Kailua Vacation Rentals

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Our top choices for Kailua vacation rentals

A/C North Shore Maui - Paia/Kuau <br>Just steps away to Mama’s and beach

A/C North Shore Maui - Paia/Kuau <br>Just steps away to Mama’s and beach
Kuau
9.4 out of 10, Exceptional, (206 reviews)
"Recently renovated and spotless! This condo had everything we needed and was comfortable and conveniently located. Highly recommend!"
United States
Allison H.
The price is CA $253
CA $612 total
includes taxes & fees
May 13 - May 14
A/C North Shore Maui - Paia/Kuau <br>Just steps away to Mama’s and beach

Yonegan Maui Getaways - Haiku

Yonegan Maui Getaways - Haiku
3.0 star property
Haiku
9.0 out of 10, Wonderful, (30 reviews)
"The location was great, especially if you plan to see the whole island! Easy check in and check out. Clean place."
United States
Weronika
The price is CA $226
CA $473 total
includes taxes & fees
May 10 - May 11
Yonegan Maui Getaways - Haiku

Stay in Hana #2

Stay in Hana #2
Hana Town Center
9.6 out of 10, Exceptional, (56 reviews)
"Great location and comfy!"
United States
Lindsay B.
The price is CA $257
CA $480 total
includes taxes & fees
May 14 - May 15
Stay in Hana #2

Ground floor oceanfront, walk out to beach

Ground floor oceanfront, walk out to beach
Central Kihei
9.0 out of 10, Wonderful, (37 reviews)
"It was a great holiday in a stunning location. We enjoyed the convenience of being in a ground floor unit. A couple of concerns/issues: the kitchen faucet needs changing and it was inconvenient that the pull out bed didn’t work, as my sister & I needed our own beds. There was also a strange outbreak of creepy wormy bugs in the bathroom one night, probably from the drains? But was beyond control is my guess? Overall, a gorgeous place to stay. "
Canada
Paula B.
The price is CA $180
CA $941 total
includes taxes & fees
May 28 - May 29
Ground floor oceanfront, walk out to beach

Fisher’s Hana Bay Hale - In Hana Town across from the Bay STHA-2017 0002

Fisher’s Hana Bay Hale - In Hana Town across from the Bay STHA-2017 0002
Hana Town Center
9.6 out of 10, Exceptional, (447 reviews)
"Food truck near."
United States
Neal
The price is CA $266
CA $525 total
includes taxes & fees
May 19 - May 20
Fisher’s Hana Bay Hale - In Hana Town across from the Bay STHA-2017 0002

Kuau Surf 2.0 Maui North Shore Locally-Owned

Kuau Surf 2.0 Maui North Shore Locally-Owned
Paia
8.8 out of 10, Excellent, (27 reviews)
"Clean and convenient"
United States
Ilya L
The price is CA $273
CA $485 total
includes taxes & fees
May 9 - May 10
Kuau Surf 2.0 Maui North Shore Locally-Owned

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
The price is CA $132
CA $849 total
includes taxes & fees
Jun 8 - Jun 9
The Ocean View Residence

Kihei · Pool / Hot Tub / Beach access / AC / Baby friendly

Kihei · Pool / Hot Tub / Beach access / AC / Baby friendly
North Kihei
9.0 out of 10, Wonderful, (7 reviews)
"Great stay, clean place. Close walk to the beach. The pool and hot tub were great and well taken care of"
United States
Danniella
The price is CA $158
CA $520 total
includes taxes & fees
May 17 - May 18
Kihei · Pool / Hot Tub / Beach access / AC / Baby friendly

Yonegan Maui Getaways - Haiku - Unit 6

Yonegan Maui Getaways - Haiku - Unit 6
Haiku-Pauwela
9.2 out of 10, Wonderful, (37 reviews)
"Great location, comfortable bed and room. "
United States
kimo
The price is CA $177
CA $440 total
includes taxes & fees
May 27 - May 28
Yonegan Maui Getaways - Haiku - Unit 6

GREAT RATES- Popular Ground Floor Unit at OCEANFRONT RESORT.

GREAT RATES- Popular Ground Floor Unit at OCEANFRONT RESORT.
North Kihei
9.4 out of 10, Exceptional, (77 reviews)
"Yes, Everything was perfect!! Very welcoming and comfortable. "
United States
Elizabeth H.
The price is CA $208
CA $649 total
includes taxes & fees
May 9 - May 10
GREAT RATES- Popular Ground Floor Unit at OCEANFRONT RESORT.

Special quiet, romantic, cozy home in a special place, Heavenly Hana. Lucky you!

Special quiet, romantic, cozy home in a special place, Heavenly Hana. Lucky you!
Kaʻeleku
9.8 out of 10, Exceptional, (243 reviews)
"30 yr anniversary - perfectly relaxing for us - would stay here again for sure."
United States
Trent H.
The price is CA $407
CA $815 total
includes taxes & fees
May 11 - May 12
Special quiet, romantic, cozy home in a special place, Heavenly Hana. Lucky you!

Tropical Romance... Lush Gardens.... in Heavenly Hana, Maui

Tropical Romance... Lush Gardens.... in Heavenly Hana, Maui
Hāna
10.0 out of 10, Exceptional, (101 reviews)
"This bungalow is perfect! It is beautiful and peaceful. I would come to Hāna just to stay here. And the host provided excellent information and was very gracious. "
United States
Catherine R.
The price is CA $424
CA $749 total
includes taxes & fees
May 24 - May 25
Tropical Romance... Lush Gardens.... in Heavenly Hana, Maui

Oceanview #204 at Hana Kai Maui - 1 Bedroom Upper Floor, Amazing View!

Oceanview #204 at Hana Kai Maui - 1 Bedroom Upper Floor, Amazing View!
Hana Town Center
9.6 out of 10, Exceptional, (77 reviews)
"Great view, excellent location. 2 -3 nights is the perfect amount of time in Hana."
United States
Jim
The price is CA $488
CA $695 total
includes taxes & fees
May 9 - May 10
Oceanview #204 at Hana Kai Maui - 1 Bedroom Upper Floor, Amazing View!

Kuau Surf North shore Maui Locally-Owned

Kuau Surf North shore Maui Locally-Owned
Paia
9.0 out of 10, Wonderful, (39 reviews)
"Cute clean and a short couple minute walk to the beach where their was seaturtles waiting "
United States
Bobby
The price is CA $273
CA $488 total
includes taxes & fees
May 20 - May 21
Kuau Surf North shore Maui Locally-Owned

Oceanfront, Exceptionally Remodeled, Split A/C, King bed, OH the sunsets

Oceanfront, Exceptionally Remodeled, Split A/C, King bed, OH the sunsets
Central Kihei
10.0 out of 10, Exceptional, (199 reviews)
"Amazing stay! Great view, clean and comfortable condo. Would stay again for sure!"
United States
Teresa F.
Oceanfront, Exceptionally Remodeled, Split A/C, King bed, OH the sunsets

Kihei Ali'i Kai Condos with Free Parking

Kihei Ali'i Kai Condos with Free Parking
4.0 star property
South Kihei
9.2 out of 10, Wonderful, (32 reviews)
"Everything was set up to be an amazing experience and we would definitely stay again."
Canada
Tamara
The price is CA $180
CA $569 total
includes taxes & fees
Jun 8 - Jun 9
Kihei Ali'i Kai Condos with Free Parking

Yonegan Maui Getaways - Haiku - Unit 4

Yonegan Maui Getaways - Haiku - Unit 4
Haiku
9.0 out of 10, Wonderful, (21 reviews)
"Great stay"
United States
Rohitkumar S.
The price is CA $219
CA $489 total
includes taxes & fees
May 11 - May 12
Yonegan Maui Getaways - Haiku - Unit 4

Oceanview #103 at Hana Kai Maui - 1 Bedroom, Amazing View - Easy Access

Oceanview #103 at Hana Kai Maui - 1 Bedroom, Amazing View - Easy Access
Hana Town Center
9.6 out of 10, Exceptional, (118 reviews)
"Great view, enjoyed location. "
United States
Tony E.
The price is CA $493
CA $702 total
includes taxes & fees
May 9 - May 10
Oceanview #103 at Hana Kai Maui - 1 Bedroom, Amazing View - Easy Access

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

Oceanview Condo in Hana-Let the ocean lull you to sleep
Hana Town Center
9.2 out of 10, Wonderful, (142 reviews)
"Great location."
United States
John
The price is CA $383
CA $688 total
includes taxes & fees
May 19 - May 20
Oceanview Condo in Hana-Let the ocean lull you to sleep

Oceanview #206 at Hana Kai Maui - Lofted Studio, Upper floor, Great View!

Oceanview #206 at Hana Kai Maui - Lofted Studio, Upper floor, Great View!
Hana Town Center
9.6 out of 10, Exceptional, (27 reviews)
"I would stay again "
United States
Bruce H.
The price is CA $521
CA $734 total
includes taxes & fees
May 19 - May 20
Oceanview #206 at Hana Kai Maui - Lofted Studio, Upper floor, Great View!
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

Find out more about Kailua

You always said you would go on a dream vacation someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannon ball into the deep end. Go ahead, unplug and unwind in style. When you book one of our vacation rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment or room. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your vacation just got upgraded.

As much as you love your short-term rental, it’s always good to get out and explore to soak up . Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in . Seeing all the best attractions is bound to make you fall in love with Kailua. Who knows, you may even be tempted to extend your vacation rental stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true.

It’s your escape so why share it? You deserve your own slice of paradise. Booking your vacation rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in short-term rentals, that won’t be hard to do.

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 Haleakala National Park. In the larger area, you’ll find Twin Falls 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.