Compare Kailua Cottage Rentals

Start date: Check-in selected.
To Date
End date: Check-out

Earn Orbucks instantly: $1 Orbuck = $1 USD, good toward hotels

Save 10% or more on select hotels with Insider Prices

Book on the app to instantly earn 5% on 350,000+ hotels

Featured Cottages in Kailua

Don't see what you're looking for?
See all available properties in Kailua
View all properties
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Hotel Options in Kailua

    Sheraton Waikiki Beach Resort

    Sheraton Waikiki Beach Resort

    2255 Kalakaua Ave Honolulu HI
    $555 nightly
    The price is $659 total per night from Jan 4 to Jan 5
    $659 total
    Jan 4 - Jan 5, 2026
    Total with taxes and fees
    9/10 Wonderful! (2,806 reviews)
    Hilton Hawaiian Village Waikiki Beach Resort

    Hilton Hawaiian Village Waikiki Beach Resort

    2005 Kalia Rd Honolulu HI
    $327 nightly
    The price is $388 total per night from Jan 3 to Jan 4
    $388 total
    Jan 3 - Jan 4, 2026
    Total with taxes and fees
    8.2/10 Very Good! (8,661 reviews)
    Hyatt Regency Waikiki Beach Resort & Spa

    Hyatt Regency Waikiki Beach Resort & Spa

    2424 Kalakaua Ave Honolulu HI
    $264 nightly
    The price is $313 total per night from Jan 5 to Jan 6
    $313 total
    Jan 5 - Jan 6, 2026
    Total with taxes and fees
    8.8/10 Excellent! (4,675 reviews)

Cottages

Book a cottage in Kailua
Spend your next getaway treating yourself to a quieter, simpler way of life in a private cottage in Kailua. Cozy and charming, cottage rentals are the ideal spot when you want the comforts of home paired with a one-of-a-kind experience. They’re perfect for a single traveler looking for peace and quiet, or small groups who want to get to know Kailua better.

Cottage apartments in Kailua range from rustic to luxurious, with just about everything in between. Orbitz gives you the best deals on all of them.

Find the best cottages in Kailua
City cottages are great if you want a cozy, comfy place to stay without being far from the all the cool spots you want to check out. A cottage makes a great home base for a day filled with adventure in Kailua and the surrounding area. Not willing to give up all the comforts of a fine hotel? A luxury cottage turns up the charm while offering perks like room service, cable television, sunken spa tubs and housekeeping.

Stay in a Kailua cottage and swap busy days for peaceful evenings. Use the kitchenette or full kitchen to come up with a meal or reheat leftovers from your afternoon in Kailua. You may even be able to use a pool and laundry facilities. Whether you’re in the mood for quiet relaxation or a night on the town, a cottage puts you right where you want to be.

Kailua Cottages essential information

Accommodation
38 Cottages
Lowest Price
$313
Highest Price
$659
Popular accommodation
An Absolute, Perfect Paradise and Affordable, Koi Palms 1 bedroom Cottage - Great location! 5 Minute Walk to Kailua Beach!, Breathtaking Ocean Views Beach Cottage, Seaside Paradise, Less than 1 min walk to Kailua Beach- NUC#1990/NUC-1760, Newly-upgraded home with Diamond Head views - walk to Waikiki Beach, Sunny Hawaii BeachFront Property, Charming Lanikai Cottage. Close to beach, A/C, parking., Newly Renovated Lanikai, steps to Ocean A/C, kayak, Detached Private cottage

More to Explore