Holiday rentals in Kaaawa

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Top-rated holiday rentals in Kaaawa

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Superhost

Home in North Shore

4.76 out of 5 average rating, 117 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.

Flat in Punaluu

4.89 out of 5 average rating, 233 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

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 Punaluu

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 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.

Flat in Kawela Bay

4.9 out of 5 average rating, 250 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 modern kitchen and living area are depicted in the image. The kitchen features sleek white cabinets and a spacious island. A stainless steel refrigerator and stove are visible. Natural light fills the area through large sliding glass doors, overlooking a green landscape.

Apartment in Kawela Bay

4.99 out of 5 average rating, 320 reviews

Modern & Contemporary North Shore Oahu Condo

Welcome to our beautiful condo nestled in the dreamy North Shore of O‘ahu. Our home is located in the gated community of Kuilima Estates West, within the renowned Turtle Bay Resort. You'll be just a 5–10 minute walk from breathtaking shorelines, world-class surf spots, romantic dining experiences, and endless adventures by land and sea. Kuilima Estates is also the only area on the North Shore where vacation rentals are legally permitted—offering you a unique and worry-free island escape.

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 Makaha

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 Punaluu

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 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 Punaluu

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

Home in Kawela Bay

4.92 out of 5 average rating, 102 reviews

Bright stay near Turtle Bay w/ pool & BBQ grill

Welcome to your North Shore escape - a relaxed stay near Turtle Bay w/ easy beach access & resort-style perks. Settle in, unwind, & enjoy island living at your own pace: - Sleeps 4 | 1 bedroom + loft | 3 beds | 2 baths - Shared outdoor pool (year-round), tennis & pickleball courts - Beach access + beach essentials & kayak - Private patio or balcony + BBQ grill - Kitchen, Wifi, workspace & in-unit washer/dryer - Family-friendly w/ Pack ’n play/Travel crib & toys