Historic Kailua Village holiday homes

We found 977 holiday rentals — enter your dates for availability
Select from 42 houses, 87 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:27 Nov - 4 Dec

Interior
Property grounds
Exterior
Room
Exceptional
(13 reviews)

Upscale Kona home in peaceful setting, ready for family gatherings.

Kailua-Kona

7% off
NZ$8,812
for 7 nights, 1 home
NZ$1,259 per night
includes taxes & fees
Upscale Kona home in peaceful setting, ready for family gatherings.
Living area
Sunset on your private lanai
Housebook and Guests Book
Kona Plaza's Facade with the Rainbow 🌈
Exceptional
(24 reviews)

Kona Rose's Hideaway in Kona Plaza #318 at the center of Kailua-Kona Town

Kailua-Kona

7% off
NZ$3,928
for 7 nights, 1 room
NZ$561 per night
includes taxes & fees
Kona Rose's Hideaway in Kona Plaza #318 at the center of Kailua-Kona Town
outdoor bar
crows nest
kitchen
kitchen island
Exceptional
(118 reviews)

OCEANFRONT BEACH HOUSE WITH SUNSET VIEWS AND PRIVATE POOL

Kailua-Kona

8% off
NZ$15,542
for 7 nights, 1 home
NZ$2,220 per night
includes taxes & fees
OCEANFRONT BEACH HOUSE WITH SUNSET VIEWS AND PRIVATE POOL
Private kitchen
Watch the cruise ship sail into the sunset while enjoying dinner on the lanai.
Living area
Living area
Exceptional
(85 reviews)

Direct Oceanfront Condo - Beach- King Bed - Free WiFi

Kailua-Kona

7% off
NZ$4,213
for 7 nights, 1 apartment
NZ$602 per night
includes taxes & fees
Direct Oceanfront Condo - Beach- King Bed - Free WiFi
popular complex close to town
view from lanai
ocean access from the pool area
comfortable furniture
Exceptional
(121 reviews)

Oceanfront Condo with Amazing View—King Bed, Lanai, Walk to Town, Free Parking

Kailua-Kona

7% off
NZ$4,960
for 7 nights, 1 apartment
NZ$709 per night
includes taxes & fees
Oceanfront Condo with Amazing View—King Bed, Lanai, Walk to Town, Free Parking
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.
A quiet tropical garden where the day slows down—sunlight through the palms, the gentle hush of the ocean beyond, and just enough shade to sit, breathe, and let the island settle in.
Exceptional
(19 reviews)

Walkable Kona Condo Oceanfront Pool Private Lanai

Kailua-Kona

7% off
NZ$2,507
for 7 nights, 1 apartment
NZ$358 per night
includes taxes & fees
Walkable Kona Condo Oceanfront Pool Private Lanai
Living area
Property grounds
Living area
Interior
Exceptional
(34 reviews)

Hale He'e - Octocondo at Alii Drive

Kailua-Kona

6% off
NZ$4,002
for 7 nights, 1 apartment
NZ$572 per night
includes taxes & fees
Hale He'e - Octocondo at Alii Drive
Pool
Exterior
Living area
Outdoor dining
Wonderful
(65 reviews)

Beautiful Views With Truly Oceanfront Condo!

Kailua-Kona

7% off
NZ$5,246
for 7 nights, 1 apartment
NZ$749 per night
includes taxes & fees
Beautiful Views With Truly Oceanfront Condo!
sunset from swimming in the pool
ocean entry when it's calm... great coral reefs to explore!
overhead visual of condominiums
Interior
Exceptional
(135 reviews)

Oceanfront Sunsets in heart of Kona

Kailua-Kona

7% off
NZ$3,091
for 7 nights, 1 apartment
NZ$442 per night
includes taxes & fees
Oceanfront Sunsets in heart of Kona
Exterior
Lanai
Living area
Interior
Exceptional
(160 reviews)

One Bedroom, First Floor, Fully Furnished Condo

Kailua-Kona

7% off
NZ$2,318
for 7 nights, 1 apartment
NZ$331 per night
includes taxes & fees
One Bedroom, First Floor, Fully Furnished Condo
Interior
Outdoor dining
Kona Reef ocean front pool and spa
Private kitchen
Exceptional
(134 reviews)

Panoramic Oceanfront! Central Air Conditioning! King Bed! Gorgeous Kitchen!

Kailua-Kona

7% off
NZ$6,374
for 7 nights, 1 apartment
NZ$911 per night
includes taxes & fees
Panoramic Oceanfront! Central Air Conditioning! King Bed! Gorgeous Kitchen!

  • 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. Bookabach 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 Bookabach 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 Bookabach 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 Bookabach. 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 Bookabach. Lazy soak or ball games and races? Leisure activities are up to you when your Bookabach 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 Bookabach 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, Bookabach 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 Bookabach 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 Bookabach 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 Bookabach, 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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