Kailua Vacation Rentals

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Vacation Rentals in Kailua

Maui Beach Vacation Club
Suite, 2 Bedrooms | Living area | TV
Maui Beach Vacation Club
2.5 star property
8.2 out of 10, Very Good, 627 reviews
"Great staff, great room. We will stay here again"
Maui Beach Vacation Club
Sugar Beach Resort
Outdoor pool
Sugar Beach Resort
3.0 star property
8.6 out of 10, Excellent, 986 reviews
"decent place to stay"
Sugar Beach Resort
Maui Schooner Resort
Outdoor pool, pool umbrellas
Maui Schooner Resort
3.5 star property
9.2 out of 10, Wonderful, 372 reviews
"The staff were friendly and sweet. The room was clean and had everything we needed for our stay."
Maui Schooner Resort
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Maui Sunset
View from property
Maui Sunset
3.5 star property
8.8 out of 10, Excellent, 328 reviews
"Maui Sunset was a dream. It comes with you would have in your kitchen at home, so you have the choice to eat out or buy groceries and cook yourself. I had a room with a partial view of the ocean and it was beautiful. The property and the pool is cleaned every day. You can sit out on a balcony and enjoy the sweet Hawaiian breeze or walk on the beach. They also have a herb garden, where if you wanted to go out and cut fresh herbs for your dinner you can do so. "
Maui Sunset
No Property Fees! Kihei Top Floor - Air Conditioned, Clean!, Turtles nearby!
Exterior
No Property Fees! Kihei Top Floor - Air Conditioned, Clean!, Turtles nearby!
10.0 out of 10, Exceptional, 223 reviews
"Lovely little place perfect for our family vacation. Very central to everything with a beach and fish pond right across the street. The owner was easy to reach if we needed anything and communication was stellar! We were surprised at all that was there when we arrived, such as stocked items in the freezer and cupboards paid forward by previous guests and playing cards and books in the drawer when you have some downtime. Absolutely all you need and more for a very good price!"
The price is $109
$403 total
includes taxes & fees
Jul 2 - Jul 3
No Property Fees! Kihei Top Floor - Air Conditioned, Clean!, Turtles nearby!
STHA-2017/0002 Across from Hana Bay
Sun loungers, beach towels
STHA-2017/0002 Across from Hana Bay
9.6 out of 10, Exceptional, 292 reviews
"Amazing. thank you. "
STHA-2017/0002 Across from Hana Bay
Oceanside condo, full kitchen, ocean view. Fully renovated 2023
Beach
Oceanside condo, full kitchen, ocean view. Fully renovated 2023
9.6 out of 10, Exceptional, 18 reviews
"The property was a great location. Quick access to downtown Kihei and not far from the airport. The property was well equipped with items needed for beach days. One recommendation would be to add an umbrella. Otherwise, very well stocked! My only negative feedback would be regarding cleanliness. The baseboards had quite a bit of dirt in the crevices and the ceiling fan was extremely dusty. My husband got up on a chair and cleaned it off because the dust was coming over the blades and it could...
The price is $110
$344 total
includes taxes & fees
Jul 2 - Jul 3
Oceanside condo, full kitchen, ocean view. Fully renovated 2023
2B/2B across from BEACH, S. Kihei, close dining & shopping, Pacific Shores
Outdoor pool
2B/2B across from BEACH, S. Kihei, close dining & shopping, Pacific Shores
9.8 out of 10, Exceptional, 139 reviews
"Nice property."
The price is $200
$503 total
includes taxes & fees
Jun 29 - Jun 30
2B/2B across from BEACH, S. Kihei, close dining & shopping, Pacific Shores
Lush Garden Charmer - Breathtaking Sunsets
Beach | Beach nearby, sun loungers, beach towels
Lush Garden Charmer - Breathtaking Sunsets
9.8 out of 10, Exceptional, 109 reviews
"Very nice! Convenient. Close to many good restaurants. Great thai! Hope to be back soon"
Lush Garden Charmer - Breathtaking Sunsets
No Property Fees! Kihei Top Floor - Air Conditioned, Clean!, Turtles nearby!
Exterior
No Property Fees! Kihei Top Floor - Air Conditioned, Clean!, Turtles nearby!
9.8 out of 10, Exceptional, 247 reviews
"Condo is very clean and in great location for beach walks, turtle sightings and just about anything you want to do on beautiful Maui. Very well equipped, pay-it-forward cabinet goodies, and very attentive host Kevin who will answer any question within minutes! I will stay again! Mahalo Kevin for a wonderful, relaxing, worry-free stay. Jacquie"
The price is $109
$403 total
includes taxes & fees
Jun 22 - Jun 23
No Property Fees! Kihei Top Floor - Air Conditioned, Clean!, Turtles nearby!
Spacious Hawaiian home 50 steps from Sugar Beach!
Beach | Sun loungers, beach towels
Spacious Hawaiian home 50 steps from Sugar Beach!
8.8 out of 10, Excellent, 58 reviews
"Thai is a fabulous location. Truth about how close to beach! Our only issue was there was no table to sit at inside. No table for cards or coffee. Outside wasn’t always appropriate. Major construction going on next door was an eyesore…"
Spacious Hawaiian home 50 steps from Sugar Beach!
Wonderful South Maui Beach Condos
Exterior
Wonderful South Maui Beach Condos
3.0 star property
9.6 out of 10, Exceptional, 14 reviews
"The location of this condo is the perfect walking distance for the beach, restaurants, coffee shops, etc. The location is central for driving out on day trips. The grounds and bbq area are well maintained. When you need a break from the beach the 2 pools are a nice alternative. The owner and management team were quick to respond when we had an issue. As with most travel to and from Maui our plane arrived and departed late at night. The owner insured that we were provided all the information...
Wonderful South Maui Beach Condos
Ocean View Condo at Beachfront Resort w/ Lanai, AC, WiFi & Shared Pool/Hot Tub
Pool
Ocean View Condo at Beachfront Resort w/ Lanai, AC, WiFi & Shared Pool/Hot Tub
9.8 out of 10, Exceptional, 129 reviews
"Nice"
Ocean View Condo at Beachfront Resort w/ Lanai, AC, WiFi & Shared Pool/Hot Tub
MAUI OCEAN VIEW 2 bed 2 bath with Air Conditioning
Sun loungers, beach towels
MAUI OCEAN VIEW 2 bed 2 bath with Air Conditioning
9.6 out of 10, Exceptional, 178 reviews
"Very comfortable unit with great view. It had everything we needed. Loved the location with beach across the street and food trucks and gardens behind the condo. The owner is very kind and responsive for any needs. Can't wait to come back!!"
MAUI OCEAN VIEW 2 bed 2 bath with Air Conditioning
Sugar Beach Resort - Maui Condo & Home
Outdoor pool
Sugar Beach Resort - Maui Condo & Home
3.0 star property
8.4 out of 10, Very Good, 502 reviews
"This property was in a greatlocation on the famed Sugar Beach. Close to the famers market and Dina's bar and grill was convenient for a good meal which was located on the property. "
Sugar Beach Resort - Maui Condo & Home
Great Rates - Clean and Cozy Condo!
Beach
Great Rates - Clean and Cozy Condo!
9.8 out of 10, Exceptional, 129 reviews
"Roger and Olive's property was the perfect stay in Maui. It was the first time in Maui for my partner and I. Communication was super smooth, even when I had questions. Directions were clear. The place was immaculate and the available towels/gear was a lifesaver. The kitchen had everything you could ever need. The shower had amazing water pressure and the bed was very comfortable. All in all, I would highly recommend to stay here and would love to stay here again."
Great Rates - Clean and Cozy Condo!
Beachy Chic Condo With Lanai, Located Across The Street From The Beach
Exterior
Beachy Chic Condo With Lanai, Located Across The Street From The Beach
9.8 out of 10, Exceptional, 8 reviews
"We visit Maui often and are well experienced with our stay on the Island. The property was lovely; amazing landscaping and friendly property management. The location is at a great spot on S Kihei Road providing access to main highways that can take you throughout Maui. We will be back soon."
Beachy Chic Condo With Lanai, Located Across The Street From The Beach
Shores of Maui - Ocean View- Top Floor Unit--Spacious! AC & WiFi
Beach nearby, sun loungers, beach towels
Shores of Maui - Ocean View- Top Floor Unit--Spacious! AC & WiFi
9.8 out of 10, Exceptional, 161 reviews
"Great location, nice big unit, giving a family of 5 enough space. Great communication with host. We will be back."
Shores of Maui - Ocean View- Top Floor Unit--Spacious! AC & WiFi
Secluded cottage on Tropical flower farm
Outdoor dining
Secluded cottage on Tropical flower farm
9.6 out of 10, Exceptional, 226 reviews
"We loved our stay here. The place was very clean, and the scenery was stunning. It was a very relaxing and enjoyable place to stay. There were issues on the island with power going out due to a fallen tree in the forest, but the owners were very responsive to texts and even drove out to give us lanterns in case there was another outage. I highly recommend staying here!"
The price is $295
$558 total
includes taxes & fees
Jun 29 - Jun 30
Secluded cottage on Tropical flower farm
Embark on a journey through Maui with Aloha Glamp
On the beach
Embark on a journey through Maui with Aloha Glamp
9.6 out of 10, Exceptional, 31 reviews
"We really enjoyed staying in the jeep tent,and traveling to top of"
The price is $155
$339 total
includes taxes & fees
Jun 19 - Jun 20
Embark on a journey through Maui with Aloha Glamp
Don't see what you're looking for?
See all available properties in Kailua
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.

Other types of properties in Kailua you may be interested in

Maui Beach Hotel
Outdoor pool, sun loungers
Maui Beach Hotel
3.0 star property
7.0 out of 10, Good, 1,008 reviews
"Rooms were decent but too noisy the guests up at all hours of the night"
The price is $219
$282 total
includes taxes & fees
Jun 23 - Jun 24
Maui Beach Hotel
Maui Beach Vacation Club
Suite, 2 Bedrooms | Living area | TV
Maui Beach Vacation Club
2.5 star property
8.2 out of 10, Very Good, 627 reviews
"Great staff, great room. We will stay here again"
Maui Beach Vacation Club
Maui Seaside Hotel
Outdoor pool, open 9:00 AM to 7:00 PM, pool umbrellas, sun loungers
Maui Seaside Hotel
3.0 star property
8.6 out of 10, Excellent, 1,149 reviews
"Gary and staff were awesome! Great Great service here"
The price is $246
$313 total
includes taxes & fees
Jul 17 - Jul 18
Maui Seaside Hotel
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.

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 $109 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?

STHA-2017/0002 Across from Hana Bay: This vacation home rental near Kailua is located in a rural location and has a patio, a garden, and a barbecue grill to put you at ease in your new surroundings. Kitchen amenities include a fridge, a stovetop, and a microwave. Make the most of the selection of games in this rental home to help you unwind.

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 Maui Garden Of Eden - Botanical Gardens & Arboretum. In the larger area, you’ll find Makawao Park and Hookipa Beach Park.

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.

Recent reviews of Kailua properties
Expedia verified reviews

Maui Schooner Resort

Maui Schooner Resort

5/5 Excellent
"The staff were friendly and sweet. The room was clean and had everything we needed for our stay."
A verified traveler stayed at Maui Schooner Resort
Posted 13 hours ago
Maui Schooner Resort