615 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, ranging from $50 to $15500 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 the perfect vacation rental for your Kailua getaway? Tripping.com’s got your trip covered. Whether you’re seeking a villa, cabin or cottage, Kailua offers 615 affordable homes to choose from, offering far more amenities, space and convenience than the average hotel room. Select from 567 properties with high-speed internet, 192 full with jacuzzi and pool, and homes complete with outdoor patio well-suited for a barbecue with loved ones. Whatever your needs, find the perfect rental that best matches your accommodation style and budget.

For travelers planning for an extended stay, long-term lodging and corporate rentals only cost an average of $16188 a month. Save hundreds with Tripping.com and even book instantly with properties marked “Instabook.” Kailua has 615 gorgeous homes with 29 pet-friendly rentals to choose from, perfect for your furry friends. Check out our listings now to get the latest deals, and book the right vacation rental for you and the whole family. Feel at home wherever you are and experience an unforgettable vacation with Tripping.com.

Search properties from 10 rental sites in Kailua where the top providers in that area are HomeAway, TripAdvisor, and Booking.com. There are 470 HomeAway rentals, 97 TripAdvisor short term rentals and 25 Booking.com vacation rentals.