Holiday rentals in Kailua

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Top-rated holiday rentals in Kailua

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Superhost

Home in Kailua

4.86 out of 5 average rating, 423 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, 108 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

Apartment in Kahuku

4.93 out of 5 average rating, 228 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

Home in Kailua

4.96 out of 5 average rating, 25 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, 279 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

Apartment in Waikiki

4.83 out of 5 average rating, 204 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, 161 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, 336 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

Apartment in Hauula

4.76 out of 5 average rating, 138 reviews

Amazing Beachfront Condo!

Welcome to the beach! Your little piece of paradise! This 1 larger bedroom, 1 bath condo has a newly remodeled kitchen! Right on a beautiful white sandy beach that is great for swimming, snorkeling, fishing & kayaking! Sea turtles & tropical fish are right out front! Fully equipped kitchen, washer/dryer & your private lanai looking out at this spectacular beach & amazing ocean views! Incredible sunrises too! Pool, gym & BBQ area, WIFI, cable & onsite FREE parking spot!

Guest favourite

Apartment in Kahuku

4.94 out of 5 average rating, 196 reviews

♥ North Shore Paradise at Turtle Bay ♥

For the discerning traveler, a designer curated space with every luxury detail thought of. When you step inside, you can feel the love poured into this space, and the exquisite detailed craftsmanship throughout. Nestled on the 3rd green of the famous Georgia Fazio course at Turtle Bay Kuilima Estates West on the North Shore of Oahu. A perfect spot to vacation, honeymoon, or spend some quality relaxation time. This magical space welcomes you with aloha.

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

Guest house in Kailua

4.79 out of 5 average rating, 153 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

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

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.

Guest house in Kailua

4.79 out of 5 average rating, 179 reviews

Absolutely Oceanfront-60'Waterfall Pool-Legal

GinaRating, 5 stars1 month 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

Cottage in North Shore

4.91 out of 5 average rating, 118 reviews

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

SusannaRating, 5 stars2 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.

Home in Kailua

4.6 out of 5 average rating, 5 reviews

Cozy Guest House

AlisaRating, 5 stars1 month ago

This is one of the best Airbnbs we’ve ever stayed at. Honestly the photos don’t do it justice because it’s full of light and feels like a high end hotel bungalow with large, spacious rooms, two queen beds, a very large TV, nice kitchen, bathroom with laundry, and in an ideal location. We loved staying in a nice, quiet neighborhood. Every convenience is right across the street; Safeway, Starbucks, gas station and a few little restaurants like L&L Hawaiian BBQ & a pizza place. A short 7 minute walk across the bridge takes you to a beach access to Castles Beach which became our new favorite spot because it’s very private with only locals. Staying in Kailua is so relaxing. It’s the lush, green side of the island away from the hustle and bustle of town. But the H3 highway gets you anywhere you want to go in 20-30 minutes. We were visiting family all over the island so it was perfect. It felt like a home away from home and our hosts couldn’t have been more helpful. We hope to be back soon!

Guest favourite

Guest suite in Hauula

5 out of 5 average rating, 15 reviews

Hauula Beach Living with Aloha

MaryRating, 5 stars2 days ago

We enjoyed our visit to Aya's guest studio. It was restful and perfectly situated for what we wanted to do. At the end of the street was a nice beach and it was a convenient drive to the Polynesian Cultural Center. It was cozy and felt like home.

Guest favourite

Apartment in Kahuku

5 out of 5 average rating, 6 reviews

The Drifter - North Shore Loft - Relaxed Luxury

KristinaRating, 5 stars1 week ago

We had a wonderful stay! The home was clean, well-equipped, and had plenty of room to relax and unwind. One of our favorite spots was the super comfy couch haha it was perfect for lounging after a long day of exploring! Short walk to the hotel and easy drive to Kahuku.

Home in Kaneohe

4.89 out of 5 average rating, 36 reviews

Relax Hawaiian Style

MaximilianRating, 5 stars1 month ago

We had small kids and a family group staying. It was a great home base, but you do need to drive to see anything so plan on renting a car. This was always our plan so it worked out great! It is very spacious for the maximum number people allowed. Would definitely stay there again, best cost value for size we could find!

Guest favourite

Flat in Hauula

4.89 out of 5 average rating, 36 reviews

Aloha Paradise Beach

KarlaRating, 5 stars1 month ago

Karon and Jacqui are amazing hosts! My family and I have been staying at their rental units for years and it never disappoints. Both Karon and Jacqui are very friendly and extremely responsive and accommodating, making sure my family and I are well taken care of. Both the condo and beach cottage was perfectly suited for our needs. I would definitely come again. We had a little staycation to celebrate our birthday’s and Karon and Jacqui’s place made it memorable!

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