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Vacation rentals in Kaaawa

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Top-rated vacation rentals in Kaaawa

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Guest favorite
The beachfront property is surrounded by lush greenery and palm trees, displaying multiple levels of residential units. The sandy beach extends to the clear blue waters, with mountain views in the background under a partly cloudy sky.
Condo in Punaluu
4.9 out of 5 average rating, 297 reviews

Secluded White Sandy beach just 30 steps away

Enjoy the 17% discount (as I pay the taxes out of the proceeds of your payment unlike most other listings that add it on) Don’t be fooled by the other smaller studios with just a niche that barely fits a bed. This is the largest true one bedroom model at Pats. This beautiful beachfront condo is the most preferred unit located at the far end on the ground floor just 30 steps to the powdery white sand beach with the only door facing East. Assigned parking close by. Avoid lengthy elevator waits

Superhost
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 Punaluu
4.77 out of 5 average rating, 275 reviews

Dreamy Beachfront Cottage with Breathtaking Views

Dream away in this romantic, sandy beachfront cottage. Perfect for couples and families! Enjoy life on the beach, in the water, or relax on the patio facing the ocean. This charming little cottage features a remodeled bathroom and galley-style kitchen. No A/C, but trade winds and ceiling fans keep you comfortable. Price temporarily reduced due to construction on the main condo complex. See spectacular sunrises, moonrises, and giant green-sea turtles sleep on this sandy beach at night until dawn.

Guest favorite
A serene beach scene is presented, with soft golden sand stretching along the shoreline. Gentle waves lap at the coast, reflecting a clear blue sky dotted with fluffy clouds. Lush palm trees line the beach, providing a tropical ambiance to the picturesque landscape.
Condo in Punaluu
4.82 out of 5 average rating, 148 reviews

"The Honu Hale" Beachfront Condo w/ View & Kitchen

SPECIAL PRICE! Welcome to your little piece of paradise! On a beautiful white sandy beach. Great for swimming, snorkeling, fishing & kayaking! Sea turtles & tropical fish are right out front! Punaluu is on the Windward side of Oahu away from all the crowds of town yet close to lots of amazing things to do! PCC, North Shore beaches & big wave surfing! There is a fully equipped kitchen, 2 beds for you & your guests. Washer/dryer in the unit & a private lanai! Keep reading for construction info...

Top guest favorite
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 Makaha
4.97 out of 5 average rating, 340 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.

Top guest favorite
The image captures a sunset view over the ocean, framed by palm trees and a neighboring cottage's overhang. A grassy area leads to the water’s edge, where calm waves meet the shore. Light reflects off the water, creating a serene ambiance.
Cottage in North Shore
4.88 out of 5 average rating, 158 reviews

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

Hawaii’s Best Kept Secret: The cottage is next to sandy coves, driftwood, shells, and forested pastures filled with polo ponies. The ocean is excellent for snorkeling and fishing; there are two surf breaks within one mile, windsurfers get wind most afternoons, and the mountains behind us offer good hiking trails. The Colony has a nice pool and a large grass chipping green, and a tennis court. We have TV and WiFi. LICENSE NO. 90/TVU-0108. GE-142-964-5312-01. TMK:1-6-8-009-001-0021.

Top guest favorite
Aerial view of a coastal property lined with homes along a sandy beach. Lush greenery and palm trees are visible, leading to a backdrop of mountains under a partly cloudy sky. Gentle waves lap against the shore, creating a serene beach environment.
Home in North Shore
4.98 out of 5 average rating, 108 reviews

Haleiwa Waterfront House

Location, location, location! This lovely DUPLEX home is perfectly situated on a beautiful white sandy beach and at the end of a quiet cull de sac. You will find all the space and privacy that one needs to enjoy a nice peaceful holiday. Historic Haleiwa Town rests in the heart of the north shore with Haleiwa being a 3 minute drive away and all the beautiful surf/swim beaches if not in front of the house then a mere 5 - 15 minute drive away (35 minute drive to the airport) .

Top guest favorite
A sea turtle glides gracefully in the clear, turquoise water, just beneath the surface. In the background, two small islands rise against a bright blue sky dotted with fluffy white clouds, creating a serene coastal atmosphere.
Place to stay in Kailua
4.96 out of 5 average rating, 131 reviews

Tropical Kailua Retreat | Walk to Beach + Gym

Walk to one of Hawaii’s most beautiful beaches, explore Kailua by kayak or bike, and relax in your own tropical retreat. The Honu (Turtle) Suite at La Bella’s Bed & Breakfast offers privacy, comfort, and island charm just minutes from the beach. Enjoy a queen bed with luxury linens, air conditioning, a full kitchen, private bathroom, private entrance, and outdoor seating area surrounded by tropical gardens on Oʻahu’s beautiful Windward Coast.

Top guest favorite
Apartment in Punaluu
5 out of 5 average rating, 12 reviews

Ocean Sounds by Turtle Bay

Be among the first guests to stay at this oceanfront getaway. Newly furnished, cozy, and designed for relaxing. Located near Turtle Bay Resort (25 min drive) on a quieter stretch of the island with fewer crowds and more calm ocean. Fall asleep to the waves and wake up to sunrise outside your window. ❗️Note: there’s construction on the parking side of the building till 9/1, so parking is limited and the curb appeal is not at its best.

Guest favorite
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, 372 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.

Top guest favorite
Apartment in Punaluu
4.93 out of 5 average rating, 14 reviews

North Shore Beachfront Studio

Wake up to breathtaking ocean views in this 4th-floor Hauʻula studio, designed for couples or solo travelers seeking the perfect North Shore escape. Step outside to sandy shores or unwind by the oceanfront pool. Minutes from Kualoa Ranch Adventures and the Polynesian Cultural Center, plus nearby food trucks, scenic hikes, and world-famous beaches. Simple, stylish, and unforgettable—your ideal base to explore Oʻahu’s North Shore.

Guest favorite
Cabin in Pupukea
4.89 out of 5 average rating, 46 reviews

The Coconut Hale

Welcome to Coconut Hale! Tucked into the lush hills of Pupukea, this simple one-bedroom cabin is perfect for extended surf trips, lazy naps, and slow mornings on the deck. Just minutes from world-famous beaches and the charm of Haleiwa Town, it’s a great place to unwind and recharge. Local laws require a minimum 30-day booking, but you don’t have to stay the full 30 days. Feel free to message us with any questions.

Superhost
The oceanfront condo is displayed from a water-level perspective, showcasing its multi-story structure. Lush palm trees surround the property, and gentle waves lap at the soft sand beach. The building features a light-colored exterior with multiple balconies overlooking the ocean.
Apartment in Punaluu
4.85 out of 5 average rating, 198 reviews

Aloha Hidden Treasure

This is the slice of Paradise. This unique ocean front condo located at the four floor, is steps away from a pristine Hawaiian soft-sand beach. Sit & enjoy the ocean. Take it easy at this unique getaway. The price has a big discount, because building is under construction, can be noisy between 8 to 4, M to F. Better be out to enjoy the beach and the island. TMK#530080020054 TA-075-900-3648-01

Popular amenities for Kaaawa vacation rentals