Kailua-Kona Vacation Rentals

261 Kailua-Kona Vacation Rentals were found matching your criteria.

1 - 25 of 261

Sort by:

Featured

$138 - $451 /night
$966 - $3106 /week

Krd32 Absolute Oceanfront Top Flr Private

Condo: 1 Bedroom, 1 Bathroom, Sleeps 4
Location: Kailua-Kona, Hawaii, United States
Description: Private, top floor, absolute oceanfront, lovely one bedroom condo at the highly acclaimed Kona Reef Resort! Why Kona Reef: ? Conveniently located...

Rates

$138 - $451 /night

$966 - $3106 /week

Featured

Add to Favorites Send Inquiry

Details and Book

Featured

$950 - $3200 /night
$6650 - $22400 /week

Hualalai~exclusive Hillside Villa 4102~upgraded 2 bd~ocea...

26 reviews Add to Favorites

Villa: 2 Bedroom, 2 Bathroom, Sleeps 4
Location: Kailua-Kona, Hawaii, United States
Description: Hualalai~exclusive Hillside Villa 4102~upgraded 2 bd~ocean Views~near Resort Location-Location-Location! This spectacular 2 bedroom, 2 bath luxur...

Rates

$950 - $3200 /night

$6650 - $22400 /week

Featured

Add to Favorites Send Inquiry

Details and Book

Featured

$629 - $695 /night
$4403 - $4865 /week

Hale Honu - Spectacular Oceanfront Home w/ central A/C - ...

73 reviews Add to Favorites

Home: 4 Bedroom, 4 Bathroom, Sleeps 8
Location: Kailua-Kona, Hawaii, United States
Description: Hale Honu - Spectacular Oceanfront Home w/ central A/C - Special Rate $499/nt Take advantage of our Fabulous Fall Special! Only $499 per night! Ef...

Rates

$629 - $695 /night

$4403 - $4865 /week

Featured

Add to Favorites Send Inquiry

Details and Book

Featured

$245 - $633 /night
$1715 - $4364 /week

Kona Makai 1-301 Direct Oceanfront, Top Floor, Best Corne...

20 reviews Add to Favorites

Condo: 2 Bedroom, 2 Bathroom, Sleeps 4
Location: Kailua-Kona, Hawaii, United States
Description: Kona Makai 1-301 Direct Oceanfront, Top Floor, Best Corner In Kona Makai! Kona Makai #1-301 is arguably the BEST condo in the entire complex! Bein...

Rates

$245 - $633 /night

$1715 - $4364 /week

Featured

Add to Favorites Send Inquiry

Details and Book

Featured

$380 - $410 /night
$2660 - $4375 /week

Private home with pool, cool elevation, unobstructed Ocea...

21 reviews Add to Favorites

Home: 3 Bedroom, 3.5 Bathroom, Sleeps 8
Location: Kailua-Kona, Hawaii, United States
Description: Private home with pool, cool elevation, unobstructed Ocean & Sunset views This beautiful home features luxury and artistic touches to add a splash...

Rates

$380 - $410 /night

$2660 - $4375 /week

Featured

Add to Favorites Send Inquiry

Details and Book

Featured

$149 - $250 /night
$1043 - $1750 /week

Updated Ocean View Condo with Additional Loft!

10 reviews Add to Favorites

Condo: 1 Bedroom, 1 Bathroom, Sleeps 4
Location: Kailua-Kona, Hawaii, United States
Description: Aloha and welcome to the ultimate tranquil Hawaiian vacation experience: Mackall?s Makai! This condo boasts a vaulted, two-story den and kitchen, w...

Rates

$149 - $250 /night

$1043 - $1750 /week

Featured

Add to Favorites Send Inquiry

Details and Book

Featured

$164 - $206 /night
$1148 - $1820 /week

Oceanfront 2 BR ground floor condo with amazing Ocean Views

49 reviews Add to Favorites

Condo: 2 Bedroom, 2 Bathroom, Sleeps 6
Location: Kailua-Kona, Hawaii, United States
Description: This unit is located in a highly desirable location just a short walk from down town Kailua Kona. A recently remodeled two bedrooms, two bath condo...

Rates

$164 - $206 /night

$1148 - $1820 /week

Featured

Add to Favorites Send Inquiry

Details and Book

Featured

$500 - $600 /night
$3500 - $4200 /week

Lymans Bay Hale-Oceanfront

33 reviews Add to Favorites

Home: 5 Bedroom, 3.5 Bathroom, Sleeps 12
Location: Kailua-Kona, Hawaii, United States
Description: For a virtual tour of this property scroll down to the bottom of the text and click on the link. As of September 20, 2015 a major renovation of Lym...

Rates

$500 - $600 /night

$3500 - $4200 /week

Featured

Add to Favorites Send Inquiry

Details and Book

$179 - $315 /night
$1113 - $2200 /week

Stunning Accessible Oceanfront Condo on the Kona Coast

Condo: 2 Bedroom, 2 Bathroom, Sleeps 6
Location: Kailua-Kona, Hawaii, United States
Description: Elegant yet simple luxury on the ocean in Kona Hawaii. * Incredible Ocean Views * Spacious 2-BR /2-BA * Central Air Conditioning (A/C)...

Rates

$179 - $315 /night

$1113 - $2200 /week

Add to Favorites Send Inquiry

View Details

$120 - $186 /night
$840 - $1540 /week

One Bedroom Condo with Amazing Ocean Views, Ac incl.

31 reviews Add to Favorites

Condo: 1 Bedroom, 1 Bathroom, Sleeps 2
Location: Kailua-Kona, Hawaii, United States
Description: This perfectly located deluxe one bedroom unit with amazing ocean views from the lanai, has been fully redecorated and upgraded. All new appliance...

Rates

$120 - $186 /night

$840 - $1540 /week

Add to Favorites Send Inquiry

Details and Book

$1285 - $1780 /night
$8995 - $12460 /week

Home: 2 Bedroom, 3 Bathroom, Sleeps 6
Location: Kailua-Kona, Hawaii, United States
Description: This beautiful, hand-crafted, custom home, with open-beam, cedar ceilings, and air-conditioned bedrooms, is the perfect getaway vacation site. The ...

Rates

$325 - $380 /night

$2275 - $2660 /week

Add to Favorites Send Inquiry

Details and Book

$1110 - $1595 /night
$7770 - $11165 /week

O'oma Plantation

Home: 7 Bedroom, 7 Bathroom, Sleeps 17
Location: Kailua-Kona, Hawaii, United States
Description: Why book individual resorts or condos when your whole group can enjoy a mansion in paradise? Enjoy exceptional panoramic coastal views from the pri...

Rates

$1110 - $1595 /night

$7770 - $11165 /week

Add to Favorites Send Inquiry

Details and Book

$148 - $344 /night
$1029 - $2282 /week

Kona Isle E23

Condo: 1 Bedroom, 1 Bathroom, Sleeps 4
Location: Kailua-Kona, Hawaii, United States
Description: E23 at the Kona Isle is a beautiful direct oceanfront property on the 2nd floor of building E. These units are in high demand. Feel the ocean breez...

Rates

$148 - $344 /night

$1029 - $2282 /week

Add to Favorites Send Inquiry

Details and Book

$135 - $190 /night
$945 - $1330 /week

Oceanfront Paradise with private lanai overlooking Kailua...

21 reviews Add to Favorites

Condo: 1 Bedroom, 1 Bathroom, Sleeps 4
Location: Kailua-Kona, Hawaii, United States
Description: Oceanfront Paradise with private lanai overlooking Kailua Bay Sea Village Resort sits right on the sea wall. Located on prestigious Alii Drive. Th...

Rates

$135 - $190 /night

$945 - $1330 /week

Add to Favorites Send Inquiry

Details and Book

$230 - $325 /night
$1610 - $2275 /week

Home: 3 Bedroom, 3 Bathroom, Sleeps 8
Location: Kailua-Kona, Hawaii, United States
Description: Hale Welo - "Sunset House" - sits above Kona at a cool elevation of 650’ with gorgeous drop dead ocean views to Kona Bay and beyond. Hale Welo is a...

Rates

$335 - $580 /night

$2345 - $4060 /week

Add to Favorites Send Inquiry

Details and Book

$175 - $315 /night
$1225 - $2205 /week

Kona Alii 504

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 1 be...

Rates

$175 - $315 /night

$1225 - $2205 /week

Add to Favorites Send Inquiry

Details and Book

$181 - $671 /night
$1253 - $4697 /week

Kona Pacific B409

Condo: 2 Bedroom, 3 Bathroom, Sleeps 6
Location: Kailua-Kona, Hawaii, United States
Description: Kona Pacific B-409 is a newly remodeled upper floor condo with breathtaking ocean views. The owners have extensively made changes that every guest ...

Rates

$181 - $671 /night

$1253 - $4697 /week

Add to Favorites Send Inquiry

Details and Book

Why Kailua-Kona?

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.

This map is intended to be used as a reference only.

Kailua-Kona Vacation Rentals

Hawaii (Big Island) Top Cities