Kailua Vacation Rentals

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Our top choices for Kailua vacation rentals

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
$435 nightly
The price is $517
Jun 3 - Jun 4
Total with taxes and fees
The Ocean View Residence

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
Jun 13 - Jun 14
Total with taxes and fees
Tropical Honeymoon Suite - BBQ, Hot Tub - Walk 2 Beach - In the Heart Of Kihei

Tracy’s Tropical Treasure #4 "Best in Kihei" 4 times and “#1 in Maui” Ocean View

Tracy’s Tropical Treasure #4 "Best in Kihei" 4 times and “#1 in Maui” Ocean View
North Kihei
10.0 out of 10, Exceptional, (40 reviews)
"Had lots of great and useful amenities "
United States
Rochelle P.
$378 nightly
The price is $442
Jun 3 - Jun 4
Total with taxes and fees
Tracy’s Tropical Treasure #4 "Best in Kihei" 4 times and “#1 in Maui” Ocean View

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, (276 reviews)
"Absolutely perfect stay! Kevin was very kind and very communicative. I highly recommend staying here when visiting Kīhei."
United States
Sylvia
$337 nightly
The price is $395
Jun 8 - Jun 9
Total with taxes and fees
10% 7 Day Discount! Kihei Studio - Split AC, Clean, Free WiFi, Turtles!

Yonegan Maui Getaways - Haiku

Yonegan Maui Getaways - Haiku
3.0 star property
Haiku
8.8 out of 10, Excellent, (31 reviews)
"Good location for the Road to Hana and exploring Paia, hot tub was enjoyable."
United States
Matt
$290 nightly
The price is $317
Jun 2 - Jun 3
Total with taxes and fees
Yonegan Maui Getaways - Haiku

Kihei Ali'i Kai Condos with Free Parking

Kihei Ali'i Kai Condos with Free Parking
4.0 star property
South Kihei
9.4 out of 10, Exceptional, (36 reviews)
"Everything was set up to be an amazing experience and we would definitely stay again."
Canada
Tamara
$379 nightly
The price is $449
Jun 22 - Jun 23
Total with taxes and fees
Kihei Ali'i Kai Condos with Free Parking

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

Kihei · Pool / Hot Tub / Beach access / AC / Baby friendly
North Kihei
8.8 out of 10, Excellent, (8 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
$302 nightly
The price is $353
Jun 2 - Jun 3
Total with taxes and fees
Kihei · Pool / Hot Tub / Beach access / AC / Baby friendly

Yonegan Maui Getaways - Haiku - Unit 3

Yonegan Maui Getaways - Haiku - Unit 3
Haiku-Pauwela
9.0 out of 10, Wonderful, (21 reviews)
"Great spot in my old home town. Very well kept yard & beautiful place to stay"
United States
Ryan H.
$319 nightly
The price is $321
Jun 2 - Jun 3
Total with taxes and fees
Yonegan Maui Getaways - Haiku - Unit 3

Ground floor oceanfront, walk out to beach

Ground floor oceanfront, walk out to beach
Central Kihei
9.0 out of 10, Wonderful, (37 reviews)
"Great location and beautiful beach"
United States
Stephanie M.
$643 nightly
The price is $670
Jun 3 - Jun 4
Total with taxes and fees
Ground floor oceanfront, walk out to beach

Stay in Hana Upstairs

Stay in Hana Upstairs
Hana Town Center
9.6 out of 10, Exceptional, (43 reviews)
"Beautiful remote location! A little short on kitchen supplies like wine glasses and Tupperware. We loved the cabin feel of the place. Great access to the Hana Road and excellent nearby waterfall hikes!"
United States
Paulina B.
$402 nightly
The price is $471
Jun 2 - Jun 3
Total with taxes and fees
Stay in Hana Upstairs

10% 7 Day Discount! Kihei 1Br Top Floor - Split AC, Clean, Free WiFi, Turtles!

10% 7 Day Discount! Kihei 1Br Top Floor - Split AC, Clean, Free WiFi, Turtles!
North Kihei
10.0 out of 10, Exceptional, (308 reviews)
"Great place, easy access and parking. Host communication was exceptional, would not hesitate to rent again."
United States
M P.
$359 nightly
The price is $419
Jun 3 - Jun 4
Total with taxes and fees
10% 7 Day Discount! Kihei 1Br Top Floor - Split AC, Clean, Free WiFi, Turtles!

Artistic Top-Floor Tropical Penthouse – Steps to Maui’s Best Beach

Artistic Top-Floor Tropical Penthouse – Steps to Maui’s Best Beach
South Kihei
9.8 out of 10, Exceptional, (125 reviews)
"Had a great time at the condo. Our host was easy to get ahold of and easy to communicate with throughout our stay. The condo was in a great location close to the beach, shopping and everything else we needed. Would highly recommend!"
Canada
Kristian
$433 nightly
The price is $507
Jun 9 - Jun 10
Total with taxes and fees
Artistic Top-Floor Tropical Penthouse – Steps to Maui’s Best Beach

Stunning South Maui Condo w/ Lanai by Beach!

Stunning South Maui Condo w/ Lanai by Beach!
North Kihei
9.8 out of 10, Exceptional, (31 reviews)
"Trudy was responsive and welcoming. The pool was perfect to swim in with my toddler. Lovely view of the ocean from the bedroom. "
United States
Melissa S.
$342 nightly
The price is $396
Jun 22 - Jun 23
Total with taxes and fees
Stunning South Maui Condo w/ Lanai by Beach!

Great location between Hana Town and Hamoa Beach, private, family-friendly

Great location between Hana Town and Hamoa Beach, private, family-friendly
Hana Town Center
9.8 out of 10, Exceptional, (239 reviews)
"Great location in Hana. Cozy and private. "
United States
Heather F.
$432 nightly
The price is $507
Jun 6 - Jun 7
Total with taxes and fees
Great location between Hana Town and Hamoa Beach, private, family-friendly

OCEAN VIEW!! Across Charley Young Beach

OCEAN VIEW!! Across Charley Young Beach
South Kihei
9.6 out of 10, Exceptional, (187 reviews)
"What a beautiful view! Whales from the couch, steps to Charley Young beach, quiet neighbors. We enjoyed our stay so very much!"
United States
Anonymous traveler
$562 nightly
The price is $658
Jun 2 - Jun 3
Total with taxes and fees
OCEAN VIEW!! Across Charley Young Beach

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, (208 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
$379 nightly
The price is $444
Jun 6 - Jun 7
Total with taxes and fees
A/C North Shore Maui - Paia/Kuau <br>Just steps away to Mama’s and beach

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, (144 reviews)
"Great location."
United States
John
$406 nightly
The price is $475
Jun 30 - Jul 1
Total with taxes and fees
Oceanview Condo in Hana-Let the ocean lull you to sleep

Oceanview #104 at Hana Kai Maui - 1 Bedroom, Easy Access, no steps, Great View!

Oceanview #104 at Hana Kai Maui - 1 Bedroom, Easy Access, no steps, Great View!
Hana Town Center
9.6 out of 10, Exceptional, (79 reviews)
"Hana Kai is very convenient place to stay. Lanai is big and great place to hang out."
United States
Ann E.
$438 nightly
The price is $514
Jun 6 - Jun 7
Total with taxes and fees
Oceanview #104 at Hana Kai Maui - 1 Bedroom, Easy Access, no steps, Great View!

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
$386 nightly
The price is $452
Jun 15 - Jun 16
Total with taxes and fees
Steps to the Beach, Affordable w/Free Parking

Beachfront ,Ground floor, Sugar Beach, Corner unit 114 - Steps to the Ocean!!!

Beachfront ,Ground floor, Sugar Beach, Corner unit 114 - Steps to the Ocean!!!
North Kihei
9.8 out of 10, Exceptional, (209 reviews)
"Gorgeous condo right on the beach! Zero complaints! Thank you for sharing your home."
United States
Susan C.
$441 nightly
The price is $516
Jun 19 - Jun 20
Total with taxes and fees
Beachfront ,Ground floor, Sugar Beach, Corner unit 114 - Steps to the Ocean!!!
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 $317 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, 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.