Kailua Vacation Rentals

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Check prices for these dates

Tonight
Jan 1 - Jan 2
Tomorrow
Jan 2 - Jan 3
This weekend
Jan 2 - Jan 4
Next weekend
Jan 9 - Jan 11

Our top choices for Kailua vacation rentals

Outdoor pool, a heated pool
BEACHFRONT condo, ocean view, steps to sea, heated pool,hot tub, AC, Sugar Beach

Condo in North Kihei

BEACHFRONT condo, ocean view, steps to sea, heated pool,hot tub, AC, Sugar Beach
10.0 out of 10, Exceptional, (129)
"Very nice condo Nice furniture Comfortable and friendly "
United States
John
The price is ￥13,940
￥52,270 total
includes taxes & fees
Jan 29 - Jan 30
BEACHFRONT condo, ocean view, steps to sea, heated pool,hot tub, AC, Sugar Beach
Outdoor pool
10% 7 Day Discount! Kihei 1Br Top Floor - Split AC, Clean, Free WiFi, Turtles!

Condo in North Kihei

10% 7 Day Discount! Kihei 1Br Top Floor - Split AC, Clean, Free WiFi, Turtles!
9.8 out of 10, Exceptional, (298)
"Great place to stay! I would stay again. Has everything you need and a pool and hot tub!"
Canada
Mary F.
The price is ￥16,185
￥62,128 total
includes taxes & fees
Jan 6 - Jan 7
10% 7 Day Discount! Kihei 1Br Top Floor - Split AC, Clean, Free WiFi, Turtles!
Exterior
AI Recommended! - Split AC, Clean, Free WiFi and Parking, Turtles!

Condo in North Kihei

AI Recommended! - Split AC, Clean, Free WiFi and Parking, Turtles!
9.6 out of 10, Exceptional, (287)
"Great room, affordable, clean, sufficient, well maintained, easy access"
United States
John K.
The price is ￥13,933
￥58,307 total
includes taxes & fees
Jan 26 - Jan 27
AI Recommended! - Split AC, Clean, Free WiFi and Parking, Turtles!
Garden
Yonegan Maui Getaways - Haiku

Vacation Home in Haiku

Yonegan Maui Getaways - Haiku
3.0 star property
9.0 out of 10, Wonderful, (16)
"It is a cozy place. It has all the amenities. It feels like home"
United States
Roberto
The price is ￥23,874
￥43,829 total
includes taxes & fees
Jan 5 - Jan 6
Yonegan Maui Getaways - Haiku
Property grounds
Modern Kihei Resort 2 Bedroom, 2 Bath Condo with AC - Steps to the Beach

Condo in North Kihei

Modern Kihei Resort 2 Bedroom, 2 Bath Condo with AC - Steps to the Beach
10.0 out of 10, Exceptional, (31)
"Clean- easy access- close to town- enjoyed our time there- mahalo!"
United States
Melodie V.
The price is ￥33,793
￥96,705 total
includes taxes & fees
Jan 5 - Jan 6
Modern Kihei Resort 2 Bedroom, 2 Bath Condo with AC - Steps to the Beach
On the beach, sun loungers, beach towels
New Central AC! Oceanfront Steps from the Beach, with Pool, Jacuzzi, & BBQ.

Condo in North Kihei

New Central AC! Oceanfront Steps from the Beach, with Pool, Jacuzzi, & BBQ.
9.6 out of 10, Exceptional, (12)
"Wonderful place to stay. Awesome host. We had a great time and hopefully be back soon!"
United States
Jennifer D.
The price is ￥23,468
￥70,301 total
includes taxes & fees
Jan 28 - Jan 29
New Central AC! Oceanfront Steps from the Beach, with Pool, Jacuzzi, & BBQ.
Beach nearby, white sand, beach towels
Kihei Ali'i Kai Condos with Free Parking

Apartment in South Kihei

Kihei Ali'i Kai Condos with Free Parking
4.0 star property
9.0 out of 10, Wonderful, (21)
"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
Kihei Ali'i Kai Condos with Free Parking
Beach towels
Fisher's Hana Bay Hale, Across from Hana Bay

Vacation Home in Hana Town Center

Fisher's Hana Bay Hale, Across from Hana Bay
9.6 out of 10, Exceptional, (410)
"Wonderful place to spend a few days in paradise! Would definitely stay again!"
United States
Steve K.
The price is ￥30,494
￥62,406 total
includes taxes & fees
Jan 24 - Jan 25
Fisher's Hana Bay Hale, Across from Hana Bay
Beach nearby, sun loungers, beach towels
Pacific Shores 2bd 2bth Kihei MAUI Condo Kamaole Beach HAWAII Vacation Rental

Condo in South Kihei

Pacific Shores 2bd 2bth Kihei MAUI Condo Kamaole Beach HAWAII Vacation Rental
4.0 star property
9.6 out of 10, Exceptional, (48)
"Good location near beach with AC in each room, many beds were good for a larger group."
Canada
Daniel C.
The price is ￥46,758
￥102,132 total
includes taxes & fees
Jan 19 - Jan 20
Pacific Shores 2bd 2bth Kihei MAUI Condo Kamaole Beach HAWAII Vacation Rental
Property grounds
Stay in Hana #1

Apartment in Hana Town Center

Stay in Hana #1
8.8 out of 10, Excellent, (60)
"Inflexible host"
United States
Nagender
The price is ￥29,428
￥54,433 total
includes taxes & fees
Jan 4 - Jan 5
Stay in Hana #1
On the beach
Embark on a journey through Maui with Aloha Glamp

Mobile Home in Haiku-Pauwela

Embark on a journey through Maui with Aloha Glamp
9.6 out of 10, Exceptional, (38)
"We booked this Jeep for our honeymoon stay on Maui. It was a wonderful drive, handled every road we were on beautiful, and provided a great place to sleep. Sebastian had all the necessities packed and it made for an easy trip. Couldn’t be happier. "
United States
Sage B.
The price is ￥20,276
￥47,886 total
includes taxes & fees
Jan 13 - Jan 14
Embark on a journey through Maui with Aloha Glamp
Property grounds
Ocean View Studio Steps to Beach - Pool, Spa & Pickleball - Free parking & Wi-Fi

Apartment in North Kihei

Ocean View Studio Steps to Beach - Pool, Spa & Pickleball - Free parking & Wi-Fi
8.8 out of 10, Excellent, (89)
"We had a great stay. It was the perfect central location to get around Maui. It’s a little noisy being right on the main Kihei road but other than that it’s a perfect place! "
United States
Matthan G.
The price is ￥26,049
￥70,307 total
includes taxes & fees
Jan 27 - Jan 28
Ocean View Studio Steps to Beach - Pool, Spa & Pickleball - Free parking & Wi-Fi
Outdoor dining
Oceanfront penthouse with amazing views at Kauhale Makai

Apartment in Central Kihei

Oceanfront penthouse with amazing views at Kauhale Makai
9.8 out of 10, Exceptional, (74)
"This was our first stay in Kihei and we had a wonderful time! The location was great and we appreciated the quietness of our space. We were able to walk to a nearby shopping plaza where we found delicious food and coffee. Our host was kind and communicated promptly and efficiently. We will be back! "
United States
Paige O.
The price is ￥20,182
￥87,129 total
includes taxes & fees
Jan 11 - Jan 12
Oceanfront penthouse with amazing views at Kauhale Makai
Outdoor dining
Beautiful 1 bedroom ocean front condo with a/c in Menehune Shores ,Kihei

Condo in North Kihei

Beautiful 1 bedroom ocean front condo with a/c in Menehune Shores ,Kihei
8.6 out of 10, Excellent, (142)
"Location and property are great! It’s exactly as you’d want on your Maui vacation!"
United States
Caelle M.
The price is ￥19,556
￥63,908 total
includes taxes & fees
Jan 20 - Jan 21
Beautiful 1 bedroom ocean front condo with a/c in Menehune Shores ,Kihei
Exterior
10% 7 Day Discount! Kihei Studio - Split AC, Clean, Free WiFi, Turtles!

Condo in North Kihei

10% 7 Day Discount! Kihei Studio - Split AC, Clean, Free WiFi, Turtles!
10.0 out of 10, Exceptional, (267)
"Great stay"
United States
Noah C.
The price is ￥15,348
￥61,316 total
includes taxes & fees
Jan 9 - Jan 10
10% 7 Day Discount! Kihei Studio - Split AC, Clean, Free WiFi, Turtles!
Property grounds
This remodeled condo earned "Best in Kihei" 4 times and “#1 in Maui” Ocean View!

Condo in North Kihei

This remodeled condo earned "Best in Kihei" 4 times and “#1 in Maui” Ocean View!
10.0 out of 10, Exceptional, (31)
"we really enjoyed our stay here. It is clean and maintained well and close to the beach."
United States
stuti s.
The price is ￥27,210
￥80,686 total
includes taxes & fees
Jan 5 - Jan 6
This remodeled condo earned "Best in Kihei" 4 times and “#1 in Maui” Ocean View!
Outdoor dining
Oceanview #103 at Hana Kai Maui - 1 Bedroom, Amazing View - Easy Access

Condo in Hana Town Center

Oceanview #103 at Hana Kai Maui - 1 Bedroom, Amazing View - Easy Access
9.6 out of 10, Exceptional, (111)
"Everything Good "
United States
Marc
The price is ￥66,491
￥93,569 total
includes taxes & fees
Jan 9 - Jan 10
Oceanview #103 at Hana Kai Maui - 1 Bedroom, Amazing View - Easy Access
Smart TV
Spacious & Remodeled Maui Vista 3213 Corner Unit!

Condo in South Kihei

Spacious & Remodeled Maui Vista 3213 Corner Unit!
9.6 out of 10, Exceptional, (138)
"Great place to stay. Cozy and cute and great location."
United States
Tad H.
The price is ￥23,468
￥67,729 total
includes taxes & fees
Jan 12 - Jan 13
Spacious & Remodeled Maui Vista 3213 Corner Unit!
Sun loungers, beach towels
Tropical Romance... Lush Gardens.... in Heavenly Hana, Maui

Cottage in Hana

Tropical Romance... Lush Gardens.... in Heavenly Hana, Maui
10.0 out of 10, Exceptional, (90)
"Very unique property near Hana. Great experience!"
United States
Keith R.
The price is ￥50,824
￥88,232 total
includes taxes & fees
Jan 19 - Jan 20
Tropical Romance... Lush Gardens.... in Heavenly Hana, Maui
Property grounds
Tropical Paradise Awaits: Steps to Sugar Beach, Pool, Hot Tub & Free WiFi!

Condo in North Kihei

Tropical Paradise Awaits: Steps to Sugar Beach, Pool, Hot Tub & Free WiFi!
9.6 out of 10, Exceptional, (160)
"It was pretty much as described and met our needs.It was in a pretty good location for our requirements, and not too far from the port for our snorkelling trip."
United Kingdom
Carole W.
The price is ￥29,556
￥84,716 total
includes taxes & fees
Jan 19 - Jan 20
Tropical Paradise Awaits: Steps to Sugar Beach, Pool, Hot Tub & Free WiFi!
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

Hampton Inn & Suites Maui North Shore

Hampton Inn & Suites Maui North Shore

10/10 Excellent
"Everyone was fantastic and the place was paradise. My mother and I really had a great time and yearn to return as soon as we can!"
Nicholas 4-night trip
Posted 2 days ago
Hampton Inn & Suites Maui North Shore

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:

  • View our selection of featured holiday rentals in Kailua
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Look no further and take a look at our great range of rental properties in Kailua!

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 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.