Holiday rentals in Kaaawa

Secret Beach with Sunrise Views

Inexpensive, all-inclusive rate for an ocean-front condo on a secret beach with stunning sunrise views! Large remodeled kitchen with full-size appliances make this condo perfect for families. Outdoor amenities include: BBQ area, pool, large lawn + picnic areas. NO A/C but lots of trade-wind breezes. The daily rate includes taxes, parking, resort fees, Smart TV, high speed WiFi. Current rates reduced due to construction nearby. A private sandy beach is just a steps away, waiting for you to enjoy.

Blue Hawaii Sandy Beachfront Cottage

Peaceful, beachfront 2nd floor cottage. Ideal for 1-4 guests. Price Includes taxes, parking, resort, and wifi. Galley kitchen with marble countertops, 2-burner cooktop, and beach house charm. NO A/C, but trade-wind breezes and ceiling fans provide comfort in this tropical paradise. This upstairs unit is 1 part of a 2-story, 4-plex building. Amenities include: BBQ, pool, fitness room, and lawn chairs. Rates reduced due to construction onsite, but no construction in the unit or on the beachside.

Nalu's Island Home • New AC • Spacious 2 Story

❄️ Brand new Split AC units! 🌺 Comfortable for large groups. A short walk from the shore, a spacious two-story home with a large fenced-in yard! Space to unwind with 4 bedrooms, 3 full bathrooms, 2 kitchens, and 2 pullout beds. Beach gear & baby essentials provided! 🌴 With Ocean & Mountain views, Wi-Fi to help to keep you connected, Family Friendly & Private Parking. 🌊 Great location on the north windward side of the island. Close to Kualoa Ranch, North Shore, food trucks, PCC and more!

"Sand & Seashore Beachfront Living" Views for Days

Incredible views! This larger 726 sq ft one bedroom is located on the Windward side of Oahu! Welcome to the country! Away from the crowded beaches & downtown, yet close to many beautiful attractions that this island has to offer! This condo has a beautifully remodeled kitchen, spacious living room, separate bedroom & full bathroom. This white sand beach is perfect for swimming, snorkeling with sea turtles, paddle boarding, fishing & just relaxing in the sun! Pool & BBQ area, free parking!

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.

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!

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.

"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.

Sea Cliff House 2 - Oceanfront Home - 30-day stays

Guests said: "Probably the BEST place I have ever stayed. Not a single downside." "This house is too beautiful for words." "Love love love the place!! Thank you!!" You'll love this oceanfront North Shore Oahu home, too. See the crystal-clear waters of Laie Bay from nearly everywhere in the house. Dine on the lanai with the ocean so close you feel like you can touch it. The Sea Cliff House is on beautiful Laie Point, a unique peninsula on the quiet side of Oahu.

Modern 1 Bed by the Beach w/Stay Discounts

Kick back and relax in this calm, stylish space. Located on the relaxing north east shore of Oahu, you're a minutes walk across the street to a beautiful and uncrowded sandy beach. Or take a drive 15 minutes up the road to the world famous surfing beaches of the north shore. If you want to stay in a bit, no problem either. Completely redone in 2022, this one bedroom apartment has a light modern feel that makes it a pleasure to just hang around.

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.

Ocean Breeze Punalu'u

Stay right on the beach in beautiful Punalu'u on Oahu's luscious east side. One bedroom condo apartment has an onsite pool, fitness center, 24 hour security, assigned parking, wifi, and cable. Recently renovated apartment is close to hiking, numerous secluded beaches, the PCC, and Oahu's North Shore. Construction is finished for the rest of 2026! Construction is set to resume some time in early 2027.