Find Vacation Rentals in Kailua

We have 228 properties to choose from
Anytime
Guests
Anytime
Guests

Popular Kailua Vacation Rentals

Find the perfect Kailua vacation rental

House Kailua
from $172 per night
House ∙ 5 guests ∙ 2 bedrooms

88 m² House

5.0
Outstanding(96 ratings)
Kailua, Honolulu County, Hawaii, United States
Details
Apartment Kailua
from $215 per night
Apartment ∙ 6 guests ∙ 3 bedrooms

121 m² Apartment

4.9
Outstanding(39 ratings)
Kailua, Honolulu County, Hawaii, United States
Details
Cabin Kailua
from $139 per night
Cabin ∙ 2 guests ∙ 1 bedroom

56 m² Cabin

4.9
Outstanding(88 ratings)
Kailua, Honolulu County, Hawaii, United States
Details
House Kailua
from $612 per night
5 guests ∙ 2 bedrooms

House

4.8
Outstanding(242 ratings)
Kailua, Honolulu County, Hawaii, United States
Details
House Kailua
from $407 per night
House ∙ 4 guests ∙ 2 bedrooms

84 m² House

5.0
Outstanding(4 ratings)
Kailua, Honolulu County, Hawaii, United States
Details
House Kailua
from $576 per night
House ∙ 6 guests ∙ 3 bedrooms

210 m² House

4.6
Excellent(30 ratings)
Kailua, Honolulu County, Hawaii, United States
Details
House Kailua
from $746 per night
House ∙ 6 guests ∙ 3 bedrooms

186 m² House

4.6
Excellent(173 ratings)
Kailua, Honolulu County, Hawaii, United States
Details
House Kailua
from $1,831 per night
House ∙ 18 guests ∙ 6 bedrooms

417 m² House

Kailua, Honolulu County, Hawaii, United States
Details
Villa Kailua
from $562 per night
12 guests ∙ 5 bedrooms

Villa

Kailua, Honolulu County, Hawaii, United States
Details
Show more

Vacation rentals and apartments with air conditioning

House  Kailua
from $1,102 per night
House ∙ 15 guests ∙ 6 bedrooms

293 m² House

5.0
Outstanding(8 ratings)
Kailua, Honolulu County, Hawaii, United States
Air conditioning
Details
Bed and breakfast  Kailua
from $367 per night
Bed and breakfast ∙ 3 guests ∙ 4 bedrooms

Award Winner - Hawaii's Hidden Hideaway - Bed and Breakfast

4.6
Excellent(145 ratings)
Kailua, Honolulu County, Hawaii, United States
Air conditioning
Details
Cabin  Kailua
from $269 per night
Cabin ∙ 4 guests ∙ 2 bedrooms

93 m² Cabin

4.7
Excellent(67 ratings)
Kailua, Honolulu County, Hawaii, United States
Air conditioning
Details
Show more

Apartments and vacation rentals with a kitchen

House  Kailua
from $1,380 per night
10 guests ∙ 5 bedrooms

House

4.9
Outstanding(54 ratings)
Kailua, Honolulu County, Hawaii, United States
Kitchen
Details
House  Kailua
from $173 per night
House ∙ 6 guests ∙ 2 bedrooms

56 m² House

4.9
Outstanding(155 ratings)
Kailua, Honolulu County, Hawaii, United States
Kitchen
Details
House  Kailua
from $414 per night
6 guests ∙ 3 bedrooms

House

Kailua, Honolulu County, Hawaii, United States
Kitchen
Details
Show more

Vacation rentals with Wi-Fi

Cabin  Kailua
from $145 per night
Cabin ∙ 2 guests ∙ 1 bedroom

47 m² Cabin

5.0
Outstanding(65 ratings)
Kailua, Honolulu County, Hawaii, United States
Internet
Details
House  Kailua
from $924 per night
House ∙ 12 guests ∙ 4 bedrooms

195 m² House

5.0
Outstanding(2 ratings)
Kailua, Honolulu County, Hawaii, United States
Internet
Details
House  Kailua
from $450 per night
House ∙ 6 guests ∙ 4 bedrooms

130 m² House

5.0
Outstanding(31 ratings)
Kailua, Honolulu County, Hawaii, United States
Internet
Details
Show 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 $130 per night.

Is it possible to compare multiple vacation rentals in Kailua?

You can find and compare 228 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