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Search for vacation rental homes in Kailua Kona

Checking Out Kailua Kona for Yourself

Up until now you’ve only seen the name written on fragrant packages of delicious coffee. Or, in a moment of wishful thinking, you have gazed at Hawaii on the map and imagined finding yourself enjoying an ocean breeze in a place as exotic sounding as Kailua Kona. Either way, now is the time to see this paradise with your own eyes…


As you get to know this Big Island locale, you’ll quickly realize why you’ve always had positive associations with it. The friendly vibes, lush scenery and ample amenities that you’ll find today have been pleasing visitors for years – in fact this was once a favorite swimming spot for Hawaiian royalty. Morphing from a quiet fishing village into a quietly buzzing town (it’s the site of the Ironman Triathlon and its oceanside pier makes it a fun place to stroll and people watch).


Traditional vacation activities like tennis, golf, swimming and shopping are all a little more fun in a land of leis and luaus, especially when that land is also outfitted with vacation rentals that aim to make you feel as if you truly belong. With your own patio, pool and kitchen as well as a view of the beach and easy access to all the highlights of the isle (Volcano National Park, Captain Cook’s Monument, Hilo Town and more) you’ll be sitting pretty and happy that you made the right choice.


Leave the kids at home and make it an escape of sorts (bring your best girlfriend or your significant other, whoever you feel like bestowing your company upon), finally letting this destination move from the land of myth to reality.

  1. Luxurious Oceanview Home with Private Pool — Property 247548

    Vacation House rental in Kailua Kona area
    • House
    • 4 bedrooms , sleeps 12
    • 3 bathrooms
    • near the ocean
    • pool
    10% off November
    S P E C I A L    O F F E R
    Rates (shown in USD)
    $2450 - $3150 per property per week
  2. Kona Alii Makai
    fabulous oceanfront estate-home with lagoon-type lap pool and ocean access — Property 255412

    Vacation House rental in Kailua Kona area
    • House
    • 5 bedrooms , sleeps 10
    • 5 bathrooms
    • beach, near the ocean
    • pool
    Rates (shown in USD)
    $6965 - $12565 per property per week
  3. Spacious 3 Story Oceanfront Home at Popular Surf Spot — Property 320057

    Vacation House rental in Kailua Kona area
    • House
    • 5 bedrooms , sleeps 12
    • 1 half bathroom
    • beach, near the ocean
    • air-conditioning
    Rates (shown in USD)
    $3675 - $3850 per property per week
  4. KEIKI BEACH HOUSE: Luxury Beach Home with Pool — Property 146358

    Vacation Estate rental in Kailua Kona area
    • Estate
    • 4 bedrooms , sleeps 10
    • 3 bathrooms
    • 1 half bathroom
    • beach, near the ocean
    • pool
    Rates (shown in USD)
    $3850 - $4550 per property per week
  5. Kona Alii Makai — Property 88547

    Vacation House rental in Kailua Kona area
    • House
    • 5 bedrooms , sleeps 10
    • 5 bathrooms
    • coffee maker
    • toaster
    Rates (shown in USD)
    $9065 per house per week
  6. Hibiscus Hale — Property 92590

    Vacation House rental in Kailua Kona area
    • House
    • 4 bedrooms , sleeps 10
    • 3 bathrooms
    • air-conditioning
    • blender
    Rates (shown in USD)
    $2800 - $3150 per house per week
  7. Stunning Kona Oceanfront Luxury Home — Property 319233

    Vacation House rental in Kailua Kona area
    • House
    • 4 bedrooms , sleeps 10
    • 4 bathrooms
    • waterfront
    • pool
    Rates (shown in USD)
    $4375 - $4550 per property per week
  8. Kona Lighthouse
    NEW LOW RATES Across from Ocean Hear/See Waves. Tropical lap pool. — Property 147230

    Vacation House rental in Kailua Kona area
    • House
    • 4 bedrooms , sleeps 10
    • 3 bathrooms
    • near the ocean, village
    • pool
    Rates (shown in USD)
    $1485 per property per week
  9. Vista Oceania : Beach Front Luxury Home — Property 172358

    Vacation Estate rental in Kailua Kona area
    • Estate
    • 3 bedrooms , sleeps 9
    • 2 bathrooms
    • 1 half bathroom
    • beach, waterfront
    • pool
    Rates (shown in USD)
    $4550 - $6650 per property per week
  10. Relaxing Oceanview Hawaiian Paradise Estate — Property 315211

    Vacation Estate rental in Kailua Kona area
    • Estate
    • 5 bedrooms , sleeps 12
    • near the ocean
    • pool
    Rates (shown in USD)

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