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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.

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  1. Beautiful Beachfront Vacation Rental Condo — Property 229279

    Vacation Condo rental in Kailua Kona area
    • Condo
    • 2 bedrooms , sleeps 4
    • 2 bathrooms
    • beach, waterfront
    • accept credit card
    1 night free with 5 night stay!!!!!!!!!!
    S P E C I A L    O F F E R
    Rates (shown in USD)
    $1505 - $1645 per property per week

  2. Kailua Kona
    7th night FREE until October 5 and free WiFi — Property 191732

    Vacation Condo rental in Kailua Kona area
    • Condo
    • 2 bedrooms , sleeps 6
    • 2 bathrooms
    • beach, near the ocean
    • accept credit card
    7th night FREE, NOW to Oct 5
    S P E C I A L    O F F E R
    Rates (shown in USD)
    $770 - $875 per property per week

  3. SALE OCEANFRONT CONDO SPRING/SUMMER $130/NT W/WIFI JAN STILL AVAILABLE! — Property 193801

    Vacation Condo rental in Kailua Kona area
    • Condo
    • 1 bedroom , sleeps 4
    • 1 bathroom
    • town, waterfront
    • accept credit card
    Sale spring/summer 2010 $130/nt !
    S P E C I A L    O F F E R
    Rates (shown in USD)
    $1085 - $1225 per property per week

  4. New-Convenient-Comfortable-Quiet-Clean. Great rates for small & large groups. — Property 149656

    Vacation House rental in Kailua Kona area
    • House
    • 4 bedrooms , sleeps 12
    • 2 bathrooms
    • near the ocean, town
    • accept credit card
    Large Group Special
    S P E C I A L    O F F E R
    Rates (shown in USD)
    $980 - $1176 per property per week

  5. Ocean Paradise on the Green - Golf-partial HDCP — Property 127773

    Vacation Condo rental in Kailua Kona area
    • Condo
    • 2 bedrooms , sleeps 6
    • 2 bathrooms
    • beach, near the ocean
    • swimming pool
    Near beach/golf lg condo $105/n sleep 6
    S P E C I A L    O F F E R
    Rates (shown in USD)
    $770 - $1015 per property per week

  6. New Million Dollar Tropical Paradise*Central Air* — Property 127780

    Vacation Townhome rental in Kailua Kona area
    • Townhome
    • 3 bedrooms , sleeps 8
    • 3 bathrooms
    • near the ocean, resort
    • swimming pool
    NEW 3BED/3BA by ocean/golf just $169/N
    S P E C I A L    O F F E R
    Rates (shown in USD)
    $1295 - $1610 per property per week

  7. Oceanfront - Vacation Rental Home next to White Sands Beach with Pool & Spa — Property 216190

    Vacation House rental in Kailua Kona area
    • House
    • 3 bedrooms , sleeps 6
    • 3 bathrooms
    • beach, waterfront
    • swimming pool
    August-September Special, $1,950 a week
    S P E C I A L    O F F E R
    Rates (shown in USD)
    $1950 - $2500 per property per week

  8. Kona Shangrila
    Oceanfront Luxury in Kona — Property 156794

    Vacation House rental in Kailua Kona area
    • House
    • 5 bedrooms , sleeps 16
    • 4 bathrooms
    • near the ocean, waterfront
    • accept credit card
    50% OFF! ABSOLUTE OCEANFRONT SUMMER SALE
    S P E C I A L    O F F E R
    Rates (shown in USD)
    $3500 - $7700 per property per week

  9. Kona Oceanview Garden Estate & Guesthouses with private tennis court & pool — Property 176615

    Vacation rental in Kailua Kona area
    • 5 bedrooms , sleeps 18
    • 4 bathrooms
    • near the ocean
    • accept credit card
    'Recession breaker discounts'
    S P E C I A L    O F F E R
    Rates (shown in USD)
    $3950 per property per week

  10. Kona Reef Oceanfront Vacation Condo Rental — Property 318447

    Vacation Condo rental in Kailua Kona area
    • Condo
    • 1 bedroom , sleeps 3
    • 1 bathroom
    • beach, waterfront
    • accept credit card
    Rates (shown in USD)
    $980 per property per week

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