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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. Keauhou Akahi
    Panoramic Ocean View Kona Country Club Luxury Condo! — Property 167675

    Vacation Condo rental in Kailua Kona area
    • Condo
    • 1 bedroom , sleeps 4
    • 2 bathrooms
    • near the ocean, town
    • garden
    Rates (shown in USD)
    $623 - $805 per property per week
  2. Paradise Condo Ocean View-on Kona Country Club 9th Fairway — Property 315891

    Vacation Condo rental in Kailua Kona area
    • Condo
    • 1 bedroom , sleeps 6
    • 2 bathrooms
    • near the ocean
    • air-conditioning
    Rates (shown in USD)
  3. 2-204 (1) The Beach Villas at Kahaluu — Property 78444

    Vacation Condo rental in Kailua Kona area
    • Condo
    • 1 bedroom , sleeps 2
    • 2 bathrooms
    • adventure
    • air-conditioning
    Rates (shown in USD)
    $1081 - $1997 per condo per week
  4. Kona Alii
    Desirable Oceanfront Condo directly across from the Ocean +Alii Drive in Kona — Property 142113

    Vacation Condo rental in Kailua Kona area
    • Condo
    • 1 bedroom , sleeps 4
    • 2 bathrooms
    • downtown, waterfront
    • tennis court
    Rates (shown in USD)
    $850 - $935 per property per week
  5. Welcome to Paradise- Kona Pacific (Newly Remodeled) DECEMBER AVAILABILITY — Property 149396

    Vacation Condo rental in Kailua Kona area
    • Condo
    • 1 bedroom , sleeps 4
    • 2 bathrooms
    • near the ocean, town
    • garden
    Rates (shown in USD)
    $665 - $840 per property per week
  6. Royal Sea Cliff #109 (1) — Property 7014452

    Vacation Condo rental in Kailua Kona area
    • Condo
    • 1 bedroom , sleeps 2
    • 2 bathrooms
    • 1 half bathroom
    • adventure
    • air-conditioning
    Rates (shown in USD)
    $1389 - $2580 per condo per week
  7. 2-103 (1) The Beach Villas at Kahaluu — Property 78443

    Vacation Condo rental in Kailua Kona area
    • Condo
    • 1 bedroom , sleeps 2
    • 2 bathrooms
    • adventure
    • air-conditioning
    Rates (shown in USD)
    $1081 - $1997 per condo per week
  8. 2-302 (1) The Beach Villas at Kahaluu — Property 7014450

    Vacation Condo rental in Kailua Kona area
    • Condo
    • 1 bedroom , sleeps 2
    • 2 bathrooms
    • adventure
    • air-conditioning
    Rates (shown in USD)
    $1081 - $1997 per condo per week
  9. 2-101 (1) The Beach Villas at Kahaluu — Property 78062

    Vacation Condo rental in Kailua Kona area
    • Condo
    • 1 bedroom , sleeps 2
    • 2 bathrooms
    • adventure
    • air-conditioning
    Rates (shown in USD)
    $1081 - $1997 per condo per week
  10. Kona Oceanview - Newly Remodeled - Luxury on a Budget!! — Property 229151

    Vacation Condo rental in Kailua Kona area
    • Condo
    • 1 bedroom , sleeps 4
    • 2 bathrooms
    • near the ocean, town
    • pool
    Rates (shown in USD)
    $700 - $840 per property per week

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