Kailua Vacation Rentals

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Vacation Rentals in Kailua

Maui Beach Vacation Club
2.5 star property
8.2 out of 10, Very good, (623)
"We love it!!! So clean n the people are really nice !! The weather really nice!!! We love the pool area! We definitely be back soon!!! "
Maui Beach Vacation Club
Sugar Beach Resort
3.0 star property
8.6 out of 10, Excellent, (986)
"decent place to stay"
Sugar Beach Resort
Maui Schooner Resort
3.5 star property
9.2 out of 10, Wonderful, (364)
"Friendly and professional staff and budget friendly property. I would recommend Maui Schooner to fellow travelers. "
Maui Schooner Resort
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Maui Sunset
3.5 star property
8.8 out of 10, Excellent, (319)
"The property is in a non-resort area, in that although there are lots of places to stay all around, their are also regular houses, apartments, and local shopping close by. Several restaurants, drug stores, and food stores are nearby, plus beaches. "
Maui Sunset
STHA-2017/0002 Across from Hana Bay
9.6 out of 10, Exceptional, (291)
"This is our second time here and it is a great place to stay. Afternoon nap on the lanai is a great way to relax. The orange cat that comes around is really sweet. Close to everything in and around Hana."
STHA-2017/0002 Across from Hana Bay
No Property Fees! Kihei Top Floor - Air Conditioned, Clean!, Turtles nearby!
10.0 out of 10, Exceptional, (223)
"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 CA $157
CA $562 total
includes taxes & fees
Jun 10 - Jun 11
No Property Fees! Kihei Top Floor - Air Conditioned, Clean!, Turtles nearby!
2B/2B across from BEACH, S. Kihei, close dining & shopping, Pacific Shores
9.8 out of 10, Exceptional, (138)
"Nice property."
The price is CA $274
CA $688 total
includes taxes & fees
Jun 30 - Jul 1
2B/2B across from BEACH, S. Kihei, close dining & shopping, Pacific Shores
Sugar Beach Resort - Maui Condo & Home
3.0 star property
8.4 out of 10, Very good, (501)
"This place is a favorite for us and have stayed here several times. Great location in Kihei. The condos are in varying condition, with some being more recently updated, which is great because you can select based on your budget. But they all have been well equipped and comfortable. The staff are available and helpful and we always enjoy our stay here. Highly recommend"
Sugar Beach Resort - Maui Condo & Home
Spacious Hawaiian home 50 steps from Sugar Beach!
8.8 out of 10, Excellent, (58)
"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!
Lush Garden Charmer - Breathtaking Sunsets
9.8 out of 10, Exceptional, (109)
"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!
9.8 out of 10, Exceptional, (246)
"I love, love this place. From the moment you walk in, you feel at home. My favorite is the " pay it forward" cabinet in the kitchen. Kevin, you really set yourself apart from other hosts. Thank you for preserving our island spirit of giving, kindness and love. Thank you"
The price is CA $157
CA $562 total
includes taxes & fees
Jun 8 - Jun 9
No Property Fees! Kihei Top Floor - Air Conditioned, Clean!, Turtles nearby!
Wonderful South Maui Beach Condos
3.0 star property
9.6 out of 10, Exceptional, (14)
"Had a very easy time booking and communicating, and really enjoyed the unit/condo/area. Close to an ideal beach, unit wasn't facing a road or parking lot, and was quiet and relaxing to use as a home base for our Maui getaway! Would stay again for sure."
Wonderful South Maui Beach Condos
Secluded cottage on Tropical flower farm
9.6 out of 10, Exceptional, (226)
"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 CA $403
CA $764 total
includes taxes & fees
Jun 9 - Jun 10
Secluded cottage on Tropical flower farm
Ocean View Condo at Beachfront Resort w/ Lanai, AC, WiFi & Shared Pool/Hot Tub
9.8 out of 10, Exceptional, (129)
"Nice"
Ocean View Condo at Beachfront Resort w/ Lanai, AC, WiFi & Shared Pool/Hot Tub
Great Rates - Clean and Cozy Condo!
9.8 out of 10, Exceptional, (128)
"The condo in which we stayed was well worth the money. Everything was excellent except for two small details: The air-conditioning was barely sufficient during the daylight hours although adequate at night. Also, the lighting in the main room (a combination living room and bedroom) was very insufficient: The lights in the ceiling fans didn't work. The only lights in the room were two simple desk lamps, one at each end of the room, making for a very dim room after the sun set."
Great Rates - Clean and Cozy Condo!
Oceanside condo, full kitchen, ocean view. Fully renovated 2023
9.6 out of 10, Exceptional, (18)
"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 CA $174
CA $499 total
includes taxes & fees
Jun 23 - Jun 24
Oceanside condo, full kitchen, ocean view. Fully renovated 2023
Sugar Beach Resort Condo w/ Private W/D, Shared Pool-Surf, Bike, Golf, More
9.6 out of 10, Exceptional, (23)
"Great stay! Beautiful location on top of sugar sand beach. thank you!"
Sugar Beach Resort Condo w/ Private W/D, Shared Pool-Surf, Bike, Golf, More
MAUI OCEAN VIEW 2 bed 2 bath with Air Conditioning
9.6 out of 10, Exceptional, (178)
"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
Beachy Chic Condo With Lanai, Located Across The Street From The Beach
9.8 out of 10, Exceptional, (8)
"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
Fabulous Beachfront Property - Ground Floor Corner Unit Steps to the Beach!
10.0 out of 10, Exceptional, (98)
"Sugar Beach is a wonderful resort. Condo 112 is just steps from the beach! The resort has beautiful landscaping, a clean pool and hot tub. Everything we needed was furnished. Kihei is also a great central location to get to anywhere on the island."
Fabulous Beachfront Property - Ground Floor Corner Unit Steps to the Beach!
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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
3.0 star property
7.0 out of 10, Good, (1008)
"Staff was very cordial and helpful. The oceanside scenery was awesome. The room was clean and just what we needed."
The price is CA $300
CA $386 total
includes taxes & fees
Jun 15 - Jun 16
Maui Beach Hotel
Maui Seaside Hotel
3.0 star property
8.6 out of 10, Excellent, (1148)
"Room was clean, staff was polite and pleasant. Loved the pool. "
The price is CA $319
CA $408 total
includes taxes & fees
Jun 8 - Jun 9
Maui Seaside Hotel
Maui Beach Vacation Club
2.5 star property
8.2 out of 10, Very good, (623)
"We love it!!! So clean n the people are really nice !! The weather really nice!!! We love the pool area! We definitely be back soon!!! "
Maui Beach Vacation Club
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, cottages, cabins, villas... 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 months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Kailua vacation rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a vacation rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Kailua vacation rentals we have selected for you start as low as CA $157 per night. Entering your travel dates in the search wizard 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 Twin Falls. In the larger area, you’ll find Maui Garden Of Eden - Botanical Gardens & Arboretum 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.

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