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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 1 - 25 of 198
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3 bedroom Vacation Rental Home in Kailua-Kona
Home: 3 Bedroom, 3 Bathroom, Sleeps 8
Location: Kailua-Kona, Hawaii, United States
Description: A newly refurnished home with stunning oceanviews, refreshing private pool, relaxing shady lanais - and all in a quiet tropical setting! Our fanta... Learn More
Rates
$249 - $299 night
$1743 - $2443 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 condo Unit Description: This one bedroom comes equipped with a queen bed and a full size wall bed in the living area. Amenities included... Learn More
Rates
$152 - $213 night
$1064 - $1491 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: The condo is located on ground level and has a Cal king bed in the bedroom, with an additional Queen Futon sofa sleeper in the living room which wi... Learn More
Rates
$105 - $115 night
$735 - $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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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 the Kona Reef Resort come with amenities to ensure ... Learn More
Rates
$161 - $999 night
$1127 - $6993 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: Located in a gated community, Surf and Racquet complex features Tennis with three well maintained courts and lighting for evening play. Great pool... Learn More
Rates
$95 - $115 night
$665 - $875 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
$130 - $255 night
$910 - $1785 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: Located on world-famous Ali'i Drive the Keauhou Kona Surf and Racquet Club is a 4-star Oceanfront Resort located 4.5 miles south of Kailua-Kona tow... Learn More
Rates
$100 - $120 night
$700 - $910 week


Non Smoking


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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 ... Learn More
Rates
$157 - $383 night
$1099 - $2681 week


Non Smoking


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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... Learn More
Rates
$265 - $355 night
$1855 - $2485 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: 12 Alii Point commands one of the best locations on the Big Island; it's an absolute ocean-front house with the best views. From the spectacular la... Learn More
Rates
$6300 - $7000 week


Non Smoking


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3 bedroom Vacation Rental Home in Kailua-Kona - Ocean View
Home: 3 Bedroom, 3 Bathroom, Sleeps 8
Location: Kailua-Kona, Hawaii, United States
Description: Situated on 5 acres of gentle hillside overlooking the Pacific, Nirmal Estates is the perfect luxury getaway. Located just south of downtown Kona, ... Learn More
Rates
$425 - $475 night
$2975 - $3500 week


Non Smoking


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3 bedroom Vacation Rental Home in Kailua-Kona - Ocean View
Home: 3 Bedroom, 3 Bathroom, Sleeps 9
Location: Kailua-Kona, Hawaii, United States
Description: A little piece of Hawaiian charm with an ocean view. Located in an authentic beach community, this home is perfect for the family looking for the i... Learn More
Rates
$250 - $295 night
$1750 - $2275 week


Non Smoking


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2 bedroom Vacation Rental Home in Kailua-Kona
Home: 2 Bedroom, 4 Bathroom, Sleeps 8
Location: Kailua-Kona, Hawaii, United States
Description: "This inviting Hale" will wow you with its open, relaxing, shady and sunny Lanai's, cool breezes and a feeling of comfort to enjoy your Hawaiian Va... Learn More
Rates
$225 - $270 night
$1575 - $1890 week


Non Smoking   Swimming Pool


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5 bedroom Vacation Rental Home in Kailua-Kona - Ocean View
Home: 5 Bedroom, 3 Bathroom, Sleeps 10
Location: Kailua-Kona, Hawaii, United States
Description: This resort-like ocean view 5 Bedroom 3 bath residence with swimming pool, stream and waterfalls is ideally located on a quiet cul-de-sac in Kailua... Learn More
Rates
$275 - $375 night
$1925 - $2800 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
$600 - $1050 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: #311 ? Top floor unit that catches the trade winds. 2 bedroom/2 bath, max. 4 people so you will have room to roam through the spacious condo and a... Learn More
Rates
$99 - $130 night
$693 - $1155 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: Treat yourself to a relaxing vacation in this beautifully furnished tropical retreat with a well-appointed kitchen, beautiful swimming pool, spa, b... Learn More
Rates
$99 - $130 night
$693 - $1155 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 Alii Villas #139 on the Big Island of Hawaii is a very nicely furnished condo that will make you feel right at home.Ocean views from your priv... Learn More
Rates
$149 - $199 night
$634 - $912 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 #239 is located in an oceanfront complex near town. Oceanfront swimmimg pool and BBQThis lovely condo is fully equipped and just waiti... Learn More
Rates
$149 - $199 night
$634 - $912 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: Spectacular 3 BR / 2 BA elegantly designed home in Garden Setting with A/C and Top of the Line Appliances. Light bright & airy with garden to ocean... 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
Condo: 1 Bedroom, 1 Bathroom, Sleeps 2
Location: Kailua-Kona, Hawaii, United States
Description: Alii Villas on Alii Drive is wonderful place to spend your holiday. Historic Kailua Village is close by where the world famous Ironman Triathlon ta... Learn More
Rates
$172 - $222 night
$740 - $1077 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 Front
Condo: 1 Bedroom, 1 Bathroom, Sleeps 4
Location: Kailua-Kona, Hawaii, United States
Description: Come and join us in paradise at unit #107 and enjoy the fragrant plumeria drifting on warm tropical Hawaiian Breezes. Relax and let the Hawaiian su... Learn More
Rates
$85 - $95 night
$595 - $840 week


Non Smoking


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5 bedroom Vacation Rental Home in Kailua-Kona
Home: 5 Bedroom, 5 Bathroom, Sleeps 10
Location: Kailua-Kona, Hawaii, United States
Description: No detail has been missed and our home is completely supplied with everything you will need to thoroughly enjoy an exceptional Hawaii vacation expe... Learn More
Rates
$625 - $725 night
$4375 - $7000 week


Non Smoking


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Listings 1 - 25 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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