Kailua Vacation Rentals

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Check prices for these dates

In two weeks
Feb 27 - Mar 1
In two months
Apr 10 - Apr 12
In three months
May 8 - May 10
In four months
Jun 5 - Jun 7

Our top choices for Kailua vacation rentals

Studio, Garden View (Haiku #6) | Terrace/patio

Yonegan Maui Getaways - Haiku

Yonegan Maui Getaways - Haiku
3.0 star property
Haiku
9.0 out of 10, Wonderful, (23 reviews)
"It is a cozy place. It has all the amenities. It feels like home"
United States
Roberto
The price is ￥23,302
￥42,779 total
includes taxes & fees
Feb 17 - Feb 18
Yonegan Maui Getaways - Haiku
Beach

Beautiful Cottage in the heart of Hana, sleeps 2 with 1bed/1bath

Beautiful Cottage in the heart of Hana, sleeps 2 with 1bed/1bath
Hana Town Center
9.6 out of 10, Exceptional, (193 reviews)
"Super lovely place, I wish we were staying longer! Has everything you need. "
United States
Nicole
The price is ￥33,670
￥74,250 total
includes taxes & fees
Feb 25 - Feb 26
Beautiful Cottage in the heart of Hana, sleeps 2 with 1bed/1bath
Beach towels

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, (197 reviews)
"Such a great place to stay! Location could not have been better. Quiet neighbors, walking distance to Mama’s Fish house and the beach. Traffic can be a little loud, but that has nothing do to with the owner or space. We would stay here again!"
United States
Allison S.
The price is ￥28,250
￥68,082 total
includes taxes & fees
Feb 16 - Feb 17
A/C North Shore Maui - Paia/Kuau <br>Just steps away to Mama’s and beach
Beach nearby, sun loungers, beach towels

Maui Modern North Shore Beach Condo - Walk to Mamas Fish House! AC, Fast WiFi

Maui Modern North Shore Beach Condo - Walk to Mamas Fish House! AC, Fast WiFi
Paia
9.8 out of 10, Exceptional, (90 reviews)
"Enjoyed our time and the food!"
United States
K G.
The price is ￥28,723
￥68,643 total
includes taxes & fees
Feb 17 - Feb 18
Maui Modern North Shore Beach Condo - Walk to Mamas Fish House! AC, Fast WiFi
Beach towels

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, (418 reviews)
"Very peaceful place to stay. Enjoyed location and would stay again if I come to Hana!"
United States
Nicholas
The price is ￥29,777
￥60,938 total
includes taxes & fees
Feb 24 - Feb 25
Fisher's Hana Bay Hale, Across from Hana Bay
Exterior

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, (131 reviews)
"Great location."
United States
John
The price is ￥39,855
￥73,275 total
includes taxes & fees
Mar 12 - Mar 13
Oceanview Condo in Hana-Let the ocean lull you to sleep
Sun loungers, beach towels

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
9.2 out of 10, Wonderful, (150 reviews)
"The location was fantastic and the house was very comfortable, especially the beds."
United States
Lisa H.
The price is ￥45,047
￥92,873 total
includes taxes & fees
Mar 3 - Mar 4
Beautiful home in the Heart of Hana, sleeps 4 with 2br/1b
Property grounds

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

Tropical Romance... Lush Gardens.... in Heavenly Hana, Maui
Hāna
10.0 out of 10, Exceptional, (92 reviews)
"Very unique property near Hana. Great experience!"
United States
Keith R.
The price is ￥49,628
￥86,314 total
includes taxes & fees
Feb 22 - Feb 23
Tropical Romance... Lush Gardens.... in Heavenly Hana, Maui
Terrace/patio

Stay in Hana #2

Stay in Hana #2
Hana Town Center
9.6 out of 10, Exceptional, (49 reviews)
"Staying here was a pleasure - from the ease of the check in process, to the cleanliness of the room, amenities and location, we're so glad we chose this home!"
United States
Jenny E.
The price is ￥28,723
￥53,450 total
includes taxes & fees
Feb 24 - Feb 25
Stay in Hana #2
Interior

Kuau Surf North shore Maui Locally-Owned

Kuau Surf North shore Maui Locally-Owned
Paia
9.0 out of 10, Wonderful, (38 reviews)
"Cute clean and a short couple minute walk to the beach where their was seaturtles waiting "
United States
Bobby
The price is ￥27,486
￥50,199 total
includes taxes & fees
Feb 27 - Feb 28
Kuau Surf North shore Maui Locally-Owned
Exterior detail

Yonegan Maui Getaways - Haiku - Unit 3

Yonegan Maui Getaways - Haiku - Unit 3
Haiku-Pauwela
9.0 out of 10, Wonderful, (19 reviews)
"It was super beautiful, and it was such a homey setting! It would be nice if it was quieter and less crowded, but overall an amazing stay for what it is!"
United States
Naveah G.
The price is ￥18,309
￥38,224 total
includes taxes & fees
Feb 17 - Feb 18
Yonegan Maui Getaways - Haiku - Unit 3
TV

Kuau Surf 2.0 Maui North Shore Locally-Owned

Kuau Surf 2.0 Maui North Shore Locally-Owned
Paia
9.2 out of 10, Wonderful, (22 reviews)
"Clean and convenient"
United States
Ilya L
The price is ￥29,013
￥52,365 total
includes taxes & fees
Mar 2 - Mar 3
Kuau Surf 2.0 Maui North Shore Locally-Owned
Interior

Kuau Plaza Paia Condo with Parking

Kuau Plaza Paia Condo with Parking
3.0 star property
Paia
The price is ￥38,328
￥88,103 total
includes taxes & fees
Feb 20 - Feb 21
Kuau Plaza Paia Condo with Parking
Property grounds

Oceanview #101 at Hana Kai Maui - 1 Bedroom Corner Unit, Amazing View!

Oceanview #101 at Hana Kai Maui - 1 Bedroom Corner Unit, Amazing View!
Hana Town Center
9.6 out of 10, Exceptional, (77 reviews)
"Nice easy check in. Easy access to black sand beach (not the State Park)."
United States
Brett
The price is ￥64,898
￥91,327 total
includes taxes & fees
Mar 1 - Mar 2
Oceanview #101 at Hana Kai Maui - 1 Bedroom Corner Unit, Amazing View!
Property grounds

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, (24 reviews)
"I would stay again "
United States
Bruce H.
The price is ￥61,844
￥87,221 total
includes taxes & fees
Mar 1 - Mar 2
Oceanview #206 at Hana Kai Maui - Lofted Studio, Upper floor, Great View!
Exterior

Yonegan Maui Getaways - Haiku - Unit 4

Yonegan Maui Getaways - Haiku - Unit 4
Haiku
8.8 out of 10, Excellent, (16 reviews)
"The property was strategically located near the Road to Hana and Haleakala National Park."
United States
C T.
The price is ￥22,508
￥43,061 total
includes taxes & fees
Feb 17 - Feb 18
Yonegan Maui Getaways - Haiku - Unit 4
Property grounds

Oceanfront penthouse with amazing views at Kauhale Makai

Oceanfront penthouse with amazing views at Kauhale Makai
Central Kihei
9.8 out of 10, Exceptional, (77 reviews)
"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 ￥20,615
￥87,411 total
includes taxes & fees
Mar 10 - Mar 11
Oceanfront penthouse with amazing views at Kauhale Makai
Sun loungers, beach towels

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 ￥16,492
￥78,223 total
includes taxes & fees
Feb 17 - Feb 18
Tropical Honeymoon Suite - BBQ, Hot Tub - Walk 2 Beach - In the Heart Of Kihei
Property grounds

Oceanview #105 at Hana Kai Maui - Sweet Studio Unit, Great View and Decor!

Oceanview #105 at Hana Kai Maui - Sweet Studio Unit, Great View and Decor!
Hana Town Center
9.8 out of 10, Exceptional, (84 reviews)
"The location was very good."
United States
Jim B.
The price is ￥60,317
￥85,250 total
includes taxes & fees
Mar 8 - Mar 9
Oceanview #105 at Hana Kai Maui - Sweet Studio Unit, Great View and Decor!
Property grounds

Enjoy Ocean Views From Lanai, Living room & Bedroom, Beachfront Pool!

Enjoy Ocean Views From Lanai, Living room & Bedroom, Beachfront Pool!
Central Kihei
9.4 out of 10, Exceptional, (85 reviews)
"Rating Details: The property manager was very helpful. The vacation rental was spotless. I was very happy with the location. I was very satisfied with the condition of the vacation rental. Overall, I recommend this vacation rental. Reviewer Comments: Beautiful condo, great views and location"
United States
Pam B.
The price is ￥29,166
￥96,982 total
includes taxes & fees
Mar 1 - Mar 2
Enjoy Ocean Views From Lanai, Living room & Bedroom, Beachfront Pool!
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

Maui Coast Hotel

Maui Coast Hotel

10/10 Excellent
"Very clean, good location, all staff are very friendly and nice."
Masako 3-night trip
Posted 2 days ago
Maui Coast Hotel

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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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, 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 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.