Vacation rentals in Kaaawa

4.86 out of 5 average rating, 444 reviews

Home in Kailua

Kailua Beach Park - 1 BR Cottage

Kailua Beach was once again been rated as the best beach in the USA for 2019, by Dr. Beach." The cottage is directly across the street from Kailua Beach Park and less than a 2-minute walk to step into the ocean. It is a legal vacation rental, license number 1990/NUC-1758. The property is tucked away one house back from the road into Lanikai, and described by guests as "a little oasis of quiet and calm." The bathroom has been remodeled with a new showers, sinks and plumbing fixtures April 2022!

Top guest favorite

Condo in Hauula

4.9 out of 5 average rating, 278 reviews

Secluded White Sandy beach just 30 steps away

Enjoy the 17% discount (as I pay the taxes out of the proceeds of your payment unlike most other listings that add it on) Don’t be fooled by the other smaller studios with just a niche that barely fits a bed. This is the largest true one bedroom model at Pats. This beautiful beachfront condo is the most preferred unit located at the far end on the ground floor just 30 steps to the powdery white sand beach with the only door facing East. Assigned parking close by. Avoid lengthy elevator waits

4.97 out of 5 average rating, 120 reviews

Place to stay in Kailua

Honu Suite at La Bella’s-Walk to Beach-Licensed

No detail is overlooked at this charming and luxurious home. La Bella’s Bed and Breakfast is the place to be if you are looking for a short walk to the beach, a beautiful garden to enjoy, great host family that lives onsite and close to amenities. Our luxury bedding and upgraded style makes you feel right at home during your Hawaii vacation. The Honu (Turtle) Suite: -AC -Queen bed -Full kitchen -Private bathroom This suite is extra private -located away from the rest of the living quarters.

4.8 out of 5 average rating, 187 reviews

Guesthouse in Kailua

Absolutely Oceanfront-60'Waterfall Pool-Legal

Kailua Absolutely Oceanfront Deluxe Vacation Rental The closest house to the Ocean in Kailua Hear waves breaking just outside Located in a quiet uncongested upscale neighborhood 60ft salt-sanitized waterfall lap pool Attached Ocean-View Deck 16-foot vaulted ceilings Wall-mounted Fujitsu air conditioning Tide pooling steps away Dramatic Sunrises Refreshing Tradewinds No Bedbugs here/Bed Bug Protective Queen Mattress and pillow covers Ozone sanitized between rentals NUC: Certificate 90-BB-0060

4.82 out of 5 average rating, 34 reviews

Place to stay in Hauula

Majestic Paradise Cabin

Tucked away in a private valley with breathtaking views, you can stay here for your retreat and be educated about this sacred land. It is a CAMPING experience. All visitors to the land will be REQUIRED to participate in our Malama Aina (care for the land) tour/program as part of your ag land education retreat. World famous beaches and food trucks within a short distance in every direction, as well as onsite activities. 10-12min walk to the beach. Make memories here that will last a lifetime!

4.97 out of 5 average rating, 295 reviews

Condo in Waianae

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.

4.88 out of 5 average rating, 48 reviews

Aloha Paradise Beach

Spectacular ocean and sunrise views. Quiet, rural area, on a pristine, sandy beach. Hear the soothing sounds of small waves. Safe for snorkeling and swimming due to a protective coral reef 1/4 mile offshore. Some construction going on at the other end of the property during weekdays. Price includes taxes, resort fees, wifi, and parking. Bonus: see giant green-sea turtles sleep on the beach at night. Perfect for remote workers and travelers who want to stay more than 30 days.

4.88 out of 5 average rating, 56 reviews

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.

4.77 out of 5 average rating, 145 reviews

Condo in Hauula

Amazing Beachfront Condo!

Welcome to the beach! Your little piece of paradise! This 1 larger bedroom, 1 bath condo has a newly remodeled kitchen! 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 kitchen, washer/dryer & your private lanai looking out at this spectacular beach & amazing ocean views! Incredible sunrises too! Pool, gym & BBQ area, WIFI, cable & onsite FREE parking spot!

5 out of 5 average rating, 3 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.

4.83 out of 5 average rating, 327 reviews

Guest suite in Hauula

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.