Holiday rentals in Kaaawa

Find and book unique accommodation on Airbnb

Top-rated holiday rentals in Kaaawa

Guests agree: these stays are highly rated for location, cleanliness and more.

%{current} / %{total}1 / 1

Superhost

Tiny home in Hauula

4.78 out of 5 average rating, 45 reviews

Rootz Wagon - North Shore Oahu

A unique cultural staycation in Sacred Valley—skip light-polluted Honolulu & enjoy nature’s sounds! Tucked in a private oasis with soaring mountain views, this is an affordable, memorable stay near Oahu’s North Shore. Just a 10-minute walk to the beach & food trucks, with essentials nearby! All visitors are required to join our free 1 hour Mālama ʻĀina (care for the land) program as part of your ag land retreat. This is an Off-grid Chevy van with solar mini fridge, outdoor shower & camping stove

Guest favourite

A tranquil outdoor area features a 60-foot lap pool surrounded by lush greenery and natural rock elements. A wooden dining table with an umbrella is positioned nearby, offering a view of the ocean in the background and a waterfall cascading into the pool.

Guest house in Kailua

4.81 out of 5 average rating, 200 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

Tall palm trees are positioned along the shoreline, framing a clear view of the vibrant blue ocean and a bright sky dotted with fluffy clouds. The gentle waves can be seen lapping at the sandy beach below.

Home in Hauula

4.92 out of 5 average rating, 37 reviews

Beachfront Condo Ocean View Haven Turtles & Whales

Welcome to the Beachfront Condo Oceanview Haven! Beautifully remodeled 1 bedroom home. FREE Parking. Dance among the waves anytime you want! 🌊 Perfect for two guests! But can sleep up to four! Pristine ocean views from the apartment. Unbeatable location! On the North Shore, close to many local attractions -Polynesian Cultural Center, Keana Zipline, Turtle Bay and Kualoa Ranch. Enjoy the spectacular views and sites of the area. Parking is included. It’s time to experience Hawaii at its finest!

Superhost

A sandy beach stretches along the shoreline, gently meeting the calm water. In the background, a multi-story building with balconies is partially surrounded by palm trees, creating a serene coastal environment under a clear blue sky with soft clouds.

Apartment in Hauula

4.82 out of 5 average rating, 130 reviews

Live like a local in HNL, HI - Pat’s at Punalu’u

New 18,000 BTU Window AC is now in the living room! Aloha 🏝 Welcome to my recently refreshed (new walk in shower and new tile floors) one bedroom condo located on the beautiful beach in Punaluu (Hauula, Hawaii). There is a lanai with a partial ocean view where you can have a meal or cocktail and relax The kitchen is open concept with a nice counter area for meals & is convenient/comfortable for working from a distance. There is some ocean equipment available to use (boogie boards, fins, etc).

Top guest favourite

A serene pathway leads toward the cottage, bordered by lush greenery and a manicured lawn. The ocean glistens in the distance under a bright blue sky, with a palm tree gently swaying nearby. Large windows of the cottage offer views of the tranquil waters.

Cottage in North Shore

5 out of 5 average rating, 73 reviews

Island Jewel, North Shore Bliss

An island jewel on the North Shore of Oahu, this cottage is situated right on the water in a quiet, serene, and peaceful setting. Surrounded by palms and gentle trade winds, the cottage is located in a gated, old-style Hawaiian setting, offering all of the amenities you’ve come to expect plus more, including a tennis court, pickleball court, basketball hoop, and an outdoor pool. Our cottage also offers an outdoor shower, and is just steps away from the ocean. Maximum occupancy — 4 individuals

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.

Apartment in Waianae

4.97 out of 5 average rating, 323 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.

Apartment in Hauula

4.77 out of 5 average rating, 266 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.

Flat in Hauula

4.89 out of 5 average rating, 66 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 tropical pathway leads from a sandy beach to the bright blue ocean, with gentle waves lapping against the shore. Lush greenery borders the scene, while distant hills are visible on the horizon under a partly cloudy sky.

Place to stay in Kailua

4.96 out of 5 average rating, 110 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

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.

Apartment 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

The image captures a serene beach scene with soft, golden sand and gentle waves lapping at the shore. Lush green mountains rise in the background, creating a striking contrast with the clear blue ocean. Fluffy white clouds drift overhead, adding to the tranquil atmosphere.

Home in Hauula

5 out of 5 average rating, 20 reviews

Ocean Views, Steps from Beach - 3 Bedroom/2 Bath

Across the street from the beach, great views of the ocean, beachy decor, clean, fully furnished, fully equipped kitchen, dining area inside and outside on patio deck with great views, window seat looking out to the ocean. AC, Wi-Fi and parking for one car included. Less than 10 min drive to grocery stores, pharmacy, gas station, Laie town, shopping and restaurants. 30 day minimum reservation (contact host to discuss your reservation dates) GET/TA-152-967-4240-01

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.

Guest house in Haleiwa

4.94 out of 5 average rating, 172 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