Holiday Rentals in Kailua

    calendar shield illustration
    Change your mind
    Book hotels with free cancellation
    deals illustration
    Treat yourself
    Sign in to save 10% or more on thousands of hotels
    Sign in
    bed illustration
    Be picky
    Search almost a million properties worldwide

Check prices for these dates

Tonight
7 Jul - 8 Jul
Tomorrow
8 Jul - 9 Jul
This weekend
11 Jul - 13 Jul
Next weekend
18 Jul - 20 Jul

Holiday Rentals in Kailua

Maui Beach Vacation Club
Suite, 2 Bedrooms | Living area

Maui Beach Vacation Club

2.5 star property
8.2 out of 10, Very good, (763)
"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, (1073)
"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, (446)
"Beautiful and centrally located. "
Maui Sunset
Ohana Paradise w/ Ocean View, Longest beach on Maui, Sugar Beach, Sleeps 4
A heated pool

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
Beautiful 3-bedroom townhome in Kihei
Private kitchen

Beautiful 3-bedroom townhome in Kihei

9.0 out of 10, Wonderful, (2)
"This stay was very nice, me and my friends enjoyed the things provided in the house specially the snorkeling equipment. Would highly recommend for any family or friends traveling to Maui. This home was convenient for any beaches, shops, or any outdoor activity."
The price is €400
includes taxes & fees
2 Aug - 3 Aug
Beautiful 3-bedroom townhome in Kihei
BEACHFRONT condo, ocean view, steps to sea, heated pool,hot tub, AC, Sugar Beach
Outdoor pool, a heated pool

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

10.0 out of 10, Exceptional, (115)
"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
Oceanview Condo in Hana-Let the ocean lull you to sleep
Outdoor dining

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

9.2 out of 10, Wonderful, (100)
"Perfect spot, comfy bed, clean and relaxing. An absolute dream thank you!"
The price is €429
includes taxes & fees
8 Jul - 9 Jul
Oceanview Condo in Hana-Let the ocean lull you to sleep
Exceptionally Remodeled Oceanfront, Sunsets, A/C, King bed Hale Kai O Kihei
Property grounds

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

10.0 out of 10, Exceptional, (137)
"Condo is right on the beach and very well kept. We enjoyed our weekend there and look forward to booking again in the future."
The price is €558
includes taxes & fees
22 Jul - 23 Jul
Exceptionally Remodeled Oceanfront, Sunsets, A/C, King bed Hale Kai O Kihei
Deluxe 4-bedroom home across from Kalepolepo Beach! Steps to the Pool & full AC!
Pool

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

10.0 out of 10, Exceptional, (1)
Deluxe 4-bedroom home across from Kalepolepo Beach! Steps to the Pool & full AC!
Can't get any closer to the Ocean#2
Property grounds

Can't get any closer to the Ocean#2

9.8 out of 10, Exceptional, (63)
"Beautiful condo right on the water. Epic sunsets and whale watching from the balcony. Building has a pool and easy access to beach."
The price is €456
includes taxes & fees
23 Jul - 24 Jul
Can't get any closer to the Ocean#2
Historic Upcountry Maui Property With Pool, 7Bedrooms, Sleeps 16
Outdoor pool

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

10.0 out of 10, Exceptional, (64)
"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 €2,433
includes taxes & fees
12 Jul - 13 Jul
Historic Upcountry Maui Property With Pool, 7Bedrooms, Sleeps 16
Dazzling Ocean View, Modern, Whole house AC. Upgraded Glass for a quiet setting
Aerial view

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
Fabulous Beachfront Property - Ground Floor Corner Unit Steps to the Beach!
Terrace/patio

Fabulous Beachfront Property - Ground Floor Corner Unit Steps to the Beach!

10.0 out of 10, Exceptional, (118)
"Great location! Perfect home base for our stay. Very nice property! Mahalo!"
Fabulous Beachfront Property - Ground Floor Corner Unit Steps to the Beach!
STUDIO: Kalama Beach Park, South Maui Gardens, Food Trucks, Hula Shows, Luaus
Outdoor pool, a heated pool

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

9.4 out of 10, Exceptional, (133)
"Location was amazing. Host also provided many amenities like beach equipment, coffee, kitchenware etc.Great air con, communication and WiFi too. "
The price is €291
includes taxes & fees
19 Jul - 20 Jul
STUDIO: Kalama Beach Park, South Maui Gardens, Food Trucks, Hula Shows, Luaus
Sugar Beach Resort Oceanview 1 bed/1 bath
Pool

Sugar Beach Resort Oceanview 1 bed/1 bath

9.6 out of 10, Exceptional, (103)
The price is €354
includes taxes & fees
10 Jul - 11 Jul
Sugar Beach Resort Oceanview 1 bed/1 bath
1BR/1BA Peaceful , relaxing , affordable Tropical South Maui Condo.
Beach nearby, sun-loungers, beach towels

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.
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, (513)
"Love this location, great beach, quiet."
Sugar Beach Resort - Maui Condo & Home
The Maui Moon Oceanfront Condo- Perfect for couples!
On the beach, sun-loungers, beach towels

The Maui Moon Oceanfront Condo- Perfect for couples!

10.0 out of 10, Exceptional, (116)
The Maui Moon Oceanfront Condo- Perfect for couples!
Private Cozy Studio walking distance to beaches, shops, restaurants and bars
Food and drink

Private Cozy Studio walking distance to beaches, shops, restaurants and bars

10.0 out of 10, Exceptional, (111)
"This was the perfect laid back property I enjoyed my stay"
Private Cozy Studio walking distance to beaches, shops, restaurants and bars
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.
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

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 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.