Kailua-Kona Vacation Rentals

Kailua-Kona is the Big Island's top vacation destination. Its sunny climate and pristine beaches make Kailua-Kona the perfect tropical destination for families and couples alike. You will find over 500 vacation rentals here, ranging from affordable studios and one-bedroom condos to spacious upscale apartments, houses and villas. There is so much to see and do in Kailua-Kona. The town is the perfect place for ocean and outdoor recreational activities. If you like watersport adventures, you can go surfing, diving, boating, snorkeling and swimming. If you enjoy shopping, you will find many shops, boutiques, art galleries and restaurants in Kailua-Kona, as well as numerous historical sites. Browse through this fine selection of Kailua-Kona vacation rentals below and find your perfect home away from home.

Browse Kailua-Kona Vacation Rentals by condo/hotel name:

» Alii Cove » Alii Lani » Alii Park Place
» Alii Villas » Banyan Tree » Casa De Emdeko
» Hale Kona Kai » Holualoa Bay Villas » Kailua Bay Resort
» Kalanikai » Kona Bali Kai » Kona Bay Estates
» Kona by the Sea » Kona Hawaiian Resort » Kona Islander Inn
» Kona Isle » Kona Magic Sands » Kona Makai
» Kona Mansions » Kona Nalu » Kona Onenalo
» Kona Reef » Kona Riviera Villas » Kona Shores
» Royal Kahili » Royal Sea Cliff » Sea Village
» White Sands Village
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  • Breathtaking View on Beautiful Sandy Beach Oceanfront

    This Oceanfront Condo has an amazing view. It has a gorgeous Great Room and a beautiful fully equipped kitchen. With the roar of the ocean just a few yards away, you will not want to leave the Lanai after relaxing on the Tropitone furniture. ...

    • 2 bedroom
    • 2 bathroom
    • Sleeps 4
    HI> Kailua-Kona
    5 night min stay5  reviews
    from $259 per night
      Book Now
  • New Property! *Hale Iki* Your Sweet Retreat - Private Home + Yard

    Hale Iki (ha-lay ee-kee) is a centrally located private home (with A/C) at the 650' elevation, making for sunny days and cool nights. We're located in a quiet neighborhood, 3 minutes from the heart of Kailua-Kona and just about everything — ...

    • 1 bedroom
    • 1 bathroom
    • Sleeps 3
    HI> Kailua-Kona
    4 night min stay22  reviews
    from $211 per night
      Book Now
  • Kona-Keauhou Sunsets+Style! Full Kitchen, Washer/Dryer, WiFi, Lanai, DVD, TV Kanaloa 2106

    Relaxing is easy when listening to the sound of the waves from this cozy two-bedroom, two-bathroom ocean view suite. You’ll love how spacious this corner unit feels, with lots of room to sprawl out with family and friends. Enjoy warm tropical...

    • 2 bedroom
    • 2 bathroom
    • Sleeps 6
    HI> KAILUA-KONA
    2 night min stay1  reviews
    from $345 per night
      Book Now
  • Kona Plaza condo (316) 1 Bedroom 1 Bath

    1 Bedroom 1 bathroom (Two Twin Beds or push together and make a King) 1 sofa bed in the living room. Also provided a portable Queen inflatable bed. Condo is in the Heart of Historic Kailua Kona village. Close and walkable, to all shops, ...

    • 1 bedroom
    • 1 bathroom
    • Sleeps 3
    HI> Kailua-Kona
    3 night min stay2  reviews
    from $127 per night
      Book Now
  • Hilltop Home w/Ocean View in Kailua-Kona!

    Experience ancient Hawaiian history over in Kaloko-Honokōhau National Historical Park, tour the royal Hulihe’e Palace and roam the rocky shoreline of Magic Sands Beach Park. All these attractions and more await within 10 miles or less of this...

    • 3 bedroom
    • 2 bathroom
    • Sleeps 6
    HI> Kailua-Kona
    3 night min stay9  reviews
    from $421 per night
      Book Now
  • Aloha Style! End Corner Unit w/Sweeping Fairway Views! –Kanaloa at Kona 1402

    Tropical decor, surfboard art and views flowing “fore-ever” make this 1,850sf suite a winner! Replay the day on the lanai with a Volcano Winery Blush and fresh catch prepped in the modern kitchen. Enjoy a washer/dryer, flat screen TVs, WiFi,...

    • 2 bedroom
    • 2 bathroom
    • Sleeps 8
    HI> KAILUA-KONA
    1 night min stay2  reviews
    from $286 per night
      Book Now
  • 99 steps to quiet beach | Centrally located | Great for families & groups

    Ideally located on iconic Alii Drive directly where the world famous Iron Man takes place annually. A number of palm trees and local landscaping on the front and side of the property add to the tropical appeal. Nearby are many of Kona's ...

    • 3 bedroom
    • 3 bathroom
    • Sleeps 8
    HI> Kailua-Kona
    4 night min stay18  reviews
    from $559 per night
      Book Now
  • Exceptional Oceanfront Luxury Condo - Fully remodeled, AC, Top Floor, Quiet

    Absolute direct oceanfront top floor, two-bedroom condo located in the heart of Kailua-Kona, Hawaii. As you walk through the door and see the blue ocean out the balcony, you have arrived in Hawaiian paradise! Fully remodeled with high ...

    • 2 bedroom
    • 2 bathroom
    • Sleeps 4
    HI> Kailua-Kona
    5 night min stay18  reviews
    from $359 per night
      Book Now
  • Kailua-Kona Condo w/ Resort Access & Ocean View!

    Treat yourself to a delightful Hawaiian getaway when you stay at this 1-bedroom, 1-bathroom Kailua-Kona vacation rental condo that sleeps 4 guests. Set along the lush landscape of Kona Coast Resort, the corner unit condo offers access to ...

    • 1 bedroom
    • 1 bathroom
    • Sleeps 4
    HI> Kailua-Kona
    3 night min stay14  reviews
    from $335 per night
      Book Now
  • Resort Perks+Homey Comforts! Kitchen+Laundry Ease, WiFi, Lanai, Flat Screens Kanaloa 201

    Welcome to your tropical haven accommodating up to six! Perfect for families or for those looking for a little extra space to unwind after a fun day, you’ll love relaxing on the lanai with dining table, wet bar and mini-fridge. The luxe master...

    • 2 bedroom
    • 2 bathroom
    • Sleeps 6
    HI> KAILUA-KONA
    1 night min stay1  reviews
    from $299 per night
      Book Now
  • Tropical Oceanfront Beauty

    COVID-19 STATE LAW OF HAWAI’I: *BEGINNING OCT 15TH TRAVEL TO HAWAI'I PERMITTED WITH NEGATIVE COVID TEST 72 HRS BEFORE FLIGHT* ~Please visit the official government of Hawai'i website for more information~ *POOL & POOL DECK/BBQ PATIO AREA ...

    • 0 bedroom
    • 1 bathroom
    • Sleeps 3
    HI> Kailua-Kona
    3 night min stay5  reviews
    from $150 per night
      Book Now
  • Kona Ali'i Condo with Ocean, Sunset, Mountain and Town Views

    Located in the heart of Kailua Kona, this special retreat makes it easy to enjoy the day and night life of Kona town with restaurants and shops within a few steps. It is also an ideal launching point for day trips to state and national parks, ...

    • 3 bedroom
    • 3 bathroom
    • Sleeps 6
    HI> Kailua-Kona
    10 night min stay14  reviews
    from $250 per night
      Book Now
  • The eruption ended.. blue skys and the best weather in 20 years !

    Centrally located in North Kona, this house is 15 minutes from the airport, downtown and sandy beaches. It is situated at a cool 1000 foot elevation, and is located in a traditional Hawaiian neighborhood with large lots, mature trees and no ...

    • 2 bedroom
    • 2 bathroom
    • Sleeps 4
    HI> Kailua-Kona
    3 night min stay36  reviews
    from $145 per night
      Book Now
  • Stunning, Romantic Cottage on Slope of Hualalai

    On the Kona side, safe and away from the volcanic activity, the Cottage awaits you. The perfect, peaceful getaway for those on a honeymoon or looking for a relaxing, romantic experience. This warm, welcoming, newly-built and finely crafted ...

    • 1 bedroom
    • 1 bathroom
    • Sleeps 2
    HI> Kailua-Kona
    5 night min stay118  reviews
    from $250 per night
      Book Now
  • Tropical Elegance overlooking the Kona Coast

    Enhance your Big Island experience with a stay at this beautiful, custom designed home on Mt. Hualalai. Located on a secluded park-like setting only 15 minutes from the Kona International Airport, at a very comfortable elevation of 1600 feet. ...

    • 2 bedroom
    • 3 bathroom
    • Sleeps 2
    HI> Kailua-Kona
    4 night min stay24  reviews
    from $325 per night
      Book Now