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. 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

  2. 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
    Ocean**Golf Condo AUG-SEPT $95/N 2/B 2/B
    S P E C I A L    O F F E R
    Rates (shown in USD)
    $125 - $805 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
    $150/NT. SPECIAL RATE FALL '08
    S P E C I A L    O F F E R
    Rates (shown in USD)

  4. Beachfront Paradise in Kona - $125/night thru Sept — Property 165750

    Vacation Townhome rental in Kailua Kona area
    • Townhome
    • 2 bedrooms , sleeps 4
    • 2 bathrooms
    • beach, waterfront
    • accept credit card
    Spectacular Oceanfront Living $120/night
    S P E C I A L    O F F E R
    Rates (shown in USD)
    $840 - $1400 per property per week

  5. Almost Oceanfront - Summer/Fall 30% OFF - AC available! — Property 138227

    Vacation Townhome rental in Kailua Kona area
    • Townhome
    • 2 bedrooms , sleeps 4
    • 2 bathrooms
    • beach, waterfront
    • accept credit card
    Listen to the surf - $89/night + A/C
    S P E C I A L    O F F E R
    Rates (shown in USD)
    $625 - $1050 per property per week

  6. Luxury Home in Kona Paradise - Private Pool - Oceanview - $275/night for summer! — 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 - $275/night! !
    S P E C I A L    O F F E R
    Rates (shown in USD)
    $2275 - $2800 per property per week

  7. Cottage, Tropical, Peaceful, Sweeping Ocean Views — Property 102135

    Vacation Cottage rental in Kailua Kona area
    • Cottage
    • 3 bedrooms , sleeps 6
    • 2 bathrooms
    • near the ocean
    • washing machine
    2008 Special
    S P E C I A L    O F F E R
    Rates (shown in USD)

  8. Kona Reef 1BR Oceanview Condo - 1 1/2 Blocks to Town — Property 182816

    Vacation Condo rental in Kailua Kona area
    • Condo
    • 1 bedroom , sleeps 4
    • 1 bathroom
    • resort, waterfront
    • accept credit card
    Rates (shown in USD)
    $795 - $875 per property per week

  9. Kona Country Club Villas — Property 214587

    Vacation Condo rental in Kailua Kona area
    • Condo
    • 2 bedrooms , sleeps 6
    • 2 bathrooms
    • beach
    • swimming pool
    Rates (shown in USD)
    $1120 - $1400 per property per week

  10. Newly Remodeled Beachfront with Ocean View Casa De Emdeko — Property 155768

    Vacation Condo rental in Kailua Kona area
    • Condo
    • 1 bedroom , sleeps 4
    • 1 bathroom
    • beach, waterfront
    • accept credit card
    Rates (shown in USD)
    $650 - $750 per property per week

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