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Kailua-Kona Vacation Rentals

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


Featured
$99 - $199 /night
$693 - $1393 /week
Beautiful Oasis !

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


Featured
$138 - $215 /night
$966 - $2915 /week
Krd32 Absolute Oceanfront Top Flr Private

  42 reviews   Add to Favorites

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


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

  71 reviews   Add to Favorites

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


Featured
$145 - $170 /night
$1015 - $1400 /week
Ocean View in heart of Kailua-Kona, 2bd/2bth

  41 reviews   Add to Favorites

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


Featured
$99 - $250 /night
$693 - $1750 /week
Book Your April - September 2017 Stay at $99/Night++! New...

  20 reviews   Add to Favorites

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


Featured
$164 - $206 /night
$1148 - $1442 /week
Oceanfront 2 BR ground floor condo with amazing Ocean Views

  47 reviews   Add to Favorites

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


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

  30 reviews   Add to Favorites

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


Featured
$1000 - $2000 /night
$5600 - $14000 /week
Hualalai Hillside Villa 4102 - Premier Location, upgraded...

  24 reviews   Add to Favorites

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


Featured
$245 - $348 /night
$1715 - $6607 /week
Kona Makai 1-301 Direct Oceanfront, Top Floor, Best Corne...

  16 reviews   Add to Favorites

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


$175 - $245 /night
$1225 - $1715 /week
Kailua Bay Resort #3301

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


$150 - $290 /night
$1050 - $2030 /week
Kona Alii 512

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


$125 - $280 /night
$875 - $2100 /week
Kksr2204 Direct Oceanfront Corner Unit!!! 2nd Floor, Wifi...

  69 reviews   Add to Favorites

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


$240 - $380 /night
$1680 - $2660 /week
Casa De Emdeko 338

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


$975 - $1100 /night
$6825 - $9450 /week
Unobstructed Oceanfront, Private Pool/Spa, Spectacular Vi...

  8 reviews   Add to Favorites

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


$199 - $350 /night
$1393 - $2450 /week
Experience VIntage Hawaii with an Ocean View and Private ...

  15 reviews   Add to Favorites

Home: 3 Bedroom, 2 Bathroom, Sleeps 6
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


$175 - $280 /night
$1225 - $1960 /week
Sea Village#1303

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


$125 - $190 /night
$875 - $1330 /week
Casa De Emdeko 223

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


$175 - $315 /night
$1225 - $2205 /week
Kona Alii 504

Condo: 1 Bedroom, 2 Bathroom, Sleeps 3
Location: Kailua-Kona, Hawaii, United States


$145 - $170 /night
$1015 - $1400 /week
Two bedroom, two bath in the heart of Kailua Kona

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


$430 - $480 /night
$3010 - $4550 /week
Beautiful single level private home with spectacular ocea...

  30 reviews   Add to Favorites

Home: 3 Bedroom, 3 Bathroom, Sleeps 6
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


$120 - $140 /night
$840 - $1085 /week
"A Slice of Paradise", Keauhou Resort #104 Townhouse, Sle...

  11 reviews   Add to Favorites

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


$175 - $265 /night
$1225 - $1855 /week
Kona Makai 6305

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.

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

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