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469 Kailua Vacation Rentals & Short Term Rentals

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Compare Kailua vacation rentals from 10 rental sites including HomeAway, TripAdvisor, Booking.com and more, from $66 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

Looking for a vacation rental in Kailua? Tripping.com has 528 vacation rental homes available in Kailua. You'll find 59 studios, 168 1-bedroom, 78 2-bedroom and 223 rentals with 3 or more bedrooms ranging from $66 a night. For extra convenience, many of these vacation homes can be booked directly online.

The average price of a nightly rental in Kailua is $603 while the average price of a weekly rental is $9301. For those looking for more than a short term rental such as corporate rentals, extended stays or long term rentals, the average monthly price of a Kailua home is $18864.

Wondering if you can bring your dog or cat along with you? There are 24 pet-friendly vacation rentals available in Kailua. In addition to accommodating pets, Kailua rentals offer a variety of amenities. In particular, 488 rentals have Internet and WiFi, 466 have TV and/or cable and 162 have a pool or hot tub.

Search properties from 10 vacation rental sites in Kailua where the top providers in that area are HomeAway, TripAdvisor, and Booking.com. There are 373 HomeAway rentals, 110 TripAdvisor short term rentals and 23 Booking.com vacation rentals.