Kailua Holiday Rentals

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Check prices for these dates

Tonight
13 Jun - 14 Jun
Tomorrow
14 Jun - 15 Jun
This weekend
13 Jun - 15 Jun
Next weekend
20 Jun - 22 Jun

Holiday Rentals in Kailua

Maui Beach Vacation Club
Living area

Maui Beach Vacation Club

2.5 star property
8.2 out of 10, Very good, (753)
"We had an amazing stay in Maui! The beachfront location was unbeatable, and the place had everything we needed for a comfortable family vacation. Super clean, kid-friendly, and close to everything. Highly recommend — we’d definitely stay here again!"
Maui Beach Vacation Club
Sugar Beach Resort
Outdoor pool

Sugar Beach Resort

3.0 star property
8.6 out of 10, Excellent, (1067)
"We enjoyed our stay.Will Visit again"
Sugar Beach Resort
Maui Sunset
View from property

Maui Sunset

3.5 star property
8.8 out of 10, Excellent, (437)
"Beautiful and centrally located. "
Maui Sunset
Maui Schooner Resort
BBQ/picnic Area

Maui Schooner Resort

3.5 star property
9.2 out of 10, Wonderful, (473)
"This property was a amazing and we are definitely going to stay here again in the future."
Maui Schooner Resort
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
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
Kihei Bay Surf B212
Property amenity

Kihei Bay Surf B212

3.5 star property
8.2 out of 10, Very good, (18)
"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
Island Surf 506
Property amenity

Island Surf 506

3.5 star property
9.4 out of 10, Exceptional, (8)
"Just across the street from a park with a beach and trail along the ocean. Beautiful sunset views. Excellent restaurants nearby. Several food trucks and shops within walking distance. "
Island Surf 506
Maui Sunset by VTrips
Pool

Maui Sunset by VTrips

3.5 star property
8.0 out of 10, Very good, (9)
"Incredible location, great apartment and 5 stars overall!"
Maui Sunset by VTrips
Chic & Elegant Oceanfront Vistas
Private kitchen

Chic & Elegant Oceanfront Vistas

4.0 star property
9.8 out of 10, Exceptional, (20)
"Good stay for the price. "
Chic & Elegant Oceanfront Vistas
Tropical & Serene Garden Vistas
Private kitchen

Tropical & Serene Garden Vistas

4.5 star property
9.6 out of 10, Exceptional, (12)
"Excellent facilities. Would stay here on Maui everytime. "
Tropical & Serene Garden Vistas
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.