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Kailua-Kona Vacation Rentals

139 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 139
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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...
Rates
$135 - $165 night
$945 - $1645 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: Kona Isle Oceanfront complex, affordable and comfortable good location #b21 Book online and receive a 5% discount excluding Ironman and end of yea...
Rates
$597 - $1273 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: Kbv 304 Top Floor Condo: Huge Oceanview, Elevators, Beach Walking Distance! This beautiful, private top floor condo at Kahaluu Bay Villas is quite...
Rates
$139 - $169 night
$973 - $1183 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 Surf & Racquet Tropical garden views, great condo in oceanfront complex Second floor beauty; recently remodeled and the decor and furnishings...
Rates
$144 - $177 night
$990 - $1587 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: $109.00 a night for ocean view in heart of Kailua-Kona, 2 BR, 2 bath Rates starting at $109.00 a night for ocean view in heart of Kailua-Kona. Thi...
Rates
$109 - $155 night
$763 - $1323 week


Non Smoking


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1 bedroom Vacation Rental Condo in Kailua-Kona - Ocean Front
Condo: 1 Bedroom, 1 Bathroom, Sleeps 6
Location: Kailua-Kona, Hawaii, United States
Description: The Kona Makai is a beautiful sunny highly sought after Ocean Front Complex located on famous Alii Drive just 1.3 miles from Kailua Village. The K...
Rates
$95 - $120 night
$665 - $840 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: Beautiful remodeled 2 BR condo located on Robert Trent Jones Golf Course This quiet beautifully remodeled 1400sf 2 bedroom condo is located at a c...
Rates
$115 - $165 night
$805 - $1155 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: 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 ...
Rates
$125 - $125 night
$875 - $1050 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 nightly gates entry, wireless internet, tennis courts a pool and...
Rates
$140 - $165 night
$980 - $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: Kona Isle A4 Beautifully upgraded condo. $69.00 special all of August-Septmbr Kona Isle Condos are located on the Kona Coast of the Big Island of ...
Rates
$75 - $90 night
$525 - $630 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: Keauhou Punahele in Kona Hawaii is a lovely tropical complex in a very nice location. The condo is quite large so you will be comfortable and it a...
Rates
$186 - $187 night
$1028 - $1548 week


Non Smoking   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: This beautiful 2 bedroom / 2 bathroom has recently undergone a full remodel and it is gorgeous! Travertine floors, granite countertops, brand new w...
Rates
$205 - $330 night
$1435 - $2310 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: Kksr#3 $119 all of June-September! Direct Oceanfront, Wifi, Amazing Location This oceanfront townhouse is beautifullly furnished, very clean, and ...
Rates
$125 - $169 night
$875 - $1183 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: Kona Makai Oceanfront complex,close to town in tropical setting #1103 Kona Makai is one of Kona's most popular resorts. Kona Makai has tennis cour...
Rates
$132 - $187 night
$909 - $1506 week


Non Smoking   High-Speed Internet


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4 bedroom Vacation Rental Home in Kailua-Kona
Home: 4 Bedroom, 5.25 Bathroom, Sleeps 10
Location: Kailua-Kona, Hawaii, United States
Description: This home sits on the bluff of one of the most pristine Bays of the Kona coast, (H) Heeia Bay. Keauhou Bay is just feet away to the South. The hom...
Rates
$525 - $595 night
$3675 - $5950 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 upgraded second floor 2bd2bth unit in Kona Bali Kai one of Kona's most popular oceanfront destinations. Watch the surfers at "Ban...
Rates
$149 - $169 night
$1043 - $1225 week


Non Smoking   High-Speed Internet


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2 bedroom Vacation Rental Condo in Kailua-Kona - Ocean Front
Condo: 2 Bedroom, 2 Bathroom, Sleeps 6
Location: Kailua-Kona, Hawaii, United States
Description: Casa De Emdeko 219 2 Bdrm Direct Ocean Front Corner unit, Wrap around Lanai! This unit has everything you will need to feel like you are rolalty a...
Rates
$199 - $250 night
$1393 - $1750 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: This a Gorgeous almost ocean front unit with beautiful updated teak furnishing and updated appliances. There is everything you need to go the beach...
Rates
$100 - $120 night
$700 - $1050 week


Non Smoking   High-Speed Internet


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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: Beautiful single level 3 BR, 3 bath home with spectacular ocean views Hale Aikáne (House of Hospitality to Family and Friends as one) a beautiful,...
Rates
$400 - $425 night
$2800 - $4025 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: The unit is fully redecorated and updated in Hawaiian decor to enhance your vacation. This beautifully maintained complex is very quaint, peaceful ...
Rates
$125 - $150 night
$875 - $1295 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: On the sun-drenched Kohala coast on the Big Island of Hawaii, the elements have come together to create a place like no other. It is at this point...
Rates
$298 - $400 night
$2086 - $4186 week


Non Smoking


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3 bedroom Vacation Rental Home in Kailua-Kona - Ocean View
Home: 3 Bedroom, 2.5 Bathroom, Sleeps 6
Location: Kailua-Kona, Hawaii, United States
Description: Oceanfront home with 180 degrees unobstructed views of the Pacific Enter the beautiful Hoku'Ea Hale named for the beautiful ocean/turtle gate that...
Rates
$495 - $545 night
$3465 - $4375 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: Kalani Kai Walk to Ocean shops and restaurants. Affordable #321 Great location right in Historic Kailua Village. Walk to Kamakahonu Beach the star...
Rates
$88 - $153 night
$597 - $1273 week


Non Smoking   High-Speed Internet


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1 bedroom Vacation Rental Cottage in Kailua-Kona
Cottage: 1 Bedroom, 1 Bathroom, Sleeps 2
Location: Kailua-Kona, Hawaii, United States
Description: "The Cottage", Mahina Meli Makai (Oceanside Honey Moon) This truly oceanfront (and we mean oceanfront) cottage, is all about a peaceful quiet Roma...
Rates
$150 - $175 night
$1050 - $1540 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...
Rates
$110 - $120 night
$770 - $1225 week


Non Smoking   Handicap Accessible


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Listings 51 - 75 of 139
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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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