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Kailua-Kona Vacation Rentals

153 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 51 - 75 of 153
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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 a Gorgeous almost ocean front unit with beautiful updated teak furnishing and updated appliances. There is everything you need to go the beach... Learn More
Rates
$100 - $120 night
$700 - $1050 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: Beautiful 4 bedroom, 4 bath home with a private pool and an outdoor shower. Unobstructed oceanview of the Kona Coast line. Spectacular stargazing ... Learn More
Rates
$450 - $525 night
$3150 - $5425 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: Keauhou Punahele B301 third floor condo with loft and ocean views Keauhou Punahele in Kona Hawaii is a lovely tropical complex in a very nice loca... Learn More
Rates
$255 - $277 night
$1097 - $1723 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: Keauhou Punahele C-201 Beautifully renovated Condo in quiet complex! This beautifully upgraded unit is breath taking. It offers a luxurious King s... Learn More
Rates
$120 - $130 night
$840 - $910 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: Fabulous Oceanview 3 BR Townhome Near Beach and Shopping! A/C Included! From the moment you step into this fabulous 3 bedroom, 2.5 bath condominiu... Learn More
Rates
$275 - $275 night
$1743 - $1925 week


Non Smoking   High-Speed Internet


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3 bedroom Vacation Rental Home in Kailua-Kona
Home: 3 Bedroom, 2 Bathroom, Sleeps 8
Location: Kailua-Kona, Hawaii, United States
Description: No Worries is a lovely newly renovated 3bd/2bth beach house with outside private shower and A/C units in the main living area and Master bedroom. T... Learn More
Rates
$229 - $249 night
$1603 - $2093 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 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   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: Sea Village Resort reflects the tranquil beauty of the Big Island. The resort is centrally located on the Kona coast close to the town of Kailua an... Learn More
Rates
$100 - $125 night
$700 - $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: Spacious Two BR, Two Bath Ocean View Elegance (Resort Fees Included) On the sun-drenched Kohala coast on the Big Island of Hawaii, the elements ha... Learn More
Rates
$220 - $240 night
$1540 - $2310 week


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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 - $321 night
$1855 - $2247 week


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6 bedroom Vacation Rental Home in Kailua-Kona - Ocean View
Home: 6 Bedroom, 6 Bathroom, Sleeps 20
Location: Kailua-Kona, Hawaii, United States
Description: Hale Pua, Private, Oceanfront Home with Pool, Spa and Spectacular Views The Hale Pua (?House of Flowers?) is maybe the only 6 bedroom/6 full bath ... Learn More
Rates
$1650 - $1950 night
$11550 - $16100 week


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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: Exceptional panoramic coastal views from this supremely private, quiet, end of the road location. Sitting high on a knoll at the very top of O'oma ... Learn More
Rates
$450 - $535 night
$3150 - $4410 week


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7 bedroom Vacation Rental Home in Kailua-Kona
Home: 7 Bedroom, 7 Bathroom, Sleeps 17
Location: Kailua-Kona, Hawaii, United States
Description: This custom home is located in O'Oma Plantation a subdivision of 19 estate-sized, 2 acre parcels. Enjoy exceptional panoramic coastal views from t... Learn More
Rates
$725 - $950 night
$5075 - $8785 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 oceanfront townhouse is beautifullly furnished, very clean, and cozy. It has Wifi, HD Television & DVR! Get lost in the sounds of the ocean, w... Learn More
Rates
$125 - $150 night
$875 - $1050 week


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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: This Keauhou Surf and Racquet unit offers a spacious family environment for your vacation. These units are approx 1200 square feet interior living ... Learn More
Rates
$160 - $180 night
$1120 - $1435 week


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Studio Vacation Rental Condo in Kailua-Kona - Ocean Front
Condo: Studio, 1 Bathroom, Sleeps 3
Location: Kailua-Kona, Hawaii, United States
Description: This unit is directly ocean front at this highly desired complex.The parking is directly in front of the unit, so no long walks to your door! Excel... Learn More
Rates
$110 - $135 night
$770 - $980 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: New Listing, Located On Alii Drive - 2 BR 2 Bath Beautiful Condo Come and enjoy a vacation in our beautiful 2 bedroom, 2 bathroom condo with priva... Learn More
Rates
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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: Kona Ohana Hale a charming single level home with a private solar heated pool. The home is part of a cul-de-sac in the small community of Hualalai ... Learn More
Rates
$350 - $398 night
$2450 - $4025 week


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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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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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3 bedroom Vacation Rental Home in Kailua-Kona - Ocean View
Home: 3 Bedroom, 3 Bathroom, Sleeps 7
Location: Kailua-Kona, Hawaii, United States
Description: The 180 degree ocean view at this gorgeous private home is where you will be spending all of your time watching for whales and dolphins. This home ... Learn More
Rates
$3500 - $3850 week


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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 B8 Spectacularly Renovated Groundfloor Condo in Oceanfront Complex! This renovated, tiled ground floor unit is excellent for a fabulous ... Learn More
Rates
$95 - $110 night
$665 - $945 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: 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   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 beautiful one bedroom, one bath air conditioned ocean front condo offers a feel of being miles away?.. with no traffic noise, but is just a ve... Learn More
Rates
$165 - $210 night
$1155 - $1785 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: The Kona Makai is one of Kona's favorite repeat destinations. This oceanfront community offers ocean views to no end. This unit is one of the 6 p... Learn More
Rates
$175 - $250 night
$1225 - $2135 week


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Listings 51 - 75 of 153
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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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