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. LOCATION LOCATION LOCATION SALE 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
    Sale Location Total 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. 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 - $125/night
    S P E C I A L    O F F E R
    Rates (shown in USD)
    $875 - $1350 per property per week

  3. Desirable Ocean Condo directly across from the Ocean /Alii Drive in Kona village — Property 142113

    Vacation Condo rental in Kailua Kona area
    • Condo
    • 1 bedroom , sleeps 4
    • 2 bathrooms
    • downtown, waterfront
    • accept credit card
    Rates (shown in USD)
    $925 - $1320 per property per week

  4. Kona Reef Oceanfront Vacation Condo Rental — Property 318447

    Vacation Condo rental in Kailua Kona area
    • Condo
    • 1 bedroom , sleeps 3
    • 1 bathroom
    • beach, waterfront
    • accept credit card
    Rates (shown in USD)
    $980 - $1085 per property per week

  5. Oceanfront Deluxe Kona Reef Condo, Watch the Whales, Dolphins and Surf — Property 313985

    Vacation Condo rental in Kailua Kona area
    • Condo
    • 1 bedroom , sleeps 4
    • 1 bathroom
    • beach, near the ocean
    • swimming pool
    Rates (shown in USD)
    $980 - $1050 per property per week

  6. Oceanview Condo at Kona Reef — Property 310265

    Vacation Condo rental in Kailua Kona area
    • Condo
    • 1 bedroom , sleeps 4
    • 1 bathroom
    • beach, village
    • swimming pool
    Rates (shown in USD)
    $693 - $945 per property per week

  7. One bedroom fully furnished condo in the heart of Kailua-Kona, Hawaii — Property 158007

    Vacation Condo rental in Kailua Kona area
    • Condo
    • 1 bedroom , sleeps 4
    • 1 bathroom
    • downtown, near the ocean
    • swimming pool
    Rates (shown in USD)

  8. 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
    • swimming pool
    Rates (shown in USD)
    $700 per property per week

  9. Affordable Luxury Home - Amazing Ocean View — Property 163569

    Vacation House rental in Kailua Kona area
    • House
    • 1 bedroom , sleeps 5
    • 1 bathroom
    • beach, near the ocean
    • swimming pool
    Rates (shown in USD)

  10. Welcome to Paradise- Kona Pacific (Newly Remodeled) SPECIALS FOR JUNE- AUG — Property 149396

    Vacation Condo rental in Kailua Kona area
    • Condo
    • 1 bedroom , sleeps 4
    • 2 bathrooms
    • near the ocean, town
    • swimming pool
    Rates (shown in USD)

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