Vacation rentals in Kaaawa

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 the patio facing the ocean. This charming little cottage features a remodeled bathroom and galley-style kitchen. No A/C, but trade winds and ceiling fans keep you comfortable. Price temporarily reduced due to construction on the main condo complex. See spectacular sunrises, moonrises, and giant green-sea turtles sleep on this sandy beach at night until dawn.

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

Island Jewel, North Shore Bliss

An island jewel on the North Shore of Oahu, this cottage is situated right on the water in a quiet, serene, and peaceful setting. Surrounded by palms and gentle trade winds, the cottage is located in a gated, old-style Hawaiian setting, offering all of the amenities you’ve come to expect plus more, including a tennis court, pickleball court, basketball hoop, and an outdoor pool. Our cottage also offers an outdoor shower, and is just steps away from the ocean. Maximum occupancy — 4 individuals

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.

8P - Hale Ohana Ali'i

Spacious 1,520 sq. ft. two-story beachfront penthouse with 3 bedrooms, 2 baths, and room for up to 10 guests. Enjoy ocean and mountain views, direct beach access, a full kitchen, and covered parking. Watch the sunrise and look for sea turtles from the lanai. The reef-protected beach offers calm water that is great for families with children. Ideal for family gatherings and relaxed North Shore stays. Please note: no AC; fans, the trade winds, and a dehumidifier help keep the condo comfortable.

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.

"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!

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

Hawaii’s Best Kept Secret: The cottage is next to sandy coves, driftwood, shells, and forested pastures filled with polo ponies. The ocean is excellent for snorkeling and fishing; there are two surf breaks within one mile, windsurfers get wind most afternoons, and the mountains behind us offer good hiking trails. The Colony has a nice pool and a large grass chipping green, and a tennis court. We have TV and WiFi. LICENSE NO. 90/TVU-0108. GE-142-964-5312-01. TMK:1-6-8-009-001-0021.

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.

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.

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.