Holiday houses in Kailua

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Top-rated holiday rentals in Kailua

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Guest favourite

Condo in Waikiki

4.83 out of 5 average rating, 310 reviews

Amazing Ocean & Beach Views - Only Steps to Beach!

There are few units closer to the ocean than this one!! Enjoy nearly ocean front at the best rate in Waikiki! Swimming pools, Lagoon, Beach & Ocean all at your doorstep. Watch the Friday Night Fireworks at 7:45pm every Friday from the comfort and privacy of your own condo! Close to Ala Moana Center - only 5 min walk! You’ll love this condo because of the Great Views, the kitchen, the comfy King bed and all of the amenities that the building offers (pool, restaurants, convenience stores, etc).

Superhost

Home in Kailua

4.86 out of 5 average rating, 426 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!

Top Guest favourite

Place to stay in Kailua

4.96 out of 5 average rating, 109 reviews

Honu Suite at La Bella’s-Walk to Beach-Licensed

No detail is overlooked at this charming and luxurious home. La Bella’s Bed and Breakfast is the place to be if you are looking for a short walk to the beach, a beautiful garden to enjoy, great host family that lives onsite and close to amenities. Our luxury bedding and upgraded style makes you feel right at home during your Hawaii vacation. The Honu (Turtle) Suite: -AC -Queen bed -Full kitchen -Private bathroom This suite is extra private -located away from the rest of the living quarters.

Guest favourite

Home in Waikiki

4.98 out of 5 average rating, 104 reviews

Waikiki Gem, Stunning Ocean View, Parking Included

Wake up to breathtaking ocean views from our newly renovated 1BR, 1BA condo. Relax on the lanai, let in the gentle breezes, and soak in the picturesque surroundings. With enough space for up to 4 guests, this retreat is perfect for couples, small families, or close friends seeking solace and tranquility. Immerse yourself in the calming ambiance of modern furnishings and a soothing color palette. Convenient parking included. Discover a blissful sanctuary where serenity and relaxation harmonize.

Guest favourite

Condo in Waianae

4.97 out of 5 average rating, 283 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.

Superhost

Condo in Waikiki

4.84 out of 5 average rating, 207 reviews

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!

Guest favourite

Cottage in North Shore

4.96 out of 5 average rating, 164 reviews

Luxurious Beach Front Oasis Steps to the Ocean

A hidden gem on the North Shore. The cottage is located on a private, gated, 2 acre ocean front property in the quiet and peaceful area of Mokuleia. The beach is the most secluded on the North Shore as there is no public access so at times it is just you and the lone turtle sunbathing on the beach. The cottage has top of the line appliances, sub-zero and viking. The bed feels like heaven and you have your choice of soaking in the free standing tub or showering under the stars.

Guest favourite

Guest suite in Kailua

4.91 out of 5 average rating, 338 reviews

Kailua Pineapple Studio. Walk to Beach! PERMITTED

Licensed 90/BB-0002 short-term rental. *not impacted by Bill 41 (2022) Hawaiian style with modern appointments. Beautiful 450 sf suite in the one of the most desirable locations in Hawaii, Kailua! An easy 8-10 min. walk to Kailua Beach, top rated in the world. Private residence at the end of a quiet cul-de-sac. Airbnb “Guest Favorite” awardee! Sister Unit: Kailua Palm Studio. Walk to Beach! PERMITTED Property managed by Cynthia Rubinstein Real Estate, Inc.(License #RB-16858)

Guest favourite

Condo in Waikiki

4.91 out of 5 average rating, 183 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

Apartment in Waikiki

4.88 out of 5 average rating, 380 reviews

Ocean View Studio in Waikiki

Ocean view studio with awesome balcony just minutes walk to the famous Waikiki Beach. Renovated bathroom with Toto Washlet system. Queen size hybrid bed with coffee maker, refrigerator and microwave. Brand new split AC. Interior of unit is small but there's a private balcony with awesome ocean views. It's hard to get a nice ocean view in Waikiki for this price! Location is in central Waikiki, only a minutes walk to the beach.

Guest favourite

Home in Kailua

4.86 out of 5 average rating, 109 reviews

Tropical Hideaway Near the Beach

We live in a quiet neighborhood which is close to the beach, bus stop or shopping. It’s a mile walking to Kailua beach. The apartment has a bedroom, living room/kitchenette and bathroom which are part of the house but has a separate entrance and private yard with a gate. We must rent on a monthly basis according to Hawaii vacation rentals. If you need a different amount of time please contact me. No pets allowed.

Superhost

Guesthouse in Kailua

4.79 out of 5 average rating, 155 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.

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Popular amenities for Kailua holiday rentals

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Pool

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Other great holiday rentals in Kailua

Guest suite in Kailua

5 out of 5 average rating, 15 reviews

Lanikai Garden Studio - Licensed Since 1985!

JohnRating, 5 stars40 months ago

Even better than we expected! (And we expected it to be great). The studio is larger than we thought and every detail is carefully thought out. The place is extremely clean and very close to the beach. Do not worry about privacy, the studio has its own gate and garden area. We hope to return soon.

Guesthouse in Kailua

4.79 out of 5 average rating, 179 reviews

Absolutely Oceanfront-60'Waterfall Pool-Legal

GinaRating, 5 stars2 months ago

Thomas’ rental was an amazing private retreat for me. The ocean front location is spectacular. Waking up to the sunrise, going to sleep with the tradewinds and crashing waves. It’s on a lava beach so it’s rocky but I discovered a swimmable beach 13 houses down where green turtles sometimes swim beside you. Gorgeous scenery and a peaceful, private location. The interior was immaculate and well cared for. After going to Whole Foods prior to my arrival, I didn’t leave the premises except to head down to the beaches!!! Highly recommend. I hope to spend a longer time there next time I’m back in Oahu.

Guest favourite

Apartment in Waikiki

4.97 out of 5 average rating, 38 reviews

17F-Beautiful & Upscale-Waikiki Beach 1BR/Parking~

LeiRating, 5 stars1 month ago

Excellent location. Close to beach , restaurants and everything. Very walkable. The hosts even provide beach umbrellas, chairs and a wagon to haul them. The unit is also nicely managed. Communication is great. Recommended for family vacations!

Guest favourite

Cottage in North Shore

4.88 out of 5 average rating, 119 reviews

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

SusannaRating, 5 stars4 weeks ago

We greatly enjoyed our time in his house. We had fantastic sunsets on the lanai. It was very relaxing to spent the afternoon on the lanai and to watch and hear the sea. You can easily reach a small beach from the house, which we only did for some late afternoon walks. We went snorkeling at Shark‘s Cove and at Waimea Beach, we could see a lot of fishes and turtles, inside and outside of the water. The location of the house was very good for us, you can easily reach different beaches, go on a sea shore hike or visit Pearl Harbour. The house was ideal for the two of us. We wanted to relax at the sea and do a lot of snorkeling and swimming which we could do every day. Peter was very friendly and helpful.

Top Guest favourite

Home in Makaha Valley

5 out of 5 average rating, 24 reviews

Kalo Homes - Breath of Life

NataliaRating, 5 stars4 weeks ago

Everything was perfect, the house looked like in the pictures, or even better, beautiful, clean and well-kept house, breathtaking views, 10 minutes from the house is the most beautiful beach on the island of oahu, the hosts were very kind, communicative and helpful, I definitely recommend it!

Guest suite in Hauula

5 out of 5 average rating, 17 reviews

Hauula Beach Living with Aloha

CharityRating, 5 stars1 week ago

Aya’s place exceeded our expectations. Her place was very clean, quiet and was fully stocked for a comfortable stay. We will be back.

Superhost

Townhouse in North Shore

4.95 out of 5 average rating, 21 reviews

Sunset Hale

AngelaRating, 5 stars3 weeks ago

Our family of four ( including a 3 & 5 y/o) had a wonderful stay! The home had everything we needed and the location was amazing! A great reef to snorkel right out front of the unit while the kiddos rested. Our favorite beaches were less than a 5 minutes drive west of the unit and had no tourists, lots of trees for shade and opportunities to snorkel with turtles. Would highly recommend for those wanting a more quiet vacation spot.

Guest favourite