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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. 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

  2. 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

  3. Oceanfront Kona Reef Vacation Condo Rental — Property 318447

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

  4. Kona Riviera Villa
    Direct Ocean Front Condo 2 Miles from Downtown Kailua Kona — Property 240383

    Vacation Condo rental in Kailua Kona area
    • Condo
    • 1 bedroom , sleeps 4
    • 1 bathroom
    • waterfront
    • pool
    Rates (shown in USD)
    $945 - $1015 per property per week

  5. Oceanfront & Steps from Town!
    Enjoy Kailua Kona Oceanfront Condo - Beautiful Views and Spectacular Sunsets! — Property 307224

    Vacation Condo rental in Kailua Kona area
    • Condo
    • 1 bedroom , sleeps 3
    • 1 bathroom
    • downtown, waterfront
    • balcony
    Rates (shown in USD)
    $945 - $1085 per property per week

  6. Kalanikai 321
    1 bedroom condo in the heart of Kona - HD TV and WiFi- $80/nt Nov-Dec Special! — Property 179684

    Vacation Condo rental in Kailua Kona area
    • Condo
    • 1 bedroom , sleeps 4
    • 1 bathroom
    • near the ocean, town
    • pool
    Rates (shown in USD)
    $560 - $700 per property per week

  7. Kona Reef
    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
    • pool
    Rates (shown in USD)
    $795 - $875 per property per week

  8. Romantic Honeymoon Cottage
    Romantic Honeymoon Cottage with Extraordinary View - on 3 Acres — Property 301982

    Vacation Cottage rental in Kailua Kona area
    • Cottage
    • 1 bedroom , sleeps 4
    • 1 bathroom
    • near the ocean, rural
    • garden
    Rates (shown in USD)
    $1050 per property per week

  9. Beautifully renovated Ocean View Condo - Kona Alii Unit# 206 — Property 171869

    Vacation Condo rental in Kailua Kona area
    • Condo
    • 1 bedroom , sleeps 4
    • 2 bathrooms
    • downtown, waterfront
    • pool
    Rates (shown in USD)

  10. Oceanview Home Away from Home - This is the Best ! — Property 189366

    Vacation Condo rental in Kailua Kona area
    • Condo
    • 1 bedroom , sleeps 4
    • 1 bathroom
    • near the ocean, town
    • garden
    Rates (shown in USD)
    $650 per property per week

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