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Kailua-Kona Vacation Rentals

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


$125 - $205 /night
$875 - $1953 /week
Kksr3202 Direct Oceanfront, Spacious, 2nd Flr

  17 reviews   Add to Favorites

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


$153 - $245 /night
$1048 - $1675 /week
Kona Surf & Racquet Tropical Gardens Views on a Private L...

  16 reviews   Add to Favorites

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


$195 - $249 /night
$1365 - $1960 /week
Oceanfront Condo with breathtaking Ocean and Sunset Views...

  92 reviews   Add to Favorites

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


$420 - $525 /night
$2940 - $4200 /week
Exquisite Three BR, Three Bath Ocean view Villa (Resort F...

  5 reviews   Add to Favorites

Condo: 3 Bedroom, 3 Bathroom, Sleeps 6
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


$425 - $450 /night
$2975 - $3150 /week
Upscale 3 bedroom bungalow in oceanfront estate

  8 reviews   Add to Favorites

Condo: 3 Bedroom, 2 Bathroom, Sleeps 8
Location: Kailua-Kona, Hawaii, United States


$116 - $150 /night
$812 - $1435 /week
Kms313 Top Floor Direct Oceanfront!!! Wifi in condo! Gorg...

  47 reviews   Add to Favorites

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


$499 - $499 /night
$3493 - $4550 /week
Alii Point - Luxury Villa in Private Oceanfront Community

  12 reviews   Add to Favorites

Home: 3 Bedroom, 2 Bathroom, Sleeps 6
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


$135 - $135 /night
$945 - $1330 /week
1 BR condo with a loft in oceanfront complex, amazing Oce...

  22 reviews   Add to Favorites

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


$105 - $105 /night
$735 - $1120 /week
One BR condo, right on the edge of town, great Ocean views

  1 reviews   Add to Favorites

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


$149 - $169 /night
$1043 - $1225 /week
Oceanfront-Incredible Views, Surf Break & Romantic Sunset...

  52 reviews   Add to Favorites

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


$250 - $300 /night
$1750 - $2450 /week
Experience VIntage Hawaii with an Ocean View and Private ...

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


$225 - $330 /night
$1575 - $2310 /week
Spacious Two BR, Two Bath Ocean View Villa (Resort Fees I...

  21 reviews   Add to Favorites

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


$153 - $245 /night
$1048 - $1675 /week
Kona Surf & Racquet Tropical garden views, great condo in...

  7 reviews   Add to Favorites

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


$100 - $125 /night
$700 - $1435 /week
Sea Village 3317 - 1 BR, Direct Oceanfront, Top Floor, Br...

  33 reviews   Add to Favorites

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


$153 - $203 /night
$1046 - $1385 /week
Kona Coast Resort Enjoy Ocean Views

  10 reviews   Add to Favorites

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


$199 - $250 /night
$1393 - $1953 /week
Casa De Emdeko 219 2 Bdrm Direct Ocean Front Corner unit,...

  18 reviews   Add to Favorites

Condo: 2 Bedroom, 2 Bathroom, Sleeps 6
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


$475 - $485 /night
$3325 - $3535 /week
Upscale 3 bedroom bungalow in an oceanfront estate

  2 reviews   Add to Favorites

Condo: 3 Bedroom, 2 Bathroom, Sleeps 8
Location: Kailua-Kona, Hawaii, United States


$125 - $125 /night
$875 - $1120 /week
Beautiful remodeled 2 BR condo located on Robert Trent Jo...

  9 reviews   Add to Favorites

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


$125 - $155 /night
$875 - $1575 /week
Large 2 bedroom, 2 bath condo right down town

  5 reviews   Add to Favorites

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


$1695 - $1850 /night
$11865 - $13300 /week
Deluxe Oceanfront 5 BR Estate with Pool & Spa, Paradise!

  1 reviews   Add to Favorites

Home: 5 Bedroom, 4 Bathroom, Sleeps 10
Location: Kailua-Kona, Hawaii, United States


$125 - $125 /night
$875 - $1050 /week
Lunapule Kona # 106 - Pool

  42 reviews   Add to Favorites

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


$110 - $120 /night
$770 - $1225 /week
Kona Plaza in Kailua-Kona town

  29 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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