Search Holiday Rentals in Kailua

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Check prices for these dates

Tonight
28 Jun - 29 Jun
Tomorrow
29 Jun - 30 Jun
Next weekend
4 Jul - 6 Jul
In two weeks
11 Jul - 13 Jul

Top Holiday Rentals in Kailua

Maui Beach Vacation Club
Suite, 2 Bedrooms | Living area | TV

Maui Beach Vacation Club

2.5 star property
8.2 out of 10, Very good, (757)
"Great place to stay!!"
Maui Beach Vacation Club
Sugar Beach Resort
Outdoor pool

Sugar Beach Resort

3.0 star property
8.6 out of 10, Excellent, (1070)
"Loved the fully stocked kitchen and amenities available. It was a delightful stay! We would stay here again."
Sugar Beach Resort
Maui Schooner Resort
BBQ/picnic Area

Maui Schooner Resort

3.5 star property
9.2 out of 10, Wonderful, (475)
"This property was a amazing and we are definitely going to stay here again in the future."
Maui Schooner Resort
Maui Sunset
View from property

Maui Sunset

3.5 star property
8.8 out of 10, Excellent, (442)
"Beautiful and centrally located. "
Maui Sunset
Kaiholo Hale
Beach nearby

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
Sugar Beach Resort - Maui Condo & Home
Outdoor pool

Sugar Beach Resort - Maui Condo & Home

3.0 star property
8.4 out of 10, Very good, (512)
"You can’t have a better view at any other resort with beach access right out the door. Spent our 40th anniversary there and had the best time."
Sugar Beach Resort - Maui Condo & Home
Chic & Elegant Oceanfront Vistas
Luxury Condo | Private kitchen | Full-sized fridge, microwave, oven, stovetop

Chic & Elegant Oceanfront Vistas

4.0 star property
9.8 out of 10, Exceptional, (20)
"Good stay for the price. "
Chic & Elegant Oceanfront Vistas
Oceanfront Penthouse Vistas
Exterior

Oceanfront Penthouse Vistas

4.5 star property
10.0 out of 10, Exceptional, (4)
"We loved this condo! Had everything we needed and then some. The views were spectacular!"
Oceanfront Penthouse Vistas
Kihei Bay Surf B212
Condo (0 Bedroom) | Property amenity

Kihei Bay Surf B212

3.5 star property
7.8 out of 10, Good, (19)
"Overall a great stay at this place. Great spot to be close to a lot of things and also very quiet. Only complaint would be that it was a little hot at times in the room but the fan really helped with that. Would recommend."
Kihei Bay Surf B212
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’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.