Historic Kailua Village holiday rentals

We found 982 holiday rentals — enter your dates for availability
Select from 43 houses, 89 apartments and other holiday rentals to find the perfect place for your stay in Historic Kailua Village. Whether you’re travelling with friends, family or even pets, holiday homes have the best amenities for hanging out with the people that matter most, which might include Wi-Fi and a washer and dryer. Whatever you're looking for, you'll be sure to find a property to rent for everyone's needs, including a place that's non-smoking or offers accessibility.

Holiday rentals with weekly discounts – Historic Kailua Village

Showing deals for:13 Nov - 20 Nov

Living area
Watch the cruise ship sail into the sunset while enjoying dinner on the lanai.
Living area
Pool
Exceptional
(85 reviews)

Direct Oceanfront Condo - Beach- King Bed - Free WiFi

Kailua-Kona

7% off
AU$3,530
for 7 nights, 1 apartment
AU$504 per night
includes taxes & fees
Direct Oceanfront Condo - Beach- King Bed - Free WiFi
Open layout connects the living area to the kitchen, making it easy to unwind, cook, or spend time together in a relaxed, airy setting.
Spacious covered lanai with dining and lounge seating, overlooking the garden—perfect for relaxing, reading, or enjoying Kona’s warm evenings.
Sun, water, and nowhere to be—just slip into the pool, stretch out under the palms, and let the day unfold at its own pace.
Spacious great room with seating, dining, and a dedicated workspace—ideal for longer stays or working remotely in comfort.
Exceptional
(19 reviews)

Walkable Kona Condo Oceanfront Pool Private Lanai

Kailua-Kona

7% off
AU$2,244
for 7 nights, 1 apartment
AU$321 per night
includes taxes & fees
Walkable Kona Condo Oceanfront Pool Private Lanai
Living area
Property grounds
Living area
Property grounds
Exceptional
(34 reviews)

Hale He'e - Octocondo at Alii Drive

Kailua-Kona

6% off
AU$2,988
for 7 nights, 1 apartment
AU$427 per night
includes taxes & fees
Hale He'e - Octocondo at Alii Drive
Kona Country Club, open to public
Sunset from your lanai
Magic Sands Beach Park 2 miles south of Sea Village
View from Open Living Area
Exceptional
(168 reviews)

SUMMER PROMO! STUNNING OCEAN VIEW WITH SUNSETS, CITY LIGHTS and A/C

Kailua-Kona

7% off
AU$3,228
for 7 nights, 1 apartment
AU$461 per night
includes taxes & fees
SUMMER PROMO! STUNNING OCEAN VIEW WITH SUNSETS, CITY LIGHTS and A/C
Living area
Exterior
Property grounds
Pool
Wonderful
(65 reviews)

Beautiful Views With Truly Oceanfront Condo!

Kailua-Kona

7% off
AU$4,074
for 7 nights, 1 apartment
AU$582 per night
includes taxes & fees
Beautiful Views With Truly Oceanfront Condo!
Exterior
Lanai
Living area
Interior
Exceptional
(160 reviews)

One Bedroom, First Floor, Fully Furnished Condo

Kailua-Kona

7% off
AU$2,079
for 7 nights, 1 apartment
AU$297 per night
includes taxes & fees
One Bedroom, First Floor, Fully Furnished Condo

  • 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

Frequently asked questions

What is the most popular type of holiday home accommodation in Historic Kailua Village?
According to our research, condos are the most in-demand holiday property type in Historic Kailua Village. But having said that, everyone's idea of an awesome trip isn't the same. Stayz has holiday homes of all shapes, sizes and budgets, and we'll help you locate your ideal match.
How much does it cost to rent a holiday home in Historic Kailua Village?
A range of things affect how much you'll pay for a holiday home in Historic Kailua Village, such as the length of stay, type of property and season. However, all Stayz homes have one thing in common — amazing value. Simply enter your travel dates to find your ideal match.
How much does it cost to rent a beach house in Historic Kailua Village?
The average price for a holiday home close to the beach in Historic Kailua Village depends on when you're visiting the area and the size and type of property you're searching for. Find prices quickly and easily on Stayz by entering your dates of travel. Then use the filters to choose the number of bedrooms and amenities that you need, like a pool, air conditioning and WiFi.
Are there pet-friendly holiday homes in Historic Kailua Village?
Yes, there are. You can pick from 304 holiday homes that welcome pets in Historic Kailua Village on Stayz. Our furry friends need a getaway too, so simply use our search function for pet-friendly holiday homes to book a perfect pad where Rover can get in on the family fun.
Can I rent a house with a pool in Historic Kailua Village?
Tick the "pool" box in our filter tool and you can choose from 278 houses with private pools in Historic Kailua Village on Stayz. Lazy soak or ball games and races? Leisure activities are up to you when your Stayz holiday property comes with a swimming pool.
What are popular home amenities in Historic Kailua Village?
When it comes to home amenities that people look for in Historic Kailua Village, a garden, a beach view and a fireplace rank the highest. With Stayz holiday homes, you'll enjoy choices to match your taste and style, whether you're planning to get away with family, friends or even pets.
Are there large group holiday homes in Historic Kailua Village?
With three properties that can host 10 people or more in Historic Kailua Village, you won't have to hold back on your invites. From fun family holidays to special events like weddings and birthday parties, Stayz can help you find a large group home that fits the occasion.
Are there holiday homes in Historic Kailua Village that welcome kids?
Gather your entire family for a fun-filled adventure in Historic Kailua Village at one of our 299 family-friendly holiday properties. A lot of these stays come with conveniences that are perfect for trips with youngsters, like laundry facilities, extra bedrooms and entertainment units. Just check the "Properties good for families" filter box and choose your favourite option.
What are the top attractions for families in Historic Kailua Village?
There are tons of fabulous things to do and see with the family in Historic Kailua Village, such as:
  • Kailua Pier
  • Magic Sands Beach
  • Kahaluu Beach Park
Are there one-bedroom holiday homes in Historic Kailua Village?
Yes, Historic Kailua Village has 185 one-bedroom homes on offer. Often situated in popular areas because of their smaller size, a one-bedroom home is ideal if you're getting away with a pal or your partner. And with plenty of home comforts like wireless internet and more privacy than a standard hotel, you'll be able to kick back while discovering this incredible destination.
Can I find two-bedroom holiday homes in Historic Kailua Village?
Gather your besties and experience complete comfort and privacy in one of the 68 two-bedroom holiday properties Historic Kailua Village has to offer.
Are there holiday homes with WiFi in Historic Kailua Village?
Historic Kailua Village has 131 holiday homes with WiFi, so you'll be able to stay connected while you're travelling. Simply check the "WiFi" box in our handy search filter for a list of properties with this feature. From streaming movies with the family to posting pics on social media, these Stayz homes make it a breeze to go online.
How can I find holiday homes with air conditioning in Historic Kailua Village?
You'll have your pick of 267 Stayz holiday homes with air conditioning in Historic Kailua Village giving you that gentle, cool breeze and extra element of comfort. Just enter your dates of travel and then use our filters to look for stays with air conditioning.
How old do you have to be to rent a holiday home in Historic Kailua Village?
The minimum age is normally 16, 18 or 21. It can differ between properties on Stayz, so check the rules of your preferred Historic Kailua Village holiday home before booking your escape.
How long can I rent a holiday home in Historic Kailua Village for?
The amount of time you can stay in a Historic Kailua Village holiday home for depends on each property. Simply put in your preferred travel dates to browse options that offer long-term stays. They have everything you need to make your extended trip more comfortable and enjoyable, like laundries and air conditioning. Some holiday homes might also offer weekly or monthly discounted prices, so you can have a longer stay for less.

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