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Kailua-Kona Holiday Rentals

156 Kailua-Kona Holiday 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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Listings 1 - 25 of 156
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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: Book online and receive a 5% discount excluding Ironman and year end holidays. Book with a licensed company to avoid any problem with your Hawaii I... Learn More
Rates
$182 - $340 night
$1030 - $1770 week


Non Smoking   High-Speed Internet


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3 bedroom Vacation Rental Home in Kailua-Kona - Ocean View
Home: 3 Bedroom, 4 Bathroom, Sleeps 6
Location: Kailua-Kona, Hawaii, United States
Description: Blue Hawaii is a lovely home with a private pool and spa/online discount Book online and receive a 5% discount excluding Ironman and year end holi... Learn More
Rates
$524 - $927 night
$3530 - $5868 week


Non Smoking   Swimming Pool   High-Speed Internet


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3 bedroom Vacation Rental Home in Kailua-Kona
Home: 3 Bedroom, 4 Bathroom, Sleeps 6
Location: Kailua-Kona, Hawaii, United States
Description: Tucked away in the quiet enclave of Kona Bay Estates, just a short walk from Kailua Bay, your oceanfront vacation home, Kona Bay Keiki Beach Oasis,... Learn More
Rates
$449 - $449 night
$3143 - $6265 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: Spectacular location, spectacular view, spectacular decor! This newly remodeled suite is committed to quality. Take your highest expectations and ... Learn More
Rates
$150 - $175 night
$1050 - $1715 week


Non Smoking   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: Oceanfront estate with breathtaking panoramic unobstructed views. 4 BR, 4 elegant baths. All bedrooms have oceanfront balconies. Walls of glass ope... Learn More
Rates
$599 - $599 night
$4193 - $4550 week


Non Smoking   High-Speed Internet


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5 bedroom Vacation Rental Home in Kailua-Kona
Home: 5 Bedroom, 4 Bathroom, Sleeps 12
Location: Kailua-Kona, Hawaii, United States
Description: A/C in every room. 180 degree unobstructed view of Lymans Bay, favorite surf spot. 2 story open floor plan with 20 foot ceilings. Downstairs includ... Learn More
Rates
$500 - $500 night
$3500 - $4200 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 spacious, upgraded and tastefully decorated three bedroom home has sweeping ocean view in the quiet gated community of Kahakai Estates. Locate... Learn More
Rates
$350 - $425 night
$2450 - $2975 week


Non Smoking   Swimming Pool   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: Keauhou Kona Surf and Racquet Club 2204 - Direct Ocean Front Corner Unit~ The Keauhou Surf and Racquet Club is a gated community of condominiums. ... Learn More
Rates
$125 - $205 night
$875 - $1435 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: 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... Learn More
Rates
$110 - $120 night
$770 - $840 week


Non Smoking


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Featured


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,... Learn More
Rates
$150 - $175 night
$1050 - $1470 week


Non Smoking


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Featured


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 ... Learn More
Rates
$179 - $295 night
$1113 - $2065 week


Non Smoking   Handicap Accessible   Swimming Pool   High-Speed Internet


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2 bedroom Vacation Rental Condo in Kailua-Kona
Condo: 2 Bedroom, 2 Bathroom, Sleeps 8
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 ... Learn More
Rates
$125 - $125 night
$875 - $1050 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: Nice clean newly furnished second floor unit with central A/C. Great in town location right on Alii Drive. Walk to shops, restaurants & ocean activ... Learn More
Rates
$110 - $120 night
$770 - $1050 week


Non Smoking   Handicap Accessible


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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: Kona Coast Resort 12201 2b/r Wonderful condo/ocean views/Kona Hawaii Book online and receive a 5% discount excluding Ironman and year end holidays... Learn More
Rates
$233 - $377 night
$1622 - $2034 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: Lovely oceanfront 2nd floor unit recently upgraded and showing beautifully. Very popular vacation complex with Oceanfront Pool and Hot Tub, BBQ and... Learn More
Rates
$159 - $189 night
$1113 - $1603 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 Makai 2102 Beautifully Renovated Ground Floor condo w/Ocean View! *new* This spectacular ground floor unit is completely renovated from top t... Learn More
Rates
$95 - $120 night
$665 - $945 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: Lunapule Kona 205 2 b/r Affordable condo great location Kona Hawaii A hidden beauty near the village of Kailua Kona on the Big Island of Hawaii. T... Learn More
Rates
$147 - $316 night
$643 - $1948 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: Kona Coast Resort 1201 2b/r Kona Coast oceanviews/Hawaii island Book online and receive a 5% discount excluding Ironman and year end holidays. Boo... Learn More
Rates
$192 - $341 night
$1061 - $1973 week


Non Smoking


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2 bedroom Vacation Rental Home in Kailua-Kona - Ocean View
Home: 2 Bedroom, 2 Bathroom, Sleeps 4
Location: Kailua-Kona, Hawaii, United States
Description: Spectacular, rare, unobstructed ocean views. Steps from surfers, snorkelers, swimmers and paddlers, all at your front door. Also within walking dis... Learn More
Rates
$229 - $229 night
$1603 - $1813 week


Non Smoking


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1 bedroom Vacation Rental Condo in Kailua-Kona
Condo: 1 Bedroom, 3 Bathroom, Sleeps 4
Location: Kailua-Kona, Hawaii, United States
Description: Kona Alii on Alii Drive in the Village of Kailua Kona has so much to offer you will not want to leave. Make this your second home and you won't be... Learn More
Rates
$169 - $334 night
$1036 - $1751 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 local has all the sights and sounds of the best Kona has to offer. Enjoy this 1 bedroom, 2 bath unit right in town. You can also enjoy the ... Learn More
Rates
$130 - $145 night
$910 - $1645 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 5
Location: Kailua-Kona, Hawaii, United States
Description: Great Views of the ocean from the Lanai. Watch whales during the season or dolphins all year around. Sip your Kona Coffee in the morning looking a... Learn More
Rates
$135 - $165 night
$945 - $1365 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: Keauhou Kona Surf & Racquet Club 36- ***new Addition to Inventory*** New appliances, furniture, granite counter tops; flat screen TV's in the livi... Learn More
Rates
$139 - $155 night
$973 - $1225 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: Really nice oceanview in this 2 bedroom 2 bath condo. Vaulted ceilings, large lanai and nicely furnished. There is a king size bed in the master b... Learn More
Rates
$159 - $310 night
$993 - $2034 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: Kona Magic Sands is one of the best complex's in town because of its ideal location right next to gorgeous white sand beach. Perfect for boogie boa... Learn More
Rates
$90 - $100 night
$630 - $700 week


Non Smoking


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Listings 1 - 25 of 156
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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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