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Kailua-Kona Vacation Rentals

148 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 1 - 25 of 148
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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...
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: 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. ...
Rates
$174 - $429 night
$1218 - $3003 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 - 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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1 bedroom Vacation Rental Condo in Kailua-Kona - Ocean View
Condo: 1 Bedroom, 1 Bathroom, Sleeps 4
Location: Kailua-Kona, Hawaii, United States
Description: 1 bedroom/1 bathroom resort suites Unit Description: The 1 bedroom/1 bathroom resort suites at Kona Reef come with amenities to ensure your stay i...
Rates
$162 - $279 night
$1134 - $1953 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 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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2 bedroom Vacation Rental Condo in Kailua-Kona
Condo: 2 Bedroom, 1 Bathroom, Sleeps 6
Location: Kailua-Kona, Hawaii, United States
Description: 2 Bedroom Bungalow Unit Description: These comfortable bungalows feature a king size bed in each bedroom, plus a queen sleeper sofa in the living ...
Rates
$229 - $599 night
$1603 - $4193 week


Non Smoking


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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: Enjoy your Hawaiian vacation at this almost oceanfront complex. This fully equipped over 1200 square foot, 2 bedroom, 2 bath condo with oversized l...
Rates
$175 - $210 night
$1225 - $1960 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: This beautiful remodeled 2 bedroom, 2 bath unit is right in the heart of Kona Village! The complex is right in the middle of town, surrounded by sh...
Rates
$120 - $145 night
$840 - $1155 week


Non Smoking


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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...
Rates
$265 - $321 night
$1855 - $2247 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 your Hawaiian vacation at this 2 bedroom, 2 bath second-floor unit in a private 15-unit shoreline complex. This unit has flawless ocean views...
Rates
$175 - $245 night
$1225 - $2100 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: Nestled along the scenic and historic Kona coast line, this completely remodeled/refurnished Unit is located in the 5-Star Kona Coast Resort, with ...
Rates
$150 - $150 night
$1050 - $1099 week


Non Smoking   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...
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 Front
Condo: 1 Bedroom, 1 Bathroom, Sleeps 4
Location: Kailua-Kona, Hawaii, United States
Description: Ali'i Villas 239 Kona Hawaii ocean front complex on the Big Island Second floor condo with great ocean views. This condo offers all the comforts ...
Rates
$103 - $216 night
$685 - $1473 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: Alii Point - Luxury Villa in Private and Gated Oceanfront Community Almost Oceanfront. Spend your vacation in a luxurious single family home withi...
Rates
$499 - $499 night
$3493 - $4550 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: Alii Villas 207 Great oceanfront complex on the Big Island Kona Hawaii Alii Villas on Alii Drive is wonderful place to spend your vacation. Histor...
Rates
$104 - $217 night
$692 - $1480 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: Alii Villas 340 Wonderful Upperfloor Condo! $95 special March 15th-31st! Alii Villas is a highly sought after condominium complex in Kona, Hawaii....
Rates
$95 - $110 night
$665 - $770 week


Non Smoking   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: 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...
Rates
$90 - $100 night
$630 - $700 week


Non Smoking


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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: Stunning direct oceanfront views in this newly remodeled one bedroom will make you never want to leave.The rhythmic sounds of crashing waves genera...
Rates
$95 - $115 night
$665 - $775 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: Beautiful 4 bedroom, 4 bath home with a private pool and an outdoor shower. Unobstructed oceanview of the Kona Coast line. Spectacular stargazing ...
Rates
$450 - $550 night
$3150 - $5565 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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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 - $450 night
$2800 - $4025 week


Non Smoking


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3 bedroom Vacation Rental Home in Kailua-Kona - Ocean View
Home: 3 Bedroom, 3.5 Bathroom, Sleeps 6
Location: Kailua-Kona, Hawaii, United States
Description: Blue Hawaii A Big Island home with amazing ocean views in Kona Hawaii You will not believe the wonderful views from this three bedroom/ three bath...
Rates
$634 - $726 night
$3589 - $4758 week


Non Smoking   Swimming Pool   High-Speed Internet


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Featured


2 bedroom Vacation Rental Condo in Kailua-Kona
Condo: 2 Bedroom, 2 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...
Rates
$140 - $155 night
$980 - $1085 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 114 - 1/1 $100.00 nightly special March 7th-10th! Casa De Emdeko offers owners and guests the perfect blend of Hawaiian ambiance wi...
Rates
$105 - $120 night
$735 - $840 week


Non Smoking


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Listings 1 - 25 of 148
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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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