442+ Vacation Rentals & Holiday Homes in Kailua |
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Kailua Accommodations - Hotels & Rentals

About Kailua Vacation Rentals

Discover More than 442 Incredible Getaway Rentals Available in Kailua. Choose from a Wide Selection of Villas, Hotels, and Other Rental Options. Explore Luxury Amenities at Affordable Prices, Creating the Ideal Base for Your Next Vacation. Plan Your Perfect Escape with Online Reservations and Uncover Fantastic Stays in Kailua.

Online Reservations Offers Numerous Last-Minute Deals on Villas, Hotels, and Rentals, Both Near You and Across the Globe. Whether You Need Accommodation for a Group or an Event, Be it a Hotel or Vacation Rental (Including Cabins and Private Luxury Villas), We're Here to Assist. With Online Reservations in Kailua, You Can Easily Compare Options from Multiple Suppliers with a Single Click to Find the Perfect Price Point, Amenities, and Style of Stay That Suit Your Needs. Looking for Group Deals, Properties with Private Pools, Hot Tubs, Pet-Friendly Options, or Spacious Master Suite Bedrooms with Open-Air Showers? You Can Find It All in the Online Reservations Vacation Rentals, Resorts, and Airbnb-Style Properties in Kailua. The Average Size of Places to Stay Near Kailua is 1332.5 ft², with Prices Averaging US $784 per Night.

Let Online Reservations Help You Discover the Ideal Holiday Rental to Create Lifelong Travel Memories in Kailua. Our Listed Prices Are Often Discounted Compared to Rack Rates. Simply Search for Your Destination and Secure the Perfect Place to Stay Today.

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Top Hotels & Vacation Rentals in Kailua

Type Count
Vacation Homes 286
Holiday Apartments 93
Cottages 38
Villas 16

Use these Quick Filters to Find a Vacation Rental in Kailua

★ Pro Tip: Online Reservations is a vacation rental website specializing in cottages, lake houses, and exclusive summer home rentals. We curate a vast selection of incredible properties from trusted suppliers, allowing you to compare prices and locations to find the perfect fit for your getaway. Create lasting memories in Kailua with Online Reservations.

Weather in Kailua, HI

View the weather forecast for Kailua before booking your Kailua Vacation Rentals to confirm your best time to go.

December - February
High 79°F       Low 64°F
March - May
High 83°F       Low 66°F
June - August
High 84°F       Low 69°F
September - November
High 84°F       Low 66°F

Activities KailuaGuest Reviews Local Attractions

A Large Selection of Hotels and Vacation Rentals from Around the World KailuaGuest Reviews Discover Exciting Activities and Must-Visit Destinations for Your Upcoming Journey


Kailua Beach
Lanikai Beach
Kalama Beach Park
Kawainui Park
Royal Hawaiian Golf Club
Kailua Bay Beach
Mokapu Point
Kaneohe Klipper Golf Course
Lanikai Pillboxes Trailhead
Olomana Three Peaks Trail
Pohakupu
Ulu Po Heiau State Monument
Ala Moana Center
Diamond Head
Moana Surfrider
Royal Hawaiian Center
Honolulu Zoo
Honolulu Harbor
Waikiki Beach
Hanauma Bay Nature Preserve

Find Hotels & Vacation Rentals in these Cities and Neighborhoods


Ulu Po Heiau State Monument 433 Properties
Pohakupu 433 Properties
Kuulei Tract 432 Properties
Kailua Bay Beach 432 Properties
Kalama Beach Park 431 Properties
Kawainui Park 426 Properties
Enchanted Lake 411 Properties
Keolu Hills 396 Properties
Coconut Grove 314 Properties
Maunawili 301 Properties
Kalama Tract 149 Properties
Lanikai 82 Properties

Frequently Asked Questions About Kailua?

What are the top hotels, lake houses & vacation rentals in Kailua?

We provide an array of great vacation destinations in Kailua. If you are looking to stay in or around the Kailua area, make sure to browse our options to find a premium rental location in a top vacation destination. Whether it is a few nights, a week, or more, we've got the luxury stays that rank among the Top Vacation Rentals in Kailua:

How many Hotels & Vacation Rentals have private pools in Kailua?

We have 77 Hotels & Vacation Rentals featuring a private pool in and near Kailua. Some of the best destinations to stay that feature or have access to a swimming pool are:

Which hotel, lake house, or vacation rental in Kailua is best for families?

Searching for a family-friendly getaway in Kailua? We've got you covered. Check out one of these luxurious getaways that are highly-rated and perfect fits for families of all sizes.

How many hotels, resorts, or rentals are available in Kailua?

Online Reservations™ offers a consistent supply of new options, combined with established great stays in top areas. Currently, the number of properties listed by Online Reservations™ in 2025 is over 442 in the Kailua area, and that number rises every day. By combining listings from multiple websites and travel providers, Online Reservations™ can provide you with a diverse amount of choices of the best luxury stays in Kailua.

Nearby Neighborhood (7) 
Neighborhood Property Count
Kalama Tract Vacation Rentals in Kailua, Hawaii 149
Lanikai Vacation Rentals in Kailua, Hawaii 82
Coconut Grove Vacation Rentals in Kailua, Hawaii 314
Enchanted Lake Vacation Rentals in Kailua, Hawaii 411
Keolu Hills Vacation Rentals in Kailua, Hawaii 396
Palolo Vacation Rentals in Kailua, Hawaii 140
Kuulei Tract Vacation Rentals in Kailua, Hawaii 432

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