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Kailua-Kona Skiing Vacation Rentals

64 Kailua-Kona Skiing Vacation Rentals were found matching your criteria.

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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
$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


$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


$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


$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


$149 - $179 /night
$1043 - $1750 /week
Updated Ocean View Condo with Additional Loft!

  2 reviews   Add to Favorites

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


$118 - $606 /night
$908 - $4150 /week
Royal Sea Cliff#704 Luxury Top Floor Penthouse with Ocean...

  5 reviews   Add to Favorites

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


$325 - $370 /night
$2275 - $2800 /week
Turtle Rock - Ocean Front Cottage with pool

  40 reviews   Add to Favorites

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


$75 - $288 /night
$525 - $1967 /week
Kona Shores#105 Beautifully Appointed Ground Floor Bungalow

  2 reviews   Add to Favorites

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


$90 - $385 /night
$630 - $2633 /week
Casa De Emdeko 324 Gorgeous Top Floor Condo with Ocean View!

  16 reviews   Add to Favorites

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


$94 - $482 /night
$691 - $3298 /week
Sea Village 3317 - 1 BR, Direct Oceanfront, Top Floor, Br...

  45 reviews   Add to Favorites

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


$199 - $300 /night
$1393 - $2450 /week
Experience VIntage Hawaii with an Ocean View and Private ...

  1 reviews   Add to Favorites

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


$1850 - $1850 /night
$12950 - $17150 /week
Oceanfront Luxury, ~ac~ in 5 King Beds+bunkrm, Private Po...

  25 reviews   Add to Favorites

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


$80 - $367 /night
$560 - $2512 /week
Alii Villas 340 Gorgeous Top floor Condo. Wifi! Great price!

  20 reviews   Add to Favorites

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


$125 - $602 /night
$875 - $3959 /week
Krd32 Absolute Oceanfront Top Flr Private

  30 reviews   Add to Favorites

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


$115 - $482 /night
$835 - $3298 /week
Remodeled In 2017! Ocean View, Huge Lanai, Walk To Town! ...

  6 reviews   Add to Favorites

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


$219 - $963 /night
$1533 - $6591 /week
Kksr5304 !! Direct Ocean Front, Top Floor, W/Loft! Best C...

  34 reviews   Add to Favorites

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


$80 - $329 /night
$560 - $2253 /week
Kalanikai- Corridor Ocean View, 1st floor in the heart of...

  6 reviews   Add to Favorites

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


$76 - $385 /night
$580 - $2633 /week
Casa De Emdeko 330 - Deluxe, Top Floor, Oceanview, Ac, Ex...

  28 reviews   Add to Favorites

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


$95 - $623 /night
$700 - $4267 /week
Kona Makai 3-302 Top Floor, Gorgeous 1 BR + Loft and 2 La...

  32 reviews   Add to Favorites

Condo: 1 Bedroom, 1 Bathroom, Sleeps 6
Location: Kailua-Kona, Hawaii, United States


$115 - $520 /night
$805 - $3559 /week
Kksr 185 Direct Oceanfront Townhome, Wifi, A True Gem

  37 reviews   Add to Favorites

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


$80 - $198 /night
$560 - $1953 /week
Kona Makai 3-203 2nd Flr, Ocean View, Remodeled BA w/ Wal...

  29 reviews   Add to Favorites

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


$139 - $575 /night
$973 - $3936 /week
Kksr#4 Direct Oceanfront Townhome! Walk to the Beach! Rem...

  3 reviews   Add to Favorites

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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