Kailua Vacation Rentals

  • Bundle & Save

    Get more, spend less whenever you see Bundle & Save deals
  • OneKeyCash

    Earn OneKeyCash on all your eligible bookings
  • Upfront pricing

    We are not like the others - we include taxes and fees

Check prices for these dates

In two weeks
In two months
In three months
In four months

Our top choices for Kailua vacation rentals

Yonegan Maui Getaways - Haiku

Yonegan Maui Getaways - Haiku
3.0 star property
Haiku
9.0 out of 10, Wonderful, (25 reviews)
"It is a cozy place. It has all the amenities. It feels like home"
United States
Roberto
$267 nightly
The price is $298
Mar 1 - Mar 2
Total with taxes and fees
Yonegan Maui Getaways - Haiku

Kuau Plaza Paia Condo with Parking

Kuau Plaza Paia Condo with Parking
3.0 star property
Paia
$529 nightly
The price is $576
Mar 8 - Mar 9
Total with taxes and fees
Kuau Plaza Paia Condo with Parking

Menehune Shores 227 2 Bedroom Condo

Menehune Shores 227 2 Bedroom Condo
3.5 star property
North Kihei
$912 nightly
The price is $1,083
Mar 1 - Mar 2
Total with taxes and fees
Menehune Shores 227 2 Bedroom Condo

The Kalama Residence

The Kalama Residence
3.0 star property
South Kihei
7.0 out of 10, Good, (2 reviews)
"My stay was okay. "
United States
Rosalba
$791 nightly
The price is $939
Mar 1 - Mar 2
Total with taxes and fees
The Kalama Residence

The Ocean View Residence

The Ocean View Residence
3.0 star property
South Kihei
10.0 out of 10, Exceptional, (1 review)
"Very nice condo for a longer-term stay. We loved being able to cook. "
United States
John
$702 nightly
The price is $834
Mar 13 - Mar 14
Total with taxes and fees
The Ocean View Residence

2BR/2BA Oceanfront Condo in Maui Sunset

2BR/2BA Oceanfront Condo in Maui Sunset
3.5 star property
Central Kihei
$636 nightly
The price is $702
Mar 1 - Mar 2
Total with taxes and fees
2BR/2BA Oceanfront Condo in Maui Sunset

Luana Kai C210 2 Bedroom Condo

Luana Kai C210 2 Bedroom Condo
3.0 star property
Central Kihei
$891 nightly
The price is $1,058
Mar 11 - Mar 12
Total with taxes and fees
Luana Kai C210 2 Bedroom Condo

Luana Kai A104 2 Bedroom Condo

Luana Kai A104 2 Bedroom Condo
3.0 star property
Central Kihei
$906 nightly
The price is $1,076
Mar 23 - Mar 24
Total with taxes and fees
Luana Kai A104 2 Bedroom Condo

Maui Vista 1315 1 Bedroom Condo

Maui Vista 1315 1 Bedroom Condo
3.0 star property
South Kihei
$623 nightly
The price is $740
Mar 15 - Mar 16
Total with taxes and fees
Maui Vista 1315 1 Bedroom Condo

Maui Vista 3307 1 Bedroom Condo

Maui Vista 3307 1 Bedroom Condo
3.0 star property
South Kihei
$605 nightly
The price is $718
Mar 12 - Mar 13
Total with taxes and fees
Maui Vista 3307 1 Bedroom Condo

Menehune Shores 601 2 Bedroom Condo

Menehune Shores 601 2 Bedroom Condo
3.0 star property
North Kihei
$998 nightly
The price is $1,185
Mar 4 - Mar 5
Total with taxes and fees
Menehune Shores 601 2 Bedroom Condo

Menehune Shores 223 2 Bedroom Condo

Menehune Shores 223 2 Bedroom Condo
3.0 star property
North Kihei
$986 nightly
The price is $1,171
Mar 26 - Mar 27
Total with taxes and fees
Menehune Shores 223 2 Bedroom Condo

Kihei Ali'i Kai Condos with Free Parking

Kihei Ali'i Kai Condos with Free Parking
4.0 star property
South Kihei
8.8 out of 10, Excellent, (27 reviews)
"I loved that it was a short walk to the beach and there were grocery stores nearby. Lots of options of places to eat and shop and explore the island!"
United States
Emma
$438 nightly
The price is $470
Mar 29 - Mar 30
Total with taxes and fees
Kihei Ali'i Kai Condos with Free Parking

Maui Vista 3213 1 Bedroom Condo

Maui Vista 3213 1 Bedroom Condo
3.0 star property
South Kihei
$617 nightly
The price is $733
Mar 25 - Mar 26
Total with taxes and fees
Maui Vista 3213 1 Bedroom Condo
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.

The Annual Vacation Sale

Members save up to 40% on hotels and homes. Plan this year’s big trip and save.
Save an average of 15% on thousands of hotels when you're signed in

Top Kailua Hotel Reviews

Find out more about Kailua

Everything you need to know about Kailua vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Kailua vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. The list goes on, and on …and on.

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Kailua vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Kailua vacation rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Kailua. If you’re looking for a little peace, consider booking during the quieter low season months. For more hustle and bustle, you may prefer to visit Kailua in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $298 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Kailua rentals

At Expedia, we put the best Kailua vacation rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia.

To find some top Kailua rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Kailua vacation.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Kailua. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.

Frequently asked questions

Can I find a vacation rental in Kailua?

Yes, there are vacation rentals near top sights in Kailua, or you can select a more secluded option if you're looking for relaxation.

What are some of the best vacation home rentals that Kailua has to offer?

Yonegan Maui Getaways - Haiku : This vacation home rental near Kailua is located near the beach and has a hot tub, a barbecue grill, and air-conditioning to put you at ease in your new surroundings. Kitchen amenities include a microwave, a coffee maker, and kitchenware.

What’s there to see and do in Kailua?

While exploring the area, visit family-friendly sights like Waikamoi Preserve, or get outside and enjoy nature at Garden of Eden Arboretum. In the larger area, you’ll find Maui Garden Of Eden - Botanical Gardens & Arboretum and Maui Spa Retreat.

What’s a vacation rental in Kailua like?

A vacation rental is a private property where you can stay for a few weeks or just a few days in Kailua. Vacation rentals feature extras such as laundry facilities and kitchens so your stay will be comfortable. If you're concerned about cleanliness, vacation rentals can provide a sense of seclusion away from shared hotel elevators and busy front desks while still allowing you a great travel experience. You'll also get more space in a vacation rental than in a hotel, which makes a vacation rental an attractive option for a small group gathering.