Owner Direct Vacation Rentals in Kailua-Kona

The Best Owner Direct Vacation Rentals in Kailua-Kona. Explore thousands of vacation home rentals, large cabins, and villas near Kailua-Kona

Affordable Luxury on One Acre From US $532
         

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10.0 (8 Reviews)
Villa
  • Parking
  • Pool
  • View
Mango Sunset Bed and Breakfast From US $281
         

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10.0 (96 Reviews)
Bed & Breakfast
  • Parking
  • View
  • Ocean View
Kailua-Kona Condo with Pool and Ocean Views From US $226
         

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10.0 (8 Reviews)
Apartment
  • Parking
  • View
  • Ocean View
Ohana Beach Retreat at the Surf and Racquet Club From US $314
         

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10.0 (7 Reviews)
Apartment
  • Air Conditioner
  • Parking
  • Pool
Kailua Village#701 From US $160
         

Luxury Places to Stay in Kailua-Kona

Over 4615+ Luxury Places to Stay in or Near Kailua-Kona
Kona Beach Bungalows From US $12,130
         

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New
House
  • Air Conditioner
  • Parking
  • Pool

Top-Rated Vacation Rentals with a Pool in Kailua-Kona

Over 3617+ Top-Rated Vacation Rentals with a Pool in or Near Kailua-Kona

Pet-Friendly Vacation Rentals in Kailua-Kona

Over 77+ Pet-Friendly Vacation Rentals in or Near Kailua-Kona
Four Seasons Resort Hualalai From US $1,440
         

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9.5 (35 Reviews)
Resort
  • Air Conditioner
  • Parking
  • Pet Friendly
Bright and Airy Beach House with Oceanfront Views From US $611
         

Bright & Airy Beach House w/Oceanfront Views From US $804
         

10.0 (22 Reviews)
House
  • Air Conditioner
  • Parking
  • Pet Friendly
Central Oceanview Modern Cozy 3 Bed House From US $309
         

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9.2 (9 Reviews)
House
  • Air Conditioner
  • Parking
  • Pet Friendly

Large Vacation Homes & Villas in Kailua-Kona

Over 415+ Large Vacation Homes & Villas in or Near Kailua-Kona
🏖️Ocean Front Villa| Concierge Included | Central AC From US $775
         

Na Hale O Keauhou Beach Views, Hot Tub & Pool From US $793
         

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10.0 (2 Reviews)
Villa
  • Air Conditioner
  • Parking
  • Pool
Luxury Kona Mansion - Infinity Pool & Epic Views From US $3,074
         

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10.0 (2 Reviews)
Villa
  • Air Conditioner
  • Parking
  • Pool
Panoramic Ocean View Home with Pool by Kona PhiLong From US $1,465
         

Hale A Kai From US $1,078
         

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10.0 (1 Review)
House
  • Air Conditioner
  • Parking
  • View

Wheelchair Accessible Vacation Homes in Kailua-Kona

Over 935+ Wheelchair Accessible Vacation Homes in or Near Kailua-Kona
Kona Bali Kai #310 From US $184
         

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9.5 (2 Reviews)
Apartment
  • Pool
  • View
  • Wheelchair Accessible
Direct Oceanview Paradise in a luxury condo 2B2B,AC From US $389
         

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9.3 (23 Reviews)
Villa
  • Air Conditioner
  • Parking
  • Pool
Country Club Villas 102 From US $430
         

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9.2 (6 Reviews)
Apartment
  • Pool
  • Wheelchair Accessible
  • Balcony/Terrace

Kailua-Kona Varoom and Airbnb Places to Stay Under $200

Over 491+ Kailua-Kona Varoom and Airbnb Places to Stay Under $200
Kona Mansions#105 From US $169
         

Breezy Condo w/Screened Lanai in Kailua-kona! From US $152
         

Kona Pacific E630 From US $150
         

Your Hawaiian Vacation Starts Here! II From US $198
         

10.0 (181 Reviews)
Condo
  • Air Conditioner
  • Parking
  • Pool
Granma's Cabin Kona coast From US $160
         

Kona Makai 5-205 From US $198
         

10.0 (2 Reviews)
House
  • Parking
  • Pool
  • View

Instantly Bookable Vacation Homes in Kailua-Kona

Over 2710+ Instantly Bookable Vacation Homes in or Near Kailua-Kona

About Kailua-Kona Vacation Rentals

With more than 4624 Kailua-Kona vacation rentals, we can help you find a place to stay. These rentals, including vacation rentals, Ownerdirect and other short-term private accommodations, have top-notch amenities with the best value, providing you with comfort and luxury at the same time. Get more value and more room when you stay at a rental property in Kailua-Kona.

Looking for last-minute deals, or finding the best deals available for cottages, condos, private villas, and large vacation homes? With Ownerdirect Kailua-Kona, you have the flexibility of comparing different options of various deals with a single click. Looking for a rental by owner with the best swimming pools, hot tubs, allows pets, or even those with huge master suite bedrooms and have large screen televisions? You can find vacation rentals by owner, and other popular Airbnb-style properties in Kailua-Kona. Places to stay near Kailua-Kona are 845.18 ft² on average, with prices averaging $617 a night.

Ownerdirect makes it easy and safe to find and compare vacation rentals in Kailua-Kona with prices often at a 30-40% discount versus the price of a hotel. Just search for your destination and secure your reservation today.

Top Rental Accommodation Types in Kailua-Kona

Type Count
Vacation Homes 1462
Holiday Apartments 579
Hotels with Suites 112
Resorts 88
Villas 79
Cottages 27
Cabin Rentals 8
B&B 6
Others 4
Hostels 1

Use these Quick Filters to Find a Vacation Rental in Kailua-Kona

Pro Tip: Ownerdirect makes it easy to compare the best listings on Ownerdirect homes from online vacation rental OTAs, including Booking.com and more. Use the Advanced Filter feature at the top to easily flip between Ownerdirect homes, vacation rentals, bed and breakfasts, private Airbnb-style rentals availability, eco-friendly properties, property type, cancellation policies, prices, and several different options. All these make it easier to find the perfect accommodation for your next vacation in Kailua-Kona.

Weather in Kailua-Kona

View the weather forecast for Kailua-Kona before booking your Kailua-Kona Vacation Rentals to confirm your best time to go.

December - February
High 79°F       Low 64°F
March - May
High 83°F       Low 66°F
June - August
High 84°F       Low 69°F
September - November
High 84°F       Low 66°F