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Kailua-Kona Holiday Rentals

149 Kailua-Kona Holiday 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 149
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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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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 - $235 night
$1050 - $1645 week


Non Smoking   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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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 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 - $200 night
$1050 - $1400 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: Blue Hawaii is a lovely home with a private pool and spa/online discount Book online and receive a 5% discount excluding Ironman and year end holi... Learn More
Rates
$524 - $858 night
$3530 - $5868 week


Non Smoking   Swimming Pool   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: Book online and receive a 5% discount excluding Ironman and year end holidays. Book with a licensed company to avoid any problem with your Hawaii I... Learn More
Rates
$182 - $277 night
$1030 - $1770 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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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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Featured


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
$350 - $449 night
$2450 - $6265 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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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
$365 - $446 night
$2555 - $3122 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: Hoku'ea Hale Oceanfront Private Home with famous Turtle Gate- New Addition! The 180 degree ocean view at this gorgeous private home is where you w... Learn More
Rates
$3500 - $3850 week


Non Smoking   High-Speed Internet


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1 bedroom Vacation Rental Condo in Kailua-Kona
Condo: 1 Bedroom, 2 Bathroom, Sleeps 3
Location: Kailua-Kona, Hawaii, United States
Description: The Kona Alii is located right in the heart of Kailua Kona. Enjoy waking up to the crashing ocean with a cup of world famous Kona Coffee! This ... Learn More
Rates
$140 - $235 night
$980 - $1645 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: 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
$140 - $155 night
$980 - $1085 week


Non Smoking   High-Speed Internet


View Details and Book Online Send Inquiry



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
$623 - $1393 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: 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
$190 - $205 night
$1330 - $1435 week


Non Smoking


View Details and Book Online Send Inquiry



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
$114 - $185 night
$668 - $1169 week


Non Smoking


View Details and Book Online Send Inquiry



4 bedroom Vacation Rental Home in Kailua-Kona
Home: 4 Bedroom, 4 Bathroom, Sleeps 8
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... Learn More
Rates
$525 - $725 night
$3675 - $5565 week


Non Smoking   High-Speed Internet


View Details and Book Online Send Inquiry



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... Learn More
Rates
$162 - $249 night
$1134 - $1743 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
$169 - $275 night
$1183 - $1925 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 2
Location: Kailua-Kona, Hawaii, United States
Description: Immaculate, beautifully furnished unit in great location. Wheel chair accessable, short walk to restaurants, shopping, and ocean activities. Solid ... Learn More
Rates
$110 - $125 night
$770 - $1050 week


Non Smoking   Handicap Accessible   High-Speed Internet


View Details and Book Online Send Inquiry



2 bedroom Vacation Rental Condo in Kailua-Kona
Condo: 2 Bedroom, 2 Bathroom, Sleeps 4
Location: Kailua-Kona, Hawaii, United States
Description: Keauhou Resort 146 is a beautiful 2/2 on the golf course in Keauhou Kona Call us for specail Summer rates at Keauhou Resort. The location of this ... Learn More
Rates
$122 - $218 night
$643 - $1389 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


View Details and Book Online Send Inquiry



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   High-Speed Internet


View Details and Book Online Send Inquiry





Listings 1 - 25 of 149
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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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