Vacation rentals in Kaaawa

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Top-rated vacation rentals in Kaaawa

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Guest favorite

Home in Kailua

4.86 out of 5 average rating, 439 reviews

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, 277 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

Guest favorite

Place to stay in Kailua

4.97 out of 5 average rating, 119 reviews

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.

Guest favorite

Guesthouse in Kailua

4.8 out of 5 average rating, 186 reviews

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

Guest favorite

Condo in Waianae

4.97 out of 5 average rating, 293 reviews

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.

Superhost

Condo in Hauula

4.77 out of 5 average rating, 13 reviews

Aloha Beachfront Suite Paradise Bound North Shore

Welcome to the Aloha Beachfront Suite! Beautifully remodeled studio condo on the water. Completely renovated in 2025! Everything is new. Dance among the waves anytime you want! Sleeps two guests comfortably. 🌊 Unbeatable location! On the North Shore, close to many local attractions -Polynesian Cultural Center, Keana Zipline, Ritz Carlton Turtle Bay Resort and Kualoa Ranch. Enjoy the spectacular views and sites of the area. Parking is included. It’s time to experience Hawaii at its finest!

Guest favorite

Condo in Hauula

4.77 out of 5 average rating, 256 reviews

Dreamy Beachfront Cottage with Breathtaking Views

Looking for a beautiful, beachfront place to stay? This is the place! Imagine a tropical beach, floating in calm ocean water, and enjoying a simple, relaxed life. This cottage has lovely ocean views, a large, covered patio facing the ocean, a newly remodeled galley-style kitchen, and it's furnished with everything you'll need for a great vacation. Watch incredible sunrises come up over the ocean, and see giant, green-sea turtles sleep on this beach before heading back out to sea at dawn.

Guest favorite

Apartment in Hauula

4.89 out of 5 average rating, 54 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.

Guest favorite

Condo in Waikiki

4.9 out of 5 average rating, 193 reviews

Amazing Waikiki Beach Views!!

Perfect vacation getaway, with amazing views of Waikiki Beach and Lagoon!! Best location, walking distance to many points of interest, Ala Moana Mall/Designer stores and many restaurants! Enjoy visiting Oahu - there's sightseeing, swimming, hiking, surfing or shopping etc! Enjoy watching the fireworks every Friday nights from the patio, sponsored by Hilton Hawaiian Village! Hotel pool is also available for our guests. Also accepting long term stays at special rates.

Guest favorite

Condo in Hauula

4.77 out of 5 average rating, 145 reviews

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!

Superhost

Guest suite in Hauula

4.83 out of 5 average rating, 325 reviews

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.

Superhost

Apartment in Hauula

4.81 out of 5 average rating, 101 reviews

The Palms at Punalu'u - North Shore

Welcome to The Palms at Punalu'u This newly renovated beachfront studio condo is ideal for a restful, relaxed, laid-back vacation. Located in the "country area" of Oahu, on the windward side of the Island, this area has a more rural, easygoing atmosphere than the hustle and bustle of Honolulu and Waikiki. You get to see the authentic charm of old Hawaii. It's a ground-floor unit, so there is no waiting for the elevator