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Kailua-Kona Vacation Rentals

127 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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Listings 76 - 100 of 127
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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: Alii Point - Luxury Villa in Private and Gated Oceanfront Community Almost Oceanfront. Spend your vacation in a luxurious single family home withi... Learn More
Rates
$499 - $499 night
$3493 - $4550 week


Non Smoking   Handicap Accessible   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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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 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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3 bedroom Vacation Rental Home in Kailua-Kona - Ocean View
Home: 3 Bedroom, 2 Bathroom, Sleeps 6
Location: Kailua-Kona, Hawaii, United States
Description: Receive a $100 per night discount for bookings between now and September 2014! Restrictions apply. Hale Akala is a beautiful custom designed 3 bed... Learn More
Rates
$298 - $398 night
$2086 - $3675 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 Condos are located on the Kona Coast of the Big Island of Hawaii, and are individually and privately owned. The gorgeous 74-unit complex ... Learn More
Rates
$105 - $140 night
$735 - $980 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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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
$135 - $155 night
$945 - $1575 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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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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1 bedroom Vacation Rental Condo in Kailua-Kona - Ocean View
Condo: 1 Bedroom, 1 Bathroom, Sleeps 4
Location: Kailua-Kona, Hawaii, United States
Description: Ali'i Villas 139 Big Island oceanfront complex/online booking discount Book online and receive a 5% discount on your reservation excluding Ironman... Learn More
Rates
$166 - $288 night
$653 - $1436 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: Hale Pua, Private, Oceanfront Home with Pool, Spa and Spectacular Views The Hale Pua (?House of Flowers?) is maybe the only 6 bedroom/6 full bath ... Learn More
Rates
$1595 - $1950 night
$11165 - $15225 week


Non Smoking   High-Speed Internet


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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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2 bedroom Vacation Rental Condo in Kailua-Kona
Condo: 2 Bedroom, 2 Bathroom, Sleeps 8
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 ... Learn More
Rates
$125 - $125 night
$875 - $1050 week


Non Smoking


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2 bedroom Vacation Rental Condo in Kailua-Kona - Ocean View
Condo: 2 Bedroom, 2 Bathroom, Sleeps 5
Location: Kailua-Kona, Hawaii, United States
Description: Kailua-Kona Oceanfront on Alii Dr.! 2nd level Ocean view, elevator, too OCEANFRONT! Panoramic ocean views, only 5 minutes from downtown and close... Learn More
Rates
$150 - $200 night
$950 - $1435 week


Non Smoking   Swimming Pool   High-Speed Internet


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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... Learn More
Rates
$95 - $120 night
$665 - $840 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: Kona Makai 1 bedroom with loft in an Ocean Front Community. Community includes a nightly gates entry, wireless internet, tennis courts a pool and... Learn More
Rates
$140 - $165 night
$980 - $1400 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
$454 - $474 night
$3178 - $4018 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: Holualoa Bay Villas 204 Kona Coast views/online booking discount Book online and receive a 5% discount excluding Ironman and year end holidays Boo... Learn More
Rates
$189 - $354 night
$948 - $1860 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: Ali'i Villas 239 Kona Coast ocean front complex/online booking discount Book online and receive a 5% discount excluding Ironman and year end holid... Learn More
Rates
$166 - $288 night
$653 - $1436 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 E105 spacious 2 b/r condo Big Island Kona Hawaii Spacious Alii Drive condo in Keauhou, quiet relaxing atmosphere. Beautiful kitch... Learn More
Rates
$222 - $246 night
$990 - $1523 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: The Keauhou Surf and Racquet Club is a gated community of condominiums. There are three professional style tennis courts with night lighting; a te... Learn More
Rates
$190 - $205 night
$1330 - $1435 week


Non Smoking


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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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Studio Vacation Rental Condo in Kailua-Kona
Condo: Studio, 1 Bathroom, Sleeps 2
Location: Kailua-Kona, Hawaii, United States
Description: This third floor condo has such a beautiful view! Sit on your lanai and sip mai tai's or just hang out to watch the sunset. Great whale watching du... Learn More
Rates
$98 - $150 night
$686 - $1050 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 Akahi 110 Great views of the ocean and golf course/Kona Hawaii Book online and receive a 5% discount excluding Ironman and year end holida... Learn More
Rates
$166 - $216 night
$653 - $1436 week


Non Smoking   High-Speed Internet


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Listings 76 - 100 of 127
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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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