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Kailua-Kona Vacation Rentals

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

Featured
$399 - $600 /night
$2793 - $5600 /week
3 Bedroom 3 Bath Luxury House with Ocean View!

  7 reviews   Add to Favorites

Home: 3 Bedroom, 3.5 Bathroom, Sleeps 6
Location: Kailua-Kona, Hawaii, United States

Featured
$100 - $165 /night
$720 - $1839 /week
Holualoa Bay Villas: 106 Beautiful Oceanview, Ac, Elevato...

  8 reviews   Add to Favorites

Condo: 2 Bedroom, 2 Bathroom, Sleeps 6
Location: Kailua-Kona, Hawaii, United States

Featured
$159 - $189 /night
$1066 - $1396 /week
Keauhou Gardens Spectacular Ocean View Condo

  19 reviews   Add to Favorites

Condo: 1 Bedroom, 1 Bathroom, Sleeps 2
Location: Kailua-Kona, Hawaii, United States

Featured
$160 - $201 /night
$1120 - $1575 /week
2 BR condo with a loft in oceanfront complex, amazing Oce...

  44 reviews   Add to Favorites

Condo: 2 Bedroom, 2 Bathroom, Sleeps 6
Location: Kailua-Kona, Hawaii, United States

Featured
$99 - $179 /night
$693 - $1750 /week
Book Your April - September 2017 Stay at $99/Night++! New...

  9 reviews   Add to Favorites

Condo: 2 Bedroom, 1.5 Bathroom, Sleeps 5
Location: Kailua-Kona, Hawaii, United States

Featured
$549 - $629 /night
$3843 - $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

Featured

$1323 - $1323 /week
Fabulous Oceanview 3 BR Townhome Near Beach From $169 per...

  38 reviews   Add to Favorites

Condo: 3 Bedroom, 2.5 Bathroom, Sleeps 6
Location: Kailua-Kona, Hawaii, United States

Featured
$131 - $178 /night
$862 - $1274 /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

Featured
$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

Featured
$89 - $307 /night
$623 - $2104 /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

Featured
$700 - $1300 /night
$4900 - $19600 /week
Summer Specials - 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

Featured
$1100 - $1300 /night
$7700 - $16800 /week
Ocean Views & short walk to beach await at this 2 bd Hual...

  20 reviews   Add to Favorites

Villa: 2 Bedroom, 2 Bathroom, Sleeps 4
Location: Kailua-Kona, Hawaii, United States

Featured
$500 - $500 /night
$3500 - $4200 /week
Lymans Bay Hale-Oceanfront

  27 reviews   Add to Favorites

Home: 5 Bedroom, 3.5 Bathroom, Sleeps 12
Location: Kailua-Kona, Hawaii, United States

Featured
$160 - $201 /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

$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

$125 - $179 /night
$875 - $1393 /week
Ocean View- great location! Free Wifi and North America C...

  16 reviews   Add to Favorites

Condo: 2 Bedroom, 2 Bathroom, Sleeps 4
Location: Kailua-Kona, Hawaii, United States

$172 - $248 /night
$1150 - $1891 /week
Tropical Oceanfront townhouse in Kona Hawaii

  28 reviews   Add to Favorites

Condo: 2 Bedroom, 2 Bathroom, Sleeps 4
Location: Kailua-Kona, Hawaii, United States

$69 - $261 /night
$483 - $1659 /week
Kona Isle A4 Beautifully appointed condo. Ground Floor, W...

  38 reviews   Add to Favorites

Condo: 1 Bedroom, 1 Bathroom, Sleeps 4
Location: Kailua-Kona, Hawaii, United States

$80 - $180 /night
$560 - $1953 /week
Kona Makai 3-203 2nd Flr, Ocean View, Remodeled BA w/ Wal...

  31 reviews   Add to Favorites

Condo: 1 Bedroom, 1 Bathroom, Sleeps 4
Location: Kailua-Kona, Hawaii, United States

$73 - $181 /night
$567 - $1656 /week
Kona Isle C24 Oceanview, 2nd floor, Wifi, Fantastic price!

  18 reviews   Add to Favorites

Condo: 1 Bedroom, 1 Bathroom, Sleeps 3
Location: Kailua-Kona, Hawaii, United States

$425 - $460 /night
$2975 - $3220 /week
Upscale 3 bedroom bungalow in oceanfront estate

  10 reviews   Add to Favorites

Condo: 3 Bedroom, 2 Bathroom, Sleeps 8
Location: Kailua-Kona, Hawaii, United States

$209 - $761 /night
$1463 - $4757 /week
Kona Makai 1-301 Direct Oceanfront, Top Floor, Best Corne...

  7 reviews   Add to Favorites

Condo: 2 Bedroom, 2 Bathroom, Sleeps 4
Location: Kailua-Kona, Hawaii, United States

$160 - $220 /night
$1120 - $1540 /week
Sea Village 1-203

Condo: 1 Bedroom, 1 Bathroom, Sleeps 4
Location: Kailua-Kona, Hawaii, United States

$299 - $400 /night
$2093 - $3500 /week
New Vacation Rental!! This Home Can Also Be Rented As A 2 BR

Home: 4 Bedroom, 3 Bathroom, Sleeps 8
Location: Kailua-Kona, Hawaii, United States

$399 - $399 /night
$2793 - $3143 /week
Kona Bay Seaclusion-Oceanfront with Pool

  22 reviews   Add to Favorites

Home: 2 Bedroom, 2.5 Bathroom, Sleeps 4
Location: Kailua-Kona, Hawaii, United States

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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