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
Sea Village
Kona Reef
Kona Shores
White Sands Village
Royal Kahili
Royal Sea Cliff

  • Punahele Penthouse Luxury Condo

    Punahele Penthouse Condo will fast become your favorite place to stay in Kailua-Kona! Punahele Penthouse is on the 7th (top) floor of the Kona Ali'i Condo Complex which is located in the heart of Kailua-Kona. You're within walking distance to ...

    • 2 bedroom
    • 2 bathroom
    • Sleeps 6
    Hawaii> Kailua-Kona
    from $504 
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  • Big Island Private Home Rental

    Guests walk in and we see wow on their faces...gourmet kitchen, ocean views, huge bedrooms.

    "perfect for a family reunion"
    "cool at night was just right"
    "close to the best beach in Hawaii"
    "your own private estate"
    "amazing...

    • 5 bedroom
    • 6 bathroom
    • Sleeps 18
    Hawaii> Kailua-Kona
    from $995 
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  • Penthouse Unit built 2007, Across from Kahaluu Beach, Fantastic Ocean Views!

    Love to snorkel and want to see over 100 species of tropical fish & turtles? Then why not stay right across the street from Hawaii's best snorkeling beach?! Our modern beachfront unit offers gorgeous ocean/sunset views and the easiest access ...

    • 2 bedroom
    • 2 bathroom
    • Sleeps 4
    Hawaii> Kailua-Kona
    from $398 
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  • Sunset in Paradise Oceanfront 1BR/1BA Condo at Kona Reef Fast WiFi & Central AC

    Enjoy sunset views every night from this beautifully updated 1br 1ba condo steps from Downtown Kailua-Kona village with AC in both the living room and bedroom (rare!).

    Sunset in Paradise is your private paradise with gorgeous ocean views ...

    • 1 bedroom
    • 1 bathroom
    • Sleeps 4
    Hawaii> Kailua-Kona
    from $372 
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  • Kona Reef A22 - Direct Ocean Front Condo - Private Lanai - Next to Honl's Beach!

    Welcome to our beautifully decorated ocean front condo in paradise - Kona Reef A-22.

    Our condo is our home away from home, so we respectfully request a maximum of 2 adult guests and no children under 18.

    Whether this is your ...

    • 1 bedroom
    • 1 bathroom
    • Sleeps 2
    Hawaii> Kailua-Kona
    from $387 
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  • Breathtaking Kona Home - Heated Pool / Air conditioning and Beautiful Sunsets

    This breathtaking 3 Bedroom plus bunkroom, 2 bath single level home is located just minutes from Kailua, Kona and some of the most beautiful beaches in Hawaii. Everything in this house is new! Fresh full remodel just completed. This includes a ...

    • 4 bedroom
    • 2 bathroom
    • Sleeps 8
    Hawaii> Kailua-Kona
    from $865 
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  • Stunning 5 Star Ocean View Condo with all the Amenities!

    Our unit is spacious with high ceilings, ceiling fans, fabulous sunlight, and gorgeous ocean views. This elevated third story unit affords a wonderful lanai with a view overlooking manicured golf courses, tropical flowers, natural lava ...

    • 3 bedroom
    • 3 bathroom
    • Sleeps 6
    Hawaii> Kailua-Kona
    from $579 
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  • Magic Sands Home, Steps From The Beach! Air Conditioned!

    Welcome to this wonderful 3 bedroom / 2 bathroom duplex home only a 3 min walk from Magic Sands Beach. Just remodeled and professionally decorated, this charming vacation getaway has all of the comforts you desire in your home away from home, ...

    • 3 bedroom
    • 2 bathroom
    • Sleeps 7
    Hawaii> Kailua-Kona
    from $622 
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  • Direct Oceanfront, Big Wave Penthouse-1,200 sq ft, Stunning View. Free WiFi

    *** For more details and more pictures, go to our website at BIGWAVEHAWAII•COM***

    The Big Wave Penthouse is arguably in the best location on the Big Island. Consider this:

    • Facing west, you're guaranteed a front-row seat every...

    • 2 bedroom
    • 2 bathroom
    • Sleeps 6
    Hawaii> Kailua-Kona
    from $745 
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  • Kona Condo at Magic Sands Beach-Ocean Views-Top Floor-Quiet

    Aloha and welcome to our condo at White Sands Village. Brand new to the rental market, this wonderfully appointed 2-bedroom, 2-bathroom top floor condo offers everything you’ll need to enjoy your stay in Kailua-Kona and the Big Island Of ...

    • 2 bedroom
    • 2 bathroom
    • Sleeps 6
    Hawaii> Kailua-Kona
    from $413 
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  • Oceanfront Condo, Free 5G Wi-Fi, King Bed, Hot Tub/Pool

    Was recently completely remodeled.
    Our oceanfront condo is 23ft. from the ocean and is located on the 2nd floor and offers spectacular sunsets.
    Watch the surfers and the dolphins from your lanai.
    A Short walk to town and over 20 ...

    • 1 bedroom
    • 1 bathroom
    • Sleeps 2
    Hawaii> Kailua-Kona
    from $361 
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  • 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 ...

    • 1 bedroom
    • 1 bathroom
    • Sleeps 2
    Hawaii> Kailua-Kona
    from $385 
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  • Private Cottage In The Rain Forest TA065882726401

    Cozy, private rain forest retreat cottage situated above Kona in the Kaloko Mauka Honua'ula Forest Reserve. Located on a 3-acre property, this cottage is set away in a lush forest of Ohia trees and Hapu'u tree ferns. Enjoy the sweet aroma of ...

    • 1 bedroom
    • 1 bathroom
    • Sleeps 2
    Hawaii> Kailua-Kona
    from $220 
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  • Red Ginger Garden Studio

    Peaceful, well appointed room with private entrance ,down a flight of stairs, overlooking our back yard garden of fruit trees and red ginger blooms. Private bath with shower, queen bed, walk in closet, kitchenette, outdoor seating; Wake up and ...

    • 1 bedroom
    • 1 bathroom
    • Sleeps 2
    Hawaii> Kailua-Kona
    from $175 
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  • Wonderful Ocean View –Totally Renovated-On Golf Course

    STVR-19-358846 - Relax and pamper yourself in luxury in this well-appointed condo. On the golf course with Spectacular Ocean views. This is NOT your average condo rental! This condo has had an extensive high-end renovation and interior ...

    • 2 bedroom
    • 2 bathroom
    • Sleeps 4
    Hawaii> Kailua-Kona
    from $266 
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  • OCEANFRONT BEACH HOUSE WITH SUNSET VIEWS AND PRIVATE POOL

    Kona Bay Estates is a gated and patrolled oceanfront community. The Sunset Beach House offers 2700 square feet of luxurious space. It is just 500 meters from the sea. Opening walls of glass offer indoor-outdoor living with spectacular views of ...

    • 3 bedroom
    • 4 bathroom
    • Sleeps 8
    Hawaii> Kailua-Kona
    from $1,489 
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  • Your Hawaiian vacation starts here!

    Kona Shores is a great location right on Alii Drive, a Hawaii Scenic Byway (Ala Loa Foot Trail). A lovely complex with an oceanfront pool & BBQ area for easy island living! Ground floor, end unit with easy access to Alii Drive and just one mile ...

    • 0 bedroom
    • 1 bathroom
    • Sleeps 4
    Hawaii> Kailua-Kona
    from $197 
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  • Your Hawaiian Vacation Starts Here! II

    Kona Shores is a great location right on Alii Drive (Hawaii Scenic Byway). A lovely complex with oceanfront pool & BBQ area for easy island living! Ground floor with easy access to Alii Drive and just one mile to downtown Kona, shopping, ...

    • 0 bedroom
    • 1 bathroom
    • Sleeps 4
    Hawaii> Kailua-Kona
    from $208 
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  • Hualalai Haliipua Villa 104

    Haliipua Villas are the newest generation of multi-family villas at Hualalai offering an array of designer finishes throughout the home. Special features include luxurious mahogany finishes, island-inspired ceiling treatments, enhanced ...

    • 3 bedroom
    • 4 bathroom
    • Sleeps 6
    Hawaii> Kailua-Kona
    from $2,723 
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  • Hualalai Waiulu Villa 137D

    This spacious 3 bedroom, 3.5 bath single-level villa is centrally located on the Resort’s popular Waiulu Street overlooking beautiful Punawai Pond, the 5th Hole of the Member’s Ke`olu Golf Course and the ocean beyond. With 2642 square feet ...

    • 3 bedroom
    • 4 bathroom
    • Sleeps 6
    Hawaii> Kailua-Kona
    from $2,227 
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