497 Kailua Vacation Rentals & Short Term Rentals

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Compare Kailua vacation rentals from 14 rental sites including HomeAway, TripAdvisor, HRS Holidays and more, ranging from $28 to $35270 a night.

Information about Kailua

About Kailua

Located on the Windward side of Oahu, Kailua is a popular destination for locals and visitors alike. Just a 30 minute drive from Waikiki, a popular beach neighbourhood in Honolulu, it is said that Kailua is “Like stepping into a post card." Kailua is home to two of the most famous beaches in America, Lanikai Beach and Kailua Beach.

Things to do in Kailua

The top of your to-do list should be to visit the world-famous beaches. Both Lanikai Beach and Kailua Beach have been rated #1 in different publications. Once you see the turquoise water and the soft, white sand, you’ll know why. Lanikai is a 5 minute drive South of Kailua Beach and both are equally as suitable for a great day of sun and sand. Grab your breakfast and sunscreen and get to these hot spots as soon as possible. Being an island favorite, these beaches get pretty crowded early on in the day. There are plenty of watersports to be enjoyed for the adventurous; kayaking, kite boarding, body boarding, parasailing, and windsurfing are among the most popular. Snorkeling is never a bad option, either! Want to spend a day off the beach? No problem! Check out Mount Olomana Three Peaks Trail for an exhilarating, challenging, yet very rewarding hike. Maunawili Falls is another scenic hike with a breathtaking waterfall at the end. If you’re looking for some history, visit the Heiau (an ancient Hawaiian temple) that can be found on the outskirts of Kailua, or head over to Pearl Harbor, a site 35 minutes away that is dedicated to those who fought and lost their lives in the Pacific during World War II. When your day comes to an end, stop in at one of the many spas for a famous Lomi Lomi massage.

Kailua Accommodations

Kailua is 19 miles from the Honolulu International Airport where you can catch a bus, a taxi, a shuttle, or rent a car. Once in Kailua, grocery stores and other amenities are all just a short distance away. Whether you’re looking for a beachfront beauty or something a few blocks back, Tripping.com has your perfect Hawaiian getaway covered!

Vacation Rentals in Kailua

Find the best Kailua vacation rentals with Tripping.com. Choose from 1057 rentals, from studio apartments to luxurious condos to entire cabin homes. Book in advance or book instantly with properties marked as “Instabook,” with prices ranging from $28 a night to $35270 a night.

Our Tripping.com vacation rentals will save you hundreds, offering more amenities than the average hotel room. Going on a business trip? 868 of homes in Kailua offer high-speed wifi internet so you won’t miss a beat. Travelling with kids? Have them splash around in any of the 360 rentals with pool or jacuzzi, or relax with the family in one of the 873 homes with cable TV.

For all those dog lovers and cat lovers, Kailua offers 64 pet-friendly vacation rentals at an affordable price. Book the perfect vacation home that best matches your budget and accommodation style. For the ultimate stay, check out our listings now to grab the latest deals.

Search properties from 14 rental sites in Kailua where the top providers in that area are HomeAway, TripAdvisor, and HRS Holidays. There are 753 HomeAway rentals, 169 TripAdvisor short term rentals and 45 HRS Holidays vacation rentals.