Kailua holiday rentals

We found 98 holiday rentals — enter your dates for availability
Scroll through and select from holiday rentals in Kailua to find one that's perfect for your trip. Holiday homes offer the amenities that you expect for you and your friends, family or even pets, such as Wi-Fi and cable TV. At the end of the day, you're sure to find a property to rent for everyone's needs, including a place that is accessible or non-smoking.

Holiday rentals with weekly discounts – Kailua

Showing deals for:13 Nov - 20 Nov

 A couple enjoying the views and sunbathing at The Waterfall House patio
Ariel view of Waterfall House with the Hanehoi valley in the background
Beautifully designed master bathroom
In-ground marble bath tub in master bathroom with spectacular views
Exceptional
(28 reviews)

Waterfall House - Private House Overlooking the Ocean!

Haiku

8% off
AU$8,144
for 7 nights, 1 home
AU$1,163 per night
includes taxes & fees
Waterfall House - Private House Overlooking the Ocean!
Living area
Outdoor dining
Private kitchen
Mana's Fishouse just 10 minutes away island favorite
Exceptional
(29 reviews)

Pineapple Cottage B&B Vacation Rental Haiku Maui, Lic#BBPH2015/0011

Haiku

7% off
AU$3,974
for 7 nights, 1 cottage
AU$568 per night
includes taxes & fees
Pineapple Cottage B&B Vacation Rental Haiku Maui, Lic#BBPH2015/0011
Pool
Living area
Private kitchen
Property grounds
Exceptional
(17 reviews)

Priv Hot Tub + Shared Jungle Pool! - Ocean Lookout

Haiku

7% off
AU$6,583
for 7 nights, 1 home
AU$940 per night
includes taxes & fees
Priv Hot Tub + Shared Jungle Pool! - Ocean Lookout
Hale Lei Aloha
Relax outside on covered lanai (deck)
Country Views in peaceful setting
Stainless steal appliances. Dining for six. Propane BBQ to prepare great meals
Exceptional
(53 reviews)

Maui Plantation Cottage Located Near Beach And Paia, Permitted Bbph 2017/0004

Haiku

7% off
AU$3,756
for 7 nights, 1 home
AU$537 per night
includes taxes & fees
Maui Plantation Cottage Located Near Beach And Paia, Permitted Bbph 2017/0004
Private kitchen
Exterior
Pool
Property grounds
Exceptional
(44 reviews)

Jump start The Road to Hana at The Lookout House!

Haiku

7% off
AU$7,813
for 7 nights, 1 home
AU$1,116 per night
includes taxes & fees
Jump start The Road to Hana at The Lookout House!
Private kitchen
Pool
Exterior
Property grounds
Exceptional
(106 reviews)

Haleakala Cottage - private hot tub, pool access

Haiku

5% off
AU$4,897
for 7 nights, 1 home
AU$700 per night
includes taxes & fees
Haleakala Cottage - private hot tub, pool access
Interior
Outdoor spa tub
Pool
Property grounds
Exceptional
(17 reviews)

Private Hot Tub + Pool Access + AC - Star Lookout

Haiku

6% off
AU$5,734
for 7 nights, 1 home
AU$819 per night
includes taxes & fees
Private Hot Tub + Pool Access + AC - Star Lookout
Interior
Exterior
Pool
Dining
Exceptional
(26 reviews)

★Rainbow Lookout - PRIVATE HOT TUB+ACCESS TO POOL

Haiku

6% off
AU$6,668
for 7 nights, 1 home
AU$953 per night
includes taxes & fees
★Rainbow Lookout - PRIVATE HOT TUB+ACCESS TO POOL
  • Peace of mind

    Our Book with Confidence Guarantee gives you 24/7 support
  • More quality time

    From booking to staying, the whole process is simple and enjoyable
  • All the privacy of home

    Enjoy full kitchens, laundry, pools, gardens and more
  • More for less

    More space, more privacy, more amenities — more value

Book a holiday rental for your Kailua getaway

Learn about the unique charm of Kailua with a stay in a holiday home rental. This city has something for everyone. Many of our holiday rentals offer full kitchens, spacious living quarters and sometimes even a hot tub—perfect for a relaxing getaway.

Activities and attractions in Kailua

Are you searching for things to do in the area? Although it can be tempting to stay in your comfortable holiday rental, you'll want to experience everything that makes Kailua a fun place to get away to. Here are some of the most popular attractions to explore, all within 30 miles (48.2 km) of the city centre:

  • Maui Spa Retreat (7.7 mi / 12.3 km)
  • Hoʻomana Spa Maui (6.3 mi / 10.2 km)
  • Pukalani Country Club (9.4 mi / 15.1 km)
  • King's Highway (15.5 mi / 25 km)
  • Haleakala Bike Company (7.1 mi / 11.4 km)
  • Enlighten Up Massage (7.3 mi / 11.8 km)

Exploring the natural features in Kailua

Whether you're looking for adventure or just want to spend some time taking in the scenery, Kailua is a great place to get out in nature. These are a few of the area's most enchanting sights, all within 30 miles (48.2 km) of the city centre:

  • Haleakala National Park (13.3 mi / 21.3 km)
  • Maui Garden Of Eden - Botanical Gardens & Arboretum (2.9 mi / 4.6 km)
  • Hoʻokipa Beach Park (9.7 mi / 15.6 km)
  • Kuau Bay Beach (10.2 mi / 16.3 km)
  • Paia Bay (11.4 mi / 18.3 km)
  • Haleakalā Visitor Center (12.5 mi / 20 km)

How to get to and around Kailua

The nearest airport is in Kahului, HI (OGG), located 14.3 mi (23 km) from the city centre. If you're unable to find a flight that fits your schedule, you could book a flight to Hana, HI (HNM), which is 14.6 mi (23.5 km) away.

Frequently asked questions

How much does it cost to rent a holiday home in Kailua?
The average price for a holiday home in Kailua depends on a number of factors, such as property type, season and length of stay. Whether you're searching for a sprawling house with room for friends and family or a quaint cabin that's perfect for two, just add your dates of travel to see some great-value stays.
How much does it cost to rent a beach house in Kailua?
When you travel and the style and size of the property will influence how much you'll pay for your beachside holiday home. Put in your Kailua travel dates to view your available options on Stayz. Looking for basics like WiFi, or perks like a private pool? Use our filters to choose the amenities and features you want.
What are the top attractions for families in Kailua?
Treat the kids to a good time at these cool family-friendly attractions in Kailua:
  • Twin Falls
  • Haiku Park
How old do you have to be to rent a holiday home in Kailua?
We advise checking with the Kailua holiday property you're considering on Stayz as the age limit differs. However, generally it's 16, 18 or 21.
How long can I rent a holiday home in Kailua for?
The length of time you can rent a holiday home in Kailua is down to the property. Simply enter your preferred dates to view a list of options offering extended stays. With a range of features like full kitchens and air conditioning, as well as some offering weekly or monthly discounted prices, you're sure to discover somewhere perfect to call your home away from home in Kailua.

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