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Kailua-Kona Vacation Rentals

122 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 26 - 50 of 122
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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: Kalani Kai 310 Heart of Kailua-Kona Village Nice condo/Kona Hawaii Book online and receive a 5% discount excluding Ironman and end of year holiday... Learn More
Rates
$140 - $194 night
$582 - $1408 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: Beautiful 4 bedroom, 4 bath home with a private unheated pool and an outdoor shower. Unobstructed oceanview of the Kona Coast line. Spectacular st... Learn More
Rates
$495 - $575 night
$3465 - $5425 week


Non Smoking   High-Speed Internet


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1 bedroom Vacation Rental Cottage in Kailua-Kona
Cottage: 1 Bedroom, 1 Bathroom, Sleeps 2
Location: Kailua-Kona, Hawaii, United States
Description: "The Cottage", Mahina Meli Makai (Oceanside Honey Moon) This truly oceanfront (and we mean oceanfront) cottage, is all about a peaceful quiet Roma... Learn More
Rates
$150 - $160 night
$1050 - $1470 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: Lovely Oceanfront 3rd floor 2bd/2bth Beautifully maintained unit in Kona Bali Kai, one of Kona's most popular oceanfront destinations. Watch the do... Learn More
Rates
$149 - $169 night
$1043 - $1225 week


Non Smoking   Handicap Accessible   High-Speed Internet


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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: Enjoy your Hawaiian vacation at this 2 bedroom, 2 bath second-floor unit in a private 15-unit shoreline complex. This unit has flawless ocean views... Learn More
Rates
$175 - $235 night
$1225 - $2100 week


Non Smoking


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2 bedroom Vacation Rental Home in Kailua-Kona - Ocean Front
Home: 2 Bedroom, 2 Bathroom, Sleeps 4
Location: Kailua-Kona, Hawaii, United States
Description: Direct Ocean Front Cottage where you can watch whales and surfers while relaxing on the large sunning deck, literally hanging over the oceans edge.... Learn More
Rates
$310 - $310 night
$2170 - $2380 week


Non Smoking   Swimming Pool


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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: This unit is directly ocean front at this highly desired complex.The parking is directly in front of the unit, so no long walks to your door! Excel... Learn More
Rates
$100 - $110 night
$700 - $770 week


Non Smoking


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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: This bottom floor unit is excellent for a fabulous hawaiian vacation.There is a great ocean view from the lanai and the living room it is also a co... Learn More
Rates
$90 - $105 night
$630 - $735 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: Sea Village Resort reflects the tranquil beauty of the Big Island. The resort is centrally located on the Kona coast close to the town of Kailua an... Learn More
Rates
$100 - $125 night
$700 - $875 week


Non Smoking


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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: Kona Coast Resort 1201 2b/r Kona Coast oceanviews/Hawaii island Book online and receive a 5% discount excluding Ironman and year end holidays. Boo... Learn More
Rates
$213 - $275 night
$916 - $1726 week


Non Smoking


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Studio Vacation Rental Condo in Kailua-Kona
Condo: Studio, 1 Bathroom, Sleeps 2
Location: Kailua-Kona, Hawaii, United States
Description: Kona Magic Sands is one of the best complex's in town because of its ideal location right next to gorgeous white sand beach. Perfect for boogie boa... Learn More
Rates
$90 - $100 night
$630 - $700 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 Kona Surf & Racquet 58 2 b/r oceanfront complex Kona Hawaii This is a very nice 2 bedroom 2 bath two story townhouse. Fully equipped for ... Learn More
Rates
$154 - $227 night
$683 - $1716 week


Non Smoking


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2 bedroom Vacation Rental Condo in Kailua-Kona - Ocean View
Condo: 2 Bedroom, 3 Bathroom, Sleeps 6
Location: Kailua-Kona, Hawaii, United States
Description: Large 2 bedroom 3 bath with full kitchen overlooking the pool area. This unit has an ocean view from the lanai. Stroll down Alii Drive and yo... Learn More
Rates
$120 - $140 night
$840 - $1470 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... Learn More
Rates
$162 - $249 night
$1134 - $1743 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 / 1 bathroom Unit Description: This 1 bedroom / 1 bathroom unit comes with one king bed, a sleeper sofa, and a fully equipped kitchen. ... Learn More
Rates
$112 - $263 night
$784 - $1841 week


Non Smoking


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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 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 ... Learn More
Rates
$130 - $145 night
$910 - $1575 week


Non Smoking   High-Speed Internet


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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... Learn More
Rates
$95 - $115 night
$665 - $775 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: The unit is fully redecorated and updated in Hawaiian decor to enhance your vacation. This beautifully maintained complex is very quaint, peaceful ... Learn More
Rates
$125 - $140 night
$875 - $1190 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 4
Location: Kailua-Kona, Hawaii, United States
Description: Keauhou Punahele D202 spacious 2 b/r Golf Course Condo Kona Hawaii Very spacious 2 bedroom 2 bath condo with golf course and ocean views and Kona ... Learn More
Rates
$189 - $211 night
$885 - $1716 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... Learn More
Rates
$750 - $1250 night
$5250 - $9800 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: Ono Hale: Beautiful 3 BR Home with Spectacular Coastline and Ocean Views We welcome you to stay at our private luxury home (Ono Hale) in the lush ... Learn More
Rates
$199 - $300 night
$1393 - $2100 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: Keauhou Kona Surf & Racquet 4204 2 b/r oceanfront Kona Hawaii Spacious absolutely direct oceanfront condo with a huge wrap around private lanai. V... Learn More
Rates
$203 - $314 night
$972 - $1983 week


Non Smoking   High-Speed Internet


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4 bedroom Vacation Rental Home in Kailua-Kona - Ocean Front
Home: 4 Bedroom, 3 Bathroom, Sleeps 8
Location: Kailua-Kona, Hawaii, United States
Description: Outstanding 4 Br / 3 Ba Oceanfront Home with saltwater "Queen's Bath" Hale Huna Kai is located within a mile of Kona town on Alli Drive. It is con... Learn More
Rates
$429 - $449 night
$3003 - $3843 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: This unit has everything you will need to feel like you are rolalty a great big king bed and two twin sized beds. It also has a fully stocked kitch... Learn More
Rates
$250 - $260 night
$1575 - $1820 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: loading photo view large image Casa De Emdeko offers owners and guests the perfect blend of Hawaiian ambiance with tropica... Learn More
Rates
$105 - $120 night
$735 - $840 week


Non Smoking   High-Speed Internet


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Listings 26 - 50 of 122
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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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