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Kailua-Kona Vacation Rentals

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


$300 - $350 /night
$2100 - $2625 /week
Ono Hale: Gorgeous Home with pool. Breathtaking ocean views.

  11 reviews   Add to Favorites

Home: 3 Bedroom, 2.5 Bathroom, Sleeps 8
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


$500 - $525 /night
$3500 - $4550 /week
Oceanfront 3 BR home with 180 degrees unobstructed views ...

  7 reviews   Add to Favorites

Home: 3 Bedroom, 2.5 Bathroom, Sleeps 7
Location: Kailua-Kona, Hawaii, United States


$165 - $185 /night
$1155 - $1540 /week
Large 2 BR, 2 bath condo with Ac, beautiful Garden and Go...

  35 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


$75 - $90 /night
$525 - $1225 /week
Kona Isle A4 Beautifully upgraded condo. Ground Floor, Wi...

  26 reviews   Add to Favorites

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


$429 - $449 /night
$3003 - $4025 /week
Outstanding 4 Br / 3 Ba Oceanfront Home with saltwater "Q...

  28 reviews   Add to Favorites

Home: 4 Bedroom, 3 Bathroom, Sleeps 8
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


$125 - $150 /night
$875 - $1435 /week
Casa De Emdeko 111 - Groundfloor, Spacious 2bed/2 bath w/...

  7 reviews   Add to Favorites

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


$499 - $499 /night
$3493 - $4550 /week
Alii Point - Luxury Villa in Private Oceanfront Community

  12 reviews   Add to Favorites

Home: 3 Bedroom, 2 Bathroom, Sleeps 6
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


$204 - $222 /night
$1108 - $1653 /week
Keauhou Punahele Ocean View condo near Kona town

  8 reviews   Add to Favorites

Condo: 2 Bedroom, 3 Bathroom, Sleeps 6
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


$160 - $160 /night
$1120 - $1995 /week
Beautifully remodeled 1 BR oceanfront condo with amazing ...

  3 reviews   Add to Favorites

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


$95 - $110 /night
$665 - $1225 /week
Kona Isle B31 Top Floor, Oceanview, & Ac!!!

  10 reviews   Add to Favorites

Condo: 1 Bedroom, 1 Bathroom, Sleeps 4
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


$135 - $135 /night
$945 - $1330 /week
1 BR condo with a loft in oceanfront complex, amazing Oce...

  22 reviews   Add to Favorites

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


$125 - $155 /night
$875 - $1575 /week
Large 2 bedroom, 2 bath condo right down town

  5 reviews   Add to Favorites

Condo: 2 Bedroom, 3 Bathroom, Sleeps 6
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


$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


$120 - $130 /night
$840 - $1435 /week
Keauhou Punahele C-201 Renovated, Wifi, 2 bed/2 bath, Spa...

  8 reviews   Add to Favorites

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


$155 - $165 /night
$1085 - $1750 /week
Oceanfront one bedroom Honeymoon Cottage, Breathtaking views

  83 reviews   Add to Favorites

Cottage: 1 Bedroom, 1 Bathroom, Sleeps 4
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


$155 - $155 /night
$1085 - $1715 /week
Oceanfront 2 bedroom ground floor condo with amazing views

  40 reviews   Add to Favorites

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


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

  31 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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