House holiday rentals in Kailua

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Top-rated house rentals in Kailua

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Guest favourite

Home in Kailua

4.86 out of 5 average rating, 439 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

Home in Waianae

4.93 out of 5 average rating, 125 reviews

Beautiful 4-BR Home| Near Beach| Mountain View

A tastefully designed 4 bed/2.5 bath home in a gated community (built in 2022), nestled in the beautiful Makaha Valley. Private back yard with breathtaking Wai’anae Mountain view and peek-a-boo oceanview. Enjoy quality time with your family and friends at this stylish, cozy home. Experience true taste of paradise on western side of Oahu, away from hustle and bustle of city. The endless beaches along the coastline, amazing sealife, and magnificent mountains will make your vacation memorable!

Guest favourite

Home in Waikiki

4.97 out of 5 average rating, 112 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.

Superhost

Home in Kailua

4.89 out of 5 average rating, 37 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

Home in Waianae

4.98 out of 5 average rating, 80 reviews

Makaha Hale - New 3 BR Home

Escape to the beautiful Makaha Valley in Hawaii and experience a truly unforgettable stay at our 3-bed 2.5-bath house. This enchanting Airbnb, nestled within a secure gated community offers a getaway for those seeking tranquility amidst the breathtaking beauty of the island. Enjoy breathtaking views of the Makaha Valley mountainside, modern amenities, and a serene ambiance. Indulge in nearby pristine beaches and immerse yourself in the beauty of the island. Your dream Hawaiian getaway awaits!

Top guest favourite

Home in Makaha Valley

4.96 out of 5 average rating, 143 reviews

Kalo Homes - Makaha's Hidden Gem

Escape to paradise in this beautiful vacation home located in Makaha Valley. Enjoy stunning panoramic ocean views and relax in the tropical backyard. Inside, you'll find a fully equipped kitchen, comfortable furnishings, and ample space for your group. Take a short drive to the beach and spend your days swimming, surfing, or lounging on the sand. Come back and enjoy a BBQ on the outdoor grill. Perfect for families or groups of friends, this vacation home is the ultimate Hawaii getaway!

Guest favourite

Home in Waianae

4.95 out of 5 average rating, 108 reviews

Oahu Perfect Vacation •Pool, Near Beach, Sleeps 14

Aloha! Welcome to Paradise Mahalo! Nestled in stunning mountains and ocean views, enjoy our modern, luxurious and cozy home located in the majestic Mākaha Valley. Whether it's a few rounds of golf, a hiking trails near by or a five minute drive down to the world famous Mākaha Beach - you got it all. From the mountains of Yosemite to the beaches of Gulf Shores, my family and I will provide you with the best experience for any vacation and occasion! (Pool available May 7th, 2025)

Guest favourite

Home in Waianae

4.96 out of 5 average rating, 109 reviews

Family Oceanview Oasis, Hot Tub, 5min to beach

Why guests LOVE our home? Why guests find it such a great VALUE? - Free parking for 5 cars (save $40–$100/car nightly) - Private SPA & BBQ, full kitchen to cut dining costs, - Spacious single-story for large family with senior and kids, 3 bedroom, 9 beds and 2 bathroom - Repeat guest favourite, peaceful spot near beaches & away from Waikiki crowds. - Gated community with Oceanview pool, gym & mountain views, - Filtered water (no bottled runs), - Washer/dryer to travel light

Guest favourite

Home in Kahuku

4.94 out of 5 average rating, 77 reviews

Spectacular golf course front steps from the beach

Enjoy the amazing experience of staying at Turtle Bay without resort pricing! Our Kuilima West condo is ideally situated just steps from the Turtle Bay Ritz Carlton Resort, and has all the amenities you need, parking, AC, free wifi More than 5 miles of secluded beaches, 3 private swimming pools, 2 private tennis and pickleball courts, charcoal BBQ, 2 PGA golf courses, horseback riding, activity rentals and fine dining all less than a 5 minute walk from your front door!

Guest favourite

Home in Hauula

5 out of 5 average rating, 16 reviews

Seabreeze:Oceanfront, AC, Outdoor Shower, 30 Day

Seabreeze is a beautiful newly designed N. Shore home w/ 110' of ocean front, spectacular sunrises & majestic mountain views. Dine on the lanai w/ turquoise ocean water so close you can almost touch it. Our home overlooks the sea & mountains (a rare & gorgeous view). We are at the water's edge w/ a lrg lanai & ample seating where sea life can often be seen. 1 home from ocean access & min. to Pounders & Kokololio Beaches; white sand gems w/ fantastic body surfing.

Superhost

Home in Makaha Valley

4.9 out of 5 average rating, 122 reviews

Slice of Paradise-3BR- Sleeps10-same $ for 2 as 10

Enjoy time w/family at this new 3 bdr 2.5 bath house in the mountains of Makaha Valley in a gated community. Minutes from year round surf&golf. This is a LEGAL vacation rental. Private yard on perimeter lot with unobstructed ocean&mountain views & just a few min. drive to clean, sand bottom beaches. Please note there is an attached studio on the property but everything is separate&private. Any combination of 10 guests is OK as long as no more than 8 adults.

Superhost

Home in Kapolei

4.74 out of 5 average rating, 206 reviews

Ko Olina Vacation 2Bdrm unit with private entrance

A beautiful clean two bedroom unit with private entrance, just a short 4 minute drive from the world famous Ko Olina Beach & Golf resort with the most beautiful sunsets on Oahu. Only 7 min from Ka Makana Ali'i shopping center with great restaurants! Costco is just 4 min away, so you can stock up the large frig with water, beer, & food! Only 25 min from airport. Kapolei is about 30 minutes from Waikiki, away from the crazy hustle & bustle.