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Kailua-Kona Holiday Rentals

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


Featured
$155 - $160 /night
$1085 - $1715 /week
Oceanfront 2 bedroom ground floor condo with amazing views

  38 reviews   Add to Favorites

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


Featured

$1323 - $2065 /week
Fabulous Oceanview 3 BR Townhome Near Beach From $169 per...

  32 reviews   Add to Favorites

Condo: 3 Bedroom, 2.5 Bathroom, Sleeps 6
Location: Kailua-Kona, Hawaii, United States


Featured

$6265 - $6265 /week
Your Own, Private Oceanfront Oasis right on Keiki Beach!

  16 reviews   Add to Favorites

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


Featured
$95 - $110 /night
$665 - $1225 /week
Kona Isle B5 Ground Floor, Very Clean, Ac, Great Price!

  21 reviews   Add to Favorites

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


Featured
$184 - $275 /night
$1256 - $2501 /week
Hawaiian Royalty's Playground is waiting for you

  4 reviews   Add to Favorites

Condo: 3 Bedroom, 2.5 Bathroom, Sleeps 6
Location: Kailua-Kona, Hawaii, United States


Featured
$686 - $686 /night
$2381 - $4729 /week
Blue Hawaii - A Big Island Home Amazing Ocean Views in Kona

  24 reviews   Add to Favorites

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


Featured
$125 - $145 /night
$875 - $1435 /week
Holualoa Bay Villas: 106 Beautiful Oceanview, Ac, Elevato...

  5 reviews   Add to Favorites

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


Featured
$399 - $600 /night
$2793 - $5600 /week
3 Bedroom 3 Bath Luxury House with Ocean View!

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


Featured
$599 - $599 /night
$4193 - $4550 /week
Hale Honu - Spectacular Oceanfront Home w/ central a/c - ...

  57 reviews   Add to Favorites

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


Featured
$89 - $119 /night
$623 - $1015 /week
Ac Included! Lovely Island Home- Casa De Emdeko #221

  5 reviews   Add to Favorites

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


Featured
$155 - $165 /night
$1085 - $1505 /week
2 BR condo with a loft in oceanfront complex, amazing Oce...

  39 reviews   Add to Favorites

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


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

  25 reviews   Add to Favorites

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


Featured
$199 - $229 /night
$1393 - $2275 /week
Spacious Three BR Home, Minutes from Town with a Panorami...

  6 reviews   Add to Favorites

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


$179 - $295 /night
$1113 - $2065 /week
Stunning Accessible Oceanfront Condo on the Kona Coast

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


$145 - $150 /night
$1015 - $1750 /week
Large Oceanfront 1 BR, 2 bath condo right down town, grea...

  25 reviews   Add to Favorites

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


$135 - $145 /night
$945 - $1540 /week
Recently remodeled 1 BR Ocean front condo, right down tow...

  25 reviews   Add to Favorites

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


$139 - $155 /night
$973 - $1225 /week
Kksr#36 Spacious, 3 BR townhome, sleeps 8!!! Amazing Price!

  11 reviews   Add to Favorites

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


$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


$85 - $120 /night
$595 - $1435 /week
Km3203 2nd Floor, Ocean View, Remodeled BA with Walk in S...

  27 reviews   Add to Favorites

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


$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


$298 - $412 /night
$2086 - $4186 /week
Spacious Two BR, Two Bath Ocean View Villa (Resort Fees I...

  4 reviews   Add to Favorites

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


$129 - $159 /night
$903 - $1743 /week
Banyan Tree 404:top Floor Direct oceanfront condo

  13 reviews   Add to Favorites

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


$895 - $925 /night
$6265 - $7665 /week
Unobstructed Oceanfront, 3 BR, Private Pool & Spa, Specta...

  2 reviews   Add to Favorites

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


$195 - $205 /night
$1365 - $1960 /week
Oceanfront Condo with breathtaking Ocean and Sunset Views...

  94 reviews   Add to Favorites

Condo: 2 Bedroom, 2 Bathroom, Sleeps 4
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


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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