Kailua-Kona holiday rentals

We found 2,919 holiday rentals — enter your dates for availability
Select from 561 houses, 1915 flats and other holiday rentals to find the perfect place for your stay in Kailua-Kona. Whether you're travelling with a group or just with your pet, holiday homes have the best amenities for spending time at your holiday home, which might include Wi-Fi and a washer and dryer. You'll be sure to find a property to rent for everyone's needs, including options that are accessible or non-smoking.

Holiday rentals with weekly discounts – Kailua-Kona

Showing deals for:8 Jan - 15 Jan

Private oceanfront estate on Ali’i Drive — rare and secluded
Pool
Open living space with sweeping ocean views
Seamless indoor-outdoor living with panoramic ocean views
Exceptional
(43 reviews)

Private Kona Oceanfront Estate · Infinity Pool & Spa

Kailua-Kona

8% off
S$31,919
for 7 nights, 1 home
S$4,560 per night
includes taxes & fees
Private Kona Oceanfront Estate · Infinity Pool & Spa
Large indoor living/dining room
View of Gazebo from Lanai
Kitchen
Pool & waterfall
Exceptional
(60 reviews)

Ultra private oceanfront gated compound with pool & spa just minutes from town.

Kailua-Kona

8% off
S$44,960
for 7 nights, 1 villa
S$6,423 per night
includes taxes & fees
Ultra private oceanfront gated compound with pool & spa just minutes from town.
Pool at Sunset
Waling to the BBQ and outdoor dinning Area
Washer & Dryer in Kitchen Area
Morning Yoga
Exceptional
(89 reviews)

Gorgeous Oceanfront Unit! Ground Floor! Greatly Updated!

Kailua-Kona

7% off
S$4,037
for 7 nights, 1 apartment
S$577 per night
includes taxes & fees
Gorgeous Oceanfront Unit! Ground Floor! Greatly Updated!
Dining area.
White Sands Beach (located across road)
Outdoor dining
Pool
Exceptional
(54 reviews)

Beach Just Steps Away/Breathtaking Mountain Views - 2 Bed/2 Bath - GREAT VALUE!!

Kailua-Kona

9% off
S$4,524
for 7 nights, 1 apartment
S$646 per night
includes taxes & fees
Beach Just Steps Away/Breathtaking Mountain Views - 2 Bed/2 Bath - GREAT VALUE!!
Living Room
Sunset over Family pool and cabana area taken from the Master lanai.
Master Bedroom
Complex waterfalls
Exceptional
(50 reviews)

Villa On The Ocean - One Of Largest Condos On Alii Drive. Directly Oceanfront.

Kailua-Kona

11% off
S$10,697
for 7 nights, 1 villa
S$1,528 per night
includes taxes & fees
Villa On The Ocean - One Of Largest Condos On Alii Drive. Directly Oceanfront.
Private kitchen
Interior
Pool
Dining
Exceptional
(34 reviews)

Kona Keauhou Newly Remodeled Home, Quiet private home on Golf course with Pool.

Kailua-Kona

8% off
S$6,129
for 7 nights, 1 home
S$876 per night
includes taxes & fees
Kona Keauhou Newly Remodeled Home, Quiet private home on Golf course with Pool.
Living area
Outdoor dining
Relax by the pool, take a swim, watch surfers, whales (in season) & turtles!
Interior
Exceptional
(123 reviews)

Romantic Penthouse Oceanfront Condo with AC and Fabulous Views

Kailua-Kona

7% off
S$4,349
for 7 nights, 1 apartment
S$621 per night
includes taxes & fees
Romantic Penthouse Oceanfront Condo with AC and Fabulous Views
The mini-split AC unit cools the entire unit; queen hide-a-bed, recliner, rocker
Dining on the lanai above the crashing waves; it just doesn't get any better.
The large tide pool in front of the condo complex with fish, eels & turtles
Master bedroom has smart TV, USB connections for devices, safe, dresser, lamps
Exceptional
(288 reviews)

Kona Oceanfront Penthouse Condo: Remodeled, AC, Crashing Waves, Sunsets, Turtles

Kailua-Kona

8% off
S$4,952
for 7 nights, 1 apartment
S$707 per night
includes taxes & fees
Kona Oceanfront Penthouse Condo: Remodeled, AC, Crashing Waves, Sunsets, Turtles
Queen size bed, looking toward sitting and dining area
Lanai at dusk
Kona Garden Studio Ohana located downstairs.
Sitting area with sliding door to private lanai
Exceptional
(26 reviews)

Kona Garden Studio Ohana - Private sunset lanai & garden views!

Kailua-Kona

7% off
S$1,761
for 7 nights, 1 apartment
S$252 per night
includes taxes & fees
Kona Garden Studio Ohana - Private sunset lanai & garden views!
Exterior
Property grounds
Living area
Room
Exceptional
(13 reviews)

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

Kailua-Kona

7% off
S$6,858
for 7 nights, 1 home
S$980 per night
includes taxes & fees
Upscale Kona home in peaceful setting, ready for family gatherings.
Living area
Living area
Pool
Room
Exceptional
(7 reviews)

Oceanside King Bed, Private Beach Access, Pool & Lanai in Kona

Kailua-Kona

7% off
S$3,228
for 7 nights, 1 apartment
S$461 per night
includes taxes & fees
Oceanside King Bed, Private Beach Access, Pool & Lanai in Kona
Property grounds
Property grounds
Private kitchen
Living area
Exceptional
(84 reviews)

Immaculate; Air Cond; Ocean/Garden views;GIG WiFi6 S

Kailua-Kona

7% off
S$2,733
for 7 nights, 1 apartment
S$390 per night
includes taxes & fees
Immaculate; Air Cond; Ocean/Garden views;GIG WiFi6 S
Hole #9 of the Kona Country Club Golf Course is Right in Front of the Property
Spectacular Views from Your Lanai
Amazing Winter Sunset from Your Lanai
Relax in Your Spacious Living Area
Exceptional
(7 reviews)

Hale Hahalua - Serenity and Ocean Views in Kailua-Kona at Keauhou Akahi

Kailua-Kona

7% off
S$3,631
for 7 nights, 1 apartment
S$519 per night
includes taxes & fees
Hale Hahalua - Serenity and Ocean Views in Kailua-Kona at Keauhou Akahi
HUGE LANAI,  OPEN SPACE, ONE OF THE FAVORITE SPOTS. FIRST IMPRESSION IS WOW!!!
HISTORICAL DISTRICT OF KAHALU'U. PLACE. SURF, CANOEING, AGRICULTURAL OF CHIEFS.!
HAPPY PLACE,  HISTORIC RESIDENCE OF HAWAIIAN CHIEFS. CANOE LANDING, SURF.
Palm Tree lined 15 yards, driveway. Sits atop the hill for Privacy. Breezy!!
Exceptional
(110 reviews)

FABULOUS BEACH HOUSE!! OCEAN FRONT VIEW! 4 MINUTE WALK TO KAHALUU BEACH PARK!!

Kailua-Kona

6% off
S$5,423
for 7 nights, 1 home
S$775 per night
includes taxes & fees
FABULOUS BEACH HOUSE!! OCEAN FRONT VIEW! 4 MINUTE WALK TO KAHALUU BEACH PARK!!
Living area
Beach
Pool
Exterior
Exceptional
(92 reviews)

Ocean Views/Mountain Views!! HUGE LANAI Directly across the road from the BEACH!

Kailua-Kona

7% off
S$4,473
for 7 nights, 1 apartment
S$639 per night
includes taxes & fees
Ocean Views/Mountain Views!! HUGE LANAI Directly across the road from the BEACH!
Interior
Lanai
Pool and Hot Tub
Living area
Exceptional
(161 reviews)

One Bedroom, First Floor, Fully Furnished Condo

Kailua-Kona

7% off
S$2,083
for 7 nights, 1 apartment
S$298 per night
includes taxes & fees
One Bedroom, First Floor, Fully Furnished Condo
Beautifully Landscaped Grounds
Kona Sunset, taken from your private lanai.
Interior
Pool
Wonderful
(71 reviews)

OCEANFRONT CONDO TOTAL REMODEL 2025 2 POOLS KONA SUNSETS PRIVATE LANAI A/C

Kailua-Kona

7% off
S$3,868
for 7 nights, 1 apartment
S$553 per night
includes taxes & fees
OCEANFRONT CONDO TOTAL REMODEL 2025 2 POOLS KONA SUNSETS PRIVATE LANAI A/C
Property grounds
Property grounds
Room
Interior
Exceptional
(109 reviews)

Immaculate; Air Cond; Ocean/Garden views; WiFi N

Kailua-Kona

7% off
S$2,555
for 7 nights, 1 apartment
S$365 per night
includes taxes & fees
Immaculate; Air Cond; Ocean/Garden views; WiFi N
  • Peace of mind

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  • 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

Delight in the oceanfront landscape of Kailua-Kona

The ocean views and other outdoor surroundings create an inviting atmosphere in Kailua-Kona. Renowned for its snorkelling, shopping and coffee shops, this city welcomes all visitors. A holiday rental can help make your stay complete—many rentals come with a full kitchen and laundry facilities.

Activities and attractions in Kailua-Kona

Do you want to find things to do while you're in the area? Travellers enjoy fun activities like snorkelling and swimming. Although it can be tempting to stay in your comfortable holiday rental, you'll want to check out everything that makes Kailua-Kona a one-of-a-kind holiday spot. These are some of the top attractions to put on your list, all within 30 miles (48.2 km) of the city centre:

  • Hula Daddy Kona Coffee Plantation (3.3 mi / 5.3 km)
  • Four Seasons Resort Hualalai Golf Course (13 mi / 20.8 km)
  • Makani Golf Club (15.9 mi / 25.7 km)
  • Waikoloa Beach Golf Course (20.8 mi / 33.5 km)
  • Waikoloa Kings Golf Course (21.4 mi / 34.5 km)
  • Mauna Lani Resort Golf Course (22.8 mi / 36.7 km)

Exploring the beaches and other natural features in Kailua-Kona

Beautiful ocean views, volcano viewpoints and breathtaking sunsets are a few of the stunning natural features that Kailua-Kona boasts. Whether you're an active traveller or just want to appreciate the scenery, you'll be sure to find the perfect setting for your holiday in Kailua-Kona. Here are some of the area’s most enchanting sights, all within 30 miles (48.2 km) of the city centre:

  • Hawaii Volcanoes National Park (28.4 mi / 45.8 km)
  • Kamakahonu Beach (0.1 mi / 0.1 km)
  • Old Kona Airport State Recreation Area (0.8 mi / 1.3 km)
  • Kaloko-Honokohau National Historical Park (3.5 mi / 5.6 km)
  • Magic Sands Beach (3.6 mi / 5.7 km)
  • Kahalu'u Beach Park (4.6 mi / 7.4 km)

Seasonal weather in Kailua-Kona

Travellers speak highly of Kailua-Kona for its snorkelling. If you're planning a holiday around the weather, August, September, October and July are the hottest months to visit, when temperatures average 24°C.

Travelling to and around Kailua-Kona

Fly into Kailua-Kona, HI (KOA-Kona Intl.), the closest airport, located 7.2 mi (11.6 km) from the city centre. If you can't find a flight that works for your travel itinerary, you might consider flying into Kamuela, HI (MUE-Waimea-Kohala), which is 32.5 mi (52.3 km) away.

Frequently asked questions

What is the best area to stay in Kailua-Kona when booking a holiday rental?
Kahaluu-Keauhou is among the most popular locations to book a holiday property in Kailua-Kona. Looking for some awesome things to see and do in this destination? Take time to visit Magic Sands Beach and Kahaluu Beach Park.
What is the most popular type of holiday rental accommodation in Kailua-Kona?
According to our research, condos are considered the most popular type of holiday rental in Kailua-Kona. But having said that, everyone's idea of the perfect trip isn't going to be the same. Vrbo has holiday rentals of all sizes and shapes, so you're bound to find the perfect match.
How much does it cost to rent a holiday rental in Kailua-Kona?
Season, length of stay and property type are some things that can influence the price of a holiday home. Simply add your travel dates to find your ideal match. From cosy country cottages to plush villas, all Vrbo holiday rentals offer incredible value.
How much does it cost to rent a beach house in Kailua-Kona?
Prices for beach houses in Kailua-Kona differ depending on the size and type of the property and when you plan to travel. All you need to do is enter your travel dates into Vrbo and how many guests to view your rental options and prices. From there you can use the filters to narrow down your search by ratings, nearby activities, amenities and more.
What are popular rental amenities in Kailua-Kona?
When it comes to rental amenities that guests are searching for in Kailua-Kona, an electric car charging station, a sauna and a beach view are at the top of the list. With Vrbo holiday homes, there are choices to suit your taste and style, whether you're planning to get away with your partner, your friends or even pets.
What are the top attractions for families in Kailua-Kona?
Keep the kids happy at these awesome family-friendly attractions in Kailua-Kona:
  • Kailua Pier
  • Magic Sands Beach
  • Kahaluu Beach Park
Can I find two-bedroom holiday rentals in Kailua-Kona?
Gather your nearest and dearest and experience complete comfort and privacy in one of the 441 two-bedroom holiday homes Kailua-Kona has to offer.
Are there holiday rentals with WiFi in Kailua-Kona?
You'll find 491 holiday rentals with WiFi in Kailua-Kona. If you want to disconnect from the world while on holiday, but still need to be connected to the internet, these properties have just what you need. Narrow your search by applying the WiFi filter on Vrbo.
How old do you have to be to rent a holiday rental in Kailua-Kona?
We advise checking with the Kailua-Kona holiday home you're looking at on Vrbo as the age limit varies. However, it's generally 16, 18 or 21.
How long can I rent a holiday rental in Kailua-Kona for?
The length of time you can rent a holiday rental in Kailua-Kona differs according to the property. Just enter your chosen dates to look at a list of options offering extended stays. With many amenities such as laundries and air conditioning, as well as some offering weekly or monthly discounted prices, you're sure to get the perfect place to call your home away from home in Kailua-Kona.

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