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Kailua-Kona Vacation Rentals

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


Featured
$380 - $410 /night
$2660 - $4375 /week
Private home with pool, cool elevation, unobstructed Ocea...

  21 reviews   Add to Favorites

Home: 3 Bedroom, 3.5 Bathroom, Sleeps 8
Location: Kailua-Kona, Hawaii, United States


Featured
$215 - $577 /night
$1595 - $3965 /week
Kona Makai 1-301 Direct Oceanfront, Top Floor, Best Corne...

  23 reviews   Add to Favorites

Condo: 2 Bedroom, 2 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
$140 - $185 /night
$980 - $1750 /week
1 BR condo with a loft in oceanfront complex, amazing Oce...

  51 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 Wa...

  74 reviews   Add to Favorites

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


Featured
$138 - $168 /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


$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


$129 - $195 /night
$903 - $2100 /week
Kksr#37 Spacious 3 BR Townhome, Sleeps 6, Close to Pool, ...

  10 reviews   Add to Favorites

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


$190 - $295 /night
$1330 - $2065 /week
Hale Alaula (Sea Village 1105)

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


$132 - $307 /night
$917 - $1883 /week
Casa De Emdeko 332

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


$129 - $199 /night
$903 - $1393 /week
Sea Village 2 Br / 2 Ba Oceanview corner unit

  35 reviews   Add to Favorites

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


$265 - $375 /night
$1855 - $2625 /week
Kona Makai 6201

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


$2160 - $2875 /night
$15120 - $20125 /week
Hale Pua

Home: 6 Bedroom, 6 Bathroom, Sleeps 20
Location: Kailua-Kona, Hawaii, United States


$161 - $492 /night
$1127 - $2933 /week
Kona Reef D32

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


$500 - $730 /night
$3500 - $5110 /week
Hale Aikane

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


$205 - $270 /night
$1435 - $1890 /week
Hale Kalena (Kanaloa 701)

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


$149 - $199 /night
$1043 - $1393 /week
Kona Bali Kai 317 Direct Oceanfront

  55 reviews   Add to Favorites

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


$140 - $170 /night
$980 - $1505 /week
1 BR condo with a loft in Oceanfront complex, amazing Oce...

  41 reviews   Add to Favorites

Condo: 1 Bedroom, 1 Bathroom, Sleeps 5
Location: Kailua-Kona, Hawaii, United States


$155 - $160 /night
$1085 - $1855 /week
Remodeled 1 bedroom Ocean front condo, right down town

  39 reviews   Add to Favorites

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


$185 - $265 /night
$1295 - $1855 /week
Sea Village 1-205-Oceanfront

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


$190 - $295 /night
$1330 - $2065 /week
Hale Ko'aniani (Sea Village 4107)

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


$149 - $279 /night
$1043 - $2100 /week
Kksr5202 Direct Oceanfront, 2Nd Floor, Best Views In The ...

  22 reviews   Add to Favorites

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


$127 - $463 /night
$889 - $2737 /week
Kona Pacific B511

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


$430 - $906 /night
$3009 - $6305 /week
New Listing! Stunning Kona Coast Haven: Ocean Views, Medi...

Home: 4 Bedroom, 4.5 Bathroom, Sleeps 8
Location: Kailua-Kona, Hawaii, United States


$80 - $240 /night
$560 - $1664 /week
Kona Isle B31 Top Floor, Oceanview, & Ac!!!

  17 reviews   Add to Favorites

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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