Kailua-Kona Vacation Home Rentals

Kailua Kona Travel Guide
On your next trip, consider a Kailua Kona vacation home rental for your accommodations. There are 15 vacation homes in Kailua Kona resorts. Vacation home rentals are generally appealing for many reasons. Some of the foremost being cost savings, more space, and no tips or service charges that are associated with hotel rooms. Vacation rental homes have kitchens for cooking, living rooms for gathering together and offer the appeal of living in a real neighborhood and soaking up the rhythm of the locals.

With our friendly, responsive customer service and extensive informational website, renting a Kailua Kona vacation home from Owner Direct Vacation Rentals is a breeze. Find your perfect location and home size to suit your needs, no matter what your criteria. We have vacation homes in Area 'A', Area 'B', Area 'C', Area 'D', Alii Cove and many more locations.

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15 Vacation Home Rentals

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  • Special Exclusive Area, Absolutely Private, Infinity Pool & Stunning Ocean View

    Special Exclusive Area

    Kailua Kona: Executive style house
    • 3 BDR
    • 3 BA
    • Sleeps 6
    • #224369
    avg $1,154 USD/night Paypal Star Rating
    Discover your private romantic paradise. The Villa itself is absolutely gorgeous with everything one could possible ask for in luxury and amenities. Twice featured in West Hawaii Today for its outstanding qualities, you will find the Villa nestled in an exclusive community overlooking the charming town of Kona. This is truly a unique destination property. Tumble out of bed to your private, secluded yard and saline solar heated infinity pool with cascading waterfalls and stunning ocean views that makes you wonder where the pool ends and the ocean begins. This luxury home enjoys the Hawaiian indoor/outdoor living plan. Its disappearing walls of glass opens to a honed limestone lanai with large built in gas barbeque, granite counter perp. Area beside the infinity pool featuring a magnificent lava rock waterfall. The home is in the “golden triangle” with the perfect elevation, climate and proximity to Kona village and local attractions. West facing panoramic ocean views from the privacy of your yard with pool side teak chaise lounge chairs, afford a perfect location to view the brilliant blue Pacific and the noted Hawaii sunset. You may even catch the “green flash. ” Ocean breezes comfortably cool this home. Each of the three suites have separate bathrooms with floor to ceiling travertine walk in showers with room for two. All suites have flat screen TV’s. Both the Aloha and Makai suites open directly to the pool, and have exotic soaker tubs with dual sink vanities. Every room is beautifully designed with the highest quality comfortable furnishings with an Asian flare. Custom designed with high end interior and exterior finish materials, including African Mahogany, travertine stone floors, and exotic granite. The gracious living room has a large screen TV and seating comfortable for a group. A designer kitchen is fully equipped for entertaining with decor to captivate a mood that inspires creativity with an eight burner gas stove, warming drawer, built in fridge and walk-in pantry. Although difficult to leave such an oasis, premier beaches, shopping and golfing is just minutes away. We provide our guests with our personal list of recommended restaurants and activities. Truly a vacation “destination” you will long remember. We want your vacation to be a memorable experience; one that will have you falling in love with Hawaii, with Kona, and with our Villa. High speed internet and cable TV are included. Central air conditioning available for a fee. Additional fee if you request a Chef, daily cleaning, grocery delivery, volcano tours, concierge services. Packages available Recent review: “Exclusive Area, Complete Privacy, Luxury Home, Heated Pool, Stunning Ocean Views” Gorgeous home with even more gorgeous views. 5 stars. We have stayed in a lot of vacation homes over the years and this one ranks right up with the best (and far more expensive) of them. Well appointed with an infinity pool to die for, the home made the 6 of us feel relaxed and happy when we returned from our near daily excursions. I really don't have anything negative to say at all other than we didn't want to leave. It is conveniently located to almost all the activities that one does on the island from surfing, scuba diving, snorkeling, horse back riding in the Waipi'o Valley and going to visit the Volcano. We spent evenings in the pool watching the sun set and then made dinner and once again, went out poolside to enjoy our meal as the last vestiges of daylight disappeared. There is a very good grill right near the pool and a fully stocked kitchen (other than food, of course). We were able to find everything we needed to cook even the most elaborate of meals. There is even a wine fridge. All in all, this place deserves 5 stars. The home owner's guide to food, beaches, shopping and other activities was an endless supply of good information though we could add a few of our own, including Luna's Cafe in the Waipi'o Valley and Big Island Divers for the night Manta ray dive (a once in a lifetime experience for the intrepid diver or snorkeler) and Paradise Helicopter for an open door ride over the active volcano. We are sad to be home but so glad we rented this home on the island of Hawaii. Date of arrival March 26, 2016
  • Gorgeous Ocean Views and Great Location

    Gorgeous Ocean Views and

    Kailua Kona: Area 'D': House
    • 2 BDR
    • 2 BA
    • Sleeps 4
    • #211648
    avg $480 USD/night Credit Card Paypal
    This gorgeous house has so much to offer, the views are incredible and the location superb. Two master suites, gourmet kitchen, spacious lanai with dining area and a BBQ Patio to enjoy some of our incredible local delicacies. This is the perfect property to relax and get away from it all.
  • * * *Private Villa , 180 Degree View from your Own Private Pool * * *

    * * *Private Villa , 180

    Kailua Kona: Villa
    • 3 BDR
    • 2 BA
    • Sleeps 8
    • #204822
    avg $483 USD/night Pet Friendly
    Mediterranean-Style VILLA 3 Bedrooms + Other (See Description), 2 Baths, Sleeps 2-8 Experience the Big Island from the comfort of this charming Mediterranean-style villa with GORGEOUS unobstructed panoramic ocean views and memorable sunsets from your own pool, living room, lanai, gazebo, private pool deck, even while YOU'RE cooking!! Resort living at the Villa is perfect for fantastic entertaining or relaxing. The Villa has been enjoyed for family vacations, reunions, honeymoons, birthdays, and holidays or to simply just getting away from it all. Perched high above the crowd taking advantage of unobstructed views theVilla is a private sanctuary with the amenities you need for a special Hawaiian vacation. "The Heart between Kailua-Kona & The Kohala Coast" where you can enjoy strolling along Kona's famous ALI'I Drive AND the Kahala Coast (home to one of Conde Nast Travelers top ten beaches on the globe). Hualalai Villa is located on a cul-DE-sac in a residential neighborhood approximately 1 MI. From Kona International Airport The Villa is approximately 10 minutes from Kailua-Kona Village and 10 minutes from one of many fabulous beaches. It's the best of both worlds!
  • Quiet, Cozy, Home Away from Home in a Tropical Setting by the Ocean

    Quiet, Cozy, Home Away

    Kailua Kona: Area 'C': House with occupied suite
    • 1 BDR
    • 1 BA
    • Sleeps 4
    • #204495
    avg $122 USD/night Credit Card Paypal
    Wonderful beach house in a quiet neighborhood. Less than 2 blocks from Magic Sands Beach in north direction and 1/4 mile from snorkel beach in the other direction. Large upstairs one bedroom with living room, full kitchen, dining room, screened in lanai and ocean views. Lots of private off street parking, coin operated washer & dryer, gazebo with bbq. Home is situated to catch the trade winds for that cooling breeze. Lush and tropical.
  • The Best Oceanviews Ever, Luxury Home. Great Rates, Kona's Best

    The Best Oceanviews Ever

    Kailua Kona: Area 'D': House
    • 3 BDR
    • 4 BA
    • Sleeps 8
    • #202679
    avg $480 USD/night Credit Card Paypal
    Wonderful views from this 3 bedroom luxury home. Located in Keauhou Estates, which is one of Kona's most prestigious gated communities. Warm and welcoming with large rooms beautifully and comfortably furnished. Gourmet kitchen and even a baby grand piano in case you have a musician in your party. Your private pool and spa will relax you after a day sightseeing on the island. Enjoy the BBQ and the outdoor kitchen. You can also enjoy 180 degree ocean views from almost anywhere in this perfect vacation home. There is a fabulous entertainment system and if you must work there is WiFi. Security gate with 24 hr guard in one of Kona's most exclusive areas. We are waiting for you in Paradise. Registration ID: W-01011238-01
  • Special Spectacular Ocean View Private 2/2 Bedroom. Location,Location

    Special Spectacular Ocean

    Kailua Kona: Malulani Gardens: Villa in a gated community
    • 2 BDR
    • 2 BA
    • Sleeps 4
    • #202391
    avg $229 USD/night Paypal Star Rating
    Nestled in an exclusive gated community, you will find our private Villa overlooking the charming village of Kona. Panoramic ocean views span the horizon for as far as your eyes will take you. This property is considered to be in a favored zone due to the perfect elevation, climate and proximity to town and local attractions. Though minutes from downtown Kona (bicycles provided), close to amenities like Starbucks, Safeway, beaches and public pool. The home is tucked away on a secluded cul de sac where underground wiring and sidewalks allow for a . The backyard is completely private, filled with tropical flowers and fruits. The ocean view is simply mesmerizing, with front row seats to watch the sea-side activities and cruise ships gliding by. You will love the space in the master bedroom which has a King-size bed, separate sitting area with desk, walk-in closet, flat screen TV and full bathroom with walk-in shower. Each of the bedroom suites are enhanced with custom furnishings, quality linens and decor to create a mood of relaxation, tranquility and comfort. The recently installed hand scraped wood floors throughout added to the beauty of this property. Best yet, the two full bathrooms (one has two sinks) lend to stress free mornings. Your senses will awaken to tropical flowers, and fruits as you walk to the private lanai and gardens that opens directly from the bedroom. We are stocked with snorkel gear, boogie boards, beach chairs and supplies. We want your vacation to be a memorable experience; one that will have you falling in love with Hawaii, with Kona, and our Villa by The Sea.
  • Elegant White Sands Estate with Pool, Ocean views.

    Elegant White Sands Estate

    Kailua Kona: Area 'C': House
    • 6 BDR
    • 4 BA
    • Sleeps 18
    • #117316
    avg $712 USD/night Credit Card Paypal
    Walk to White Sands Beach! With both a large swimming pool and spa, home is surrounded by an expansive lawn, tropical plantings and lanais. There is a formal dining room plus areas on the lanais and near the swimming pool for you to enjoy both indoor and outdoor dining. Home has two full kitchens, one upstairs and one downstairs, perfect for accommodating multiple families. The living room features a large screen TV, VCR, DVD and stereo entertainment center. WI-FI and unlimited long distance is also provided.
  • Oceanviews Forever, Private Pool 4 Bedrooms

    Oceanviews Forever

    Kailua Kona: Area 'B': Home
    • 4 BDR
    • 3 BA
    • Sleeps 8
    • #39582
    avg $482 USD/night Credit Card Paypal
    Outstanding views, beautiful pool plus two master bedroom suites. This home is very private and is close to everything in Kona. It is approximately a 2 hour drive to Volcanoes National Park and most folks make this a day trip. Water activities abound in the area including self-piloted pontoon boat rentals, sailing and snorkeling cruises, glassbottom boat adventure cruises, 24' zodiac raft trips to Captain Cooks monument, and the always popular whale watching cruises. Private home rentals offer great values over hotels. Your family and friends can enjoy being together yet enjoy your own space for a fraction of the price you would pay in a hotel. Eat your meals in or al fresco. We are waiting for you in Paradise Registration ID: W-10718730-01
  • Old Hawaii Charm, Private Gated Property with Great View and a Private Pool

    Old Hawaii Charm, Private

    Kailua Kona: Area 'C': Executive style house
    • 4 BDR
    • 4 BA
    • Sleeps 10
    • #151245
    avg $325 USD/night Star Rating
    This property offers Old Hawaii plantation feel with all the modern conveniences. The property occupies one half acre of beautifully landscaped gardens. The swimming pool is very private and full sized. All rooms in the house are large and spacious with most rooms having high ceilings. Each bedroom has french doors into a lanai or garden. Perfect for multi generation families or several couples as each has privacy. The property is close to shopping, golf courses and beaches but seems set apart in a very private location. The kitchen is huge and supplied for entertaining. We have had several weddings on the property and it ideal for such occasions with a large grassy lawn and big pool deck for dancing.
  • Panoramic Ocean and City View  Hale Imy Ii  Brand New Home

    Panoramic Ocean and City

    Kailua Kona: House
    • 3 BDR
    • 2 BA
    • Sleeps 5
    • #224356
    avg $154 USD/night Credit Card Paypal Pet Friendly
    This beautiful home has one of the most breath taking views of the Kailua-Kona Coastline. This home has formal dining, living, three bedrooms (two queen beds and a twin) to accommodate 2 couples for 5 guests very comfortably. It is a high elevation so it is cooler in the evening and at night. Spend all you time at the beach and drive up the hill to a cooler climate with a wonderful view.
  • Panoramic Ocean and City View Hale Imy Ii

    Panoramic Ocean and City

    Kailua Kona: Kona-Palisades: House
    • 2 BDR
    • 2 BA
    • Sleeps 4
    • #207198
    avg $132 USD/night Credit Card Paypal Pet Friendly
    This home is located at a slightly higher elevation so you can enjoy the warm days and the cooler nights. Great place to sit and watch the sunsets, whales and fishing boats leaving the Harbor. There is a wonderful day bed on the Lanai that is calling your name for a refreshing nap......
  • Truly the Traditional Hawaiian Home

    Truly the Traditional

    Kailua Kona: House
    • 3 BDR
    • 2 BA
    • Sleeps 8
    • #213824
    avg $155 USD/night Credit Card Paypal Pet Friendly
    This Traditional Hawaiian Home sits on the historic Alii Drive which fronts the Pacific Ocean. Being across the street from the Ocean there is really no view to speak of. It is Truly A Gem in the Pacific. This three bedroom 2 bath home is large enough for 8 guests. The pool table is a wonderful delight as a way of relaxing. Close enough to walk to Kahaluu Beach Park.
  • 4-Bed Studio Unit with Mini Kitchen/Dining, Possible Pool/Jacuzzi Access

    4-Bed Studio Unit with

    Kailua Kona: Area 'B': Island style cottage
    • 1 BA
    • Sleeps 5
    • #87353
    avg $200 USD/night Credit Card
    This 4-bed Studio unit with mini kitchen/dining is suitable for a small group looking for a good deal and depending upon the rental situation of the main house, the backyard pool, jacuzzi, BBQ area may also be available. The outdoor pool has a waterfall, and jacuzzi. The BBQ area has separate charcoal (1) & gas units (2). There is a basketball hoop (ask greeters for the ball) in the carport area. This property has an electric gate with full security alarm. The property is on a 19,000 sq ft lot and has trees and greenery separating the nearest 3 neighbors' property to the east and the south. To the west (ocean direction) and north, the property sits on top of a thirty foot high wall and overlooks the properties far below (no neighbors) and Lako street to the north.
  • Large Kona Home W/Pool & Jacuzzi, 3 Bedrooms, 13 Beds (Max 16 Persons), 4 Baths

    Large Kona Home W/Pool &

    Kailua Kona: Area 'B': House
    • 3 BDR
    • 4 BA
    • Sleeps 16
    • #57130
    avg $672 USD/night Credit Card
    Escape the hotel crowds and enjoy the privacy of this large family home with FULL amenities for your home-stay away from home. Incredible panoramic views of the ocean from the pool/lanai deck backyard, close to town and ocean (5 minutes by car). This home is perfect for that 2-3 family holiday together, small wedding or company team getaway. Main house has 3 bedrooms, 4 baths, 13 beds and if needed, the separate 'Ohana' studio unit has 4 beds, bath, mini kitchen & dining. If available, 'House Next Door' (HND) can be rented adding another 3 queen rooms (3 couples + kids) and same great views. There is a separate dining room (289 sq ft) with seating for 8. High vaulted ceilings with fans in all rooms. The lanai is 434 square feet with tables/chairs for seating >25 people. The outdoor pool has a waterfall, and jacuzzi. The BBQ area has separate charcoal (1) & gas units (2). There is a basketball hoop (ask greeters for the ball) in the car port area. This property has an electric gate with full security alarm. The property is on a 19,000 sq ft lot and has trees and greenery separating the nearest 3 neighbors' property to the east and the south. To the west (ocean direction) and north, the property sits on top of a thirty foot high wall and overlooks the properties far below (no neighbors) and Lako street to the north. There is a second unit located on this property. Please see also OwnerDirect unit ID# 8489 for 4-bedroom offering which includes a separate studio unit.
  • Large Kona Home w/Pool & Jacuzzi, 4 Bedrooms, 17 Beds (max 22 persons), 5 Baths

    Large Kona Home w/Pool &

    Kailua Kona: Area 'B': House
    • 3 BDR
    • 5 BA
    • Sleeps 22
    • #8489
    avg $788 USD/night Credit Card
    Escape the hotel crowds and enjoy the privacy of this large family home with FULL amenities for your home-stay away from home. Incredible panoramic views of the ocean from the pool/lanai deck backyard, close to town and ocean (5 minutes by car). This home is perfect for that 2-4 family holiday together, small wedding or company team getaway. Main house has 3 bedrooms, 4 baths, 13 beds and separate 'Ohana' studio unit has 4 beds, bath, mini kitchen & dining. If available, 'House Next Door' (HND) can also be rented adding another 3 queen rooms (3 couples + kids) and same great views. There is a separate dining room (289 sq ft) with seating for 8. High vaulted ceilings with fans in all rooms. The lanai is 434 square feet with tables/chairs for seating >25 people. The outdoor pool has a waterfall, and jacuzzi. The BBQ area has separate charcoal (1) & gas units (2). There is a basketball hoop (ask greeters for the ball) in the car port area. This property has an electric gate with full security alarm. The property is on a 19,000 sq ft lot and has trees and greenery separating the nearest 3 neighbors' property to the east and the south. To the west (ocean direction) and north, the property sits on top of a thirty foot high wall and overlooks the properties far below (no neighbors) and Lako street to the north. This four bedroom offering INCLUDES a separate studio unit.

Can't find what you are looking for? Try these nearby vacation rental regions

Kailua Kona News and Events


Owner Direct Vacation Rentals Article:

The Big Island experience begins on the beautiful Kona Coast. It's enticing appeal has captivated Hawaiian royalty and visitors for over 200 years. This area is know as the "Gold Coast" because of it's excellent sunsets and reliable sunshine. In addition, the Kona area is known for it's steep hillsides where Kona coffee grows. The scenic bay front fishing village of Kailua, is a blend of old Hawaii and a modern resort town.

Kona-Kohala Chamber of Commerce:

IronMan Triathlon World Championship held in October, which brings the world’s top triathletes here to compete for the title as top man and top woman in this now-famous endurance event consisting of a 2.4-mile swim, 112 mile bike and 26.2 mile run.

Kona-Kohala Chamber of Commerce:

Hawaiian International Billfish Tournament ("HIBT"), founded in 1959 and held every August. The HIBT is one of the most prestigious international fishing tourneys, where angler teams from many countries compete along the Kona Coast to catch, tag and release the largest Pacific Blue marlin.

No matter what your preferences, activities and sports are, you will find lots to do on the Big Island! Check the events website for the latest information ...
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Experience the difference, no waiting
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