Holiday rentals in Kaaawa

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

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

Hibiscus Hale on Gated Estate + Walk to the Beach

Take it easy at this tranquil getaway on Oahu's North Shore. This eclectic container-turned-guesthouse is insulated & cooled with 2 split A/C units, has a cozy queen bed with all the amenities - Wifi, smart TV, off-street parking right in front of your unit & outdoor dining and gazebo area. Located on a large orchard, you'll be literally surrounded by avocado, mango and lemon trees that are free for the picking. The beach for surfing, snorkeling, shell-collecting is an easy 10 minute walk away.

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 a large, covered patio facing the ocean. This charming cottage features a remodeled galley-style kitchen, and bathroom. No A/C, but trade winds and ceiling fans keep you comfortable. Price includes all taxes, resort fees, and parking fees. See spectacular sunrises, moonrises, and giant, green-sea turtles that sleep on this sandy beach at night until dawn.

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.

"Hina Hideaway", Views, AC, Walkable to Beach

This listing represents one unit from "Hina Hideaway," a collection of comparable duplex 3BR/2BA rentals. You'll be assigned one specific unit upon booking. While decor and finishes may vary between individual units, all offer comparable quality, size, configuration, sleeping arrangements, and amenities. Enjoy A/C bedrooms, full kitchen, fast Wi-Fi, washer/dryer, and beach gear. Close to Polynesian Cultural Center, North Shore surf, Turtle Bay, and local food trucks. Walkable to the beach.

Newly Renovated Villa Walk to Beach + Pool

Welcome to your serene island retreat on O‘ahu’s North Shore. Nestled within Turtle Bay Resort and just steps from the Ritz-Carlton, Kaia Villa is a NEWLY RENOVATED modern organic retreat where boutique luxury meets effortless island living. Enjoy nearby beaches, oceanfront dining, horseback rides, and a heated pool. The villa includes beach gear, a full kitchen, an enclosed lanai for slow mornings, washer/dryer, and curated details designed to make your stay effortless and unforgettable.

"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!

♥ North Shore Paradise at Turtle Bay ♥

For the discerning traveler, a designer curated space with every luxury detail thought of. When you step inside, you can feel the love poured into this space, and the exquisite detailed craftsmanship throughout. Nestled on the 3rd green of the famous Georgia Fazio course at Turtle Bay Kuilima Estates West on the North Shore of Oahu. A perfect spot to vacation, honeymoon, or spend some quality relaxation time. This magical space welcomes you with aloha.

NOW $50/NIGHT - Plumeria Place

NOW - MAY 10th, $50/night Currently recovering from recent flooding and offering discounted nights! Bathroom facility is still under repair—NO showers available. NO electricity. Clean porta potty is on-site. Thanks for your understanding as we finish up repairs! ⚠️NOTE: This is not a luxury resort—it’s a rugged, back-to-nature experience. Expect bugs, geckos, and the occasional rainstorm. Ideal for travelers craving nature, simplicity and adventure.

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.

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.