Holiday rentals in Kaaawa

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.

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.

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.

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.

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.

"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!

Sunset Hale

Experience paradise at Mokuleia Beach Colony in our oceanfront 2 bedroom, 1 bath beach cottage with panoramic ocean and coastline views. Enjoy a remodeled kitchen, walk-in shower, and a spacious living area. Amenities include secured and gated community, a heated pool, tennis and Pickleball courts. NOTE: Rates are for for 2 people. You may add up to 2 more people max w/ a $25 fee per person per night plus tax. LEGAL Vacation Rental NUC No.90/TVU-0631

♥ 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.

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.

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