92 out of 5 average rating, 142 reviews

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.

Guest favourite

Cottage in North Shore

4.97 out of 5 average rating, 101 reviews

Tiny living! Quaint Haleiwa cottage

****Calendar is not always accurate, please inquire for availability. ******* Newly built cottage, equipped with everything to make your vacation a home away from home. High vaulted ceilings make the small home feel spacious, full kitchen for home cooked meals, a large covered deck for outdoor dining. In the heart of historic Haleiwa town, near Starbucks and 7-11, shopping and food trucks are down the street. We are located on site should you have any issues.

Hotel room in Waikiki

4.81 out of 5 average rating, 883 reviews

Cute Private Studio in Waikiki

Fully renovated to modern-retro style, with breathtaking views of ocean, Diamondhead and mountains. Desirable location -in Waikiki - minutes walking distance to Convention Center, beach, shopping, dining, entertainment... Sleeps two in full size bed. With kitchenette, suitable for long- and short-stays. Condohotel with 24/7 security, pool, jacuzzi, BBQ, laundry, shops, bar, ATM.... Parking and fitness is available, but must be paid separately. TA-029-819-2896-01

Guest house in Kailua

4.78 out of 5 average rating, 140 reviews

Kailua Beach Cottage - 90/TVU-0287

WE HAVE PERMIT - 90/TVU-0287 FROM THE CITY & COUNTY WE WERE RATED BY AIRBNB AS A SUPERHOST. KAILUA BEACH RATED #1 BEACH IN AMERICA! This place is good for couples, business travelers, and families. (On the 2nd floor - upstairs) *Additional guest fee of $90 per person per day applies to parties over 4 people. Additional service fee and tax will apply. Visit the 8 Bdrm Villa website for a larger family group.

Guest favourite

Guest house in Kailua

4.85 out of 5 average rating, 348 reviews

Kailua Palm Studio. Walk to Beach! PERMITTED

Licensed, legal 90/BB-0002 short term rental. *not impacted by Bill 41 (2022) **NEWLY 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 Cynthia Rubinstein Real Estate, Inc. (License #RB-16858)

Guest favourite

Guest house in Ewa

4.95 out of 5 average rating, 359 reviews

Plumeria Resurt at the Beach

Beach front Glamping at it's best! Located on an oceanfront gated property. 100ft to the ocean's edge! Brand new construction with beatiful gardens, full bathroom and laundry ~~ no out house here...This romantic setting with plush comforts and a view of the stars from the dome skylight above the bed makes this private retreat the best of Hawaii getaways.

Holiday rentals for every style

Get the amount of space that is right for you

Bungalows

Intimate homes, inviting architecture

Villas

Luxurious estates for the ultimate escape

Flats

Convenient locations with everyday essentials

Popular amenities for Kailua holiday rentals

Free parking on premises

Air conditioning

Stay near Kailua's top sights

Kailua Beach Park200 locals recommend

Whole Foods Market370 locals recommend

Buzz's Steakhouse136 locals recommend

Pillbox Hike178 locals recommend

Boots & Kimo's Homestyle Kitchen51 locals recommend

Kailua Beach Adventures40 locals recommend

Other great holiday rentals in Kailua

Guest favourite

Cottage in Kailua

4.92 out of 5 average rating, 37 reviews

Kailua Ohana Cottage close to beach

Guest favourite

Guest house in Kailua

5 out of 5 average rating, 69 reviews

Lanikai Plumeria Beach Cottage (Close to beach!)

Guest favourite

Guest suite in Kailua

5 out of 5 average rating, 18 reviews

Aniutea’s Lodge

Guest favourite

Villa in Kailua

5 out of 5 average rating, 70 reviews

Nai’a Suite at La Bella’s-Walk to Beach-Licensed

Guest favourite

Guest house in Kailua

4.96 out of 5 average rating, 70 reviews

Kailua Surf Shack: Your Hawaiian Adventure!

Guest favourite

Home in Kaaawa

4.86 out of 5 average rating, 97 reviews

Enjoy the Ocean View from Tropical Paradise Condo!

Home in Kailua

4.88 out of 5 average rating, 17 reviews

Amazing Lanikai Beachfront Guest House!!

Guest favourite

Guest house in Kailua

5 out of 5 average rating, 12 reviews

Lovely Private Kailua Cottage

Quick stats about holiday rentals in Kailua

Total rentals
380 properties
Total number of reviews
11K reviews
Family-friendly rentals
200 properties are a good fit for families
Pet-friendly rentals
50 properties allow pets
Rentals with a pool
100 properties have a pool
Rentals with dedicated workspaces
180 properties have a dedicated workspace

Destinations to explore