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Kailua-Kona Vacation Rentals

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

Featured
$175 - $201 /night
$1225 - $1575 /week
2 BR condo with a loft in oceanfront complex, amazing Oce...

  43 reviews   Add to Favorites

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

Featured
$599 - $629 /night
$4193 - $4865 /week
Hale Honu - Spectacular Oceanfront Home w/ central A/C

  63 reviews   Add to Favorites

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

Featured
$99 - $179 /night
$693 - $1750 /week
Book Your April - September 2017 Stay at $99/Night++! New...

  9 reviews   Add to Favorites

Condo: 2 Bedroom, 1.5 Bathroom, Sleeps 5
Location: Kailua-Kona, Hawaii, United States

Featured
$89 - $89 /night
$623 - $1120 /week
Ac Included! Lovely Island Home- Casa De Emdeko #221

  12 reviews   Add to Favorites

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

Featured

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

  38 reviews   Add to Favorites

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

Featured
$242 - $304 /night
$1666 - $2100 /week
Kona Surf & Racquet Tropical, oceanfront paradise. Perfec...

  30 reviews   Add to Favorites

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

Featured
$125 - $482 /night
$875 - $3298 /week
Holualoa Bay Villas: 106 Beautiful Oceanview, Ac, Elevato...

  8 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!

  7 reviews   Add to Favorites

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

Featured
$170 - $191 /night
$1190 - $1750 /week
Oceanfront 2 BR ground floor condo with amazing Ocean Views

  40 reviews   Add to Favorites

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

Featured
$124 - $173 /night
$843 - $1268 /week
Keauhou Palena Golfers Delight Great location in Kona Par...

  6 reviews   Add to Favorites

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

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

  26 reviews   Add to Favorites

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

Featured
$95 - $140 /night
$665 - $1435 /week
Kona Isle B5 Ground Floor, Very Clean, Ac, Great Price!

  23 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

$115 - $289 /night
$805 - $2449 /week
Casa De Emdeko 211 - 2/2 Ocean View, Ac, Elevators, Spaci...

  16 reviews   Add to Favorites

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

$85 - $110 /night
$595 - $1435 /week
Kona Isle A4 Beautifully appointed condo. Ground Floor, W...

  37 reviews   Add to Favorites

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

$145 - $145 /night
$1015 - $1505 /week
Ocean View in heart of Kailua-Kona, 2bd/2bth

  28 reviews   Add to Favorites

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

$995 - $995 /night
$6965 - $7875 /week
Unobstructed Oceanfront, 3 BR, Private Pool & Spa, Specta...

  3 reviews   Add to Favorites

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

$150 - $230 /night
$1050 - $1610 /week
Sea Village 3-212

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

$170 - $170 /night
$1190 - $2086 /week
Beautifully remodeled 1 BR oceanfront condo with amazing ...

  10 reviews   Add to Favorites

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

$199 - $275 /night
$1393 - $2800 /week
Kilohana Hale *new Vacation Rental* with a Panoramic Ocea...

  2 reviews   Add to Favorites

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

$165 - $191 /night
$1155 - $1750 /week
Oceanfront 2 BR ground floor condo with amazing Ocean views

  45 reviews   Add to Favorites

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

$145 - $160 /night
$1015 - $1386 /week
1 BR condo with a loft in Oceanfront complex, amazing Oce...

  27 reviews   Add to Favorites

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

$175 - $205 /night
$1225 - $1435 /week
Kona Bali Kai 317 - Oceanfront

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

$125 - $482 /night
$875 - $3298 /week
Kksr2204 Direct Oceanfront Corner Unit!!! 2nd Floor, Wifi...

  58 reviews   Add to Favorites

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


$636 - $1350 /week
Kona Isle is great for Whale Watching & relaxing by the o...

  6 reviews   Add to Favorites

Condo: 1 Bedroom, 1 Bathroom, Sleeps 2
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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