Kailua Holiday Rentals

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Holiday Rentals in Kailua

Maui Beach Vacation Club

2.5 star property
8.2 out of 10, Very good, (766)
"Great place to stay. "
Maui Beach Vacation Club

Maui Sunset

3.5 star property
8.8 out of 10, Excellent, (447)
"Beautiful and centrally located. "
Maui Sunset

Sugar Beach Resort

3.0 star property
8.6 out of 10, Excellent, (1074)
"Loved the fully stocked kitchen and amenities available. It was a delightful stay! We would stay here again."
Sugar Beach Resort

Maui Schooner Resort

3.5 star property
9.2 out of 10, Wonderful, (477)
"This property was a amazing and we are definitely going to stay here again in the future."
Maui Schooner Resort

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$708
includes taxes & fees
2 Aug - 3 Aug
Beautiful 3-bedroom townhome in Kihei

Ohana Paradise w/ Ocean View, Longest beach on Maui, Sugar Beach, Sleeps 4

9.8 out of 10, Exceptional, (114)
"Great view, ocean sounds. "
Ohana Paradise w/ Ocean View, Longest beach on Maui, Sugar Beach, Sleeps 4

Wonderful South Maui Beach Condos

3.5 star property
9.4 out of 10, Exceptional, (22)
"Exactly what we needed with beach access right across the street"
The price is AU$774
includes taxes & fees
4 Aug - 5 Aug
Wonderful South Maui Beach Condos

Completely remodeled 2 bedroom King bed AC Kauhale Makai on the top floor

10.0 out of 10, Exceptional, (78)
"6th floor great view of water. Nice beach and pool. Two bedrooms with plenty of space. Comfortable beds. Great kitchen. Remodeled and looks great. AC works well. Close to everything. Parking was great. Would stay again. "
Completely remodeled 2 bedroom King bed AC Kauhale Makai on the top floor

Oceanview Condo in Hana-Let the ocean lull you to sleep

9.2 out of 10, Wonderful, (101)
"Perfect spot, comfy bed, clean and relaxing. An absolute dream thank you!"
The price is AU$752
includes taxes & fees
11 Aug - 12 Aug
Oceanview Condo in Hana-Let the ocean lull you to sleep

1BR/1BA Peaceful , relaxing , affordable Tropical South Maui Condo.

9.4 out of 10, Exceptional, (112)
"I enjoyed how close of a walk it was to stores, restaurants and several beaches. "
1BR/1BA Peaceful , relaxing , affordable Tropical South Maui Condo.

Exceptionally Remodeled Oceanfront, Sunsets, A/C, King bed Hale Kai O Kihei

10.0 out of 10, Exceptional, (137)
"Well stocked in a great location. Fantastic beach location."
The price is AU$925
includes taxes & fees
22 July - 23 July
Exceptionally Remodeled Oceanfront, Sunsets, A/C, King bed Hale Kai O Kihei

STUDIO: Kalama Beach Park, South Maui Gardens, Food Trucks, Hula Shows, Luaus

9.4 out of 10, Exceptional, (135)
"Location was amazing. Host also provided many amenities like beach equipment, coffee, kitchenware etc.Great air con, communication and WiFi too. "
The price is AU$524
includes taxes & fees
19 July - 20 July
STUDIO: Kalama Beach Park, South Maui Gardens, Food Trucks, Hula Shows, Luaus

Kaiholo Hale

3.0 star property
9.4 out of 10, Exceptional, (199)
"We stayed here 4 nights, perfect location for our activities. We did sunrise bike ride down Haleakala and Road to Hana. "
Kaiholo Hale

Tropical Gated Oceanfront Estate, Pool, Privacy, and huge ocean view on 2/3 acre

9.8 out of 10, Exceptional, (201)
"great for large groups"
Tropical Gated Oceanfront Estate, Pool, Privacy, and huge ocean view on 2/3 acre

BEACHFRONT condo, ocean view, steps to sea, heated pool,hot tub, AC, Sugar Beach

10.0 out of 10, Exceptional, (116)
"Fantastic spot. Nothing but positive to say with this stay. Host had everything and more we could’ve needed. Home was sparking clean and the view was Beautiful! The crowd at pool and hottub were all pleasant to be around. We especially enjoyed walking the beach at night which was a 30 second walk from the condo. "
BEACHFRONT condo, ocean view, steps to sea, heated pool,hot tub, AC, Sugar Beach

Deluxe 4-bedroom home across from Kalepolepo Beach! Steps to the Pool & full AC!

10.0 out of 10, Exceptional, (2)
"This location was perfect for our group of two families. The pool area was lovely and located close to lots of beaches. The amenities of the condo were updated and fantastic. We enjoyed our time in Maui in this location immensely. "
Deluxe 4-bedroom home across from Kalepolepo Beach! Steps to the Pool & full AC!

The Maui Moon Oceanfront Condo- Perfect for couples!

10.0 out of 10, Exceptional, (116)
"This condo is spectacular. The views are amazing and they have made sure to have everything you could possibly need for any day trips or excursions you take. Highly recommend staying here and hope to be back someday. "
The Maui Moon Oceanfront Condo- Perfect for couples!

Dazzling Ocean View, Modern, Whole house AC. Upgraded Glass for a quiet setting

10.0 out of 10, Exceptional, (259)
"The place was clean and nice, in an excellent location with a great view."
Dazzling Ocean View, Modern, Whole house AC. Upgraded Glass for a quiet setting

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

9.8 out of 10, Exceptional, (279)
"Convenient great location for the price"
The price is AU$582
includes taxes & fees
30 July - 31 July
10% 7 Day Discount! Kihei Studio - Split AC, Clean, Free WiFi, Turtles!

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
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.