An aerial view of a coastal town with clear turquoise waters, two prominent islands, and lush green hills.

Kailua Vacation Rentals

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Our top choices for Kailua vacation rentals

Paradise: Ocean View Cottage Solar Power Tropical Flower Gardens - 10% off JULY!

Paradise: Ocean View Cottage Solar Power Tropical Flower Gardens - 10% off JULY!
Hana
10.0 out of 10, Exceptional, (515 reviews)
"Beautiful place. Excellent host. "
United States
Darryl S.
The price is CA $350
CA $630 total
includes taxes & fees
Jul 1 - Jul 2
Paradise: Ocean View Cottage Solar Power Tropical Flower Gardens - 10% off JULY!

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, (455 reviews)
"Great place to stay while exploring Hana"
Canada
Igor G.
The price is CA $276
CA $546 total
includes taxes & fees
Jul 10 - Jul 11
Fisher’s Hana Bay Hale - In Hana Town across from the Bay STHA-2017 0002

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, (212 reviews)
"Great location near Paia shops and short walk to Mama's Fish House, & beach. Enjoyed our stay at Kuau Plaza. The condo was just as described and pictured. Nicely furnished & decorated. Comfy bed, everything you could need in the kitchen, nice bathroom...all looked brand new! Although right next to the road, we barely heard the traffic. We would stay here again."
United States
Kimberly
The price is CA $262
CA $634 total
includes taxes & fees
Jul 16 - Jul 17
A/C North Shore Maui - Paia/Kuau <br>Just steps away to Mama’s and beach

Fisher's Hana Bay Hale, Across from Hana Bay

Fisher's Hana Bay Hale, Across from Hana Bay
Hana Town Center
9.6 out of 10, Exceptional, (439 reviews)
"Great stay thanks! "
United States
Stephanie C.
The price is CA $276
CA $575 total
includes taxes & fees
Jul 16 - Jul 17
Fisher's Hana Bay Hale, Across from Hana Bay

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, (146 reviews)
"Nice location, comfortable accommodations. We loved the view off the lanai. "
United States
Kelly J.
The price is CA $337
CA $638 total
includes taxes & fees
Jul 6 - Jul 7
Oceanview Condo in Hana-Let the ocean lull you to sleep

Beautiful home in the Heart of Hana, sleeps 4 with 2br/1b

Beautiful home in the Heart of Hana, sleeps 4 with 2br/1b
Hana Town Center
9.4 out of 10, Exceptional, (158 reviews)
"The host communicated clearly and the accommodations were exactly what we were looking for. "
United States
Angie F.
The price is CA $325
CA $737 total
includes taxes & fees
Jul 1 - Jul 2
Beautiful home in the Heart of Hana, sleeps 4 with 2br/1b

Yonegan Maui Getaways - Haiku - Unit 6

Yonegan Maui Getaways - Haiku - Unit 6
Haiku-Pauwela
9.2 out of 10, Wonderful, (38 reviews)
"Everything was great."
United States
Bryan
The price is CA $174
CA $443 total
includes taxes & fees
Jun 28 - Jun 29
Yonegan Maui Getaways - Haiku - Unit 6

Sugar Beach 314 Front Row Ocean Views in Beautifully Upgraded Beachfront Condo

Sugar Beach 314 Front Row Ocean Views in Beautifully Upgraded Beachfront Condo
North Kihei
9.6 out of 10, Exceptional, (57 reviews)
"This is a great unit. Excellent location and easy access to everything on Maui. "
United States
scott s.
The price is CA $337
CA $851 total
includes taxes & fees
Jul 8 - Jul 9
Sugar Beach 314 Front Row Ocean Views in Beautifully Upgraded Beachfront Condo

Tropical Honeymoon Suite - BBQ, Hot Tub - Walk 2 Beach - In the Heart Of Kihei

Tropical Honeymoon Suite - BBQ, Hot Tub - Walk 2 Beach - In the Heart Of Kihei
North Kihei
9.8 out of 10, Exceptional, (109 reviews)
"This place was in a good location in Kihei. You are within 5 mins of dozen of beaches. All the beach gear a person needs is provided(towels, chairs, snorkels, flippers, coolers and more)! Jon is super friendly and a great host!"
United States
Troy s.
The price is CA $137
CA $704 total
includes taxes & fees
Jul 6 - Jul 7
Tropical Honeymoon Suite - BBQ, Hot Tub - Walk 2 Beach - In the Heart Of Kihei

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, (10 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 $156
CA $488 total
includes taxes & fees
Jul 5 - Jul 6
Kihei · Pool / Hot Tub / Beach access / AC / Baby friendly

Locally-owned, eco-friendly condo on Road to Hāna. 2-min walk to beach & seafood

Locally-owned, eco-friendly condo on Road to Hāna. 2-min walk to beach & seafood
Paia
10.0 out of 10, Exceptional, (12 reviews)
"We had a wonderful stay, our host was sweet"
United States
Nancy k.
The price is CA $275
CA $557 total
includes taxes & fees
Jul 4 - Jul 5
Locally-owned, eco-friendly condo on Road to Hāna. 2-min walk to beach & seafood

Ocean View 2-bedroom condo with pool and AC in wonderful Kihei

Ocean View 2-bedroom condo with pool and AC in wonderful Kihei
North Kihei
9.8 out of 10, Exceptional, (29 reviews)
"Nice place"
Canada
PC SHOP
The price is CA $215
CA $666 total
includes taxes & fees
Jun 29 - Jun 30
Ocean View 2-bedroom condo with pool and AC in wonderful Kihei

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 $93
CA $787 total
includes taxes & fees
Jun 25 - Jun 26
The Ocean View Residence

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)
"Beautiful grounds, great location close to secluded beach."
United States
Mark S.
The price is CA $439
CA $773 total
includes taxes & fees
Jul 12 - Jul 13
Tropical Romance... Lush Gardens.... in Heavenly Hana, Maui

Unit 25 Waena Inn - Maui Private Suite

Unit 25 Waena Inn - Maui Private Suite
Wailuku
9.8 out of 10, Exceptional, (16 reviews)
"Had a great time, even with the rain ."
United States
Kevin M.
The price is CA $277
CA $411 total
includes taxes & fees
Jun 28 - Jun 29
Unit 25 Waena Inn - Maui Private Suite

Yonegan Maui Getaways - Haiku - Unit 4

Yonegan Maui Getaways - Haiku - Unit 4
Haiku
9.0 out of 10, Wonderful, (21 reviews)
"Great location for driving the Road to Hana."
United States
Lisa
The price is CA $216
CA $491 total
includes taxes & fees
Jun 28 - Jun 29
Yonegan Maui Getaways - Haiku - Unit 4

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, (247 reviews)
"I appreciated everything as advertised. Would have preferred mini splits or AC in the bedrooms, but still a nice peaceful spot."
United States
Robert
The price is CA $421
CA $847 total
includes taxes & fees
Jul 1 - Jul 2
Special quiet, romantic, cozy home in a special place, Heavenly Hana. Lucky you!

Steps to the Beach, Affordable w/Free Parking

Steps to the Beach, Affordable w/Free Parking
North Kihei
9.6 out of 10, Exceptional, (171 reviews)
"Clean, across the street from beach and whale center. Great location to get to other places on the island. "
Canada
wayneiversonphotosk
The price is CA $166
CA $613 total
includes taxes & fees
Jun 28 - Jun 29
Steps to the Beach, Affordable w/Free Parking

Hale Nihi - Paia, Maui

Hale Nihi - Paia, Maui
Paia
9.6 out of 10, Exceptional, (63 reviews)
"Very convenient place to stay within walking distance to activities and beach. "
United States
Chameil H.
The price is CA $253
CA $629 total
includes taxes & fees
Jun 26 - Jun 27
Hale Nihi - Paia, Maui

Oceanfront, Hale Kai O Kihei, incredible sunsets, King bed, AC, remodeled 2023

Oceanfront, Hale Kai O Kihei, incredible sunsets, King bed, AC, remodeled 2023
Central Kihei
10.0 out of 10, Exceptional, (114 reviews)
"Beautiful views, lovely beach, convenient parking and good amenities nearby. "
United States
Tesha T.
The price is CA $228
CA $662 total
includes taxes & fees
Jun 25 - Jun 26
Oceanfront, Hale Kai O Kihei, incredible sunsets, King bed, AC, remodeled 2023
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 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.