Vacation rentals in Kaaawa

4.76 out of 5 average rating, 169 reviews

A private lanai is seen through sliding glass doors, featuring two chairs and a small table overlooking the ocean. Lush palm trees are visible, with water glistening under the clear sky. The space has green turf flooring, providing a vibrant touch.

Condo in Punaluu

"Endless Summer" Beachfront Condo w/ Full Kitchen!

Welcome to the beach! Your little piece of paradise! 1 bed w/ king bed & queen bed in the living room too! Directly on a beautiful white sandy beach that is great for swimming, snorkeling, fishing & kayaking! Sea turtles & tropical fish are right out front! Fully equipped kitchen, washer/dryer in the condo & private lanai looking out at a spectacular beach with amazing ocean views! Enjoy incredible sunrises too! Pool, gym, BBQ area & WIFI. Close to may attractions like PCC, Kualoa Ranch & More!

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

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

Hawaii’s Best Kept Secret! The cottage is next to sandy coves, driftwood, shells, and Polo ponies in forested pastures. The ocean is excellent for snorkeling and fishing; there are 2 surf spots, & world-class windsurfing within 2 mile. Mountains behind us offer good hiking trails. The Colony has a nice pool, and a Pickle Ball court. We have TV and WiFi. LICENSE NO. 90/TVU-0108. GE-142-964-5312-01. TMK:1-6-8-009-001-0021. Note: We have NO Air Conditioner, 3 ceiling fans, 2 desk fans & ocean

4.88 out of 5 average rating, 164 reviews

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.

4.89 out of 5 average rating, 247 reviews

Aloha Beach Front Cottage

This is the slice of Paradise you are looking for. This unique beach cottage (NO AC) at the second floor is steps from a pristine Hawaiian 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

An expansive view of the ocean is captured from a balcony, showcasing gentle waves lapping against the sandy beach. Lush palm trees line the shore, and distant greenery is visible along the coastal landscape under a clear blue sky.

4.71 out of 5 average rating, 52 reviews

Beautiful Beachfront Family Condo for 4-8 guests

Great ocean views from every room. Sandy beach is great for swimming. The condo can accommodate up to 7 guests. (Base rate is for 4 guests.) NO A/C, but lush green forests, trade-wind breezes, and ceiling fans keep you comfortable in this tropical location. Price includes taxes, parking, and resort fees. Perfect for families, and groups who want privacy and a sandy beach. The condo features an open-concept kitchen with a large dining/living room. Price is discounted due to construction nearby.

4.97 out of 5 average rating, 344 reviews

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

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.

Condo in Punaluu

Beachfront Condo Hawaii Retreat Turtles & Whales

New Listing! Welcome to the Aloha Beachfront Condo directly on the sand! Time to reset and recharge! Beautifully remodeled. Dance among the waves anytime you want! 🌊 Sleep peacefully to the ocean waves from the comfort of your bed. 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 the true Hawaii!

4.97 out of 5 average rating, 29 reviews

Home in Laie

Perfect for Big Groups | A/C + Short Walk to Beach

Bring your ohana to this beautifully updated Hawaiian retreat! Just steps from the beach and minutes from local favorites, this spacious, modern home combines island charm with sleek, contemporary comfort. Enjoy open living spaces, a fully equipped kitchen, ample seating for large groups, and beautiful mountain views...perfect for gathering after a day of exploring. Ideal for families and groups seeking a relaxing tropical escape filled with warmth, comfort, and the true spirit of aloha.

4.73 out of 5 average rating, 41 reviews

Tall palm trees stand against a vibrant sunset sky, showcasing shades of pink, purple, and orange. The tranquil ocean reflects the sunset colors, with gentle waves lapping the shore in the background. The scene conveys a serene coastal environment.

Apartment in Hauula

4C Pat's at Punalu'u - Palama Paradise

End unit with 3 lanai doors to bring in all the beautiful view and sounds of the sea. It is on a reef-protected, calm beach which is perfect for families with children. Best of all it is away from the busy tourist areas of Waikiki. Note: This building is undergoing work that may involve noise and off-property, nearby parking If you choose to stay and find these issues to be unacceptable, please contact me and a full refund will be given for any unoccupied nights.

4.92 out of 5 average rating, 63 reviews

Home in Hauula

"Hina Hideaway", Views, A/C, ~5 min Walk 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.

Top guest favorite

5.0 out of 5 average rating, 18 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.

The serene beach shoreline is depicted at sunset, with gentle waves lapping against the sandy edge. Clouds hover in the sky, tinged with soft golden light. Palm trees stand to the right, contributing to the tranquil coastal scene.

4.93 out of 5 average rating, 15 reviews

Cozy Hauula Studio Getaway!

Experience breathtaking ocean views from this 4th-floor studio, offering a perfect blend of comfort and convenience. Featuring a fully equipped kitchen for home-cooked meals, a dedicated workstation for productivity, and direct access to the beach, this studio is ideal for both relaxation and work. Whether you're enjoying the sunrise from your private space or exploring the coastline, this oceanfront retreat offers the perfect getaway.