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Kailua-Kona Vacation Rentals

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

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
$89 - $313 /night
$623 - $2146 /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
$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
$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
$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
$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
$1100 - $11000 /night
$7700 - $77000 /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
$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
$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
$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
$175 - $175 /night
$1225 - $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
$170 - $170 /night
$1190 - $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

Featured
$600 - $1300 /night
$4200 - $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
$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

$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

$199 - $300 /night
$1393 - $2450 /week
Experience VIntage Hawaii with an Ocean View and Private ...

  4 reviews   Add to Favorites

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

$160 - $160 /night
$1120 - $1470 /week
2 bedroom condo in oceanfront complex, great Ocean views

  32 reviews   Add to Favorites

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

$154 - $201 /night
$1027 - $1562 /week
Lunapule Kona Affordable Condo near Kona Town & Beach!

  9 reviews   Add to Favorites

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


$653 - $1575 /week
Beautifully decorated two bedroom, two bath condo

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


$6650 - $7525 /week
Premier Estate featuring 6 BRs, Private Pool & Spa, Ocean...

Home: 6 Bedroom, 4.5 Bathroom, Sleeps 12
Location: Kailua-Kona, Hawaii, United States

$275 - $275 /night
$1925 - $2275 /week
Two BR Beach House Within Walking Distance to Kahalu'u Beach

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

$125 - $259 /night
$875 - $2450 /week
Sv4205 2 BR, Direct Oceanfront, Wifi, Breathtaking View.

  45 reviews   Add to Favorites

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

$195 - $265 /night
$1365 - $2205 /week
Oceanfront 2 BR condo with amazing Ocean and Sunset views

  57 reviews   Add to Favorites

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

$730 - $805 /night
$5110 - $5635 /week
Hale Honu-Oceanfront

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

$145 - $200 /night
$1015 - $1400 /week
Keauhou Gardens #11-101 at Kona Coast Resort

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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