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Kailua-Kona Vacation Rentals

151 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 26 - 50 of 151
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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
$160 - $232 night
$1081 - $1783 week


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2 bedroom Vacation Rental Home in Kailua-Kona - Ocean View
Home: 2 Bedroom, 2 Bathroom, Sleeps 4
Location: Kailua-Kona, Hawaii, United States
Description: SUPER SPECIAL RATES FOR APRIL, MAY & JUNE 250 PER NIGHT AND 1,500 PER WEEK ?KONA SUNSETS VISTAS? IS A WONDERFUL VACATION HOME IN A QUIET, CENTRALL...
Rates
$267 - $378 night
$1803 - $2583 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: Oceanfront Condo with breathtaking Ocean and Sunset Views, 2 BR, 2 bath Casa De Emdeko, an oceanfront condominium complex, is located on famous Al...
Rates
$195 - $242 night
$1365 - $1960 week


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1 bedroom Vacation Rental Condo in Kailua-Kona - Ocean Front
Condo: 1 Bedroom, 1 Bathroom, Sleeps 4
Location: Kailua-Kona, Hawaii, United States
Description: Kona Isle E23 Direct Ocean Front, Wifi, 2nd floor, Gorgeous 1/1 E23 at the Kona Isle is a beautiful DIRECT OCEANFRONT property on the 2nd floor of...
Rates
$105 - $140 night
$735 - $1435 week


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Studio Vacation Rental Condo in Kailua-Kona - Ocean Front
Condo: Studio, 1 Bathroom, Sleeps 3
Location: Kailua-Kona, Hawaii, United States
Description: Kms109 Groundfloor, Direct Oceanfront, Wifi, Kona Magic Sands Welcome to DIRECT oceanfront living! Unit#109 is a wonderful ground floor property a...
Rates
$110 - $135 night
$770 - $1435 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: The Kona Makai is one of Kona's favorite repeat destinations. This oceanfront community offers ocean views to no end. This unit is one of the 6 p...
Rates
$180 - $265 night
$1260 - $2170 week


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2 bedroom Vacation Rental Cabin in Kailua-Kona - Ocean Front
Cabin: 2 Bedroom, 2 Bathroom, Sleeps 4
Location: Kailua-Kona, Hawaii, United States
Description: This recently remodeled estate offers the finest in accommodations without having to leave Kona. Enjoy this estate, located on a private cove featu...
Rates
$265 - $321 night
$1855 - $2247 week


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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: B8 at the Kona Isle is a wonderful option for your Hawaiian Vacation! TAKE A VIRTUAL TOUR OF THE PROPERTY! **If link is not seen above, please in...
Rates
$95 - $110 night
$665 - $1225 week


Non Smoking


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3 bedroom Vacation Rental Home in Kailua-Kona - Ocean View
Home: 3 Bedroom, 3 Bathroom, Sleeps 6
Location: Kailua-Kona, Hawaii, United States
Description: This lavishly appointed single level home with 3 air-conditioned bedroom suites comes with all the modern bells and whistles made just for entertai...
Rates
$750 - $1250 night
$5250 - $9800 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: Kona Makai is one of Kona's most popular resorts. Kona Makai has tennis courts, a gorgeous oceanfront pool plus hot tub and a super location. Enjoy...
Rates
$141 - $197 night
$936 - $1521 week


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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


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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: Kanaloa at Kona offers a lushly landscaped 18-acre oceanfront setting overlooking stunning Keauhou Bay. The complex offers 24 hour gated security, ...
Rates
$165 - $185 night
$1155 - $1540 week


Non Smoking


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1 bedroom Vacation Rental Condo in Kailua-Kona - Ocean Front
Condo: 1 Bedroom, 1 Bathroom, Sleeps 2
Location: Kailua-Kona, Hawaii, United States
Description: This perfectly located deluxe one bedroom unit with amazing ocean views from the lanai, has been fully redecorated and upgraded. All new appliance...
Rates
$145 - $164 night
$1015 - $1400 week


Non Smoking


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1 bedroom Vacation Rental Condo in Kailua-Kona - Ocean Front
Condo: 1 Bedroom, 1 Bathroom, Sleeps 4
Location: Kailua-Kona, Hawaii, United States
Description: Remodeled 1 BR Ocean View condo in Oceanfront Complex Close to Town This recently remodeled perfectly located one bedroom, one bath ocean view con...
Rates
$97 - $120 night
$679 - $945 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 Coast Resort#8-204 is a gem in the resort. Beautifully maintained. Spacious. Air conditioning, King Sized bed, Big lanai for entertaining! Gue...
Rates
$120 - $150 night
$840 - $1225 week


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1 bedroom Vacation Rental Condo in Kailua-Kona
Condo: 1 Bedroom, 1.5 Bathroom, Sleeps 4
Location: Kailua-Kona, Hawaii, United States
Description: Right in the middle of town in walking distance from the Kona Pier. Remodeled and AC included. The pictures say it all! The unit has a Queen siz...
Rates
$145 - $170 night
$1015 - $1540 week


Non Smoking


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2 bedroom Vacation Rental Cottage in Kailua-Kona - Ocean View
Cottage: 2 Bedroom, 3 Bathroom, Sleeps 6
Location: Kailua-Kona, Hawaii, United States
Description: Under new management, Pacific Edge Kona, a gracious oceanfront island style beach home! From the lanai of this waterfront Cottage see breaching hum...
Rates
$250 - $265 night
$1750 - $1855 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 A4 Beautifully upgraded condo. Ground Floor, Wifi, Ac! A4 at the Kona Isle is undeniably one of the BEST valued property in the complex....
Rates
$75 - $90 night
$525 - $1225 week


Non Smoking


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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: 1 bedroom/1 bathroom resort suites Unit Description: The 1 bedroom/1 bathroom resort suites at Kona Reef come with amenities to ensure your stay i...
Rates
$162 - $249 night
$1134 - $1743 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: Sea Village 2nd floor Direct Oceanfront unit with extensive upgrades & A/C Lovely oceanfront 2nd floor unit totally upgraded and showing beautiful...
Rates
$159 - $189 night
$1113 - $1603 week


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1 bedroom Vacation Rental Condo in Kailua-Kona - Ocean Front
Condo: 1 Bedroom, 1 Bathroom, Sleeps 4
Location: Kailua-Kona, Hawaii, United States
Description: Kona Makai 5305 Top Floor, Ocean View, 1 BR + Loft and 2 Lanais! **new** This is a newer condo in our inventory! Top floor, spacious condo with a ...
Rates
$95 - $120 night
$665 - $1435 week


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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: Kona Surf & Racquet Tropical Gardens Views on a Private Lanai. Sit on your private lanai with a delicious cup of Kona coffee and enjoy the birds s...
Rates
$149 - $232 night
$1003 - $1588 week


Non Smoking


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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: C21 at the Kona Isle is a great place to have your Hawaiian Vacation! 2nd floor unit in building C, gives you a nice partial ocean view on your lan...
Rates
$95 - $110 night
$665 - $1225 week


Non Smoking   High-Speed Internet


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1 bedroom Vacation Rental Condo in Kailua-Kona - Ocean Front
Condo: 1 Bedroom, 1 Bathroom, Sleeps 2
Location: Kailua-Kona, Hawaii, United States
Description: Tastefully furnished ; you will love this first floor condo on Alii Drive. C3 is on the first floor so no stairs and you can walk from your lanai r...
Rates
$165 - $165 night
$612 - $1274 week


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1 bedroom Vacation Rental Condo in Kailua-Kona - Ocean View
Condo: 1 Bedroom, 2 Bathroom, Sleeps 4
Location: Kailua-Kona, Hawaii, United States
Description: This local has all the sights and sounds of the best Kona has to offer. Enjoy this 1 bedroom, 2 bath unit right in town. You can also enjoy the ...
Rates
$135 - $170 night
$945 - $1680 week


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Listings 26 - 50 of 151
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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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