Holiday Rentals in Kailua

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Our top choices for Kailua holiday 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
The price is €457
includes taxes & fees
3 Jun - 4 Jun
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.
The price is €427
includes taxes & fees
13 Jun - 14 Jun
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.
The price is €385
includes taxes & fees
9 Jun - 10 Jun
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
The price is €339
includes taxes & fees
8 Jun - 9 Jun
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
The price is €265
includes taxes & fees
2 Jun - 3 Jun
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
The price is €403
includes taxes & fees
6 Jun - 7 Jun
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
The price is €303
includes taxes & fees
2 Jun - 3 Jun
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.
The price is €276
includes taxes & fees
2 Jun - 3 Jun
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.
The price is €572
includes taxes & fees
3 Jun - 4 Jun
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.
The price is €412
includes taxes & fees
2 Jun - 3 Jun
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.
The price is €360
includes taxes & fees
3 Jun - 4 Jun
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
The price is €493
includes taxes & fees
24 Jun - 25 Jun
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.
The price is €342
includes taxes & fees
22 Jun - 23 Jun
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.
The price is €446
includes taxes & fees
6 Jun - 7 Jun
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 traveller
The price is €566
includes taxes & fees
2 Jun - 3 Jun
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, (210 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 €385
includes taxes & fees
6 Jun - 7 Jun
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
The price is €406
includes taxes & fees
30 Jun - 1 Jul
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.
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
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.
The price is €443
includes taxes & fees
19 Jun - 20 Jun
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 holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Kailua holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, apart-hotels, cabins, villas... 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 holiday rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search. 

Kailua holiday 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 months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Kailua holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Kailua holiday rentals we have selected for you start as low as €265 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on Kailua rentals

At Expedia, we put the best Kailua holiday 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 holiday.

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 holiday rental in Kailua?

Yes, there are holiday rentals close to the most popular sights in Kailua, or you can select a more secluded option if you're looking for a relaxing stay.

What are some of the best holiday rentals that Kailua has to offer?

Yonegan Maui Getaways - Haiku : This holiday home rental outside of Kailua is located near the beach, and has 1 hot tub, a BBQ 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 wider area, you’ll find Maui Garden Of Eden - Botanical Gardens & Arboretum and Maui Spa Retreat.

What’s a holiday rental in Kailua like?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in Kailua. Holiday rentals offer amenities such as WiFi and washers and dryers so you'll feel just like you're at home. If you're concerned about a clean environment, holiday rentals can offer a sense of seclusion away from shared hotel lifts and bustling concierge desks while still allowing you a great travel experience. You'll also get more space in a holiday rental than in a hotel, which makes a holiday rental a great option for a small group gathering.