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. 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)

  2. Oceanfront Spectacular in Kona - On Sale thru Sept — Property 165750

    Vacation Townhome rental in Kailua Kona area
    • Townhome
    • 2 bedrooms , sleeps 4
    • 2 bathrooms
    • beach, waterfront
    • accept credit card
    Spectacular Ocean/Beachfront $145/night
    S P E C I A L    O F F E R
    Rates (shown in USD)
    $840 - $1400 per property per week

  3. 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

  4. Aug-Nov Sale Totally Oceanfront Condo w/WiFi and breathtaking sunsets — Property 193801

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

  5. Lovely 2bdrm/2bth Oceanfront Condo — Property 149038

    Vacation Condo rental in Kailua Kona area
    • Condo
    • 2 bedrooms , sleeps 4
    • 2 bathrooms
    • beach, waterfront
    • accept credit card
    Oceanfront Delight - $125/night Special
    S P E C I A L    O F F E R
    Rates (shown in USD)
    $840 - $1350 per property per week

  6. 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
    Rates (shown in USD)
    $1050 - $1260 per property per week

  7. 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
    Rates (shown in USD)

  8. 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
    Rates (shown in USD)

  9. Oceanfront Luxury Suites of Casa Del Sol — Property 190991

    Vacation Villa rental in Kailua Kona area
    • Villa
    • 2 bedrooms , sleeps 9
    • beach, waterfront
    • accept credit card
    Rates (shown in USD)
    $1113 - $1253 per property per week

  10. BLUE WATER HOUSE:Luxury Home, Oceanfront with Pool in Gated Community — Property 169257

    Vacation Estate rental in Kailua Kona area
    • Estate
    • 3 bedrooms , sleeps 10
    • 3 bathrooms
    • beach, village
    • accept credit card
    Rates (shown in USD)
    $7000 per property per week

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