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Kailua-Kona Vacation Rentals

140 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 140
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2 bedroom Vacation Rental Condo in Kailua-Kona
Condo: 2 Bedroom, 1 Bathroom, Sleeps 6
Location: Kailua-Kona, Hawaii, United States
Description: 2 Bedroom Bungalow Unit Description: These comfortable bungalows feature a king size bed in each bedroom, plus a queen sleeper sofa in the living ...
Rates
$204 - $599 night
$1428 - $4193 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: $109.00 a night for ocean view in heart of Kailua-Kona, 2 BR, 2 bath Rates starting at $109.00 a night for ocean view in heart of Kailua-Kona. Thi...
Rates
$109 - $155 night
$763 - $1323 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: Alii Villas 221 Gorgeous 2nd flr condo with Ocean View, Wifi, & Close to Pool Alii Villas#221 is an amazing spot for your Vacation. With a spectac...
Rates
$95 - $115 night
$665 - $1050 week


Non Smoking   High-Speed Internet


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3 bedroom Vacation Rental Condo in Kailua-Kona
Condo: 3 Bedroom, 2 Bathroom, Sleeps 8
Location: Kailua-Kona, Hawaii, United States
Description: New appliances, furniture, granite counter tops; TV in the living room & in all the bedrooms. There are 2 queen beds upstairs with a window A/C un...
Rates
$139 - $155 night
$973 - $1225 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: Beautiful single level 3 BR, 3 bath home with spectacular ocean views Hale Aikáne (House of Hospitality to Family and Friends as one) a beautiful,...
Rates
$400 - $425 night
$2800 - $4025 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: Kona Isle E23 Direct Ocean Front, Wifi, 2nd floor, Gorgeous 1/1 Kona Isle Condos are located on the Kona Coast of the Big Island of Hawaii, and ar...
Rates
$105 - $140 night
$735 - $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: Kksr 185 $119.00 special Aug-September!! Direct Oceanfront, Wifi, A True Gem The Keauhou Surf and Racquet Club is a gated community of condominium...
Rates
$125 - $169 night
$875 - $1953 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 C24 Partial Oceanview, 2nd floor condo, Excellant Price! This condo is a comfortable spot for your Hawaiian Vacation. Great partial ocea...
Rates
$95 - $110 night
$665 - $1050 week


Non Smoking   High-Speed Internet


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3 bedroom Vacation Rental Home in Kailua-Kona - Ocean View
Home: 3 Bedroom, 3.5 Bathroom, Sleeps 6
Location: Kailua-Kona, Hawaii, United States
Description: Spectacular coastline views from this home located right above Kailua-Kona Village at about a 700 feet elevation, which offers comfortable cooler n...
Rates
$350 - $385 night
$2450 - $4025 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: Casa De Emdeko 330 - Extra spacious, Top Floor, Oceanview, Air Conditioning! Casa De Emdeko offers owners and guests the perfect blend of Hawaiian...
Rates
$100 - $120 night
$700 - $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: Kksr2103 $115.00 spcl Aug-September!! Direct Oceanfront, Ground Floor, Wifi! The Keauhou Surf and Racquet Club is a gated community of condominium...
Rates
$125 - $205 night
$875 - $1953 week


Non Smoking   High-Speed Internet


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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....
Rates
$325 - $325 night
$2275 - $2800 week


Non Smoking   Swimming Pool


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3 bedroom Vacation Rental Home in Kailua-Kona - Ocean View
Home: 3 Bedroom, 2.5 Bathroom, Sleeps 8
Location: Kailua-Kona, Hawaii, United States
Description: Ono Hale: Gorgeous Home with pool $229 nightly special all of Aug-September We welcome you to stay at our private luxury home (Ono Hale) in the lu...
Rates
$275 - $325 night
$1925 - $2450 week


Non Smoking   Swimming Pool


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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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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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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...
Rates
$149 - $169 night
$1043 - $1225 week


Non Smoking   Handicap Accessible   High-Speed Internet


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4 bedroom Vacation Rental Home in Kailua-Kona
Home: 4 Bedroom, 4 Bathroom, Sleeps 10
Location: Kailua-Kona, Hawaii, United States
Description: Beautiful 4 bedroom, 4 bath home with a private pool and an outdoor shower. Unobstructed oceanview of the Kona Coast line. Spectacular stargazing ...
Rates
$450 - $550 night
$3150 - $5565 week


Non Smoking   High-Speed Internet


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3 bedroom Vacation Rental Condo in Kailua-Kona - Ocean View
Condo: 3 Bedroom, 3 Bathroom, Sleeps 6
Location: Kailua-Kona, Hawaii, United States
Description: Exquisite Three BR, Three Bath Oceanview Halii Kai (Resort Fees Incl.) On the sun-drenched Kohala coast on the Big Island of Hawaii, the elements ...
Rates
$420 - $510 night
$2940 - $4200 week


Non Smoking   High-Speed Internet


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4 bedroom Vacation Rental Home in Kailua-Kona
Home: 4 Bedroom, 5.25 Bathroom, Sleeps 10
Location: Kailua-Kona, Hawaii, United States
Description: This home sits on the bluff of one of the most pristine Bays of the Kona coast, (H) Heeia Bay. Keauhou Bay is just feet away to the South. The hom...
Rates
$525 - $595 night
$3675 - $5950 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: Kksr#3 $119 all of Augst-September! Direct Oceanfront, Wifi, Amazing Location This oceanfront townhouse is beautifullly furnished, very clean, and...
Rates
$125 - $169 night
$875 - $1953 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...
Rates
$750 - $1250 night
$5250 - $9800 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 - $279 night
$1134 - $1953 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: Keauhou Punahele C-201 Renovated, Wifi, 2 bed/2 bath, Spacious This beautifully upgraded unit is breath taking. It offers a luxurious King sized m...
Rates
$120 - $130 night
$840 - $1435 week


Non Smoking


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3 bedroom Vacation Rental Home in Kailua-Kona - Ocean Front
Home: 3 Bedroom, 4 Bathroom, Sleeps 10
Location: Kailua-Kona, Hawaii, United States
Description: Perfectly located on the Kona "Gold Coast" of the Big Island, this home offers you your own personal paradise. This dramatic gated, Ocean Front Est...
Rates
$3300 - $4400 night
$23100 - $30800 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: Kpb409 Upgrded, High Flr, Ocean View, Big Lanai, Walk To Town! Elevator, Ac!! ***NEW PROPERTY IN INVENTORY, & NEW OWNERSHIP!****Kona Pacific B409 ...
Rates
$125 - $179 night
$875 - $1603 week


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Listings 26 - 50 of 140
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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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