Kailua Holiday Rentals

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Holiday Rentals in Kailua

Oceanfront Hana Bay Manini Cottage! Pet-friendly, 5-minute walk to the beach!

10.0 out of 10, Exceptional, (18)
"Awesome place for a couple nights in Hāna. "
The price is AU$1,126
includes taxes & fees
15 July - 16 July
Oceanfront Hana Bay Manini Cottage! Pet-friendly, 5-minute walk to the beach!

Amazing Hana Bay Beach Cottage Location! 5-Minute Walk to Hana town & beaches!

10.0 out of 10, Exceptional, (17)
"nice place"
The price is AU$2,035
includes taxes & fees
30 July - 31 July
Amazing Hana Bay Beach Cottage Location! 5-Minute Walk to Hana town & beaches!

Hana Homestead by the Beach

9.8 out of 10, Exceptional, (134)
"This property is amazing! Not right on the water but great view of the ocean, can hear the ocean and 3minute walk to the beach!! Beautiful property and plenty of extras such as a jacuzzi, sauna, boogie boards, beach chairs, beach toys for the kids, and an on-site private outside shower to clean up after walking or playing in the beach. "
The price is AU$2,130
includes taxes & fees
12 Aug - 13 Aug
Hana Homestead by the Beach

Fisher's Hana Bay Hale, Across from Hana Bay

9.4 out of 10, Exceptional, (387)
"Just as described and perfect for our 1 night in Hāna. Loved being able to walk to the beach across the street and down the road a bit"
The price is AU$608
includes taxes & fees
22 July - 23 July
Fisher's Hana Bay Hale, Across from Hana Bay

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

9.2 out of 10, Wonderful, (142)
"For Hana, this was a great find. AC in both bedrooms. Nice porch with a great view. Full kitchen. Modern rain shower was great after the long drive. Check and out was easy. "
The price is AU$887
includes taxes & fees
18 July - 19 July
Beautiful home in the Heart of Hana, sleeps 4 with 2br/1b

Beautiful Home in paradise!

9.6 out of 10, Exceptional, (168)
"Wanted a place for my family to stay while we enjoyed the road to Hana in Maui. This place checked the boxes. "
The price is AU$1,013
includes taxes & fees
20 July - 21 July
Beautiful Home in paradise!

Special quiet, romantic, cozy home in a special place, Heavenly Hana. Lucky you!

9.8 out of 10, Exceptional, (226)
"What an amazing place to stay and enjoy beautiful Hana. The home is clean, comfortable and updated. We loved the property and how well kept the landscaping - it gives you a feeling of a high-end resort! Will stay her again!"
The price is AU$1,063
includes taxes & fees
3 Aug - 4 Aug
Special quiet, romantic, cozy home in a special place, Heavenly Hana. Lucky you!

3 Bedroom Ocean View Private Home in Hana Permit#SUP2 2019/0006

9.8 out of 10, Exceptional, (75)
"This place was more than enough for our family of 5! We could have fit another family with us! Very clean, easy check in. The instructions on finding the place were spot on. We would definitely stay here again!"
The price is AU$1,880
includes taxes & fees
13 July - 14 July
3 Bedroom Ocean View Private Home in Hana Permit#SUP2 2019/0006

Yonegan Maui Getaways - Haiku

3.0 star property
The price is AU$393
includes taxes & fees
14 July - 15 July
Yonegan Maui Getaways - Haiku

Haiku Hale - 3 Bedroom Maui Getaway!

10.0 out of 10, Exceptional, (4)
"Clean, well lit, private, Haiku is a sweet town. Note that there are a few steep steps to master bedroom."
The price is AU$1,507
includes taxes & fees
14 July - 15 July
Haiku Hale - 3 Bedroom Maui Getaway!

Historic Upcountry Maui Property With Pool, 7Bedrooms, Sleeps 16

10.0 out of 10, Exceptional, (65)
"16 of us stayed at this beautiful property. Two Families, 12 children total. We have nothing bad to say. All of our expectations were met. The listing is true and accurate. Communication with the property manager was always prompt and efficient.We would definitely stay her again."
The price is AU$4,160
includes taxes & fees
17 July - 18 July
Historic Upcountry Maui Property With Pool, 7Bedrooms, Sleeps 16

Charming Direct Oceanfront North Shore Beach House

9.0 out of 10, Wonderful, (32)
"We had a great time at this VRBO! It was so clean and was the perfect lay out for our family. The beds were comfortable and the views were gorgeous! We will definitely be staying again. "
The price is AU$1,237
includes taxes & fees
13 July - 14 July
Charming Direct Oceanfront North Shore Beach House

Beautiful 3-bedroom townhome in Kihei

9.6 out of 10, Exceptional, (4)
"We loved our stay! The place had everything the family needed for visiting the beach and the place was clean and comfortable. Would stay again! "
The price is AU$704
includes taxes & fees
2 Aug - 3 Aug
Beautiful 3-bedroom townhome in Kihei

Maaleaa Surf C5 Oceanfront townhouse on miles of Sandy Beach

10.0 out of 10, Exceptional, (6)
"Clean, cozy and nicely designed. This condo has an amazing view and access to the beach and pool. Kitchen is well equipped, even has a milk warmer/frother which I appreciate so much as a lover of lattes. We'll happily stay here again on our next trip to Maui. "
The price is AU$1,113
includes taxes & fees
27 July - 28 July
Maaleaa Surf C5 Oceanfront townhouse on miles of Sandy Beach

Sugar Beach 417 Direct Row Beach Views in Beautifully Upgraded Ocean front Condo Home

The price is AU$883
includes taxes & fees
15 July - 16 July
Sugar Beach 417 Direct Row Beach Views in Beautifully Upgraded Ocean front Condo Home

Tropical Garden Family Home & Penthouse - Sleeps 8 Walk to Beach, BBQ, Hot Tub

10.0 out of 10, Exceptional, (1)
"Place was great and would definitely stay again! There was a nice yard and a closet full of beach gear, chairs and coolers we made use of. Only thing that would have been better was if the hot tub was not on a timer that shuts off later at night. Great spot!!"
The price is AU$2,873
includes taxes & fees
15 July - 16 July
Tropical Garden Family Home & Penthouse - Sleeps 8 Walk to Beach, BBQ, Hot Tub

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

9.8 out of 10, Exceptional, (109)
"Quiet neighborhood setting. Nice backyard for relaxing. Well equipped with beach accessories including snorkel gear. Large whirlpool tub and comfortable bed. Be prepared for carrying luggage to second floor."
The price is AU$989
includes taxes & fees
27 July - 28 July
Tropical Honeymoon Suite - BBQ, Hot Tub - Walk 2 Beach - In the Heart Of Kihei

Tropical Garden Family Home - Sleeps 6 - Walk to Beach, BBQ, Hot Tub

9.6 out of 10, Exceptional, (106)
"Nice property with plenty of space, great location on the island, super communicative and polite host, and such a great backyard/outdoor area. Would highly recommend!"
The price is AU$2,067
includes taxes & fees
15 July - 16 July
Tropical Garden Family Home - Sleeps 6 - Walk to Beach, BBQ, Hot Tub

Menehune Shores 121: 2 BR, 2 BA Condominium in Kihei, Sleeps 4

10.0 out of 10, Exceptional, (186)
"We all loved it!"
The price is AU$1,065
includes taxes & fees
7 Aug - 8 Aug
Menehune Shores 121: 2 BR, 2 BA Condominium in Kihei, Sleeps 4
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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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?

Kaiholo Hale: This holiday home rental outside of Kailua is by the ocean, and equipped with free WiFi and a TV to help you feel perfectly comfortable in your new surroundings. Kitchen amenities include a full-sized fridge, a stovetop and a microwave.

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 Twin Falls. In the wider area, you’ll find Garden of Eden Arboretum and Maui Garden Of Eden - Botanical Gardens & Arboretum.

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.