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.

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  1. Executive Ocean View Condo — Property 322656

    Vacation Condo rental in Kailua Kona area
    • Condo
    • 2 bedrooms , sleeps 6
    • 2 bathrooms
    • near the ocean, resort
    • accept credit card
    10% off the nightly rate!!
    S P E C I A L    O F F E R
    Rates (shown in USD)

  2. Opulent Executive Vacation Home — Property 219163

    Vacation House rental in Kailua Kona area
    • House
    • 2 bedrooms , sleeps 6
    • 2 bathrooms
    • beach, near the ocean
    • accept credit card
    10% off the nightly rate!!
    S P E C I A L    O F F E R
    Rates (shown in USD)

  3. Absolue Oceanfront, just 25' from shore. A luxurious, peaceful Island Retreat ! — Property 134526

    Vacation Condo rental in Kailua Kona area
    • Condo
    • 2 bedrooms , sleeps 5
    • 2 bathrooms
    • beach, waterfront
    • accept credit card
    Fall Special for Oceanfront condo
    S P E C I A L    O F F E R
    Rates (shown in USD)
    $1380 - $1450 per property per week

  4. Desirable Ocean Condo directly across from the Ocean +Alii Drive in Kona Village — Property 142113

    Vacation Condo rental in Kailua Kona area
    • Condo
    • 1 bedroom , sleeps 4
    • 2 bathrooms
    • downtown, waterfront
    • accept credit card
    Fall Special for Kona Alii
    S P E C I A L    O F F E R
    Rates (shown in USD)
    $925 - $1320 per property per week

  5. Grand Opening Special $239/nt Million Dollar Luxury Oceanfront Condo Kona Hawaii — Property 209356

    Vacation Condo rental in Kailua Kona area
    • Condo
    • 2 bedrooms , sleeps 4
    • 2 bathrooms
    • beach, waterfront
    • accept credit card
    Grand Opening Special $239/nt.
    S P E C I A L    O F F E R
    Rates (shown in USD)
    $2093 per property per week

  6. Amazing Oceanfront Luxury. 2 BR 2 BA Condo on famous Ali'I Dr. — Property 134335

    Vacation Condo rental in Kailua Kona area
    • Condo
    • 2 bedrooms , sleeps 9
    • 2 bathrooms
    • beach, waterfront
    • accept credit card
    FALL SAVINGS OFFER
    S P E C I A L    O F F E R
    Rates (shown in USD)
    $1365 - $1645 per property per week

  7. CHRISTMAS WEEK STILL AVAILABLE! - Spectacular Private Oceanfront Estate — Property 156794

    Vacation House rental in Kailua Kona area
    • House
    • 5 bedrooms , sleeps 16
    • 4 bathrooms
    • near the ocean, waterfront
    • accept credit card
    $199/Nt - Oceanfront! 2 Br/2Ba Sleeps 6
    S P E C I A L    O F F E R
    Rates (shown in USD)

  8. Kona Grand Oceanview Twin Villas — Property 163580

    Vacation Villa rental in Kailua Kona area
    • Villa
    • 7 bedrooms , sleeps 16
    • 10 bathrooms
    • near the ocean
    • accept credit card
    $2000 off Weekly-Grand Opening Special!
    S P E C I A L    O F F E R
    Rates (shown in USD)

  9. Fall Special $350 per nt. for Luxury Oceanfront Condo / Villa in Sunny Kona — Property 155739

    Vacation Condo rental in Kailua Kona area
    • Condo
    • 3 bedrooms , sleeps 6
    • 3 bathrooms
    • resort, waterfront
    • accept credit card
    Rates (shown in USD)
    $2450 - $3850 per property per week

  10. Availability Starts April 2008 Reserve Now!! — Property 189282

    Vacation Condo rental in Kailua Kona area
    • Condo
    • 2 bedrooms , sleeps 4
    • 2 bathrooms
    • downtown, near the ocean
    • swimming pool
    Rates (shown in USD)

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