Holiday rentals in Kaaawa

Majestic Paradise Cabin

Tucked away in a private valley with breathtaking views, you can find some rest while being educated about this special and historical land. All visitors to the land will be REQUIRED to participate in our Aina Program (a short land conservation project), as part of your stay. It is a CAMPING experience. World famous local food trucks and beaches within a short distance in every direction, as well as onsite activities. 10-12min walk to the beach. A memorable experience and a chance to give back.

"Endless Summer" Beachfront Condo w/ Full Kitchen!

Welcome to the beach! Your little piece of paradise! This 1 large bedroom has a new king bed, and there is a bed in the living room as well. Right on a beautiful white sandy beach that is great for swimming, snorkeling, fishing & kayaking! Sea turtles & tropical fish are right out front! Fully equipped remodeled kitchen, washer/dryer & private lanai looking out at this spectacular beach & amazing ocean views! Incredible sunrises too! Pool, gym & BBQ area, WIFI, cable & onsite FREE parking spot!

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

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

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

Looking for a beautiful, sandy beachfront place to stay? This is the place! Enjoy a simple, relaxed life on the beach or sitting on a covered patio facing the ocean. The cottage has a newly remodeled galley kitchen, and bath room. NO A/C, but tropical forests, trade winds, and ceiling fans keep you comfortable. Price includes taxes, resort fees, wifi, and parking. See spectacular sunrises over the ocean and moon-lit nights. Rates are discounted, due to construction next to this cottage.

Aloha Beachfront Condo Paradise Bound Turtle Haven

New Listing! Welcome to the Aloha Beachfront Suite! Beautifully remodeled condo on the sand and water! Completely renovated in 2025! Dance among the waves anytime you want! Sleeps two guests comfortably. 🌊 Unbeatable location! On the North Shore, close to many local attractions -Polynesian Cultural Center, Keana Zipline, Ritz Carlton Turtle Bay Resort and Kualoa Ranch. Enjoy the spectacular views and sites of the area. Parking is included. It’s time to experience Hawaii at its finest!

30 Steps to the beach! Sleeps 4 TA154-814-0544-01

My place is close to Kaya's Country General Store across the Street Polynesian Cultural Center Laie Temple Laie Point Shark's Cove Marine Sanctuary (snorkeling) Sunset Beach Pipeline Waimea Falls Park Waimea Bay Kahana Bay The Crouching Lion The Old Sugar Mill Kualoa Ranch-horseback riding, 3 wheeling, mountain biking. Where Jurassic Park and Lost were filmed., public transport. My place is good for couples, solo adventurers, business travelers, and families (with kids).

3M - Pat's at Punalu 'u - Pikaki Paradise

This end unit has 3 sets of doors to bring in the light, and the beautiful trade winds. It has the largest lanai in the building. Note: This building is undergoing work that may involve noise at times. If you choose to stay and find the noise 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.

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.

Studio- Ocean View Hideaway

Aloha and welcome to our home away from home in Makaha!! Newly built and luxuriously appointed, this beautiful studio with kitchen and patio area, is the ideal spot on the west side of Oahu. Located in the private gated community, with the amazing views of ocean and mountains. This is the most desirable location to escape, relax and enjoy a rejuvenating and memorable vacation! Kick back and relax in this calm, peaceful space.

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.