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Kailua-Kona Vacation Rentals

147 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 1 - 25 of 147
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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: 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... Learn More
Rates
$412 - $837 night
$2810 - $5538 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 6
Location: Kailua-Kona, Hawaii, United States
Description: Tucked away in the quiet enclave of Kona Bay Estates, just a short walk from Kailua Bay, your oceanfront vacation home, Kona Bay Keiki Beach Oasis,... Learn More
Rates
$449 - $449 night
$3143 - $6265 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: This spacious, upgraded and tastefully decorated three bedroom home has sweeping ocean view in the quiet gated community of Kahakai Estates. Locate... Learn More
Rates
$350 - $425 night
$2450 - $2975 week


Non Smoking   Swimming Pool   High-Speed Internet


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5 bedroom Vacation Rental Home in Kailua-Kona
Home: 5 Bedroom, 4 Bathroom, Sleeps 12
Location: Kailua-Kona, Hawaii, United States
Description: A/C in every room. 180 degree unobstructed view of Lymans Bay, favorite surf spot. 2 story open floor plan with 20 foot ceilings. Downstairs includ... Learn More
Rates
$500 - $500 night
$3500 - $4200 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
$110 - $120 night
$770 - $840 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: Come and enjoy this community at the Kona Makai, vacationers number one choice for return guests. The Kona Makai offers guests lovely lush grounds,... Learn More
Rates
$150 - $195 night
$1050 - $1470 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: Spectacular location, spectacular view, spectacular decor! This newly remodeled suite is committed to quality. Take your highest expectations and ... Learn More
Rates
$150 - $200 night
$1050 - $1715 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: The Kona Coast Resort is one of the premier resorts in Kona and this condo fits right in. The condo has been completely remodeled with all new floo... Learn More
Rates
$162 - $278 night
$981 - $1736 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: Oceanfront estate with breathtaking panoramic unobstructed views. 4 BR, 4 elegant baths. All bedrooms have oceanfront balconies. Walls of glass ope... Learn More
Rates
$599 - $599 night
$4193 - $4550 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: Keauhou Kona Surf and Racquet Club 2204 - Direct Ocean Front Corner Unit~ The Keauhou Surf and Racquet Club is a gated community of condominiums. ... Learn More
Rates
$125 - $205 night
$875 - $1435 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: Elegant yet simple luxury on the ocean in Kona Hawaii. And ONE OF ONLY TWO ACCESSIBLE OCEANFRONT CONDOS ON THE KONA COAST * Incredible Ocean ... Learn More
Rates
$179 - $295 night
$1113 - $2065 week


Non Smoking   Handicap Accessible   Swimming Pool   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 is a highly sought after condominium complex in Kona, Hawaii. The location is perfect. It is in walking distance to town where there ar... Learn More
Rates
$95 - $110 night
$665 - $770 week


Non Smoking   High-Speed Internet


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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 182 2 b/r Oceanfront condo Kona Hawaii One of a kind, like a cottage by the sea. Enjoy the crashing surf and one of Ko... Learn More
Rates
$163 - $323 night
$1060 - $2221 week


Non Smoking   High-Speed Internet


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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 58 2 b/r condo in oceanfront complex Kona Hawaii This is a very nice 2 bedroom 2 bath two story townhouse. Fully equi... Learn More
Rates
$107 - $279 night
$728 - $1915 week


Non Smoking


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3 bedroom Vacation Rental Condo in Kailua-Kona
Condo: 3 Bedroom, 3 Bathroom, Sleeps 6
Location: Kailua-Kona, Hawaii, United States
Description: Mauna Loa Village Lovely 3 b/r in a tropical setting. luxury at a good price Live where Hawaii's royalty played, Mauna Loa Village at the Honua Re... Learn More
Rates
$197 - $279 night
$1349 - $1672 week


Non Smoking   High-Speed Internet


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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 - $1255 night
$5075 - $8785 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: Ali'i Villas 139 Great oceanfront complex on the Big Island Kona Hawaii Kona Alii Villas #139 on the Big Island of Hawaii is a very nicely furnish... Learn More
Rates
$93 - $216 night
$612 - $1473 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: 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 ... Learn More
Rates
$168 - $284 night
$997 - $1927 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 Punahele C102 Spacious, serene, 2 b/r Kona Hawaii condo This condo is beautifully furnished.in a nice location. The master suite is huge w... Learn More
Rates
$147 - $279 night
$960 - $1915 week


Non Smoking   High-Speed Internet


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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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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: Gorgeous 3 BR Home with pool & breathtaking views ***new*** We welcome you to stay at our private luxury home (Ono Hale) in the lush hil... Learn More
Rates
$275 - $275 night
$1925 - $2275 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: Keauhou Kona Surf & Racquet 6103 Oceanfront complex 2 BR lovely condo Surf & Racquet Club 6103 has wonderful amenities, high speed internet, three... Learn More
Rates
$138 - $279 night
$941 - $1915 week


Non Smoking   High-Speed Internet


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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
$300 - $525 night
$2100 - $3675 week


Non Smoking   High-Speed Internet


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1 bedroom Vacation Rental Condo in Kailua-Kona
Condo: 1 Bedroom, 3 Bathroom, Sleeps 4
Location: Kailua-Kona, Hawaii, United States
Description: Kona Alii on Alii Drive in the Village of Kailua Kona has so much to offer you will not want to leave. Make this your second home and you won't be... Learn More
Rates
$150 - $272 night
$988 - $1718 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 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... Learn More
Rates
$95 - $120 night
$665 - $840 week


Non Smoking   High-Speed Internet


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Listings 1 - 25 of 147
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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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