More Filters

Price per Night Range

$0
$1000+


Accommodations


Interest


Kailua-Kona Vacation Rentals

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


$165 - $245 /night
$1130 - $1881 /week
Kona Surf & Racquet Amazing Oceanfront townhouse Kona

  10 reviews   Add to Favorites

Condo: 2 Bedroom, 2 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


$184 - $304 /night
$1256 - $2089 /week
Kona Surf & Racquet Townhouse Rare 3 Bd

  16 reviews   Add to Favorites

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


$147 - $215 /night
$1007 - $1552 /week
Awesome Condo in a Great Central Location

  6 reviews   Add to Favorites

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


$105 - $140 /night
$735 - $1435 /week
Kona Isle D4 Ground Floor, Oceanfront Unit, Wifi!

  17 reviews   Add to Favorites

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


$175 - $185 /night
$1225 - $1995 /week
Spacious two BR, two Bath Ocean View condo, close to town

  5 reviews   Add to Favorites

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


$162 - $249 /night
$1134 - $1743 /week
1 bedroom/1 bathroom resort suites

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


$100 - $120 /night
$700 - $1225 /week
Casa De Emdeko 324 Gorgeous Top Floor Condo with Ocean View!

  15 reviews   Add to Favorites

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


$145 - $207 /night
$977 - $1604 /week
Kona Makai Oceanfront complex on Alii Dr

  2 reviews   Add to Favorites

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


$95 - $120 /night
$665 - $1435 /week
Km3302 Top Floor, Gorgeous 1 Bedroom + Loft and 2 Lanais!

  21 reviews   Add to Favorites

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


$145 - $170 /night
$1015 - $1750 /week
Large Oceanfront 1 BR, 2 bath condo right down town, grea...

  24 reviews   Add to Favorites

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


$200 - $225 /night
$1400 - $2135 /week
Spacious three bedroom, home with beautiful Ocean views

  23 reviews   Add to Favorites

Home: 3 Bedroom, 2.25 Bathroom, Sleeps 6
Location: Kailua-Kona, Hawaii, United States


$153 - $245 /night
$1048 - $1675 /week
Oceanfront Complex Lovely Condo

  3 reviews   Add to Favorites

Condo: 2 Bedroom, 2 Bathroom, Sleeps 6
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


$250 - $275 /night
$1750 - $2100 /week
Pacific Edge Kona, a rustic Oceanfront Cottage

  2 reviews   Add to Favorites

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


$174 - $174 /night
$634 - $1344 /week
Great for Whale Watching!

  3 reviews   Add to Favorites

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


$210 - $225 /night
$1470 - $2135 /week
Completely Remodeled, Spacious Oceanfront 2 BR condo w/ A...

  6 reviews   Add to Favorites

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


$149 - $169 /night
$1043 - $1225 /week
Kona Bali Kai 317 Bamboo - Oceanfront

  38 reviews   Add to Favorites

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


Contact Owner
Directly For Rates
Kaulana at Kona, an upscale spacious 3 BR with 190 degree...

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


$450 - $535 /night
$3150 - $4410 /week
Piko Nani (Hilltop Beauty) Estate

  10 reviews   Add to Favorites

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


$88 - $179 /night
$593 - $1385 /week
Kona Big Island Oceanfront Complex - Alii Villas

  7 reviews   Add to Favorites

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


$350 - $350 /night
$2450 - $2765 /week
2 bedroom, 2 bath upscale bungalow in an oceanfront estate

  6 reviews   Add to Favorites

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


$153 - $185 /night
$1046 - $1385 /week
Lovely Affordable Condo in Great Location for Vacation

  2 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...

  44 reviews   Add to Favorites

Condo: 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


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: