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Kailua-Kona Vacation Rentals

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


$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


$1695 - $1850 /night
$11865 - $13300 /week
Deluxe Oceanfront 5 BR Estate with Pool & Spa, Paradise!

  1 reviews   Add to Favorites

Home: 5 Bedroom, 4 Bathroom, Sleeps 10
Location: Kailua-Kona, Hawaii, United States


$139 - $179 /night
$973 - $1750 /week
2/1.5 Two Story Ocean View Condo! *take Advantage Of Our ...

  1 reviews   Add to Favorites

Condo: 2 Bedroom, 1.5 Bathroom, Sleeps 5
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


$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


$100 - $120 /night
$700 - $1050 /week
Casa De Emdeko 321 Remodeled , Wifi, Top Floor, Ac includ...

  8 reviews   Add to Favorites

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


$129 - $191 /night
$903 - $2100 /week
Oceanfront one bedroom unit with amazing views

  8 reviews   Add to Favorites

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


$110 - $120 /night
$770 - $1225 /week
Kona Plaza

  29 reviews   Add to Favorites

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


$117 - $162 /night
$799 - $1344 /week
Kalani Kai Walk to Ocean shops and restaurants. Affordabl...

  13 reviews   Add to Favorites

Condo: 1 Bedroom, 1 Bathroom, Sleeps 3
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


$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


$241 - $304 /night
$1665 - $2087 /week
Kona Surf & Racquet Tropical, oceanfront paradise. Perfec...

  23 reviews   Add to Favorites

Condo: 2 Bedroom, 2 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


$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


$120 - $135 /night
$840 - $1050 /week
Kona Pacific Value

  35 reviews   Add to Favorites

Condo: 1 Bedroom, 2 Bathroom, Sleeps 2
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


$895 - $925 /night
$6265 - $7665 /week
Unobstructed Oceanfront, 3 BR, Private Pool & Spa, Specta...

  2 reviews   Add to Favorites

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



$1393 - $1925 /week
Luxurious 3 BR Townhome with Lovely Ocean Views! Close to...

  6 reviews   Add to Favorites

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


$425 - $450 /night
$2975 - $3150 /week
Upscale 3 bedroom bungalow in oceanfront estate

  8 reviews   Add to Favorites

Condo: 3 Bedroom, 2 Bathroom, Sleeps 8
Location: Kailua-Kona, Hawaii, United States


$1660 - $1750 /night
$11620 - $16100 /week
Oceanfront Luxury, a/c in 5 King Beds+bunkrm, Private Poo...

  19 reviews   Add to Favorites

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


$184 - $275 /night
$1256 - $2501 /week
Mauna Loa Village 55 Luxury condo near Kona town, ocean a...

  4 reviews   Add to Favorites

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


$3425 - $4565 /night
$23975 - $31955 /week
Alii Honu Kai

Home: 3 Bedroom, 4 Bathroom, Sleeps 10
Location: Kailua-Kona, Hawaii, United States


$425 - $450 /night
$2975 - $4165 /week
Large 4 BR home, Private Pool, Spectacular Ocean & Sunset...

  3 reviews   Add to Favorites

Home: 4 Bedroom, 3.5 Bathroom, Sleeps 9
Location: Kailua-Kona, Hawaii, United States


$140 - $186 /night
$980 - $1400 /week
2 bedroom condo in oceanfront complex, great Ocean views

  27 reviews   Add to Favorites

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


$125 - $145 /night
$875 - $1435 /week
Holualoa Bay Villas: 106 Beautiful Oceanview, Ac, Elevato...

  4 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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