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

4.9 out of 5 average rating, 317 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!

Superhost

Guest house in Kailua

4.79 out of 5 average rating, 180 reviews

Absolutely Oceanfront-60'Waterfall Pool-Legal

Kailua Absolutely Oceanfront Deluxe Vacation Rental The closest house to the Ocean in Kailua Hear waves breaking just outside Located in a quiet uncongested upscale neighborhood 60ft salt-sanitized waterfall lap pool Attached Ocean-View Deck 16-foot vaulted ceilings Wall-mounted Fujitsu air conditioning Tide pooling steps away Dramatic Sunrises Refreshing Tradewinds No Bedbugs here/Bed Bug Protective Queen Mattress and pillow covers Ozone sanitized between rentals NUC: Certificate 90-BB-0060

Guest favourite

Home in Kailua

4.93 out of 5 average rating, 30 reviews

Large Kailua Beach Home - Steps To The Beach!

Spacious home for the entire family to enjoy! Just a few minutes walk to the soft sand & clear water of Kailua beach. Spend your days at the beach with your private, air conditioned oasis awaiting you for rest and relaxation. A short bike ride to Kailua Town with restaurants and shops. Lanikai Beach is less than a 5 minute drive away. Hike, bike ride, snorkel, swim, surf, boogie board, kayak, paddle board, kite surf, wind surf, and much more!! Some dates not shown - reach out to confirm avail!

Guest favourite

Apartment in Waianae

4.97 out of 5 average rating, 286 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.

Top guest favourite

Flat in Waikiki

4.98 out of 5 average rating, 411 reviews

Six Thousand Waves

I put a lot of heart & soul into designing this place, I hope you like it :-) - 3 min walk to Waikiki beach - Central location - minutes to food/booze/stores - 1G Internet + Top of the line router (fastest internet you can get!) - Powerful Split-unit AC - Epic wood art + Hawaiian shaped surfboards - Top-of the line modern appliances - 55inch 4K TV + 4K Chromecast + SNES classic I welcome ALL with open arms. All religions, nationalities, genders. You won't regret booking here! -Take

Top guest favourite

Place to stay in Kailua

5 out of 5 average rating, 100 reviews

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.

Guest favourite

Apartment in Kahuku

4.88 out of 5 average rating, 138 reviews

The Coloradoan

One bed, one bath, close to parking, walk out lanai to large yard area facing 18th hole of Fazio golf course. Five minute walk to beach. Hawaiian country furnishings are deceptively simple but supremely comfortable. Owned by retired Colorado couple that spend winter months in Turtle Bay. Sleeps two only. Lots of amenities. Sorry, no pets, kids or surf boards. Can be rented for 1 to 3 months by tourists for deep discount. Has been popular with seniors and newly weds.

Guest favourite

Guest house in Makaha Valley

4.94 out of 5 average rating, 111 reviews

Studio- Ocean View Hideaway

Aloha and welcome to our home away from home in Makaha!! Newly built and luxuriously appointed, this beautiful studio with kitchen and patio area, is the ideal spot on the west side of Oahu. Located in the private gated community, with the amazing views of ocean and mountains. This is the most desirable location to escape, relax and enjoy a rejuvenating and memorable vacation! Kick back and relax in this calm, peaceful space.

Guest favourite

Guest house in Kailua

4.8 out of 5 average rating, 158 reviews

Kailua Beach Cottage - 1990/NUC-1797

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

Flat in Waikiki

4.97 out of 5 average rating, 134 reviews

High FL-Upscale Ocean View w/ Easy Beach Access~

Situated in one of the most vibrant neighborhoods in all of Waikiki, you'll be within steps away from many local restaurants, and shopping plazas. Most importantly, a quick 2 min walk to Waikiki beach, surrounded by cultural activities such as surf lessons and rentals. This stunning apartment is truly one of a kind, and it's the perfect choice for couples & memorable occasions.

Superhost

Home in Kailua

4.77 out of 5 average rating, 78 reviews

Lanikai Ohana Hale: Tropical Cottage w/Pool, Lanai

Charming Cottage in beautiful Lanikai that has been totally renovated in 2021. Everything in the Cottage is new including the furnishings! Short walk to the beach. Enjoy the comforts of home with an efficient kitchen and own washer and dryer. Large lanai to extend the living space and room to BBQ and dine. One split AC unit adequate to quickly provide comfort.

Guest favourite

Guest house in Kailua

4.86 out of 5 average rating, 403 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 Kupono Services.