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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 101 - 125 of 198
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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: Relax in our convenient Deluxe Sized condo on the ground floor at Casa De Emdeko. Close to the cabana and barbeque areas. Just steps away from poo... Learn More
Rates
$150 - $188 night
$1050 - $1316 week


Non Smoking   Swimming Pool   High-Speed Internet


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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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2 bedroom Vacation Rental Condo in Kailua-Kona
Condo: 2 Bedroom, 2 Bathroom, Sleeps 6
Location: Kailua-Kona, Hawaii, United States
Description: The Keauhou Surf and Racquet Club is a gated community of condominiums. There are three professional style tennis courts with night lighting; a te... Learn More
Rates
$125 - $205 night
$875 - $1435 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: Welcome to Paradise. Paradise Found. Stay in this fabulous, large home with all the amenities! Private pool, coastal views, everything you could... Learn More
Rates
$350 - $634 night
$1765 - $3691 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 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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1 bedroom Vacation Rental Condo in Kailua-Kona - Ocean View
Condo: 1 Bedroom, 1 Bathroom, Sleeps 3
Location: Kailua-Kona, Hawaii, United States
Description: Great location rignt in Historic Kailua Village. Walk to Kamakahonu Beach the start of the Kona Ironman Triathlon. Explore Hulihee Palace where Ha... Learn More
Rates
$138 - $196 night
$623 - $961 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: Enjoy spectacular sunsets from this beautifully decorated 2 bedroom 2 bath condo located in Sea Village; a superbly maintained oceanfront holiday r... Learn More
Rates
$125 - $140 night
$875 - $1260 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 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
$120 - $210 night
$840 - $1470 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 - Ocean View
Condo: 2 Bedroom, 2 Bathroom, Sleeps 4
Location: Kailua-Kona, Hawaii, United States
Description: Great location on Alii Drive very close to town and Honl's beach. All new interior and there is a peek a boo view of the ocean from the lanai. A h... Learn More
Rates
$181 - $285 night
$606 - $1388 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: 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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3 bedroom Vacation Rental Home in Kailua-Kona - Ocean View
Home: 3 Bedroom, 3 Bathroom, Sleeps 6
Location: Kailua-Kona, Hawaii, United States
Description: Spacious 3/2 home with views of the Kona Coast and the blue Pacific Ocean. Enjoy tropical breezes while relaxing in this gorgeous three bedroom va... Learn More
Rates
$380 - $562 night
$2178 - $3403 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: Located in the Kailua Bay Resort complex just a short walk from the center of Kailua-Kona, this unit was renovated in March of this year. There are... Learn More
Rates
$99 - $125 night
$693 - $1225 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 pri... 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, 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
$395 - $475 night
$2765 - $3500 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. ... Learn More
Rates
$104 - $332 night
$728 - $2324 week


Non Smoking


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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


View Details and Book Online Send Inquiry



2 bedroom Vacation Rental Condo in Kailua-Kona
Condo: 2 Bedroom, 2 Bathroom, Sleeps 6
Location: Kailua-Kona, Hawaii, United States
Description: The Keauhou Surf and Racquet Club is a gated community of condominiums. There are three professional style tennis courts with night lighting; a te... Learn More
Rates
$190 - $205 night
$1330 - $1435 week


Non Smoking


View Details and Book Online Send Inquiry



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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3 bedroom Vacation Rental Home in Kailua-Kona - Ocean Front
Home: 3 Bedroom, 2 Bathroom, Sleeps 8
Location: Kailua-Kona, Hawaii, United States
Description: The soaring ocean views from almost every room will take your breath away at this luxury Hawaiian resort home Located in the award winning gated ... Learn More
Rates
$275 - $325 night
$1925 - $2625 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: Keauhou Kona Surf & Racquet Club has such a great location just 5 miles from Kona town. There is a large swimming pool, 3 lighted tennis courts an... Learn More
Rates
$163 - $243 night
$744 - $1154 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: 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 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
$193 - $255 night
$948 - $1154 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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Listings 101 - 125 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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