Kailua Vacation Rentals

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Check prices for these dates

In two weeks
Oct 10 - Oct 12
In one month
Oct 24 - Oct 26
In two months
Nov 21 - Nov 23
In three months
Dec 19 - Dec 21

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, (800)
"Just a great stay! "
Maui Beach Vacation Club
Yonegan Maui Getaways - Haiku
Garden

Yonegan Maui Getaways - Haiku

3.0 star property
9.2 out of 10, Wonderful, (5)
"Loved having the hot tub to come home to!!"
The price is ￥16,848
￥34,674 total
includes taxes & fees
Oct 5 - Oct 6
Yonegan Maui Getaways - Haiku
Maui Schooner Resort
BBQ/picnic area

Maui Schooner Resort

3.5 star property
9.2 out of 10, Wonderful, (489)
"Beautiful grounds, clean facility, and friendly people. Small Resort that's maintained very well! Lots of nice views! Will book there again.Very tropical with a real sense you are in Hawaii. Only two buildings. One faces the ocean and the other faces the pool area with tropical views. Some have views of the ocean as well. "
Maui Schooner Resort
Maui Sunset
Premium Condo, 2 Bedrooms, Kitchen, Ocean View | Terrace/patio

Maui Sunset

3.5 star property
8.8 out of 10, Excellent, (473)
"Good place to spend your vacation "
Maui Sunset
Sugar Beach Resort
Outdoor pool

Sugar Beach Resort

3.0 star property
8.6 out of 10, Excellent, (1089)
"We loved it there! "
Sugar Beach Resort
Oceanview Condo in Hana-Let the ocean lull you to sleep
Outdoor dining

Oceanview Condo in Hana-Let the ocean lull you to sleep

9.2 out of 10, Wonderful, (107)
"An idyllic setting where we could see the bay, hear the waves, with a short walk to the beach (black rocky sands). Neighbors a bit loud, but still one of the best spots in Hāna. Easy drive to the 7 sacred pools. Good food trucks nearby. "
The price is ￥29,898
￥59,321 total
includes taxes & fees
Oct 2 - Oct 3
Oceanview Condo in Hana-Let the ocean lull you to sleep
Kaiholo Hale
Beach nearby

Kaiholo Hale

3.0 star property
9.4 out of 10, Exceptional, (200)
"Area was quiet but close to amenities. We could drive anywhere on Maui easily. There was a lovely beach less than a block from the suite with good snorkeling and friendly locals. Bed in the suite was very comfortable, and it had everything we needed for a relaxing vacation."
Kaiholo Hale
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, (514)
"Love this location, great beach, quiet."
Sugar Beach Resort - Maui Condo & Home
Kihei Bay Surf 227
Condo (0 Bedroom) | Property amenity

Kihei Bay Surf 227

3.5 star property
9.4 out of 10, Exceptional, (17)
"Loved having the beach chairs, towels, and umbrellas! Wish there was an additional life jacket! "
Kihei Bay Surf 227
Kihei Bay Surf B212
Condo (0 Bedroom) | Property amenity

Kihei Bay Surf B212

3.5 star property
7.8 out of 10, Good, (21)
"Overall a great stay at this place. Great spot to be close to a lot of things and also very quiet. Only complaint would be that it was a little hot at times in the room but the fan really helped with that. Would recommend."
Kihei Bay Surf B212
Maui Sunset B123 Beachfront, Ocean View, Ground Floor Families! Pool! 3 Bedrooms
Outdoor pool, a heated pool

Maui Sunset B123 Beachfront, Ocean View, Ground Floor Families! Pool! 3 Bedrooms

9.8 out of 10, Exceptional, (55)
"The place is in a perfect location. The condo was super spacious and great views"
Maui Sunset B123 Beachfront, Ocean View, Ground Floor Families! Pool! 3 Bedrooms
Koa Resort 2 Bed Ground Floor Condo -Air Conditioning
Interior

Koa Resort 2 Bed Ground Floor Condo -Air Conditioning

9.4 out of 10, Exceptional, (175)
"Like everything Except a few island bugs "
Koa Resort 2 Bed Ground Floor Condo -Air Conditioning
Sleeps 4, Full kitchen & AC. Pool, hot tub, tennis court, bbq grills! And Beach!
Outdoor dining

Sleeps 4, Full kitchen & AC. Pool, hot tub, tennis court, bbq grills! And Beach!

9.8 out of 10, Exceptional, (72)
"We enjoyed our stay. Pool was easily accessible and quiet everyday. Great location "
Sleeps 4, Full kitchen & AC. Pool, hot tub, tennis court, bbq grills! And Beach!
Luxury Ocean Front Living -- 180 Degree Direct Ocean View -- Best in Kihei
Property grounds

Luxury Ocean Front Living -- 180 Degree Direct Ocean View -- Best in Kihei

9.8 out of 10, Exceptional, (102)
"The place was outstanding and very clean and beautiful!"
Luxury Ocean Front Living -- 180 Degree Direct Ocean View -- Best in Kihei
Fall Sale! Oceanfront/Ocean view condo in S. Maui,Free A/C, Wifi, Parking, Pool!
Property grounds

Fall Sale! Oceanfront/Ocean view condo in S. Maui,Free A/C, Wifi, Parking, Pool!

10.0 out of 10, Exceptional, (149)
"This lovely home was as advertised, and then some. Convenient location, comfortable and attractive living, fantastic views and perhaps the most well-stocked rental we’ve ever visited. Jean is an excellent host, providing lots of information to help enhance the stay (eg great restaurant picks) and very responsive, yet unintrusive. We hope to return someday!"
Fall Sale! Oceanfront/Ocean view condo in S. Maui,Free A/C, Wifi, Parking, Pool!
2B/2B across from BEACH, S. Kihei, close dining & shopping, Pacific Shores
Outdoor dining

2B/2B across from BEACH, S. Kihei, close dining & shopping, Pacific Shores

9.8 out of 10, Exceptional, (184)
"Had a wonderful experience staying here! A sweet, cozy and comfortable little getaway for our family and little one!"
The price is ￥24,352
￥68,139 total
includes taxes & fees
Oct 21 - Oct 22
2B/2B across from BEACH, S. Kihei, close dining & shopping, Pacific Shores
Island Sunset Villa: Your Maui Escape with Ocean & Stunning Sunsets Views
Fridge, microwave, oven, stovetop

Island Sunset Villa: Your Maui Escape with Ocean & Stunning Sunsets Views

10.0 out of 10, Exceptional, (178)
"Great place !!"
The price is ￥84,499
￥171,833 total
includes taxes & fees
Oct 21 - Oct 22
Island Sunset Villa: Your Maui Escape with Ocean & Stunning Sunsets Views
Exceptional Upcountry Villa with breathtaking views
Outdoor pool

Exceptional Upcountry Villa with breathtaking views

10.0 out of 10, Exceptional, (44)
"Beautiful views and beautiful accommodations! We loved being in the up country and this house was perfect for my family of five. "
Exceptional Upcountry Villa with breathtaking views
Best Oceanfront Value in Kihei - Kealia Resort!
On the beach

Best Oceanfront Value in Kihei - Kealia Resort!

9.6 out of 10, Exceptional, (107)
"The condo was exactly as described and in a great location, we loved the grassy area right in front of the beach if we didn’t feel like sitting in the sand! Tim had all the essentials for us and was quick to respond if we had any questions- we would definitely stay here again in the future! "
The price is ￥19,135
￥68,411 total
includes taxes & fees
Oct 15 - Oct 16
Best Oceanfront Value in Kihei - Kealia Resort!
Dazzling Ocean View, Modern, Whole house AC. Upgraded Glass for a quiet setting
On the beach, sun loungers, beach towels

Dazzling Ocean View, Modern, Whole house AC. Upgraded Glass for a quiet setting

10.0 out of 10, Exceptional, (266)
"Our family had a great time at the condo in Kihei. The rooms were spacious, the place had everything you need for cooking and the beach (minus life jackets but those were easy to rent). The location was perfect and within walking distance of tons of restaurants, shops, and the ocean. I would definitely recommend this place and if we're ever in the area again would happily stay there."
Dazzling Ocean View, Modern, Whole house AC. Upgraded Glass for a quiet setting
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.
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Top Kailua Hotel Reviews

Yonegan Maui Getaways - Haiku

Yonegan Maui Getaways - Haiku

10/10 Excellent
"Loved having the hot tub to come home to!!"
Pedro 1-night trip
Posted 3 days ago
Yonegan Maui Getaways - Haiku

Find out more about Kailua

Find out more about Kailua

Search for holiday rentals in Kailua on Expedia! You can easily find your home rentals, villas, holiday apartments in Kailua using one of the methods below:

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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, kitchenware, and a coffee maker.

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 Garden of Eden Arboretum and Maui Garden Of Eden - Botanical Gardens & Arboretum.

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.