Kailua-Kona Vacation Rentals

274 Kailua-Kona Vacation Rentals were found matching your criteria.

1 - 25 of 274

Sort by:

Featured

$89 - $89 /night
$623 - $1120 /week

Ac Included! Lovely Island Home- Casa De Emdeko #221

Condo: 1 Bedroom, 1 Bathroom, Sleeps 4
Location: Kailua-Kona, Hawaii, United States
Description: AC Included! Lovely, One Bedroom, One Bathroom! The condo is tiled throughout with wood floors in the bedroom. The bedroom has a Queen size bed wi...

Rates

$89 - $89 /night

$623 - $1120 /week

Featured

Add to Favorites Send Inquiry

Details and Book

Featured

$135 - $240 /night
$900 - $1200 /week

Kona Luna 106

Condo: 3 Bedroom, 2 Bathroom, Sleeps 6
Location: Kailua-Kona, Hawaii, United States
Description: Immerse yourself in beautiful Kailua Village on the Big Island of Hawaii. Enjoy the vibrance of town, just 10 minutes from your own vacation home. ...

Rates

$135 - $240 /night

$900 - $1200 /week

Featured

Add to Favorites Send Inquiry

Details and Book

Featured

$120 - $172 /night
$804 - $1194 /week

Keauhou Palena Golfers Delight Great location in Kona Par...

6 reviews Add to Favorites

Condo: 1 Bedroom, 2 Bathroom, Sleeps 4
Location: Kailua-Kona, Hawaii, United States
Description: Keauhou Palena Golfers Delight Great location in Kona Paradise Keauhou Palena is located in a lovely quiet community but still close to Keauhou Ba...

Rates

$120 - $172 /night

$804 - $1194 /week

Featured

Add to Favorites Send Inquiry

Details and Book

Featured

$114 - $165 /night
$798 - $1839 /week

Holualoa Bay Villas: 106 Beautiful Oceanview, Ac, Elevato...

9 reviews Add to Favorites

Condo: 2 Bedroom, 2 Bathroom, Sleeps 6
Location: Kailua-Kona, Hawaii, United States
Description: Holualoa Bay Villas: 106 Beautiful Oceanview, Ac, Elevators, Wifi! Holualoa Bay Villas#106 is a brand new rental in our inventory, that Knutson & ...

Rates

$114 - $165 /night

$798 - $1839 /week

Featured

Add to Favorites Send Inquiry

Details and Book

Featured

$160 - $207 /night
$1120 - $1750 /week

Oceanfront 2 BR ground floor condo with amazing Ocean Views

41 reviews Add to Favorites

Condo: 2 Bedroom, 2 Bathroom, Sleeps 6
Location: Kailua-Kona, Hawaii, United States
Description: This unit is located in a highly desirable location just a short walk from down town Kailua Kona. A recently remodeled two bedrooms, two bath condo...

Rates

$160 - $207 /night

$1120 - $1750 /week

Featured

Add to Favorites Send Inquiry

Details and Book

Featured

$89 - $247 /night
$623 - $1690 /week

Kona Isle B5 Ground Floor, Ac, Close to Pool!

23 reviews Add to Favorites

Condo: 1 Bedroom, 1 Bathroom, Sleeps 4
Location: Kailua-Kona, Hawaii, United States
Description: B5 at the Kona Isle is a fantastic ground floor unit that you will absolutely love. AIR CONDITIONING, Great Price, Clean, & very comfortable! You w...

Rates

$89 - $247 /night

$623 - $1690 /week

Featured

Add to Favorites Send Inquiry

Details and Book

Featured

$147 - $188 /night
$998 - $1309 /week

Keauhou Gardens Spectacular Ocean View Condo

20 reviews Add to Favorites

Condo: 1 Bedroom, 1 Bathroom, Sleeps 2
Location: Kailua-Kona, Hawaii, United States
Description: The Kona Coast Resort is one of the premier resorts in Kona and this condo fits right in. The condo has been completely remodeled with all new floo...

Rates

$147 - $188 /night

$998 - $1309 /week

Featured

Add to Favorites Send Inquiry

Details and Book

Featured

$900 - $1300 /night
$6300 - $16800 /week

Ocean Views & short walk to beach await at this 2 bd Hual...

21 reviews Add to Favorites

Villa: 2 Bedroom, 2 Bathroom, Sleeps 4
Location: Kailua-Kona, Hawaii, United States
Description: Ocean Views & short walk to beach await at this 2 bd Hualalai Hillside Villa Location-Location-Location! This spectacular 2 bedroom, 2 bath luxur...

Rates

$900 - $1300 /night

$6300 - $16800 /week

Featured

Add to Favorites Send Inquiry

Details and Book

Featured

$499 - $629 /night
$3493 - $4865 /week

Hale Honu - Spectacular Oceanfront Home w/ central A/C - ...

64 reviews Add to Favorites

Home: 4 Bedroom, 4 Bathroom, Sleeps 8
Location: Kailua-Kona, Hawaii, United States
Description: Hale Honu - Spectacular Oceanfront Home w/ central A/C - Special Rate $499/nt Take advantage of our Fabulous Fall Special! Only $499 per night! Ef...

Rates

$499 - $629 /night

$3493 - $4865 /week

Featured

Add to Favorites Send Inquiry

Details and Book

Featured

$1183 - $1925 /week

9 reviews Add to Favorites

Home: 3 Bedroom, 3.5 Bathroom, Sleeps 6
Location: Kailua-Kona, Hawaii, United States
Description: Experience Island Lifestyle in one of Kona's most desirable gated neighborhood.. This single-level custom built home with elegant appointments thro...

Rates

$399 - $600 /night

$2793 - $5600 /week

Featured

Add to Favorites Send Inquiry

Details and Book

$179 - $315 /night
$1113 - $2200 /week

Stunning Accessible Oceanfront Condo on the Kona Coast

Condo: 2 Bedroom, 2 Bathroom, Sleeps 6
Location: Kailua-Kona, Hawaii, United States
Description: Elegant yet simple luxury on the ocean in Kona Hawaii. * Incredible Ocean Views * Spacious 2-BR /2-BA * Central Air Conditioning (A/C)...

Rates

$179 - $315 /night

$1113 - $2200 /week

Add to Favorites Send Inquiry

View Details

$320 - $320 /night
$2240 - $2240 /week

Ali'i Drive Condo #228768

Condo: 2 Bedroom, 2 Bathroom, Sleeps 6
Location: Kailua-Kona, Hawaii, United States
Description: A Step Back to Authentic Hawaiian Pleasures. When you stay at Kona Hawaiian Resort in Kailua-Kona on the Big Island’s west coast, you’ll feel as if...

Rates

$320 - $320 /night

$2240 - $2240 /week

Add to Favorites Send Inquiry

Details and Book

$85 - $117 /night
$595 - $875 /week

Ocean view 1 bedroom, 1 bath right in the heart of town!

Condo: 1 Bedroom, 1 Bathroom, Sleeps 4
Location: Kailua-Kona, Hawaii, United States
Description: This beautifully remodeled 1 bedroom 1 bathroom unit makes for the perfect retreat for a Big Island Vacation. Enjoy breath taking views from the sp...

Rates

$85 - $117 /night

$595 - $875 /week

Add to Favorites Send Inquiry

Details and Book

$300 - $475 /night
$2100 - $3325 /week

Pahukoa Hale - Direct Ocean Front Hawaiian Style home in ...

42 reviews Add to Favorites

Home: 3 Bedroom, 3 Bathroom, Sleeps 8
Location: Kailua-Kona, Hawaii, United States
Description: Pahukoa Hale - Direct Ocean Front Hawaiian Style home in Kona Bay Estates This vintage Hawaiian beach house is nestled in a private gated communit...

Rates

$300 - $475 /night

$2100 - $3325 /week

Add to Favorites Send Inquiry

Details and Book

$653 - $1575 /week

Beautifully decorated two bedroom, two bath condo

Condo: 2 Bedroom, 2 Bathroom, Sleeps 4
Location: Kailua-Kona, Hawaii, United States
Description: Relax and enjoy the excitement of Ali?i Drive from this beautifully remodeled spacious 2 bedroom, 2 bath condo with private Lanai. Not your typical...

Rates

$653 - $1575 /week

Add to Favorites Send Inquiry

Details and Book

$165 - $200 /night
$1155 - $2086 /week

Beautifully remodeled 1 BR oceanfront condo with amazing ...

11 reviews Add to Favorites

Condo: 1 Bedroom, 2 Bathroom, Sleeps 4
Location: Kailua-Kona, Hawaii, United States
Description: Beautifully remodeled 1 BR oceanfront condo with amazing views, in town This newly remodeled oceanfront condo located right in the heart of Kailua...

Rates

$165 - $200 /night

$1155 - $2086 /week

Add to Favorites Send Inquiry

Details and Book

$1110 - $1595 /night
$7770 - $11165 /week

Hahalua Hale

Home: 6 Bedroom, 4.5 Bathroom, Sleeps 12
Location: Kailua-Kona, Hawaii, United States
Description: Welcome to "Hahalua Hale" (House of the Manta Ray) located in a quiet gate community. Located at a perfect coffee growing elevation that receives t...

Rates

$1110 - $1595 /night

$7770 - $11165 /week

Add to Favorites Send Inquiry

Details and Book

$440 - $700 /night
$3080 - $4900 /week

Ho'o Maluhia

Home: 3 Bedroom, 3.5 Bathroom, Sleeps 8
Location: Kailua-Kona, Hawaii, United States
Description: This beautiful home features luxury and artistic touches to add a splash of sophistication to your vacation. The beautiful layout, wood floors and ...

Rates

$440 - $700 /night

$3080 - $4900 /week

Add to Favorites Send Inquiry

Details and Book

$160 - $220 /night
$1120 - $1540 /week

Kona Makai 1304

Condo: 2 Bedroom, 2 Bathroom, Sleeps 4
Location: Kailua-Kona, Hawaii, United States
Description: Great Views of the ocean from the Lanai. Watch whales during the season or dolphins all year around. Sip your Kona Coffee in the morning looking at...

Rates

$160 - $220 /night

$1120 - $1540 /week

Add to Favorites Send Inquiry

Details and Book

$125 - $347 /night
$875 - $2246 /week

Kksr3202 Direct Oceanfront, Spacious, 2nd Flr

29 reviews Add to Favorites

Condo: 2 Bedroom, 2 Bathroom, Sleeps 6
Location: Kailua-Kona, Hawaii, United States
Description: Welcome to Keauhou Kona Surf & Racquet Club, Unit #3-202! This beautiful, DIRECT oceanfront condo is Hawaiian Living at it's finest! Hear the ocean...

Rates

$125 - $347 /night

$875 - $2246 /week

Add to Favorites Send Inquiry

Details and Book

Why Kailua-Kona?

Why stay in a vacation rental or villa in Kailua-Kona? One word: relaxation. You'll be far not just from the urban setting of Hilo, but from the bustling Honolulu and Oahu. You'll be far from the maddening tourists on Maui. But you'll be on the Big Island, with lots to see and do. And if you decided to stay in your vacation villa in Kona, you'll be blessed with some of the best weather found anywhere. The weather is so good there that over the centuries, Hawaiian monarchs made this area their home. You can even see a reconstruction of King Kamehameha's beach quarters outside the hotel that bears his name. There's also Hulihe'e Palace, the last home of native Hawaiian Royals before the islands were absorbed into the United States.

Kailua-Kona is a great home base from which to explore the Big Island of Hawaii. You may have to drive a bit, but the scenery is worth it. Plus there are plenty of interesting stops along the way. Drive north and you'll see cowboys as you travel through Waimea. Head south and you'll see coffee plantations and quaint places to stop for lunch and shopping, as well as black sand and green sand beaches. Since you've come all this way, perhaps check out the Kapoho vacation rentals and spend a few days on the easy side of the island before heading back to Kona.

Or, just hang around Kailua-Kona. Mark Twain summed up Kailua best: "We landed at Kailua, a little collection of native grass houses reposing under tall cocoanut trees - the sleepiest, quietest, Sundayest looking place you can imagine. Ye weary ones that are sick of the labor and care, and the bewildering turmoil of the great world, and sigh for a land where ye may fold your tired hands and slumber your lives peacefully away, pack up your carpet sacks and go to Kailua! A week there ought to cure the saddest of you all.”

While you may not find yourself resting in a grass house, you’ll certainly feel as if you don’t have to do anything at all when you’re in Kailua-Kona. But if the urge to get active does overcome you, there’ll be plenty to do. Kailua-Kona offers everything you’d expect from a popular beach community—lots of great shopping, fantastic restaurants, friendly locals, welcoming bars and pubs, fishing, beachcombing, parasailing, surfing and whatever else you might want to do under the warm, Hawaii sun.

This map is intended to be used as a reference only.

Kailua-Kona Vacation Rentals

Hawaii (Big Island) Top Cities