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Kailua-Kona Vacation Rentals

136 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 136
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3 bedroom Vacation Rental Home in Kailua-Kona - Ocean View
Home: 3 Bedroom, 2.25 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...
Rates
$175 - $225 night
$1225 - $2065 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 Amazing views from your private oceanfront lanai This recently upgraded and remodeled, direct oceanfront condo at Kona Keauhou...
Rates
$144 - $232 night
$990 - $1977 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 Pacific Lovely Affordable Condo in Great Location for Vacation Everything you need for an unforgettable Hawaiian vacation! All brand new furn...
Rates
$121 - $153 night
$831 - $1312 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: Orchid House at Kona Bay - Perfect Beach Hideaway! $99 special all September! Perfect beach hideaway for two! Tropical entrance. No stairs to cl...
Rates
$225 - $275 night
$1575 - $1925 week


Non Smoking


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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: Luxurious 3 BR Townhome with Lovely Ocean Views! Close to Everything! Privacy abounds in the quiet, gated neighborhood of Na Hale O Keauhou. This ...
Rates
$1673 - $2065 week


Non Smoking   High-Speed Internet


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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...
Rates
$120 - $150 night
$840 - $1540 week


Non Smoking


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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: Kona Isle A4 Beautifully upgraded condo. $69.00 special all of May-June! Kona Isle Condos are located on the Kona Coast of the Big Island of Hawai...
Rates
$75 - $90 night
$525 - $630 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 3317 - 1 BR Direct Oceanfront $95.00 special May-July! Sea Village Resort reflects the tranquil beauty of the Big Island. The resort i...
Rates
$100 - $125 night
$700 - $875 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...
Rates
$750 - $1250 night
$5250 - $9800 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 ...
Rates
$95 - $110 night
$665 - $770 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: Nestled along the scenic and historic Kona coast line, this completely remodeled/refurnished Unit is located in the 5-Star Kona Coast Resort, with ...
Rates
$150 - $150 night
$1050 - $1099 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
Condo: 1 Bedroom, 2 Bathroom, Sleeps 4
Location: Kailua-Kona, Hawaii, United States
Description: Upgraded one bedroom oasis looking right over the ocean. You will love the unit, you will love the location, walking distance to everywhere in town...
Rates
$130 - $165 night
$910 - $1505 week


Non Smoking


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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 June-September We welcome you to stay at our private luxury home (Ono Hale) in the l...
Rates
$275 - $275 night
$1925 - $2275 week


Non Smoking   Swimming Pool


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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: Kona Surf & Racquet Tropical oceanfront luxury condo in Kona Hawaii Absolutely wonderful oceanfront 2 bedroom 2 bath townhouse. Great swimming po...
Rates
$144 - $232 night
$990 - $1782 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 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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1 bedroom Vacation Rental Condo in Kailua-Kona
Condo: 1 Bedroom, 1 Bathroom, Sleeps 2
Location: Kailua-Kona, Hawaii, United States
Description: Banyan Tree 404:top Floor Direct oceanfront $119.00 special June-July! *new!* Knutson & Associates is very proud to represent this recently acquir...
Rates
$129 - $159 night
$903 - $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: Casa De Emdeko offers owners and guests the perfect blend of Hawaiian ambiance with tropical gardens and the songs of the many colorful birds enjoy...
Rates
$140 - $155 night
$980 - $1085 week


Non Smoking


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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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1 bedroom Vacation Rental Condo in Kailua-Kona - Ocean Front
Condo: 1 Bedroom, 1 Bathroom, Sleeps 4
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...
Rates
$95 - $120 night
$665 - $840 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: 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 - $770 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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Listings 26 - 50 of 136
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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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