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Kailua-Kona Vacation Rentals

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

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

  74 reviews   Add to Favorites

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

Featured
$138 - $250 /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

  35 reviews   Add to Favorites

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

Featured
$240 - $501 /night
$1685 - $3441 /week
Kona Makai 1-301 Direct Oceanfront, Top Floor, Best Corne...

  24 reviews   Add to Favorites

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

$100 - $300 /night
$700 - $2100 /week
Kona Pacific B511 High Flr, Ac, Elevators, Walk to Town, ...

  20 reviews   Add to Favorites

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

$350 - $580 /night
$2450 - $4060 /week
Hale Nui Ohana

Home: 4 Bedroom, 4 Bathroom, Sleeps 14
Location: Kailua-Kona, Hawaii, United States

$90 - $238 /night
$650 - $1655 /week
New Listing! Oceanfront Resort Condo w/ Pacific Views & Pool

  1 reviews   Add to Favorites

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

$100 - $279 /night
$805 - $1953 /week
Holualoa Bay Villas: 106 Beautiful Oceanview, Ac, Elevato...

  22 reviews   Add to Favorites

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

$149 - $199 /night
$1043 - $1393 /week
Oceanfront-Incredible Views, Surf Break & Romantic Sunset...

  79 reviews   Add to Favorites

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

$93 - $279 /night
$663 - $1953 /week
Direct Oceanfront Corner Ground Floor Kona Isle D-4!

  32 reviews   Add to Favorites

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

$499 - $649 /night
$3493 - $4543 /week
Outstanding 4 Br / 3 Ba Oceanfront Home with saltwater "Q...

  35 reviews   Add to Favorites

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

$132 - $400 /night
$992 - $2800 /week
Royal Sea Cliff#704 Luxury Top Floor Penthouse with Ocean...

  14 reviews   Add to Favorites

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

$129 - $199 /night
$903 - $1393 /week
Surf & Racquet Club Lovely open and airy 2bd/2bth 2nd flo...

  8 reviews   Add to Favorites

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

$489 - $1085 /night
$3423 - $7383 /week
Hale Lani-Private Majestic Gated Property w/Resort Size P...

  14 reviews   Add to Favorites

Home: 4 Bedroom, 4 Bathroom, Sleeps 14
Location: Kailua-Kona, Hawaii, United States

$175 - $205 /night
$1225 - $1435 /week
Kona Bali Kai 223 - Oceanfront

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

$112 - $300 /night
$870 - $2100 /week
Kksr#37 Spacious 3 BR Townhome, Sleeps 6, Close to Pool, ...

  11 reviews   Add to Favorites

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

$159 - $229 /night
$1113 - $1603 /week
Sea Village 2nd floor Direct Oceanfront unit with extensi...

  72 reviews   Add to Favorites

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

$134 - $326 /night
$938 - $2282 /week
Holualoa Bay Villas #106

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

$135 - $300 /night
$945 - $2100 /week
Kksr2103 Direct Oceanfront, Ground Floor, Remodeled Kitch...

  53 reviews   Add to Favorites

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

$125 - $326 /night
$868 - $2282 /week
Kona Isle D4

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

$102 - $271 /night
$772 - $1895 /week
Tropical Oasis w/ Pool, Spa & Private Lanai - Walk to Coast!

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

$150 - $401 /night
$1138 - $2441 /week
Lanai w/ Dazzling Oceanfront Views! Luxe 2Br + Loft w/ Po...

  2 reviews   Add to Favorites

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

$175 - $374 /night
$1225 - $2450 /week
Kona Makai 1-204

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

$162 - $427 /night
$1134 - $2583 /week
Kahaluu Bay Villas #304

Condo: 2 Bedroom, 2 Bathroom, Sleeps 6
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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