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Popular Kailua Vacation Rentals

Find the perfect Kailua vacation rental

House Kailua
from $435 per night
4 guests ∙ 2 bedrooms

House

5.0
Outstanding(10 ratings)
Kailua, Honolulu County, Hawaii, United States
Vrbo
Details
House Kailua
from $252 per night
House ∙ 7 guests ∙ 3 bedrooms

139 m² House

4.8
Outstanding(4 ratings)
Kailua, Honolulu County, Hawaii, United States
HomeToGo
Details
House Kailua
from $1,134 per night
House ∙ 10 guests ∙ 5 bedrooms

167 m² House

5.0
Outstanding(9 ratings)
Kailua, Honolulu County, Hawaii, United States
Vrbo
Details
House Kailua
from $128 per night
House ∙ 10 guests ∙ 5 bedrooms

167 m² House

5.0
Outstanding(9 ratings)
Kailua, Honolulu County, Hawaii, United States
HomeToGo
Details
House Kailua
from $183 per night
House ∙ 5 guests ∙ 2 bedrooms

88 m² House

5.0
Outstanding(93 ratings)
Kailua, Honolulu County, Hawaii, United States
Vrbo
Details
House Kailua
from $1,047 per night
House ∙ 20 guests ∙ 8 bedrooms

465 m² House

4.8
Outstanding(85 ratings)
Kailua, Honolulu County, Hawaii, United States
Vrbo
Details
Cottage Kailua
from $137 per night
Cottage ∙ 2 guests ∙ 1 bedroom

56 m² Cottage

4.9
Outstanding(85 ratings)
Kailua, Honolulu County, Hawaii, United States
Vrbo
Details
House Kailua
from $2,290 per night
House ∙ 14 guests ∙ 8 bedrooms

465 m² House

4.7
Excellent(102 ratings)
Kailua, Honolulu County, Hawaii, United States
Vrbo
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House Kailua
from $542 per night
7 guests ∙ 3 bedrooms

House

4.9
Outstanding(39 ratings)
Kailua, Honolulu County, Hawaii, United States
Vrbo
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Vacation rentals and apartments with air conditioning

House  Kailua
from $1,124 per night
10 guests ∙ 5 bedrooms

House

5.0
Outstanding(46 ratings)
Kailua, Honolulu County, Hawaii, United States
Air conditioning
Vrbo
Details
Bed and breakfast  Kailua
from $362 per night
Bed and breakfast ∙ 3 guests ∙ 4 bedrooms

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

4.6
Excellent(101 ratings)
Kailua, Honolulu County, Hawaii, United States
Air conditioning
Vrbo
Details
House  Kailua
from $360 per night
House ∙ 5 guests ∙ 2 bedrooms

93 m² House

4.7
Excellent(86 ratings)
Kailua, Honolulu County, Hawaii, United States
Air conditioning
Vrbo
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Apartments and vacation rentals with a kitchen

Apartment  Kailua
from $109 per night
Apartment ∙ 2 guests ∙ 1 bedroom

48 m² Apartment

Kailua, Honolulu County, Hawaii, United States
Kitchen
HomeToGo
Details
House  Kailua
from $763 per night
House ∙ 6 guests ∙ 4 bedrooms

116 m² House

4.9
Outstanding(86 ratings)
Kailua, Honolulu County, Hawaii, United States
Kitchen
Vrbo
Details
House  Kailua
from $189 per night
House ∙ 5 guests ∙ 3 bedrooms

56 m² House

4.9
Outstanding(151 ratings)
Kailua, Honolulu County, Hawaii, United States
Kitchen
Vrbo
Details
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Vacation rentals with Wi-Fi

House  Kailua
from $308 per night
House ∙ 8 guests ∙ 5 bedrooms

186 m² House

4.9
Outstanding(50 ratings)
Kailua, Honolulu County, Hawaii, United States
Internet
Vrbo
Details
House  Kailua
from $481 per night
House ∙ 4 guests ∙ 1 bedroom

88 m² House

4.9
Outstanding(95 ratings)
Kailua, Honolulu County, Hawaii, United States
Internet
Vrbo
Details
Apartment  Kailua
from $128 per night
Apartment ∙ 3 guests ∙ 1 bedroom

37 m² Apartment

5.0
Outstanding(24 ratings)
Kailua, Honolulu County, Hawaii, United States
Internet
Vrbo
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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 $109 per night.

Is it possible to compare multiple vacation rentals in Kailua?

You can find and compare 448 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!

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