Find Vacation Rentals in Kailua

We have 305 properties to choose from
Anytime
Guests
Anytime
Guests

Popular Kailua Vacation Rentals

Find the perfect Kailua vacation rental

Villa Kailua
from $956 per night
Villa ∙ 12 guests ∙ 6 bedrooms
Kailua, Honolulu County, Hawaii, United States
Vrbo
Details
House Kailua
from $349 per night
House ∙ 4 guests ∙ 2 bedrooms
3.3
Kailua, Honolulu County, Hawaii, United States
Agoda
Details
Villa Kailua
from $1,050 per night
Villa ∙ 14 guests ∙ 6 bedrooms
5.0
Outstanding(4 ratings)
Kailua, Honolulu County, Hawaii, United States
Vrbo
Details
Cottage Kailua
from $133 per night
Cottage ∙ 2 guests ∙ 1 bedroom
4.9
Outstanding(85 ratings)
Kailua, Honolulu County, Hawaii, United States
Vrbo
Details
House Kailua
from $177 per night
House ∙ 5 guests ∙ 2 bedrooms
5.0
Outstanding(93 ratings)
Kailua, Honolulu County, Hawaii, United States
Vrbo
Details
House Kailua
from $340 per night
House ∙ 7 guests ∙ 3 bedrooms
4.9
Outstanding(39 ratings)
Kailua, Honolulu County, Hawaii, United States
Vrbo
Details
House Kailua
from $148 per night
House ∙ 4 guests ∙ 1 bedroom
5.0
Outstanding(1 rating)
Kailua, Honolulu County, Hawaii, United States
Vrbo
Details
House Kailua
from $665 per night
House ∙ 7 guests ∙ 3 bedrooms
4.7
Excellent(150 ratings)
Kailua, Honolulu County, Hawaii, United States
Vrbo
Details
House Kailua
from $292 per night
House ∙ 7 guests ∙ 3 bedrooms
Kailua, Honolulu County, Hawaii, United States
Vrbo
Details
View more

Vacation rentals and apartments with air conditioning

House  Kailua
from $874 per night
House ∙ 10 guests ∙ 5 bedrooms
5.0
Outstanding(6 ratings)
Kailua, Honolulu County, Hawaii, United States
Air conditioning
Vrbo
Details
House  Kailua
from $1,091 per night
House ∙ 7 guests ∙ 3 bedrooms
5.0
Outstanding(70 ratings)
Kailua, Honolulu County, Hawaii, United States
Air conditioning
Vrbo
Details
House  Kailua
from $611 per night
House ∙ 2 guests ∙ 1 bedroom
4.7
Excellent(169 ratings)
Kailua, Honolulu County, Hawaii, United States
Air conditioning
Vrbo
Details
View more

Vacation rentals with Wi-Fi

House  Kailua
from $256 per night
House ∙ 7 guests ∙ 3 bedrooms
4.8
Outstanding(4 ratings)
Kailua, Honolulu County, Hawaii, United States
Internet
HomeToGo
Details
House  Kailua
from $257 per night
House ∙ 7 guests ∙ 3 bedrooms
5.0
Outstanding(6 ratings)
Kailua, Honolulu County, Hawaii, United States
Internet
Vrbo
Details
Cottage  Kailua
from $501 per night
Cottage ∙ 5 guests ∙ 2 bedrooms
4.7
Excellent(146 ratings)
Kailua, Honolulu County, Hawaii, United States
Internet
Vrbo
Details
View more

Apartments and vacation rentals with a kitchen

House  Kailua
from $748 per night
House ∙ 6 guests ∙ 4 bedrooms
4.9
Outstanding(73 ratings)
Kailua, Honolulu County, Hawaii, United States
Kitchen
Vrbo
Details
Bed and breakfast  Kailua
from $438 per night
Bed and breakfast ∙ 2 guests ∙ 1 bedroom
5.0
Outstanding(172 ratings)
Kailua, Honolulu County, Hawaii, United States
Kitchen
Vrbo
Details
House  Kailua
from $190 per night
House ∙ 5 guests ∙ 2 bedrooms
4.9
Outstanding(148 ratings)
Kailua, Honolulu County, Hawaii, United States
Kitchen
Vrbo
Details
View more

Frequently Asked Questions

How much does it cost to book a vacation rental in Kailua?

You can book a vacation rental in Kailua for as little as $113 per night.

Is it possible to compare multiple vacation rentals in Kailua?

You can find and compare 305 offers in Kailua and book an ideal place for your next getaway.

Finding the perfect vacation home has never been easier. Tripping.com searches the world's top vacation rental sites to find the best properties in 190 countries worldwide. One search lets you filter, compare and sort over 10 million available vacation rentals from trusted partners including HomeAway, VRBO, TripAdvisor, Booking.com and more. When you use Tripping.com to plan your trip and book your vacation rental, you never have to wonder if you're getting the best deal.

Kailua Information

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!

Popular Day Trips Near Kailua

What are the trendiest neighborhoods in Kailua?

image-tag