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Kailua-Kona Vacation Rentals

198 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
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Listings 101 - 125 of 198
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1 bedroom Vacation Rental Condo in Kailua-Kona - Ocean View
Condo: 1 Bedroom, 1 Bathroom, Sleeps 2
Location: Kailua-Kona, Hawaii, United States
Description: Stellar ocean views, quiet, secluded, lovely. Bedding Configuration: 1 King Additional Features: * Convenience: Nearby Grocery, Shopping, Snorkel... Learn More
Rates
$125 - $185 night
$875 - $1295 week


Non Smoking   High-Speed Internet


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1 bedroom Vacation Rental Cabin in Kailua-Kona - Ocean Front
Cabin: 1 Bedroom, 1 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 luxurious estate located on a private c... Learn More
Rates
$239 - $315 night
$1673 - $2205 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 4
Location: Kailua-Kona, Hawaii, United States
Description: Come and join us in paradise at unit #107 and enjoy the fragrant plumeria drifting on warm tropical Hawaiian Breezes. Relax and let the Hawaiian su... Learn More
Rates
$85 - $95 night
$595 - $840 week


Non Smoking


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3 bedroom Vacation Rental Home in Kailua-Kona - Ocean View
Home: 3 Bedroom, 4 Bathroom, Sleeps 6
Location: Kailua-Kona, Hawaii, United States
Description: Welcome to Blue Hawaii. Luxury is really affordable in Kona and Blue Hawaii has it all. Kona's premier vacation home overlooking the beautiful blu... Learn More
Rates
$2905 - $3992 week


Non Smoking   Swimming Pool   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: This charming and completely renovated one bedroom, one bath condo is a short distance to downtown Kailua Kona on the Big Island of Hawaii. From yo... Learn More
Rates
$89 - $109 night
$623 - $1050 week


Non Smoking


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3 bedroom Vacation Rental Cabin in Kailua-Kona - Ocean Front
Cabin: 3 Bedroom, 2 Bathroom, Sleeps 8
Location: Kailua-Kona, Hawaii, United States
Description: This recently remodeled estate offers the finest in accommodations without having to leave Kona. Enjoy this luxurious estate, located on a private ... Learn More
Rates
$365 - $470 night
$2555 - $3290 week


Non Smoking   High-Speed Internet


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3 bedroom Vacation Rental Home in Kailua-Kona - Ocean View
Home: 3 Bedroom, 4 Bathroom, Sleeps 6
Location: Kailua-Kona, Hawaii, United States
Description: This impressive home boasts 3800 sq-ft of interior living area, inc: great room, dining room, totally equipped kitchen, 3 bedrooms all with en-suit... Learn More
Rates
$2765 - $6265 week


Non Smoking


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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... Learn More
Rates
$265 - $355 night
$1855 - $2485 week


Non Smoking   High-Speed Internet


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2 bedroom Vacation Rental Condo in Kailua-Kona - Ocean Front
Condo: 2 Bedroom, 2 Bathroom, Sleeps 4
Location: Kailua-Kona, Hawaii, United States
Description: This oceanfront townhouse is beautifullly furnished, very clean, and cozy.Get lost in the sounds of the ocean, while you sit on your lanai or lay i... Learn More
Rates
$95 - $150 night
$665 - $1050 week


Non Smoking   High-Speed Internet


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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: This unit will provide you with a calm and relaxing Hawaiian vacation. It's on the 5th Floor (top floor) and is quiet. The Master Bedroom is quite ... Learn More
Rates
$95 - $110 night
$665 - $910 week


Non Smoking


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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: This newer home is the perfect vacation destination for families coming to the Big Island of Hawaii. Located halfway between the Kona International... Learn More
Rates
$229 - $249 night
$1603 - $2275 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: You?ve found your most ideal place to spend your next vacation or even your honeymoon here on the Big Island of Hawaii! And it?s very affordable! P... Learn More
Rates
$125 - $140 night
$875 - $980 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: Only a palm tree and a stone's throw separate you from the Pacific sunsets at this beautiful, newly-renovated oceanfront condominium. The upscale 1... Learn More
Rates
$135 - $165 night
$945 - $1393 week


Non Smoking


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4 bedroom Vacation Rental Condo in Kailua-Kona
Condo: 4 Bedroom, 3 Bathroom, Sleeps 8
Location: Kailua-Kona, Hawaii, United States
Description: SPECTACULAR OCEANFRONT TOWNHOME - Welcome to Hale Kai O'Kona #7, an Oceanfront Island Home. Hale Kai O'Kona is an exclusive oceanfront Hawaii vacat... Learn More
Rates
$350 - $350 night
$2450 - $2975 week


Non Smoking


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4 bedroom Vacation Rental Home in Kailua-Kona
Home: 4 Bedroom, 4 Bathroom, Sleeps 8
Location: Kailua-Kona, Hawaii, United States
Description: This home embodies iconic and liveable Lucky Bennett design. An exquisite 4 bedroom 3.5 bath home, gated & found in the small beach community of Ka... Learn More
Rates
$350 - $420 night
$2450 - $2940 week


Non Smoking   Swimming Pool   High-Speed Internet


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2 bedroom Vacation Rental Condo in Kailua-Kona - Ocean Front
Condo: 2 Bedroom, 2 Bathroom, Sleeps 4
Location: Kailua-Kona, Hawaii, United States
Description: This 2 bedroom 2 bath at Kona Alii is a penthouse unit. Fully equiped to also include a sun deck! Star gaze or get a serious tan! The Ocean Front... Learn More
Rates
$130 - $255 night
$910 - $1785 week


Non Smoking


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3 bedroom Vacation Rental Home in Kailua-Kona - Ocean View
Home: 3 Bedroom, 2 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... Learn More
Rates
$175 - $250 night
$1225 - $1750 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: Welcome to Casa de Emdeko #311 ~ a two bedroom, two baths, which was recently remodeled.This great island-style vacation rental rests in a lush tro... Learn More
Rates
$120 - $150 night
$840 - $1120 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: Country Club Villas has 3 swimming pools and 3 jacuzzis that all have wonderful ocean and golf course views. There are also 2 tennis courts. Spect... Learn More
Rates
$145 - $165 night
$1015 - $1365 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: 1 bedroom condo Unit Description: This one bedroom comes equipped with a queen bed and a full size wall bed in the living area. Amenities included... Learn More
Rates
$152 - $213 night
$1064 - $1491 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: Lovely oceanfront townhouse. Enjoy the waves breaking right in front on your lanai. This is a beautiful well maintained oceanfront condo with all... Learn More
Rates
$217 - $315 night
$1062 - $1693 week


Non Smoking   High-Speed Internet


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3 bedroom Vacation Rental Condo in Kailua-Kona
Condo: 3 Bedroom, 3 Bathroom, Sleeps 8
Location: Kailua-Kona, Hawaii, United States
Description: The grounds of the complex are lush with palm trees and flowering bushes. There is a wonderful pool and Jacuzzi on the grounds. It is conveniently ... Learn More
Rates
$175 - $190 night
$1225 - $1330 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: Welcome to Hui o Kulia, where the view from A-15 at the Kona Reef will take your breath away. Relax and watch the whales and dolphins swim by, crui... Learn More
Rates
$145 - $165 night
$1015 - $1393 week


Non Smoking


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1 bedroom Vacation Rental Condo in Kailua-Kona - Ocean View
Condo: 1 Bedroom, 2 Bathroom, Sleeps 2
Location: Kailua-Kona, Hawaii, United States
Description: This is a 1 bedroom, 2 bath condo in the Kona Pacific condo in the town of Kailua Kona on the Big Island. This condo has been renovated beautifully... Learn More
Rates
$109 - $119 night
$763 - $1050 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: Alii Villas is a highly sought after condominium complex in Kona, Hawaii. The location is perfect. It is in walking distance to town where there ar... Learn More
Rates
$95 - $110 night
$665 - $770 week


Non Smoking   High-Speed Internet


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Listings 101 - 125 of 198
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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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