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Kailua-Kona Vacation Rentals

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


$125 - $169 /night
$875 - $1953 /week
Kksr#3 Direct Oceanfront Townhome! Wifi, Amazing Location

  29 reviews   Add to Favorites

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


$3425 - $5020 /night
$23975 - $35140 /week
Alii Honu Kai

Home: 3 Bedroom, 4 Bathroom, Sleeps 10
Location: Kailua-Kona, Hawaii, United States



$1393 - $1925 /week
Luxurious 3 BR Townhome with Lovely Ocean Views! Close to...

  6 reviews   Add to Favorites

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


$295 - $305 /night
$2065 - $2765 /week
Quaint upscale 1 bedroom bungalow in oceanfront estate

  5 reviews   Add to Favorites

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


$95 - $110 /night
$665 - $1225 /week
Kona Isle C21 2nd floor, Oceanview, Ac, Amazing Price!

  6 reviews   Add to Favorites

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


$125 - $169 /night
$875 - $1953 /week
Kksr 185 Direct Oceanfront Townhome, Wifi, A True Gem

  34 reviews   Add to Favorites

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


$450 - $795 /night
$3150 - $5565 /week
Beautiful 4 BR home with Private Pool and unobstructed Oc...

  13 reviews   Add to Favorites

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


$100 - $120 /night
$700 - $1050 /week
Casa De Emdeko 321 Remodeled , Wifi, Top Floor, Ac includ...

  8 reviews   Add to Favorites

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


$100 - $110 /night
$700 - $1050 /week
Keauhou Akahi 210- Top floor spacious condo that sleeps 4...

  5 reviews   Add to Favorites

Condo: 1 Bedroom, 2 Bathroom, Sleeps 4
Location: Kailua-Kona, Hawaii, United States


$735 - $850 /night
$5145 - $8855 /week
Large 7 BR custom home, Private Pool & Spa, Spectacular O...

  36 reviews   Add to Favorites

Home: 7 Bedroom, 7 Bathroom, Sleeps 17
Location: Kailua-Kona, Hawaii, United States


$105 - $140 /night
$735 - $1435 /week
Kona Isle E23 Direct Ocean Front, Wifi, 2nd floor, Gorgeo...

  15 reviews   Add to Favorites

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


$129 - $191 /night
$903 - $2100 /week
Oceanfront one bedroom unit with amazing views

  8 reviews   Add to Favorites

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


$241 - $304 /night
$1665 - $2087 /week
Kona Surf & Racquet Amazing views from your private ocean...

  14 reviews   Add to Favorites

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


$204 - $222 /night
$1108 - $1653 /week
Keauhou Punahele Ocean View condo near Kona town

  8 reviews   Add to Favorites

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


$279 - $400 /night
$1894 - $2728 /week
Amazing Kona Sunsets House

  1 reviews   Add to Favorites

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


$145 - $145 /night
$1015 - $1470 /week
1 BR condo with a loft in oceanfront complex, amazing Oce...

  34 reviews   Add to Favorites

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


$159 - $189 /night
$1113 - $1603 /week
Sea Village 2nd floor Direct Oceanfront unit with extensi...

  41 reviews   Add to Favorites

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


$100 - $120 /night
$700 - $1225 /week
Casa De Emdeko 332- Amazing Oceanview, Top Floor, Ac incl...

  18 reviews   Add to Favorites

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


$184 - $304 /night
$1256 - $2089 /week
Kona Surf & Racquet Townhouse Rare 3 Bd

  16 reviews   Add to Favorites

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


$175 - $185 /night
$1225 - $1995 /week
Spacious two BR, two Bath Ocean View condo, close to town

  5 reviews   Add to Favorites

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


$100 - $120 /night
$700 - $1225 /week
Casa De Emdeko 330 - Deluxe, Top Floor, Oceanview, Ac, Ex...

  23 reviews   Add to Favorites

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


$325 - $325 /night
$2275 - $2800 /week
Turtle Rock - Ocean Front Cottage with pool

  40 reviews   Add to Favorites

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


$425 - $475 /night
$2975 - $4025 /week
Beautiful single level 3 BR, 3 bath home with spectacular...

  11 reviews   Add to Favorites

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


$135 - $160 /night
$945 - $1365 /week
$109.00 a night for ocean view in heart of Kailua-Kona, 2...

  18 reviews   Add to Favorites

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


$125 - $150 /night
$875 - $1435 /week
Casa De Emdeko 111 - Groundfloor, Spacious 2bed/2 bath w/...

  7 reviews   Add to Favorites

Condo: 2 Bedroom, 2 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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