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Kailua Vacation Rentals and Short Term Rentals

Tripping.com is the world's top vacation rental search engine, rated 9.6 out of 10 based on 50 user reviews. Compare Kailua vacation homes and short term rentals from 7 rental sites including HomeAway, VRBO, FlipKey and more, ranging from $65 to $6,000 a night.
Showing 983 personalized results
 
    $249 / night
    Kailua Beachfront - All New Apartment!
    Kailua Beachfront - All New Apartment!
    1 bed / 1 bath
    Kailua, HI
    $155 / night
    Ginger Gazebo: Luxurious Setting with Salt Pool
    Ginger Gazebo: Luxurious Setting with Salt Pool
    1 bed / 1 bath
    Kailua, HI
    $1800 / night
    Kailua Beachfront Retreat
    Kailua Beachfront Retreat
    6 bed / 5 bath
    Kailua, HI
    $249 / night
    Hawaiian Plantation Style Studio Cabana
    Hawaiian Plantation Style Studio Cabana
    1 bed / 1 bath
    Kailua, HI
    $500 / night
    Kailua Hale Nalu Palekaiko, Best Beaches, Pool
    Kailua Hale Nalu Palekaiko, Best Beaches, Pool
    4 bed / 3 bath
    Kailua, HI
    $199 / night
    KAILUA DREAMS-PALI, the perfect mix of Beach/Town Life
    KAILUA DREAMS-PALI, the perfect mix of Beach/Town Life
    1 bed / 1 bath
    Kailua, HI
    $325 / night
    Peerless Luxury Beach Apartment 900sf (From $275)
    Peerless Luxury Beach Apartment 900sf (From $275)
    Studio
    Waimanalo, HI
    $799 / night
    Pulelehua - Pool, Spa, Waterfront, View Home!
    Pulelehua - Pool, Spa, Waterfront, View Home!
    4 bed / 3 bath
    Kane‘ohe, HI
    $300 / night
    Peacock House on Kaneohe Bay Private Waterfront
    Peacock House on Kaneohe Bay Private Waterfront
    1 bed / 1 bath
    Kane‘ohe, HI
    $6000 / night
    Royal Kailua Estate - Upscale Private Beachfront Resort with Stunning Courtyard
    Royal Kailua Estate - Upscale Private Beachfront Resort with Stunning Courtyard
    7 bed / 8 bath
    Kailua, HI
    $799 / night
    Pulelehua - Pool, Spa, Waterfront, View Home!
    Pulelehua - Pool, Spa, Waterfront, View Home!
    4 bed / 3 bath
    Kane‘ohe, HI
    $150 / night
    Vacation Rental in Oahu Hawiia, the Aloha State
    Vacation Rental in Oahu Hawiia, the Aloha State
    1 bed / 1 bath
    Kane‘ohe, HI

    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

    Save hundreds with a Tripping.com vacation rental and forget about the expensive hotel room. For the ultimate getaway trip, Kailua offers 943 vacation home rentals for an affordable price to match your budget and accommodation needs. Book one now for an average price of $313 a night, or a long-term rental for an average price of $5,341 a month.

    These homes offer a range of amenities, giving you more bang for your buck. For those looking to stay in a corporate rental, 889 of Kailua’s rentals offer high speed internet so you can easily keep in touch with your company or team. Go for a swim at one of the 382 properties complete with pool or jacuzzi, or relax with a night of cable TV in any of our 880 cozy homes.

    Search properties from 8 rental sites in Kailua where the top providers in that area are HomeAway, VRBO, and TripAdvisor. There are 472 HomeAway rentals, 384 VRBO short term rentals and 57 TripAdvisor vacation rentals.

    Traveling with pets? Choose from 48 pet-friendly rentals in Kailua for a quality experience. Tripping.com’s home rentals offer far more room and comfort than a hotel, providing a safe and spacious place for you and your furry buddy. Book instantly with properties marked “Instabook”, and check out our other listings now to find the perfect vacation home for you.

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