Kailua Vacation Rentals

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Our top choices for Kailua vacation rentals

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, (196 reviews)
"Had a very nice stay. The cottage was well equipped. I spent 8 days there. Loved this location in Hana."
United States
Lon S.
$413 nightly
The price is $483
Mar 14 - Mar 15
Total with taxes and fees
Beautiful Cottage in the heart of Hana, sleeps 2 with 1bed/1bath

Yonegan Maui Getaways - Haiku

Yonegan Maui Getaways - Haiku
3.0 star property
Haiku
9.0 out of 10, Wonderful, (27 reviews)
"It is a cozy place. It has all the amenities. It feels like home"
United States
Roberto
$271 nightly
The price is $304
Mar 22 - Mar 23
Total with taxes and fees
Yonegan Maui Getaways - Haiku

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, (199 reviews)
"Recently renovated and spotless! This condo had everything we needed and was comfortable and conveniently located. Highly recommend!"
United States
Allison H.
$378 nightly
The price is $443
Mar 15 - Mar 16
Total with taxes and fees
A/C North Shore Maui - Paia/Kuau <br>Just steps away to Mama’s and beach

Embark on a journey through Maui with Aloha Glamp

Embark on a journey through Maui with Aloha Glamp
Haiku-Pauwela
9.6 out of 10, Exceptional, (40 reviews)
"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.
$249 nightly
The price is $291
Apr 2 - Apr 3
Total with taxes and fees
Embark on a journey through Maui with Aloha Glamp

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, (135 reviews)
"Great location."
United States
John
$400 nightly
The price is $468
Apr 4 - Apr 5
Total with taxes and fees
Oceanview Condo in Hana-Let the ocean lull you to sleep

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, (421 reviews)
"Very peaceful place to stay. Enjoyed location and would stay again if I come to Hana!"
United States
Nicholas
$349 nightly
The price is $408
Apr 9 - Apr 10
Total with taxes and fees
Fisher's Hana Bay Hale, Across from Hana Bay

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
$516 nightly
The price is $613
Mar 13 - Mar 14
Total with taxes and fees
The Ocean View Residence

[RARE] Upscale 2BR/2BA Kuau Paia - Walk to Beach

[RARE] Upscale 2BR/2BA Kuau Paia - Walk to Beach
Paia
9.8 out of 10, Exceptional, (41 reviews)
"Wonderful Property"
United States
Kristin M.
$804 nightly
The price is $873
Mar 13 - Mar 14
Total with taxes and fees
[RARE] Upscale 2BR/2BA Kuau Paia - Walk to Beach

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
$511 nightly
The price is $598
Mar 23 - Mar 24
Total with taxes and fees
Oceanview #204 at Hana Kai Maui - 1 Bedroom Upper Floor, Amazing View!

Yonegan Maui Getaways - Haiku - Unit 3

Yonegan Maui Getaways - Haiku - Unit 3
Haiku-Pauwela
9.0 out of 10, Wonderful, (19 reviews)
"Host was very welcoming. "
United States
Douglas M.
$271 nightly
The price is $272
Mar 22 - Mar 23
Total with taxes and fees
Yonegan Maui Getaways - Haiku - Unit 3

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, (25 reviews)
"I would stay again "
United States
Bruce H.
$488 nightly
The price is $571
Mar 15 - Mar 16
Total with taxes and fees
Oceanview #206 at Hana Kai Maui - Lofted Studio, Upper floor, Great View!

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
$364 nightly
The price is $366
Mar 17 - Mar 18
Total with taxes and fees
Kuau Surf 2.0 Maui North Shore Locally-Owned

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, (116 reviews)
"Everything Good "
United States
Marc
$511 nightly
The price is $598
Mar 15 - Mar 16
Total with taxes and fees
Oceanview #103 at Hana Kai Maui - 1 Bedroom, Amazing View - Easy Access

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

Tropical Romance... Lush Gardens.... in Heavenly Hana, Maui
Hāna
10.0 out of 10, Exceptional, (96 reviews)
"Very unique property near Hana. Great experience!"
United States
Keith R.
$483 nightly
The price is $565
Mar 18 - Mar 19
Total with taxes and fees
Tropical Romance... Lush Gardens.... in Heavenly Hana, Maui

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.
$414 nightly
The price is $485
Mar 19 - Mar 20
Total with taxes and fees
Tropical Honeymoon Suite - BBQ, Hot Tub - Walk 2 Beach - In the Heart Of Kihei

Stay in Hana #2

Stay in Hana #2
Hana Town Center
9.6 out of 10, Exceptional, (50 reviews)
"Spent a night in Hana to avoid being rushed and having to drive the challenging road both ways in one day. Great place just off the main road but feels very secluded. "
United States
Dean M.
$297 nightly
The price is $348
Mar 12 - Mar 13
Total with taxes and fees
Stay in Hana #2

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, (154 reviews)
"The location was fantastic and the house was very comfortable, especially the beds."
United States
Lisa H.
$538 nightly
The price is $630
Mar 25 - Mar 26
Total with taxes and fees
Beautiful home in the Heart of Hana, sleeps 4 with 2br/1b

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, (239 reviews)
"30 yr anniversary - perfectly relaxing for us - would stay here again for sure."
United States
Trent H.
$513 nightly
The price is $600
Mar 22 - Mar 23
Total with taxes and fees
Special quiet, romantic, cozy home in a special place, Heavenly Hana. Lucky you!

Sugar Beach Resort Oceanview 1 bed/1 bath

Sugar Beach Resort Oceanview 1 bed/1 bath
North Kihei
9.6 out of 10, Exceptional, (115 reviews)
"Condo is fully stocked and decorated beautifully! "
United States
erin t.
$380 nightly
The price is $445
Mar 14 - Mar 15
Total with taxes and fees
Sugar Beach Resort Oceanview 1 bed/1 bath

10% 7 Day Discount! Kihei Studio - Split AC, Clean, Free WiFi, Turtles!

10% 7 Day Discount! Kihei Studio - Split AC, Clean, Free WiFi, Turtles!
North Kihei
10.0 out of 10, Exceptional, (272 reviews)
"Great stay"
United States
Noah C.
$345 nightly
The price is $404
Mar 15 - Mar 16
Total with taxes and fees
10% 7 Day Discount! Kihei Studio - Split AC, Clean, Free WiFi, Turtles!
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

Everything you need to know about Kailua vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Kailua vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. The list goes on, and on …and on.

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Kailua vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Kailua vacation rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Kailua. If you’re looking for a little peace, consider booking during the quieter low season months. For more hustle and bustle, you may prefer to visit Kailua in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $304 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Kailua rentals

At Expedia, we put the best Kailua vacation rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia.

To find some top Kailua rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Kailua vacation.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Kailua. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.

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 Haleakala National Park. 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.