More Filters

Price per Night Range

$0
$1000+


Accommodations


Interest


Kailua-Kona Skiing Vacation Rentals

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

Filters Applied:
  • clear filterSkiing
Search results are filtered by the criteria above. Click "clear filter" next to criteria to remove. Or clear all filters.

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
$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
$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


$100 - $110 /night
$700 - $1050 /week
Keauhou Akahi 210- Top floor spacious condo that sleeps 4...

  5 reviews   Add to Favorites

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


$85 - $85 /night
$595 - $1435 /week
Kalanikai- Corridor Ocean View, 1st floor in the heart of...

  4 reviews   Add to Favorites

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


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

  34 reviews   Add to Favorites

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


$95 - $110 /night
$665 - $1225 /week
Kona Isle C21 2nd floor, Oceanview, Ac, Amazing Price!

  6 reviews   Add to Favorites

Condo: 1 Bedroom, 1 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


$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


$95 - $115 /night
$665 - $1435 /week
Amazing Oceanfront Kona Isle D21

  26 reviews   Add to Favorites

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


$139 - $169 /night
$973 - $1435 /week
Kbv 304 Top Floor Condo: Huge Oceanview, Elevators, Beach...

  12 reviews   Add to Favorites

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


$95 - $110 /night
$665 - $1225 /week
Kona Isle B8 Ground Floor, Updated, Amazing Price

  16 reviews   Add to Favorites

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


$120 - $150 /night
$840 - $1225 /week
5-Star Kona Coast Resort Gorgeous, King Bed, Ac, Spacious!

  15 reviews   Add to Favorites

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


$189 - $219 /night
$1323 - $2093 /week
New to the Vacation Rental Market! Oceanview Walua Rd Vac...

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


$169 - $209 /night
$1183 - $1953 /week
Royal Sea Cliff#704 Luxury Top Floor Penthouse with Ocean...

  4 reviews   Add to Favorites

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


$100 - $120 /night
$700 - $1225 /week
Casa De Emdeko 332- Amazing Oceanview, Top Floor, Ac incl...

  18 reviews   Add to Favorites

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


$125 - $205 /night
$875 - $1953 /week
Kksr2204 Direct Oceanfront Corner Unit!!! 2nd Floor, Wifi...

  45 reviews   Add to Favorites

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


$95 - $115 /night
$665 - $1435 /week
Alii Villas 221 Gorgeous 2nd flr condo with Ocean View, W...

  1 reviews   Add to Favorites

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


$150 - $175 /night
$1050 - $1953 /week
Sv4205 2 BR, Direct Oceanfront, Wifi, Breathtaking View.

  33 reviews   Add to Favorites

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


$325 - $325 /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


$125 - $169 /night
$875 - $1953 /week
Kksr 185 Direct Oceanfront Townhome, Wifi, A True Gem

  34 reviews   Add to Favorites

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


$95 - $110 /night
$665 - $1435 /week
Alii Villas 340 Gorgeous Top floor Condo. Wifi! Great price!

  17 reviews   Add to Favorites

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


$95 - $120 /night
$665 - $1435 /week
Km2102 Beautifully Renovated, Ground Floor, Wifi!

  33 reviews   Add to Favorites

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


$340 - $340 /night
$2380 - $2800 /week
Pahukoa Hale - Direct Ocean Front Hawaiian Style home in ...

  35 reviews   Add to Favorites

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


$110 - $135 /night
$770 - $1435 /week
Kms109 Groundfloor, Direct Oceanfront, Wifi, Kona Magic S...

  36 reviews   Add to Favorites

Condo: Studio, 1 Bathroom, Sleeps 3
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.

Hawaii (Big Island) Top Cities

Vacation Rental Deals and Specials

Find additional Vacation Rentals: