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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Guest favourite

Home in Kailua

4.89 out of 5 average rating, 266 reviews

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!

Guest favourite

Apartment in Kahuku

5 out of 5 average rating, 153 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

Rental unit in Waikiki

4.87 out of 5 average rating, 295 reviews

Jewel in Sky near Hilton Hawaiian Village

Cozy quiet privately owned studio, view of ocean and Diamond-head crater. 7 min walk to beach! Next to famous Hilton Hawaii Village beach and lagoon. Address: 1920 AlaMoana Blvd. 17th floor, access to outdoor common terrace / pool on 5th floor overlooking park. AC, fans, windows open for fresh air, bathtub, etc. Queen bed, cotton sheets, beach towels + many amenities, small "kitchenette". NOTE: Paid Parking only — in our building or next door. We take care of concerns immediately!

Guest favourite

Apartment in Waianae

4.97 out of 5 average rating, 241 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

Apartment in Waikiki

4.89 out of 5 average rating, 270 reviews

Newly Renovated Cozy Home

Experience the charm of our newly renovated studio, legally permitted for your peace of mind. Revel in the modern ambiance featuring wood-like floors, luxurious marble countertops, and a stylishly tiled bathroom. Immaculately maintained for your comfort, the studio boasts SUPER CLEAN interiors and offers FANTASTIC CANAL VIEWS. Conveniently located within walking distance to the famous beaches, shopping malls, delectable dining options, and all your essentials. Your dream getaway begins here!

Guest favourite

Home in Haleiwa

4.96 out of 5 average rating, 178 reviews

Oceanfront Oahu North Shore Hawaii Private 3b Home

For rates less than 90 days. Please call or DM. Nestled on the shore of legendary Waimea Bay Point, this home is the gateway to an authentic Hawaiian experience. Lounge on the covered lanai feet from lapping surf watching whales, dolphins, turtles, surfers, and incredible sunsets. Extremely clean with all the necessities. Steps to 3 sandy beaches Waimea Bay, Shark’s Cove and Three Tables. This is the perfect family getaway, allowing you to live the true North Shore lifestyle.

Guest favourite

Apartment in Waikiki

4.92 out of 5 average rating, 148 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.

Superhost

Hotel room in Waikiki

4.81 out of 5 average rating, 902 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

Superhost

Rental unit in Waikiki

4.85 out of 5 average rating, 118 reviews

Cute Studio, Close to Beach, WI-FI

Enjoy easy access to everything from this perfectly located home base. Everyone will enjoy this paradise for swimming, surfing, snorkeling, and more. The beautiful tropical climate with tons of activities and events for all ages. Walking distance to the nightlife with Hawaiian bars, clubs, and lively entertainment. Or a low-key night along Waikiki Beach. You can absolutely walk Waikiki Beach at night with the sound of the waves right next to you.

Superhost

Guest house in Kailua

4.78 out of 5 average rating, 143 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.

Superhost

Guest house in Kailua

4.85 out of 5 average rating, 352 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 suite in Haleiwa

4.83 out of 5 average rating, 201 reviews

Hale Nalu a/c, beach, bike path, food trucks, cook

Come experience all the North Shore of Oahu has to offer. Our hale has all you need to relax comfortably and in style! Whether you want to cook all your meals or find a near by restaurant or food truck we’ve got you covered! We’re located by the beautiful North Shore bike path on the ocean side of the “Kam Hwy.” and a short 3 minute walk via deeded access to the beach.