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Kailua-Kona Vacation Rentals

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


Featured
$235 - $577 /night
$1645 - $3966 /week
Kona Makai 1-301 Direct Oceanfront, Top Floor, Best Corne...

  21 reviews   Add to Favorites

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


Featured
$380 - $410 /night
$2660 - $4375 /week
Private home with pool, cool elevation, unobstructed Ocea...

  21 reviews   Add to Favorites

Home: 3 Bedroom, 3.5 Bathroom, Sleeps 8
Location: Kailua-Kona, Hawaii, United States


Featured
$950 - $3200 /night
$6650 - $22400 /week
Hualalai~exclusive Hillside Villa 4102~upgraded 2 bd~ocea...

  26 reviews   Add to Favorites

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


Featured
$138 - $168 /night
$966 - $1750 /week
Krd32 Absolute Oceanfront Top Flr Private

  45 reviews   Add to Favorites

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


Featured
$500 - $600 /night
$3500 - $4200 /week
Lymans Bay Hale-Oceanfront

  33 reviews   Add to Favorites

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


Featured
$164 - $200 /night
$1148 - $1820 /week
Oceanfront 2 BR ground floor condo with amazing Ocean Views

  50 reviews   Add to Favorites

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


Featured
$629 - $695 /night
$4403 - $4865 /week
Hale Honu - Spectacular Oceanfront Home w/ central A/C - ...

  73 reviews   Add to Favorites

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


Featured
$120 - $189 /night
$840 - $1323 /week
New to the rental Market !!! Book now

Condo: 2 Bedroom, 2 Bathroom, Sleeps 4
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


$800 - $2000 /night
$5600 - $14000 /week
Fairway Villa 110C~2bd~ garden level~15th Fairway w/signa...

  4 reviews   Add to Favorites

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


$148 - $344 /night
$1029 - $2282 /week
Kona Isle E23

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


$215 - $265 /night
$1505 - $2450 /week
Oceanfront with breathtaking Ocean & Sunset Views, 2 BR, ...

  109 reviews   Add to Favorites

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


$140 - $175 /night
$980 - $1225 /week
Kona Pacific

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


$209 - $482 /night
$1435 - $2940 /week
Royal Sea Cliff #704

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


$116 - $307 /night
$812 - $2111 /week
Kona Magic Sands#313 Top Floor Direct Beachbront, Best Vi...

  56 reviews   Add to Favorites

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


$200 - $400 /night
$1400 - $2800 /week
Kksr5303 Direct Oceanfront, Top Floor W/Loft, Remodeled, ...

  28 reviews   Add to Favorites

Condo: 2 Bedroom, 3 Bathroom, Sleeps 4
Location: Kailua-Kona, Hawaii, United States


$265 - $467 /night
$1820 - $3269 /week
Casa De Emdeko 219

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


$125 - $199 /night
$875 - $1393 /week
Ocean View- great location! Free Wifi and North America C...

  36 reviews   Add to Favorites

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


$185 - $205 /night
$1295 - $1890 /week
2 BR condo in oceanfront complex, great Ocean views, *new...

  36 reviews   Add to Favorites

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


$300 - $345 /night
$2100 - $2800 /week
Two BR Beach House Within Walking Distance to Kahalu'u Beach

  20 reviews   Add to Favorites

Home: 2 Bedroom, 3 Bathroom, Sleeps 6
Location: Kailua-Kona, Hawaii, United States


$1200 - $3200 /night
$8400 - $22400 /week
Hualalai Haliipua Villa~newly Updated 3 bd Luxury Villa~s...

  2 reviews   Add to Favorites

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


$250 - $475 /night
$1750 - $3325 /week
New Vacation Rental!

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


$1150 - $1460 /night
$8050 - $12075 /week
Absolute Ocean & Beach Front Estate with Pool and Spa w/ ...

  13 reviews   Add to Favorites

Home: 4 Bedroom, 4 Bathroom, Sleeps 10
Location: Kailua-Kona, Hawaii, United States


$325 - $380 /night
$2275 - $2660 /week
Kahalu'u Hale

Home: 2 Bedroom, 3 Bathroom, Sleeps 6
Location: Kailua-Kona, Hawaii, United States


$140 - $185 /night
$980 - $1750 /week
1 BR condo with a loft in oceanfront complex, amazing Oce...

  51 reviews   Add to Favorites

Condo: 1 Bedroom, 1 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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