home
oahu
maui
kauai
big-island
lanai
molokai

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 Shores » Sea Village
» Royal Kahili » Royal Sea Cliff » White Sands Village
 
List
Map
  •

    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
    163  reviews
    from $270 
      View Property   Book Now

  • Hualalai Haliipua Villa 104 - Spectacular Sunset Views + Newly Renovated 2023

    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
    7  reviews
    from $1,729 
      View Property   Book Now

  • OCEAN VIEWS* LUXURY AND LOCATION AT HUALALAI RESORT ** TWO GOLF CARTS**

    Located in the Award Winning Resort Community of Hualalai Four Seasons.

    Enjoy the sounds of the ocean serenade, the magic of sunsets, and whale watching during the winter months, from this recently updated garden level Hillside Villa. ...

    • 3 bedroom
    • 3 bathroom
    • Sleeps 6
    Hawaii> Kailua-Kona
    6  reviews
    from $1,614 
      View Property   Book Now

  • Keauhou Convenience, Ocean Views, Newly Renovated, AC in Bedrooms, Wrap-Around Lanai

    Welcome to Keauhou Lani an exquisite private residence located in the desirable gated community of Keauhou Estates.

    Step into the grand entry of Keauhou Lani's 4 bedroom, 3 bathrooms, 4750 square foot home (plus an additional 1700 square ...

    • 4 bedroom
    • 4 bathroom
    • Sleeps 8
    Hawaii> Kailua-Kona
    80  reviews
    from $760 
      View Property   Book Now

  • **Summer Specials** Beautiful Estate Home at Hualalai Resort ** Luxury ** Views ** Location ** 2 Golf Carts**

    ** Special Offer ** Book a stay for 7 nights at the advertised rate and enjoy the 7th night free! This offer is valid for travel dates between July 10 and October 31, 2023. (Daily Resort Guest Fees not included in the nightly rental ...

    • 5 bedroom
    • 6 bathroom
    • Sleeps 10
    Hawaii> Kailua-Kona
    4  reviews
    from $5,000 
      View Property   Book Now

  • Tranquil Kaloko Cottage nestled in the forest overlooking the Kona coast.

    We know you'll just love this cozy guest apartment. We've been told it feels like a rather sophisticated tree house. Pretty rooms and comfy beds. Just a quick drive to the beach and activities, but none of the hustle-bustle or crowds. The ...

    • 3 bedroom
    • 1 bathroom
    • Sleeps 6
    Hawaii> Kailua-Kona
    15  reviews
    from $200 
      View Property   Book Now

  • Ocean and Golf Course Views ! Three Bedroom,Split Level Townhouse ** 2 Golf Carts **

    Located in the Award Winning Resort Community of Hualalai Four Seasons.

    3 Bedrooms / 3 Baths
    Living Area: 2,657 sqft and 940 sqft of Lanai
    Ocean,Golf Course and Mountain Views
    Spilt Level Townhouse
    2 ~ 4 person Golf ...

    • 3 bedroom
    • 3 bathroom
    • Sleeps 6
    Hawaii> Kailua-Kona
    5  reviews
    from $1,500 
      View Property   Book Now

  • Ocean Views ! Excellent Proximity to Resort Amenities ! Includes Golf Cart

    Located in the Award Winning Resort Community of Hualalai Four Seasons.

    Beautiful ocean views from this delightful two bedroom Garden Level Villa. Spacious Lanai with lounge seating extends seamlessly to a large lawn area. Enjoy the ...

    • 2 bedroom
    • 2 bathroom
    • Sleeps 4
    Hawaii> Kailua-Kona
    6  reviews
    from $1,300 
      View Property   Book Now

  • ‘Kona Aloha Aina’: Home w/ Lanai < 3 Mi to Beaches

    Fall in love with the Aloha Spirit in this 3-bedroom, 2-bath vacation rental home in Kailua-Kona. Located at an elevation of 450 feet, this home boasts gorgeous hillside views of the sunsets over the Pacific Ocean and a comfortable year-round ...

    • 3 bedroom
    • 2 bathroom
    • Sleeps 6
    Hawaii> Kailua-Kona
    9  reviews
    from $281 
      View Property   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. Set along the lush landscape of Kona Coast Resort, the corner unit condo offers access to pristine pools, hot tubs, ...

    • 1 bedroom
    • 1 bathroom
    • Sleeps 4
    Hawaii> Kailua-Kona
    27  reviews
    from $274 
      View Property   Book Now

  • Great Location - Snorkel, Surf & Sunsets!

    Beach Villas at Kahalu’u is right across the street from the best snorkeling beach on the Big Island! See green turtles and reef fish!

    The ground floor condo has 2 bedrooms, one with a king bed, the other with twin beds, and 2 ...

    • 2 bedroom
    • 2 bathroom
    • Sleeps 5
    Hawaii> Kailua-Kona
    11  reviews
    from $270 
      View Property   Book Now

  • FALL SPECIAL; 2 NIGHTS FREE WHEN BOOKING 7 NIGHTS OR MORE 9/1 - 11/15/23.

    This beautiful and meticulously maintained home situated on the 9th hole of Hualalai's Jack Nicklaus golf course with Pacific Ocean views is available for private rentals. Perfectly located, the home is just a short walk or golf cart ride (two ...

    • 3 bedroom
    • 3 bathroom
    • Sleeps 6
    Hawaii> Kailua-Kona
    6  reviews
    from $3,200 
      View Property   Book Now

  • Beach House: Oversized Lanai with Indoor/Outdoor Flow. EZ Stroll to Magic Sands!

    Check out this drone video showing the home, neighborhood and proximity to the ocean: https://youtu.be/4d2V5HbQ1cY

    Upgrade your Vacation at our Magic Sands Beach House! Best Location, Lifestyle & Amenities! Maximizing Kona's beaches & ...

    • 2 bedroom
    • 2 bathroom
    • Sleeps 5
    Hawaii> Kailua-Kona
    21  reviews
    from $405 
      View Property   Book Now

  • Stunning Ocean Views from the 18th Fairway at Hualalai Resort

    Magnificent Garden Level Villa located on the #18 hole of the Hualalai Jack Nicklaus Signature Course. Enjoy white water views and spectacular sunsets from this highly desirable location at Hualalai Resort. Listen to the ocean and whale watch ...

    • 3 bedroom
    • 4 bathroom
    • Sleeps 6
    Hawaii> Kailua-Kona
    8  reviews
    from $2,718 
      View Property   Book Now

  • Ocean View Home

    This 2740 square foot custom designed home is located in the gated community of Bayview Estates on the Kona coast. A great home with an open floor plan consisting of glass sliding pocket doors to bring the outdoors into the living area. This ...

    • 3 bedroom
    • 4 bathroom
    • Sleeps 8
    Hawaii> Kailua-Kona
    16  reviews
    from $550 
      View Property   Book Now

  • AMAZING OCEAN VIEW Popular White Sands Village Steps To The Beach!!!

    Hale Lihi Lani
    Ocean View Vacation Rental at White Sands Village.

    We are located 4 miles south of charming Kailua-Kona Village and directly across from Kona's spectacular Magic Sands Beach. You will enjoy beautiful ocean views and ...

    • 2 bedroom
    • 2 bathroom
    • Sleeps 6
    Hawaii> Kailua-Kona
    7  reviews
    from $175 
      View Property   Book Now

  • Stunning Kona home with salt water pool will take your breath away

    Floor to ceiling window walls retract completely to let you take in the view of the serene Pacific, and enjoy true indoor-outdoor living. Relax by the salt-water pool surrounded by tropical plants and flowers. Pick fresh papayas, citrus and ...

    • 4 bedroom
    • 5 bathroom
    • Sleeps 8
    Hawaii> Kailua-Kona
    24  reviews
    from $690 
      View Property   Book Now

  • Hillside Penthouse Villa Hualalai - Celebrate Thanksgiving with Ocean Views!

    *Note: A Host Fee of 3.5% of your rent will be added to the automated quote provided by VRBO. This includes our administration fee and your $20,000 damage waiver.
    * * * * * *

    One of only seven Hualalai Penthouse Villas. ...

    • 3 bedroom
    • 4 bathroom
    • Sleeps 6
    Hawaii> Kailua-Kona
    27  reviews
    from $2,671 
      View Property   Book Now

  • Ocean View Kona Hideaway - Pool - Sleeps up to 8

    The Kona Hideaway is a beautiful private one acre home... It has a 180 degree ocean view and lots of privacy. Pool , fruit orchard with mango , papaya ,orange grape fruit and much more .Also, ping pong , weight equipment and lots of beach ...

    • 3 bedroom
    • 2 bathroom
    • Sleeps 8
    Hawaii> Kailua-Kona
    6  reviews
    from $450 
      View Property   Book Now

  • The Moon&Stars@Konarado

    Rest and recharge in one of the best, quietest, relaxed, and established vacation rentals in Kailua Kona. Konarado is an environment that has not disappointed. At Konarado, you can have your own peaceful paradise.

    Located in a very quiet ...

    • 0 bedroom
    • 2 bathroom
    • Sleeps 4
    Hawaii> Kailua-Kona
    22  reviews
    from $158 
      View Property   Book Now

  • Waiulu Estate Villa / Hualalai / New Decor / Personal Concierge

    *Note: A Host Fee of 3.5% of your rent will be added to the automated quote provided by VRBO. This includes our administration fee and your $20,000 damage waiver.
    * * * * * *

    Welcome to the exquisite Waiulu Estate Villa at ...

    • 5 bedroom
    • 6 bathroom
    • Sleeps 10
    Hawaii> Kailua-Kona
    4  reviews
    from $8,000 
      View Property   Book Now

  • Luxurious Condo on Ali’i Drive with Ocean view.

    Complete your visit to the islands by staying in this Samoan-inspired 3-bedroom, 2-bathroom condo at Ali'i Cove. Featuring Polynesian interior design, the vibrant color scheme warms your spirits, setting in the reality that you are truly in ...

    • 3 bedroom
    • 2 bathroom
    • Sleeps 6
    Hawaii> Kailua-Kona
    3  reviews
    from $198 
      View Property   Book Now

  • Spacious Ranch Cottage with private hot tub and VIEW!

    Our Ranch House Cottage sits above the town of Kona with beautiful views of the Kona Coast. We are a 10-acre gated estate. This unit has a private Hot Tub/Jacuzzi with magnificent views. We a working farm with miniature goats, sheep and ...

    • 1 bedroom
    • 1 bathroom
    • Sleeps 2
    Hawaii> Kailua-Kona
    16  reviews
    from $200 
      View Property   Book Now

  • Mountain Thunder Coffee Plantation Retreat with FREE 4x4 Tour

    Discover Mountain Thunder Retreat, a tranquil and serene get-away nestled on the cool slopes of dormant volcano, Hualalai.

    This vintage-style plantation home is located on a 20-acre organic coffee farm. We are a quick 20-minute drive ...

    • 4 bedroom
    • 3 bathroom
    • Sleeps 8
    Hawaii> Kailua-Kona
    19  reviews
    from $556 
      View Property   Book Now

  • Wyndham Kona Hawaiian Resort


    Please note, some holiday weeks require a seven night stay, please confirm with agent. Prime weeks and holiday weeks have higher rates, your agent will send you an initial quote based on the dates you have chosen.

    DASH REALTY GROUP, ...

    • 2 bedroom
    • 2 bathroom
    • Sleeps 6
    Hawaii> Kailua-Kona
    2  reviews
    from $516 
      View Property   Book Now

  • Gorgeous Oceanview Townhome at Na Hale O Keauhou

    A beautifully landscaped, quiet, and one of the newest properties in Kona. The townhome is in an upscale gated community. It is a 3 bedroom and 2.5 bath townhouse with a garage. The condo has 1700 sq. ft. not including 2 large lanais. It is ...

    • 3 bedroom
    • 3 bathroom
    • Sleeps 6
    Hawaii> Kailua-Kona
    38  reviews
    from $393 
      View Property   Book Now

  • Live, work & play in paradise year-round - beautiful condo, beaches and sunsets

    Welcome to paradise made easy! BEAUTIFUL, SPACIOUS CONDO: 2 story, 3 bedroom, 3 bathroom, tastefully appointed condo, amply furnished, high ceilings and tall windows, hardwood floors, air conditioning. Main floor and upper floor balconies/lanais...

    • 3 bedroom
    • 3 bathroom
    • Sleeps 6
    Hawaii> Kailua-Kona
    5  reviews
    from $277 
      View Property   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
    Hawaii> Kailua-Kona
    32  reviews
    from $325 
      View Property   Book Now

  • Waiulu Grand Estate / Hualalai / 2-Min Walk to Beach / Personal Concierge

    *Note: A Host Fee of 3.5% of your rent will be added to the automated quote provided by VRBO. This includes our administration fee and your $20,000 damage waiver.
    * * * * * *

    Welcome to your home away from home at the ...

    • 4 bedroom
    • 5 bathroom
    • Sleeps 8
    Hawaii> Kailua-Kona
    3  reviews
    from $6,500 
      View Property   Book Now

  • Beautiful Fairway Villa 104A at Hualalai w/Resort Pool, AC & Two Golf Carts

    This exquisite villa is perfect for sophisticated travelers. Whether vacationing with friends or family, this elegantly appointed upper level three bedroom will meet your needs and exceed your expectations! Find your inner child as you cruise ...

    • 3 bedroom
    • 4 bathroom
    • Sleeps 6
    Hawaii> Kailua-Kona
    14  reviews
    from $1,034 
      View Property   Book Now

Showing 1 of 42 pages.

Home
About
Privacy Policy
Terms
Disclaimer
Sitemap
To-Hawaii.com © 2006-2024
back-top