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Kailua-Kona Vacation Rentals

144 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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Listings 51 - 75 of 144
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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
$187 - $250 night
$1037 - $1930 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: 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
$105 - $120 night
$735 - $840 week


Non Smoking


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3 bedroom Vacation Rental Condo in Kailua-Kona - Ocean View
Condo: 3 Bedroom, 2 Bathroom, Sleeps 8
Location: Kailua-Kona, Hawaii, United States
Description: This estate, located on a private cove features a pool, spa and koi pond and offers the finest in accommodations without having to leave Kona. Th... Learn More
Rates
$435 - $534 night
$3045 - $3738 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: Ono Hale: Beautiful 3 BR Home with Spectacular Coastline and Ocean Views We welcome you to stay at our private luxury home (Ono Hale) in the lush ... Learn More
Rates
$199 - $199 night
$1393 - $2275 week


Non Smoking


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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 - $575 night
$3150 - $4410 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 1103 Alii drive almost oceanfront Great Kona Hawaii condo Kona Makai is one of Kona's most popular resorts. Kona Makai has tennis court... Learn More
Rates
$192 - $232 night
$1140 - $1768 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 2
Location: Kailua-Kona, Hawaii, United States
Description: Casa De Emdeko, an oceanfront condominium complex, is located on famous Alii Drive just 1.5 miles south of Kailua Kona Village. Casa offers guests... Learn More
Rates
$110 - $125 night
$770 - $1330 week


Non Smoking   High-Speed Internet


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1 bedroom Vacation Rental Condo in Kailua-Kona - Ocean View
Condo: 1 Bedroom, 2 Bathroom, Sleeps 4
Location: Kailua-Kona, Hawaii, United States
Description: This Keauhou Akahi condo with beautiful sweeping ocean views overlooks the newly resurfaced Akahi swimming pool and 9th tee of the famous Kona Coun... Learn More
Rates
$125 - $140 night
$875 - $980 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: Nestled along the scenic and historic Kona coast line, this completely remodeled/refurnished Unit is located in the 5-Star Kona Coast Resort, with ... Learn More
Rates
$150 - $150 night
$1050 - $1099 week


Non Smoking   High-Speed Internet


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3 bedroom Vacation Rental Home in Kailua-Kona - Ocean Front
Home: 3 Bedroom, 3 Bathroom, Sleeps 6
Location: Kailua-Kona, Hawaii, United States
Description: Hale Kipa - Ocean Front Dream Home. Rent Either as a 3/3 Or a 5/4! Just 4.5 miles from Kailua Village, this Oceanfront house with pool and fountai... Learn More
Rates
$412 - $412 night
$2884 - $2884 week


Non Smoking   Swimming Pool   High-Speed Internet


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3 bedroom Vacation Rental Home in Kailua-Kona - Ocean Front
Home: 3 Bedroom, 3 Bathroom, Sleeps 8
Location: Kailua-Kona, Hawaii, United States
Description: Pahukoa Hale - Direct Ocean Front Hawaiian Style home in Kona Bay Estates This vintage Hawaiian beach house is nestled in a private gated communit... Learn More
Rates
$340 - $340 night
$2380 - $2625 week


Non Smoking   Swimming Pool   High-Speed Internet


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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
$686 - $1050 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 2
Location: Kailua-Kona, Hawaii, United States
Description: This bottom floor unit is excellent for a fabulous hawaiian vacation.There is a great ocean view from the lanai and the living room it is also a co... Learn More
Rates
$90 - $105 night
$630 - $735 week


Non Smoking


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1 bedroom Vacation Rental Cabin in Kailua-Kona - Ocean Front
Cabin: 1 Bedroom, 1 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 luxurious estate located on a private c... Learn More
Rates
$239 - $305 night
$1673 - $2135 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: Upgraded one bedroom oasis looking right over the ocean. You will love the unit, you will love the location, walking distance to everywhere in town... Learn More
Rates
$130 - $155 night
$910 - $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
$105 - $120 night
$735 - $840 week


Non Smoking


View Details and Book Online Send Inquiry



2 bedroom Vacation Rental Condo in Kailua-Kona - Ocean View
Condo: 2 Bedroom, 2 Bathroom, Sleeps 6
Location: Kailua-Kona, Hawaii, United States
Description: Sea Village 1102 - 2 BR Direct Oceanfront - New Addition to Inventory! This beautiful oceanfront condo has two bedrooms, two baths on the first fl... Learn More
Rates
$149 - $175 night
$1043 - $1225 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: Kona Isle C3 great first floor condo all remodeled & no stairs Beautifully furnished and all remodeled; you will love this first floor condo on Al... Learn More
Rates
$144 - $144 night
$559 - $1004 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: Book online and receive a 5% discount excluding Ironman and year end holidays Book with a licensed company to avoid any problems with your Hawaii I... Learn More
Rates
$111 - $156 night
$653 - $1480 week


Non Smoking


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2 bedroom Vacation Rental Home in Kailua-Kona - Ocean Front
Home: 2 Bedroom, 2 Bathroom, Sleeps 4
Location: Kailua-Kona, Hawaii, United States
Description: Direct Ocean Front Cottage where you can watch whales and surfers while relaxing on the large sunning deck, literally hanging over the oceans edge.... Learn More
Rates
$325 - $325 night
$2275 - $2450 week


Non Smoking   Swimming Pool


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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 ... Learn More
Rates
$125 - $140 night
$875 - $1190 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: Kona Reef D32 Absolute Oceanfront Top Floor Private Kona Reef! *new Addition* Private, top floor, absolute oceanfront, lovely one bedroom condo at... Learn More
Rates
$138 - $168 night
$966 - $1176 week


Non Smoking   High-Speed Internet


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2 bedroom Vacation Rental Condo in Kailua-Kona - Ocean Front
Condo: 2 Bedroom, 3 Bathroom, Sleeps 6
Location: Kailua-Kona, Hawaii, United States
Description: Keahou Kona Surf and Racquet Club 5304- Direct Ocean Front 2 BR + Loft The Keauhou Surf and Racquet Club is a gated community of condominiums. Th... Learn More
Rates
$250 - $300 night
$1750 - $2100 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: This spacious private three bedroom two and a quarter bath home offers lots of wide-open spaces and million dollar oceanviews for your tropical get... Learn More
Rates
$175 - $225 night
$1225 - $1750 week


Non Smoking


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3 bedroom Vacation Rental Condo in Kailua-Kona
Condo: 3 Bedroom, 2 Bathroom, Sleeps 6
Location: Kailua-Kona, Hawaii, United States
Description: Keauhou Kona Surf & Racquet 24 3 b/r oceanfront complex Kona Hawaii This is a very nice 3 bedroom 2 bath townhouse close to Kahaluu Beach Park. Ve... Learn More
Rates
$181 - $298 night
$1091 - $2418 week


Non Smoking


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Listings 51 - 75 of 144
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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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