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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. Pauls' Almost Perfect Magic Sands Beach Pool House — Property 310700

    Vacation House rental in Kailua Kona area
    • House
    • 4 bedrooms , sleeps 12
    • 4 bathrooms
    • beach, near the ocean
    • pool
    Rates (shown in USD)
  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. Tu'Tu's Beach House with Huge Pool and Back Yard — Property 312920

    Vacation House rental in Kailua Kona area
    • House
    • 5 bedrooms , sleeps 10
    • 4 bathrooms
    • beach, near the ocean
    • garden
    Rates (shown in USD)
    $2000 - $2450 per property per week
  4. Kaloko Ranch House
    Cool, tranquil home with a comfortable elegance in the Ohia forest. — Property 254168

    Vacation House rental in Kailua Kona area
    • House
    • 4 bedrooms , sleeps 10
    • 4 bathrooms
    • mountain, near the ocean
    • balcony
    Rates (shown in USD)
    $2000 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. 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
  7. Hale Malihini - a Family-Oriented Vacation Retreat Home — Property 170046

    Vacation House rental in Kailua Kona area
    • House
    • 5 bedrooms , sleeps 12
    • 4 bathrooms
    • beach, near the ocean
    • pool
    Rates (shown in USD)
  8. Steps from Fabulous Kahaluu Beach, Kailua-Kona — Property 167633

    Vacation House rental in Kailua Kona area
    • House
    • 4 bedrooms , sleeps 12
    • 4 bathrooms
    • beach, near the ocean
    • internet access
    Rates (shown in USD)
  9. Oceanfront Dolphin House Estate — Property 221634

    Vacation House rental in Kailua Kona area
    • House
    • 4 bedrooms , sleeps 10
    • 4 bathrooms
    • 1 half bathroom
    • beach, waterfront
    • pool
    Rates (shown in USD)
    $6825 per property per week
  10. Moana Hale — Property 210119

    Vacation Estate rental in Kailua Kona area
    • Estate
    • 5 bedrooms , sleeps 10
    • 4 bathrooms
    • beach, waterfront
    Rates (shown in USD)
    $12600 per property per week

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