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Kailua-Kona Vacation Rentals

141 Kailua-Kona Vacation Rentals were found matching your criteria. These vacation rentals are presented by their owners or managers. Please click on the photos or links below, then contact them directly with your inquiries. Use the search criteria box on the left of the page to refine your search within Kailua-Kona, Hawaii (Big Island), Hawaii, United States.
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Hawaii (Big Island) Top Cities
Listings 101 - 125 of 141
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4 bedroom Vacation Rental Home in Kailua-Kona - Ocean View
Home: 4 Bedroom, 3 Bathroom, Sleeps 8
Location: Kailua-Kona, Hawaii, United States
Description: Kona Ohana Hale a charming single level home with a private solar heated pool. The home is part of a cul-de-sac in the small community of Hualalai ...
Rates
$295 - $405 night
$2065 - $3675 week


Non Smoking   High-Speed Internet


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2 bedroom Vacation Rental Condo in Kailua-Kona
Condo: 2 Bedroom, 2 Bathroom, Sleeps 4
Location: Kailua-Kona, Hawaii, United States
Description: Keauhou Punahele Spacious Kona Condo, Nice View, good location This condo is beautifully furnished.in a nice location. The master suite is huge wi...
Rates
$1029 - $1393 week


Non Smoking   High-Speed Internet


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1 bedroom Vacation Rental Condo in Kailua-Kona - Ocean View
Condo: 1 Bedroom, 1 Bathroom, Sleeps 4
Location: Kailua-Kona, Hawaii, United States
Description: Second floor condo with great ocean views. This condo offers all the comforts of home in a tropical paradise. Enjoy the beautiful pool with amazi...
Rates
$88 - $153 night
$597 - $1312 week


Non Smoking


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6 bedroom Vacation Rental Home in Kailua-Kona - Ocean View
Home: 6 Bedroom, 6 Bathroom, Sleeps 20
Location: Kailua-Kona, Hawaii, United States
Description: Luxury Oceanfront Home, with Private Pool, Spa and Spectacular Views Hale Pua (?House of Flowers?) features five king bedrooms plus one bunkroom w...
Rates
$1650 - $2095 night
$11550 - $16100 week


Non Smoking   Swimming Pool


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1 bedroom Vacation Rental Condo in Kailua-Kona
Condo: 1 Bedroom, 2 Bathroom, Sleeps 4
Location: Kailua-Kona, Hawaii, United States
Description: Upgraded one bedroom oasis looking right over the ocean. You will love the unit, you will love the location, walking distance to everywhere in town...
Rates
$130 - $165 night
$910 - $1505 week


Non Smoking


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1 bedroom Vacation Rental Condo in Kailua-Kona - Ocean Front
Condo: 1 Bedroom, 1 Bathroom, Sleeps 6
Location: Kailua-Kona, Hawaii, United States
Description: The Kona Makai is a beautiful sunny highly sought after Ocean Front Complex located on famous Alii Drive just 1.3 miles from Kailua Village. The K...
Rates
$95 - $120 night
$665 - $1050 week


Non Smoking   High-Speed Internet


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3 bedroom Vacation Rental Condo in Kailua-Kona - Ocean View
Condo: 3 Bedroom, 2 Bathroom, Sleeps 8
Location: Kailua-Kona, Hawaii, United States
Description: This estate, located on a private cove features a pool, spa and koi pond and offers the finest in accommodations without having to leave Kona. Th...
Rates
$365 - $446 night
$2555 - $3122 week


Non Smoking


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1 bedroom Vacation Rental Condo in Kailua-Kona
Condo: 1 Bedroom, 1 Bathroom, Sleeps 4
Location: Kailua-Kona, Hawaii, United States
Description: Kona Isle Oceanfront complex, affordable and comfortable good location #b21 Book online and receive a 5% discount excluding Ironman and end of yea...
Rates
$1299 - $1312 week


Non Smoking


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1 bedroom Vacation Rental Condo in Kailua-Kona
Condo: 1 Bedroom, 1 Bathroom, Sleeps 4
Location: Kailua-Kona, Hawaii, United States
Description: This lovely, recently remodeled vacation condo offers first floor connivance at Kona Makai. The interior is nicely furnished is and the condo of co...
Rates
$132 - $164 night
$909 - $1350 week


Non Smoking


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3 bedroom Vacation Rental Condo in Kailua-Kona
Condo: 3 Bedroom, 2.5 Bathroom, Sleeps 6
Location: Kailua-Kona, Hawaii, United States
Description: Mauna Loa Village 55 Luxury condo near Kona town, ocean and beach Affordable Live where Hawaii's royalty played, Mauna Loa Village at the Honua Re...
Rates
$156 - $228 night
$1070 - $1785 week


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2 bedroom Vacation Rental Condo in Kailua-Kona - Ocean View
Condo: 2 Bedroom, 2 Bathroom, Sleeps 6
Location: Kailua-Kona, Hawaii, United States
Description: Holualoa Bay Villas: 106 Beautiful Oceanview, Ac, Elevators, Wifi! Holualoa Bay Villas#106 is a brand new rental in our inventory, that Knutson & ...
Rates
$125 - $145 night
$875 - $1435 week


Non Smoking   High-Speed Internet


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3 bedroom Vacation Rental Home in Kailua-Kona
Home: 3 Bedroom, 4 Bathroom, Sleeps 8
Location: Kailua-Kona, Hawaii, United States
Description: This plantation style home is centrally located on Alii Drive. Walk downtown to Kailua-Kona for dinner or to enjoy a nearby beach. It's fully furn...
Rates
$568 - $739 night
$3654 - $5501 week


Non Smoking   Swimming Pool


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2 bedroom Vacation Rental Condo in Kailua-Kona
Condo: 2 Bedroom, 2 Bathroom, Sleeps 6
Location: Kailua-Kona, Hawaii, United States
Description: Oceanfront-Incredible Views, Surf Break & Romantic Sunsets at Bali Kai 223 Lovely Oceanfront upgraded second floor 2bd2bth unit in Kona Bali Kai o...
Rates
$149 - $169 night
$1043 - $1225 week


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2 bedroom Vacation Rental Condo in Kailua-Kona
Condo: 2 Bedroom, 2 Bathroom, Sleeps 4
Location: Kailua-Kona, Hawaii, United States
Description: This experience is one of a kind- looks like a cottage by the sea. Enjoy the crashing surf at one of Kona's best resorts. If you need more space yo...
Rates
$144 - $232 night
$990 - $1782 week


Non Smoking   High-Speed Internet


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1 bedroom Vacation Rental Condo in Kailua-Kona - Ocean View
Condo: 1 Bedroom, 1 Bathroom, Sleeps 4
Location: Kailua-Kona, Hawaii, United States
Description: Kona Isle B8 Ground Floor, Updated, Amazing Price $79.00 all of September!! This renovated, tiled ground floor unit is excellent for a fabulous ha...
Rates
$95 - $110 night
$665 - $1050 week


Non Smoking


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2 bedroom Vacation Rental Condo in Kailua-Kona
Condo: 2 Bedroom, 2 Bathroom, Sleeps 6
Location: Kailua-Kona, Hawaii, United States
Description: Across from the ocean on Alii Drive. Close to living area with 2 bedrooms and 2 baths and a loft with bed and lounge area. Enclosed swimming pool ...
Rates
$125 - $125 night
$875 - $1050 week


Non Smoking


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1 bedroom Vacation Rental Condo in Kailua-Kona - Ocean View
Condo: 1 Bedroom, 2 Bathroom, Sleeps 3
Location: Kailua-Kona, Hawaii, United States
Description: The Kona Alii is located right in the heart of Kailua Kona. Enjoy waking up to the crashing ocean with a cup of world famous Kona Coffee! This ...
Rates
$140 - $165 night
$980 - $1715 week


Non Smoking


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2 bedroom Vacation Rental Condo in Kailua-Kona
Condo: 2 Bedroom, 2 Bathroom, Sleeps 4
Location: Kailua-Kona, Hawaii, United States
Description: Keauhou Punahele is a very spacious condo offering two bedrooms and two bathrooms. With terrific views of the golf course, the Pacific. And of co...
Rates
$133 - $188 night
$912 - $1393 week


Non Smoking


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1 bedroom Vacation Rental Condo in Kailua-Kona
Condo: 1 Bedroom, 1 Bathroom, Sleeps 2
Location: Kailua-Kona, Hawaii, United States
Description: Stunning direct oceanfront views in this newly remodeled one bedroom will make you never want to leave.The rhythmic sounds of crashing waves genera...
Rates
$95 - $115 night
$665 - $1435 week


Non Smoking   High-Speed Internet


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2 bedroom Vacation Rental Condo in Kailua-Kona
Condo: 2 Bedroom, 2 Bathroom, Sleeps 6
Location: Kailua-Kona, Hawaii, United States
Description: Beautiful remodeled 2 BR condo located on Robert Trent Jones Golf Course This quiet beautifully remodeled 1400sf 2 bedroom condo is located at a c...
Rates
$115 - $165 night
$805 - $1155 week


Non Smoking


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2 bedroom Vacation Rental Condo in Kailua-Kona - Ocean View
Condo: 2 Bedroom, 2 Bathroom, Sleeps 4
Location: Kailua-Kona, Hawaii, United States
Description: Spacious Two BR, Two Bath Ocean View Elegance (Resort Fees Included) On the sun-drenched Kohala coast on the Big Island of Hawaii, the elements ha...
Rates
$220 - $250 night
$1540 - $2310 week


Non Smoking   High-Speed Internet


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2 bedroom Vacation Rental Condo in Kailua-Kona - Ocean View
Condo: 2 Bedroom, 2 Bathroom, Sleeps 6
Location: Kailua-Kona, Hawaii, United States
Description: Holualoa Bay Villas Great Ocean View Close to Turtle Beach #203 An almost oceanfront condo with great views. There is a small beach across the ro...
Rates
$144 - $177 night
$990 - $1587 week


Non Smoking   High-Speed Internet


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1 bedroom Vacation Rental Condo in Kailua-Kona
Condo: 1 Bedroom, 1 Bathroom, Sleeps 4
Location: Kailua-Kona, Hawaii, United States
Description: Casa De Emdeko 204 - Air Conditioning! Elevators! Oceanfront Complex! Casa De Emdeko offers owners and guests the perfect blend of Hawaiian ambian...
Rates
$100 - $120 night
$700 - $1435 week


Non Smoking


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3 bedroom Vacation Rental Home in Kailua-Kona - Ocean View
Home: 3 Bedroom, 2.25 Bathroom, Sleeps 6
Location: Kailua-Kona, Hawaii, United States
Description: This spacious private three bedroom two and a quarter bath home offers lots of wide-open spaces and million dollar oceanviews for your tropical get...
Rates
$175 - $225 night
$1225 - $2065 week


Non Smoking


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1 bedroom Vacation Rental Condo in Kailua-Kona - Ocean View
Condo: 1 Bedroom, 1 Bathroom, Sleeps 3
Location: Kailua-Kona, Hawaii, United States
Description: Kalani Kai Walk to Ocean shops and restaurants. Affordable #321 Great location right in Historic Kailua Village. Walk to Kamakahonu Beach the star...
Rates
$88 - $153 night
$597 - $1273 week


Non Smoking   High-Speed Internet


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Listings 101 - 125 of 141
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This map is intended to be used as a reference only.
Please confirm the exact location with the property owner or manager.
 
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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