Vacation rentals in Kaaawa

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

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.

Large Kailua Beach Home - Steps To The Beach!

Spacious home for the entire family to enjoy! Just a few minutes walk to the soft sand & clear water of Kailua beach. Spend your days at the beach with your private, air conditioned oasis awaiting you for rest and relaxation. A short bike ride to Kailua Town with restaurants and shops. Lanikai Beach is less than a 5 minute drive away. Hike, bike ride, snorkel, swim, surf, boogie board, kayak, paddle board, kite surf, wind surf, and much more!! Some dates not shown - reach out to confirm avail!

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!

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.

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.

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.

Cozy retreat w/golf views & beach

Experience a relaxed North Shore escape at Turtle Bay, where sweeping golf course vistas blend with gentle beach breezes for the perfect Hawaiian getaway. - Sleeps 6 | 3 bedrooms | 4 beds | 2 baths - Golf course views & sunlit outdoor dining area - Fenced backyard w/ cozy BBQ grill & seating - Beach access & beach essentials provided - Family‑friendly: crib, toys, workspace & WiFi - Fully equipped kitchen & dining space

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.

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