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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. Executive Ocean View Condo — Property 322656

    Vacation Condo rental in Kailua Kona area
    • Condo
    • 2 bedrooms , sleeps 6
    • 2 bathrooms
    • near the ocean, resort
    • garden
    November $100 per Night Special
    S P E C I A L    O F F E R
    Rates (shown in USD)
    $805 - $1085 per property per week

  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
    • sauna
    November $100 Per Night Special
    S P E C I A L    O F F E R
    Rates (shown in USD)
    $945 - $1365 per property per week

  3. Oceanfront Kona Condo;Ocean View-Private Lanai;Sandy Beach/Picnic Area — Property 127018

    Vacation Condo rental in Kailua Kona area
    • Condo
    • 1 bedroom , sleeps 4
    • beach, waterfront
    • garden
    10% Discount 1 week (or more) rental
    S P E C I A L    O F F E R
    Rates (shown in USD)
    $735 - $770 per property per week

  4. 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
    • internet access
    March 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

  5. Kona Bali Kai
    Absolute OCEAN FRONT unit on famous Banyon's surfing beach! 6th night FREE — Property 259272

    Vacation Condo rental in Kailua Kona area
    • Condo
    • 2 bedrooms , sleeps 5
    • 2 bathrooms
    • beach, waterfront
    • internet access
    Last Minute Deal Drops $25.00 Per Night!
    S P E C I A L    O F F E R
    Rates (shown in USD)
    $1000 - $1500 per property per week

  6. Spring Sale $130/nt TOTALLY OCEANFRONT CONDO w/ Free Wi-Fi & BEAUTIFUL SUNSETS!! — Property 193801

    Vacation Condo rental in Kailua Kona area
    • Condo
    • 1 bedroom , sleeps 4
    • 1 bathroom
    • town, waterfront
    • pool
    Spring/Summer Sale only $130/nt!
    S P E C I A L    O F F E R
    Rates (shown in USD)
    $1085 - $1260 per property per week

  7. 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
    • garden
    10% off Special (limited time offer)
    S P E C I A L    O F F E R
    Rates (shown in USD)
    $1400 - $1750 per property per week

  8. Aloha Island Dreams - Kona 101
    Almost Oceanfront Luxury - Listen to the Surf! — Property 138227

    Vacation Condo rental in Kailua Kona area
    • Condo
    • 2 bedrooms , sleeps 4
    • 2 bathrooms
    • beach, waterfront
    • tennis court
    Almost Oceanfront & Gorgeous - On Sale!
    S P E C I A L    O F F E R
    Rates (shown in USD)
    $665 - $1050 per property per week

  9. Sunset spectacular
    Holiday Special for Luxury Oceanfront Condo / Villa — Property 155739

    Vacation Condo rental in Kailua Kona area
    • Condo
    • 3 bedrooms , sleeps 6
    • 3 bathrooms
    • resort, waterfront
    • pool
    7th night free on a six night minimum.
    S P E C I A L    O F F E R
    Rates (shown in USD)
    $3500 - $3850 per property per week

  10. Spectacular Ocean view Condo — Property 136162

    Vacation Condo rental in Kailua Kona area
    • Condo
    • 3 bedrooms , sleeps 6
    • 2 bathrooms
    • beach, near the ocean
    • tennis court
    Sale! Hurry on this one! $130 per night!
    S P E C I A L    O F F E R
    Rates (shown in USD)
    $1085 - $1365 per property per week

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