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. Oceanfront Spectacular in Kona - Special Rates!! — Property 165750

    Vacation Townhome rental in Kailua Kona area
    • Townhome
    • 2 bedrooms , sleeps 4
    • 2 bathrooms
    • beach, waterfront
    • accept credit card
    Spectacular Ocean/Beachfront $135/night
    S P E C I A L    O F F E R
    Rates (shown in USD)
    $910 - $1400 per property per week

  2. Last Minute Special for Totally Oceanfront Condo at Sea Village — Property 193801

    Vacation Condo rental in Kailua Kona area
    • Condo
    • 1 bedroom , sleeps 4
    • 1 bathroom
    • town, waterfront
    • swimming pool
    LAST MINUTE OCEANFRONT SPECIAL $100/nt !
    S P E C I A L    O F F E R
    Rates (shown in USD)
    $980 - $1155 per property per week

  3. Spectacular Private Oceanfront Estate with Pool and Hot Tub — Property 156794

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

  4. Luxury Home in Kona Paradise - Private Pool - Oceanview ! — Property 165874

    Vacation House rental in Kailua Kona area
    • House
    • 4 bedrooms , sleeps 12
    • 3 bathrooms
    • near the ocean, town
    • accept credit card
    Luxury Oceanview & Pool - $250/night! !
    S P E C I A L    O F F E R
    Rates (shown in USD)
    $1850 - $2800 per property per week

  5. Oceanfront Delight - One of a Kind Master Suite! — Property 186982

    Vacation Townhome rental in Kailua Kona area
    • Townhome
    • 1 bedroom , sleeps 4
    • 2 bathrooms
    • beach, waterfront
    • accept credit card
    Oceanfront with MasterSuite - $115/night
    S P E C I A L    O F F E R
    Rates (shown in USD)
    $980 - $1350 per property per week

  6. Vista Oceania : Beach Front Luxury Home — Property 172358

    Vacation Estate rental in Kailua Kona area
    • Estate
    • 3 bedrooms , sleeps 9
    • 2 bathrooms
    • 1 half bathroom
    • beach, waterfront
    • accept credit card
    Rates (shown in USD)
    $6300 - $8400 per property per week

  7. 'Malu Wahi' - A place of calmness, tropical paradise! — Property 204176

    Vacation House rental in Kailua Kona area
    • House
    • 4 bedrooms , sleeps 10
    • 3 bathrooms
    • near the ocean, rural
    • swimming pool
    Rates (shown in USD)
    $1960 - $2100 per property per week

  8. Ocean views and the waters edge are just steps away in Kona, Hawaii — Property 191732

    Vacation Condo rental in Kailua Kona area
    • Condo
    • 2 bedrooms , sleeps 6
    • 2 bathrooms
    • beach, near the ocean
    • swimming pool
    Rates (shown in USD)
    $770 - $875 per property per week

  9. Tu'Tu's Beach House with Huge Pool and Back Yard — Property 312920

    Vacation House rental in Kailua Kona area
    • House
    • 3 bedrooms , sleeps 8
    • 4 bathrooms
    • beach, near the ocean
    • accept credit card
    Rates (shown in USD)
    $1925 - $2450 per property per week

  10. Hot Summer Deals - Min 3 Days — Property 155010

    Vacation Condo rental in Kailua Kona area
    • Condo
    • 1 bedroom , sleeps 5
    • 2 bathrooms
    • beach, downtown
    • accept credit card
    Rates (shown in USD)
    $539 per property per week

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