Historic Kailua Village holiday rentals

We found 886 holiday rentals — enter your dates for availability

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October 2025

November 2025

Select from 41 houses, 88 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:16 Jan - 23 Jan

Exceptional

(12 reviews)

Beautiful Kona Hawaiian Resort - 2BR/2BA Deluxe Unit

Kailua-Kona, HI

8% off

for 7 nights, 1 room

S$784 per night

includes taxes & fees

Exceptional

(97 reviews)

Enjoy Panoramic Ocean Sunset Views From Your Private, Gated Residence

Kailua-Kona, HI

10% off

for 7 nights, 1 home

S$2,370 per night

includes taxes & fees

Exceptional

(19 reviews)

Manta Ray Manor - Oceanfront Gated Community, short walk to beach and town.

Kailua-Kona, HI

7% off

for 7 nights, 1 home

S$2,638 per night

includes taxes & fees

Exceptional

(9 reviews)

Island Glow Kailua Village, AC and ocean views in the heart of Kailua Kona

Kailua-Kona, HI

6% off

for 7 nights, 1 apartment

S$439 per night

includes taxes & fees

Exceptional

(13 reviews)

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

Kailua-Kona, HI

7% off

for 7 nights, 1 home

S$978 per night

includes taxes & fees

Exceptional

(16 reviews)

Poolside Cozy 1br, 1Qbed plus 1QSofa bed, Med refrig, sm kitchen,2min to Ocean

Kailua-Kona, HI

7% off

for 7 nights, 1 apartment

S$290 per night

includes taxes & fees

Excellent

(46 reviews)

Amazing Oceanfront Condo 🤿 Fresh Island Flavor in Style and Comfort!🐠 - Hale Kona Kai 306

Kailua-Kona, HI

5% off

for 7 nights, 1 apartment

S$603 per night

includes taxes & fees

Beautiful sunsets, oceanside, pool, hot tub, coco palms; our lanai view C31

Exceptional

(131 reviews)

Seaside Kona Condo/Top Fl, Sunsets, Private Lanai,Best Kona Location, Sleeps 2

Kailua-Kona, HI

7% off

for 7 nights, 1 apartment

S$564 per night

includes taxes & fees

The lanai overlooks the pool area. There is also a hot tub, chairs and BBQ.

Exceptional

(5 reviews)

Kona Islander Inn - #316 - Located in beachfront town of Kailua Kona Hawaii.

Kailua-Kona, HI

7% off

for 7 nights, 1 apartment

S$371 per night

includes taxes & fees

Wonderful

(39 reviews)

🍍Oceanfront Condo & Walking Distance to Beach and Town! 🏖 - Hale Kona Kai 207

Kailua-Kona, HI

5% off

for 7 nights, 1 apartment

S$571 per night

includes taxes & fees

Exceptional

(9 reviews)

Charming Condo Hotel in lovely Beach front Kailua-Kona with AC, WiFi

Kailua-Kona, HI

7% off

for 7 nights, 1 apartment

S$371 per night

includes taxes & fees

Wonderful

(6 reviews)

Luxury Beachfront Gated retreat in-town SPA/AC/BBQ accessible to the public pool

Kailua-Kona, HI

6% off

for 7 nights, 1 home

S$1,951 per night

includes taxes & fees

Absolute oceanfront almost hangs over the ocean.

Wonderful

(43 reviews)

Amazing Oceanfront Condo 🐠 with Out of this World Ocean Views! 🌅 - Hale Kona Kai 203

Kailua-Kona, HI

5% off

for 7 nights, 1 apartment

S$515 per night

includes taxes & fees

Very good

(34 reviews)

Oceanfront Blissful Sanctuary 🐳 Balcony that Almost Hangs Over The Ocean! 🐠 Hale Kona Kai 308

Kailua-Kona, HI

5% off

for 7 nights, 1 apartment

S$571 per night

includes taxes & fees

Find spaces that suit your style

House

Condo/Apartment

Find properties near top attractions in Historic Kailua Village

Kailua Pier

Find the best place to stay - Historic Kailua Village

Hale Kona Kai by Casago Kona

Sleeps 3 · 1 bedroom

Premier Host

Exotic Kona Bay Hawaii Beachfront Tropical Paradise Stunning Home.

Sleeps 12 · 4 bedrooms · 3+ bathrooms

Spacious Lanai with breath taking views!

Premier Host

Kona Alii 201: Tropical Oceanfront Condo w/ AC & Pool in Downtown Kona

Sleeps 4 · 1 bedroom · 2 bathrooms

Top rated rentals - Historic Kailua Village

View looking north from your oceanfront lanai towards Kailua-Kona Bay

Premier Host

Super nice condo!!

Awesome!!! Very clean. Just as advertised. Location was perfect. Pool area very clean and secure. Grounds well maintained. Well equipped.

JANET L.

Stayed Jun 2023

Premier Host

Fabulous

Absolutely wonderful. Would stay again in a minute.

Michael N.

Stayed Sept 2021

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 rental 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. Vrbo 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 rental in Historic Kailua Village?

A range of things affect how much you'll pay for a holiday rental in Historic Kailua Village, such as the length of stay, type of property and season. However, all Vrbo 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 rental 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 Vrbo 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 rentals in Historic Kailua Village?

Yes, there are. You can pick from 304 holiday rentals that welcome pets in Historic Kailua Village on Vrbo. Our furry friends need a getaway too, so simply use our search function for pet-friendly holiday rentals 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 Vrbo. Lazy soak or ball games and races? Leisure activities are up to you when your Vrbo holiday property comes with a swimming pool.

What are popular rental amenities in Historic Kailua Village?

When it comes to rental amenities that people look for in Historic Kailua Village, a garden, a beach view and a fireplace rank the highest. With Vrbo 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 rentals 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, Vrbo can help you find a large group rental that fits the occasion.

Are there holiday rentals 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 rentals in Historic Kailua Village?

Yes, Historic Kailua Village has 185 one-bedroom rentals on offer. Often situated in popular areas because of their smaller size, a one-bedroom rental 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 rentals 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 rentals with WiFi in Historic Kailua Village?

Historic Kailua Village has 131 holiday rentals 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 Vrbo homes make it a breeze to go online.

How can I find holiday rentals with air conditioning in Historic Kailua Village?

You'll have your pick of 267 Vrbo holiday rentals 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 rental in Historic Kailua Village?

The minimum age is normally 16, 18 or 21. It can differ between properties on Vrbo, so check the rules of your preferred Historic Kailua Village holiday home before booking your escape.

How long can I rent a holiday rental in Historic Kailua Village for?

The amount of time you can stay in a Historic Kailua Village holiday rental 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.