Holiday houses in Kaaawa

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Top-rated holiday rentals in Kaaawa

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Superhost

Home in North Shore

4.75 out of 5 average rating, 118 reviews

North shore Studio with sauna! - Walk to beach!

Legal Nightly Vacation Rental (No 30-day contracts) A cozy, island-style unit with a loft bed, perfect for an authentic Hawaiian getaway. The unit includes High speed WiFi, 65 inch Smart TV, Split unit AC, sauna, an outdoor shower, an outdoor gym, a sun deck, and private access. Located within walking distance to famous Waimea Bay and other beautiful spots, this space offers convenience, comfort, and island charm. **Please note bookings after may 15th the sauna will be removed for renovations!

Guest favourite

A multistory beach cottage is viewed from the shoreline, showcasing its white and turquoise façade. Lush palm trees line the beachfront, complementing the soft sand. The clear turquoise waters reflect the building, creating a serene coastal scene.

Apartment in Hauula

4.89 out of 5 average rating, 234 reviews

Aloha Beach Front Cottage

This is the slice of Paradise you are looking for. This unique beach cottage at the second floor is steps away from a pristine Hawaiian soft-sand beach. It is extremely calming to sit & enjoy the ocean while your loved ones play in this secret sandy beach, protected by the reef. Is a perfect getaway. Enjoy the secret beach and all the island attractions. Price has discount, because main building is under construction, can be very noisy between 8 to 4, M to F. TMK#530080020132 TA-143-890-4320-01

Guest favourite

Apartment in Kahuku

5 out of 5 average rating, 8 reviews

North Shore Hideaway

Elevated, design-forward retreat at Turtle Bay. This stylish, retro surf–inspired condo overlooks the golf course and mountains, filled with natural light and calming, earthy tones. AC in living room & bedroom, high-speed Wi-Fi, Samsung Frame TV, Quince linen bedding, premium Slowtide towels, and a fully stocked kitchen. Enjoy pools, tennis & pickleball courts, plus walk to Ritz-Carlton dining. Surf, snorkeling, hikes, horseback rides, & golf right here. Adventure, comfort, and serenity await.

Top Guest favourite

A two-story building is framed by lush greenery and large windows. A white staircase leads to the upper level, while balconies are visible. The exterior showcases a light-colored facade that blends with the natural surroundings, creating a serene residential setting.

Apartment in Kahuku

4.9 out of 5 average rating, 251 reviews

Turtle Bay Corner Condo With A Fairway View!

Resort-style amenities at your doorstep, including snorkeling beach access, pool, tennis courts, & 2 world-class golf courses. East Side of Kuilima Estates, on the Fazio 17th w/cool breezes, new washer & dryer, and A/C in bedroom & living room for comfort. The unit is locally owned and operated by longtime North Shore residents. After you have experienced all of the attractions O’ahu has to offer, check out our place on Molokai. Relax there and enjoy a true authentic Hawaiian experience!

Top Guest favourite

A scenic sunset view highlights the horizon over calm waters, with soft waves lapping against the sandy beach. In the foreground, a decorative dolphin sculpture adds a touch of charm to the balcony railing, while lush greenery frames the view.

Condo in Waianae

4.97 out of 5 average rating, 324 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

Two individuals float in calm, clear ocean water, each using a brightly colored inflatable inner tube. The water appears inviting and tranquil, and the sandy bottom is visible beneath the surface.

Condo in Hauula

4.77 out of 5 average rating, 267 reviews

Dreamy Beachfront Cottage with Breathtaking Views

Dream away in this romantic, sandy beachfront cottage. (Not affected by recent rain in Hawaii.) Perfect for couples and families! Enjoy life on the beach, or relaxing on a large patio facing the ocean. This charming cottage features a remodeled galley-style kitchen, and bath. No A/C, but trade winds and ceiling fans keep you comfortable. Price includes all taxes, resort and parking fees. See spectacular sunrises, moonrises, and giant, green-sea turtles sleep on the beach at night until dawn.

Guest favourite

A scenic outdoor area features multiple turquoise umbrellas providing shade over a set of tables and chairs. Lush green landscaping surrounds the space, while the ocean waves gently lap against the shore in the background, framed by swaying palm trees under a clear blue sky.

Apartment in Hauula

4.9 out of 5 average rating, 67 reviews

3M - Pat's at Punalu 'u - Pikaki Paradise

This end unit has 3 sets of doors to bring in the light, and the trade winds. It has the largest lanai in the building. Note: This building is undergoing work that may involve noise and off-property, nearby parking. If you choose to stay and find these issues to be unacceptable, please contact me and a full refund will be given for any unoccupied nights. Feel free to drop host a message (scroll to the bottom) if you cannot find dates on the calendar. I have other condos on island.

Guest favourite

A dining table is placed in front of large windows, offering a view of the ocean and a palm tree swaying gently. The clear blue sky contrasts with the water's gentle waves, creating a serene atmosphere.

Condo in Hauula

4.88 out of 5 average rating, 109 reviews

"Coconut Cottage by the Sea" Steps to the beach!

Aloha & Welcome to Punaluu! Enjoy a memorable visit when you stay in this unique sandy beachfront cottage! Important! Please keep reading for information about the renovations going on at the property. Incredible view of the ocean & you will love amazing sunrises right out your window! This special condo has a great little kitchen & new king bed. Perfect for swimming, snorkeling, paddleboarding & just relaxing on the beach! BBQ area, pool, gym, security & FREE parking!

Guest favourite

An outdoor seating area is featured, with a wooden table and four white metal chairs. A comfortable lounge area, furnished with a wooden bench and colorful cushions, is visible to the right. The background includes lush greenery, enhancing the setting's natural feel.

Guesthouse in Haleiwa

4.94 out of 5 average rating, 173 reviews

Dreamy Surf Shack

If you are looking for a dreamy modern surf shack on the North Shore of Oahu then this is the ultimate spot! Located on a quiet private street across from the famous surf breaks and the best beaches. Sunset Beach, BackYards and Velzyland - which offers perfect swimming in the summer and amazing surf all winter, turtle sighting on the sand and spectacular sunsets are all only a 3 minute bike ride away and about a 5-10 minute walk away. @dreamysurfshack

Guest favourite

The kitchen area features white cabinetry, a black refrigerator, and stainless-steel appliances. A butcher block countertop serves as a preparation space, complemented by a wooden island and a black stool. Natural light fills the room through windowed doors, enhancing the modern design.

Guesthouse in Hauula

4.93 out of 5 average rating, 83 reviews

Modern 1 Bed by the Beach w/Stay Discounts

Kick back and relax in this calm, stylish space. Located on the relaxing north east shore of Oahu, you're a minutes walk across the street to a beautiful and uncrowded sandy beach. Or take a drive 15 minutes up the road to the world famous surfing beaches of the north shore. If you want to stay in a bit, no problem either. Completely redone in 2022, this one bedroom apartment has a light modern feel that makes it a pleasure to just hang around.

Guest favourite

A cozy studio space features a spacious bed with a patterned blanket, complemented by wooden cabinetry. A kitchenette area is equipped with a refrigerator, microwave, coffee maker, and meal preparation essentials. Natural light filters in through a window, draped with a teal curtain.

Guest suite in Hauula

4.85 out of 5 average rating, 357 reviews

Hauula Studio

Hauula Hale Studio quietly sits against the mountains in the small town of Hauula, which is just a 5 minute drive from Laie and the Polynesian Cultural Center. Located in the charming country setting of Oahu's windward coast, you can enjoy a quiet and relaxing stay in our comfortable studio. With only a 5 minute walk to hiking trails or the beach or a 20 minute drive to the beautiful North Shore, there is plenty to explore and do.

Guest favourite

A spacious sleeping area is highlighted by a king-size bed dressed in a white coverlet. A futon is positioned alongside, complemented by decorative pillows. Soft natural light enters through multiple windows, while indoor plants add a touch of greenery to the peaceful ambiance.

Guesthouse in Kailua

4.87 out of 5 average rating, 440 reviews

Kailua Palm Studio. Walk to Beach! PERMITTED

Licensed, legal (NUC short term rental #1990/NUC-1819, Tax map key: 43073024) *not impacted by Honolulu ordinances banning short term **RECENTLY 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.