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Kailua-Kona Vacation Rentals

139 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 1 - 25 of 139
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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


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...
Rates
$239 - $305 night
$1673 - $2135 week


Non Smoking   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: 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 ...
Rates
$95 - $110 night
$665 - $770 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: Kksr2204 $115.00 special August-September! Direct Oceanfront Corner Unit!!! The Keauhou Surf and Racquet Club is a gated community of condominiums...
Rates
$125 - $205 night
$875 - $1435 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: Come and enjoy this community at the Kona Makai, vacationers number one choice for return guests. The Kona Makai offers guests lovely lush grounds,...
Rates
$150 - $185 night
$1050 - $1470 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 Coast Resort Spectacular condo Oceanview Resort, Affordable Luxury #5203 The Kona Coast Resort is one of the premier resorts in Kona and this...
Rates
$143 - $176 night
$987 - $1312 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: Spectacular location, spectacular view, spectacular decor! This newly remodeled suite is committed to quality. Take your highest expectations and ...
Rates
$150 - $185 night
$1050 - $1715 week


Non Smoking   High-Speed Internet


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3 bedroom Vacation Rental Condo in Kailua-Kona - Ocean View
Condo: 3 Bedroom, 2.5 Bathroom, Sleeps 6
Location: Kailua-Kona, Hawaii, United States
Description: Fabulous Oceanview 3 BR Townhome Near Beach Summer Special $175 per nt! From the moment you step into this fabulous 3 bedroom, 2.5 bath condominiu...
Rates
$275 - $275 night
$1225 - $1925 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 6
Location: Kailua-Kona, Hawaii, United States
Description: Elegant yet simple luxury on the ocean in Kona Hawaii. And ONE OF ONLY TWO ACCESSIBLE OCEANFRONT CONDOS ON THE KONA COAST * Incredible Ocean ...
Rates
$179 - $295 night
$1113 - $2065 week


Non Smoking   Handicap Accessible   Swimming Pool   High-Speed Internet


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Studio Vacation Rental Condo in Kailua-Kona
Condo: Studio, 1 Bathroom, Sleeps 2
Location: Kailua-Kona, Hawaii, United States
Description: Kms313 Top Floor Direct Oceanfront!!! Wifi in condo! Gorgeous! This third floor condo has such a beautiful view! Sit on your lanai and sip mai tai...
Rates
$98 - $150 night
$686 - $1050 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
$144 - $177 night
$990 - $1587 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. ...
Rates
$174 - $499 night
$1218 - $3493 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: 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 - $1183 week


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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: On the sun-drenched Kohala coast on the Big Island of Hawaii, the elements have come together to create a place like no other. It is at this point...
Rates
$298 - $400 night
$2086 - $4186 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: 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 - $775 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: 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 ...
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 4
Location: Kailua-Kona, Hawaii, United States
Description: Kona Surf & Racquet Tropical, oceanfront paradise. Perfect vacation condo Gorgeous, absolutely direct oceanfront condo with a huge wrap around pri...
Rates
$144 - $232 night
$990 - $1977 week


Non Smoking   High-Speed Internet


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3 bedroom Vacation Rental Condo in Kailua-Kona - Ocean View
Condo: 3 Bedroom, 2 Bathroom, Sleeps 8
Location: Kailua-Kona, Hawaii, United States
Description: This estate, located on a private cove features a pool, spa and koi pond and offers the finest in accommodations without having to leave Kona. Th...
Rates
$435 - $534 night
$3045 - $3738 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
Condo: 1 Bedroom, 1 Bathroom, Sleeps 4
Location: Kailua-Kona, Hawaii, United States
Description: Affordable Oceanfront Complex Perfect Big Island Location - Alii Villas Alii Villas on Alii Drive is wonderful place to spend your vacation. Histo...
Rates
$88 - $153 night
$597 - $1312 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 Makai 1 bedroom with loft in an Ocean Front Community. Community includes a nightly gates entry, wireless internet, tennis courts a pool and...
Rates
$140 - $165 night
$980 - $1435 week


Non Smoking   High-Speed Internet


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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
$194 - $599 night
$1358 - $4193 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: 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
$144 - $232 night
$990 - $1782 week


Non Smoking   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: Kona Isle A4 Beautifully upgraded condo. $69.00 special all of August-Septmbr Kona Isle Condos are located on the Kona Coast of the Big Island of ...
Rates
$75 - $90 night
$525 - $630 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 beautiful 2 bedroom / 2 bathroom has recently undergone a full remodel and it is gorgeous! Travertine floors, granite countertops, brand new w...
Rates
$205 - $330 night
$1435 - $2310 week


Non Smoking


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Listings 1 - 25 of 139
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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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