Kailua-Kona Vacation Rentals

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

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$500 - $500 /night
$3500 - $4200 /week

Lymans Bay Hale-Oceanfront

Home: 5 Bedroom, 3.5 Bathroom, Sleeps 12
Location: Kailua-Kona, Hawaii, United States
Description: For a virtual tour of this property scroll down to the bottom of the text and click on the link. As of September 20, 2015 a major renovation of Lym...

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$500 - $500 /night

$3500 - $4200 /week

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$87 - $234 /night
$615 - $1603 /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...

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$87 - $234 /night

$615 - $1603 /week

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

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

12 reviews Add to Favorites

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...

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$89 - $89 /night

$623 - $1120 /week

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$99 - $250 /night
$693 - $1750 /week

Book Your April - September 2017 Stay at $99/Night++! New...

10 reviews Add to Favorites

Condo: 2 Bedroom, 1.5 Bathroom, Sleeps 5
Location: Kailua-Kona, Hawaii, United States
Description: Book Your April - September 2017 Stay at $99/Night++! New Photos!! Book Your April - September 2017 at a special rate of $99/night!! ++ Welcome t...

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$99 - $250 /night

$693 - $1750 /week

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$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...

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$900 - $1300 /night

$6300 - $16800 /week

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$125 - $165 /night
$875 - $1953 /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 & ...

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$125 - $165 /night

$875 - $1953 /week

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

Kona Luna by the Sea 106

Condo: 2 Bedroom, 2 Bathroom, Sleeps 2
Location: Kailua-Kona, Hawaii, United States
Description: Perfect for vacationing couple interested in exploring the wonders of the Big Island of Hawaii! Also Special Offer available for family with childr...

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$135 - $240 /night

$900 - $1200 /week

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$160 - $207 /night
$1120 - $1820 /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...

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$160 - $207 /night

$1120 - $1820 /week

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$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...

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$499 - $629 /night

$3493 - $4865 /week

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$399 - $600 /night
$2793 - $5600 /week

3 Bedroom 3 Bath Luxury House with Ocean View!

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...

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$399 - $600 /night

$2793 - $5600 /week

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$800 - $1300 /night
$5600 - $19600 /week

Fall Special - Amazing 3 BR Hualalai Villa, 2 golf carts

8 reviews Add to Favorites

Villa: 3 Bedroom, 3.5 Bathroom, Sleeps 6
Location: Kailua-Kona, Hawaii, United States
Description: Convenientally located 3 bedroom, 3.5 bath luxury villa overlooks the 15th hole of the Jack Nicklaus designed Hualalai Golf Course. Ground floor si...

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$800 - $1300 /night

$5600 - $19600 /week

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$160 - $219 /night
$1120 - $1750 /week

2 BR condo with a loft in oceanfront complex, amazing Oce...

46 reviews Add to Favorites

Condo: 2 Bedroom, 2 Bathroom, Sleeps 6
Location: Kailua-Kona, Hawaii, United States
Description: 2 BR condo with a loft in oceanfront complex, amazing Ocean views Come and enjoy this community at the Kona Makai, vacationers number one choice f...

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$160 - $219 /night

$1120 - $1750 /week

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$192 - $225 /night
$1309 - $1543 /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...

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$192 - $225 /night

$1309 - $1543 /week

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$1183 - $1925 /week

Nahale B3--Fabulous Ocean view 3Br Town home Near Beach F...

39 reviews Add to Favorites

Condo: 3 Bedroom, 2.5 Bathroom, Sleeps 6
Location: Kailua-Kona, Hawaii, United States
Description: Nahale B3--Fabulous Ocean view 3Br Town home Near Beach From $169 per night! From the moment you step into this fabulous 3 bedroom, 2.5 bath condo...

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$1183 - $1925 /week

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$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...

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$120 - $172 /night

$804 - $1194 /week

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

13 reviews Add to Favorites

Condo: 2 Bedroom, 3 Bathroom, Sleeps 6
Location: Kailua-Kona, Hawaii, United States
Description: Remodeled In 2017! Ocean View, Huge Lanai, Walk To Town! Elevator, Ac!! Kona Pacific B-409 is a newly remodeled upper floor condo with breathtakin...

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$120 - $300 /night

$840 - $2100 /week

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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.

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Kailua-Kona Vacation Rentals

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