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Kailua-Kona Vacation Rentals

198 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 76 - 100 of 198
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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: Minutes from the picturesque town of Kailua-Kona where you will find restaurants, shops, and beautiful beaches. Relax and enjoy the ocean sunset o... Learn More
Rates
$145 - $165 night
$1015 - $1295 week


Non Smoking   Handicap Accessible


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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


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3 bedroom Vacation Rental Home in Kailua-Kona
Home: 3 Bedroom, 4 Bathroom, Sleeps 8
Location: Kailua-Kona, Hawaii, United States
Description: New to the Vacation Rental program! This beautiful oceanfront home is located next to the keiki pond at the Kona Bay Estates gated community. Enjoy... Learn More
Rates
$700 - $700 night
$4900 - $7000 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: This home sits on the bluff of one of the most pristine historic Bays of the Kona coast, Keauhou and (H) Heeia Bay. Famous Heeia Bay is located ju... Learn More
Rates
$525 - $855 night
$3675 - $5985 week


Non Smoking   High-Speed Internet


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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... Learn More
Rates
$130 - $200 night
$910 - $1400 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: Recently remodeled, top (third) floor unit. One bedroom (queen-size bed), vacation rental. Quiet oceanfront complex. Within walking distance of Kai... Learn More
Rates
$90 - $99 night
$630 - $903 week


Non Smoking


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3 bedroom Vacation Rental Home in Kailua-Kona - Ocean Front
Home: 3 Bedroom, 3 Bathroom, Sleeps 8
Location: Kailua-Kona, Hawaii, United States
Description: This Direct Ocean Front home is located just steps from the beach, conveniently located close to Kailua Pier, restaurants, shopping, and beaches. ... Learn More
Rates
$340 - $408 night
$2380 - $2856 week


Non Smoking   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: 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
$600 - $1050 week


Non Smoking   High-Speed Internet


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2 bedroom Vacation Rental Home in Kailua-Kona
Home: 2 Bedroom, 2 Bathroom, Sleeps 6
Location: Kailua-Kona, Hawaii, United States
Description: The home is approximately 100 feet from Keauhou Bay and located within walking distance of the Keauhou shopping center.Sit back and enjoy this home... Learn More
Rates
$325 - $385 night
$2275 - $2940 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: Casa de Emdeko, affectionately known as the 'Crown Jewel of the Kona Coast' is an oceanfront complex located on Alii Drive-One and a half miles sou... Learn More
Rates
$99 - $109 night
$693 - $910 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 gated nightly pass, wireless internet, tennis courts a pool and ... Learn More
Rates
$140 - $195 night
$980 - $1365 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: Excellent ocean views from your private lanai.Small beach just across the road for you to enjoy.This complex offers tennis a lovely pool and an exe... Learn More
Rates
$169 - $213 night
$924 - $1004 week


Non Smoking   High-Speed Internet


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1 bedroom Vacation Rental Condo in Kailua-Kona - Ocean View
Condo: 1 Bedroom, 2 Bathroom, Sleeps 2
Location: Kailua-Kona, Hawaii, United States
Description: Immaculate, beautifully furnished unit in great location. Wheel chair accessable, short walk to restaurants, shopping, and ocean activities. Solid ... Learn More
Rates
$95 - $110 night
$665 - $840 week


Non Smoking   Handicap Accessible   High-Speed Internet


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2 bedroom Vacation Rental Condo in Kailua-Kona
Condo: 2 Bedroom, 3 Bathroom, Sleeps 6
Location: Kailua-Kona, Hawaii, United States
Description: The Keauhou-Kona Surf and Racquet Club is a private garden style community situated on 17 acres. Other amenities include: three lighted tennis cour... Learn More
Rates
$140 - $180 night
$980 - $1330 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: Quiet community on the golf course in Keauhou. This second floor condo has a relaxing view of the course. Spacious floor plan, large lanai, free pa... Learn More
Rates
$191 - $207 night
$946 - $972 week


Non Smoking   High-Speed Internet


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4 bedroom Vacation Rental Home in Kailua-Kona - Ocean View
Home: 4 Bedroom, 3 Bathroom, Sleeps 8
Location: Kailua-Kona, Hawaii, United States
Description: This newer home is the perfect vacation destination for families coming to the Big Island of Hawaii. Located halfway between the Kona International... Learn More
Rates
$229 - $249 night
$1603 - $2275 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: Sea Village, an environmentally-respecting development of four buildings (none higher than 3 stories) surrounding a lovely grassy garden courtyard,... Learn More
Rates
$125 - $140 night
$875 - $1155 week


Non Smoking


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1 bedroom Vacation Rental Condo in Kailua-Kona
Condo: 1 Bedroom, 2 Bathroom, Sleeps 2
Location: Kailua-Kona, Hawaii, United States
Description: This complex is a great location for being near downtown Kailua Kona, yet you are right across the street from the beautiful Kona Coast Sunsets, fu... Learn More
Rates
$80 - $90 night
$560 - $875 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: Kona Coast Resort is one of the most spectacular locations on the Kona Coast. And this is one of the best condos in the complex. Enjoy the sounds ... Learn More
Rates
$265 - $345 night
$1563 - $1873 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: This oceanfront corner condo boasts fantastic ocean views from every angle; the living room and kitchen have a large side picture window and glass ... Learn More
Rates
$130 - $150 night
$910 - $1050 week


Non Smoking


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1 bedroom Vacation Rental Condo in Kailua-Kona
Condo: 1 Bedroom, 2 Bathroom, Sleeps 2
Location: Kailua-Kona, Hawaii, United States
Description: Relax in this large one bedroom 2 bath condo located within Keauhou Palena! The condo features a remodeled kitchen, a large floor plan, in unit W/D... Learn More
Rates
$99 - $110 night
$693 - $875 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: Stellar ocean views, quiet, secluded, lovely. Bedding Configuration: 1 King Additional Features: * Convenience: Nearby Grocery, Shopping, Snorkel... Learn More
Rates
$125 - $185 night
$875 - $1295 week


Non Smoking   High-Speed Internet


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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 unit will provide you with a calm and relaxing Hawaiian vacation. It's on the 5th Floor (top floor) and is quiet. The Master Bedroom is quite ... Learn More
Rates
$95 - $110 night
$665 - $910 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: Welcome to Hui o Kulia, where the view from A-15 at the Kona Reef will take your breath away. Relax and watch the whales and dolphins swim by, crui... Learn More
Rates
$145 - $165 night
$1015 - $1393 week


Non Smoking


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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: This great townhouse has been completely renovated through-out. New appliances, furniture, granite counter tops; flat screen TV's in the living roo... Learn More
Rates
$139 - $155 night
$973 - $1225 week


Non Smoking


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Listings 76 - 100 of 198
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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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