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
  • **AWESOME 7TH FLOOR PENTHOUSE CONDO - OCEAN, SUNRISE & SUNSET VIEWS**

    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
    95  reviews
    from $399 
      View Property   Book Now
  • VERY PRIVATE, expansive ocean VIEWS, close to BEST BEACH

    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
    76  reviews
    from $735 
      View Property   Book Now
  • 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
    106  reviews
    from $275 
      View Property   Book Now
  • 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
    140  reviews
    from $624 
      View Property   Book Now
  • 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
    86  reviews
    from $225 
      View Property   Book Now
  • Magic Sands Home Steps From The Beach. Air Conditioned. No Cleaning Fee!

    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
    90  reviews
    from $419 
      View Property   Book Now
  • 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
    162  reviews
    from $395 
      View Property   Book Now
  • 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
    75  reviews
    from $299 
      View Property   Book Now
  • 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
    206  reviews
    from $269 
      View Property   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 ...

    • 1 bedroom
    • 1 bathroom
    • Sleeps 2
    Hawaii> Kailua-Kona
    180  reviews
    from $261 
      View Property   Book Now
  • 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
    104  reviews
    from $160 
      View Property   Book Now
  • 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
    105  reviews
    from $138 
      View Property   Book Now
  • 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
    82  reviews
    from $190 
      View Property   Book Now
  • 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
    100  reviews
    from $1,100 
      View Property   Book Now
  • 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
    138  reviews
    from $118 
      View Property   Book Now
  • 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
    146  reviews
    from $118 
      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
    5  reviews
    from $1,750 
      View Property   Book Now
  • Hualalai Waiulu Villa 137D~Great views overlooking Punawai Pond+Golf Course

    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
    17  reviews
    from $1,700 
      View Property   Book Now
  • Hualalai Palm Villa130A ~ Stunning Sunset Views~Signature Garden Shower

    One of the largest floor plans of any villa at Hualalai, this spacious and centrally located 3 bedroom, 3 bath villa is ideal for your Hawaii getaway. Extra bedding available with a "bonus" living room on the first level. The down-stairs suite ...

    • 3 bedroom
    • 3 bathroom
    • Sleeps 6
    Hawaii> Kailua-Kona
    26  reviews
    from $1,650 
      View Property   Book Now
  • Hualalai Palm Villa 140C~popular townhome on the 15th Fairway~2 golf carts

    The spacious floor plan includes a downstairs primary bedroom suite with king bed and luxury spa-like bath. Just off the master is a large living room with queen sized sofa pull out that opens to the downstairs lanai, leading to the lawn and ...

    • 3 bedroom
    • 3 bathroom
    • Sleeps 6
    Hawaii> Kailua-Kona
    21  reviews
    from $1,500 
      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
    8  reviews
    from $1,679 
      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, 3.5 bathrooms, 4,750 sq. ft. home plus, 1,700 sq. ft. covered ...

    • 4 bedroom
    • 4 bathroom
    • Sleeps 8
    Hawaii> Kailua-Kona
    79  reviews
    from $899 
      View Property   Book Now
  • Gorgeous Luxury Estate Home- Hualalai Resort - Spectacular Ocean and Golf Course Views- Private Pool and Spa- 3 Golf Carts

    Gorgeous, Contemporary, Newer Home Exemplifies Luxury and ease of Living in our Island Paradise. This 5-bedroom, 5 1/2 bath pod-style estate home is exceptionally appointed and designed to take full advantage of the temperate climate and island ...

    • 5 bedroom
    • 6 bathroom
    • Sleeps 10
    Hawaii> Kailua-Kona
    4  reviews
    from $4,583 
      View Property   Book Now
  • Hualalai Fairway Villa 116C - NEWLY Renovated, 2 golf carts, BEST LOCATION.

    Newly renovated villa from top to bottom. A 3 bedroom, 3.5 bath luxury villa conveniently located in the heart of Hualalai Resort overlooking the 15th hole of the Jack Nicklaus designed Hualalai Golf Course. Ground floor single level floor plan ...

    • 3 bedroom
    • 4 bathroom
    • Sleeps 6
    Hawaii> Kailua-Kona
    14  reviews
    from $1,769 
      View Property   Book Now
  • 🏖️Ocean View | Private | AC | Child Friendly | Salt Water Pool | vrKCV

    vrKCV - Hawaiian Honu House, Professionally Managed by Kona Coast Vacations

    Hawaiian Honu House is a winner in so many ways. This updated home is fully air conditioned, with individual temperature controls for each bedroom. This is the ...

    • 3 bedroom
    • 2 bathroom
    • Sleeps 6
    Hawaii> Kailua-Kona
    73  reviews
    from $549 
      View Property   Book Now
  • Live Aloha! Pacific View, Lanai and Laundry-Kanaloa

    Kanaloa at Kona #2203: Inside, you’ll find a bright living area with generous seating and a large flat screen television, perfect for entertaining your friends and family! The suite’s full size galley kitchen has Koa wood cabinetry, ...

    • 2 bedroom
    • 2 bathroom
    • Sleeps 4
    Hawaii> KAILUA-KONA
    12  reviews
    from $303 
      View Property   Book Now
  • Central A/C Double Master Suite Home in the Exclusive Ali'i Point community!

    Exquisite 2-bedroom, 2.5 bath house located in a private gated community on Ali'i Drive! With only 16 homes in this community, you can expect peace and serenity staying here on your Hawaiian vacation.

    Featuring an air-conditioned home ...

    • 2 bedroom
    • 3 bathroom
    • Sleeps 6
    Hawaii> Kailua-Kona
    19  reviews
    from $400 
      View Property   Book Now
  • Beautiful 180 Degree Ocean View With Spa And Pool.

    Unbelievable views from almost every room in the house!

    Located just minutes above Kailua-Kona town, this spacious two-story home is a beautiful island getaway for your whole family. Two master bedrooms with king size beds and private ...

    • 4 bedroom
    • 5 bathroom
    • Sleeps 10
    Hawaii> Kailua-Kona
    32  reviews
    from $800 
      View Property   Book Now
  • 306-AirCon. Upgraded Corner Unit w/Expansive Ocean Views and Extra Large Lanai.

    STVR-19-347215. This is a direct oceanfront corner unit with one of the largest lanais in Kona. The unit was recently remodeled with a new kitchen, bathrooms, living & dining areas, as well as the bedrooms. All new appliances in October 2023. ...

    • 2 bedroom
    • 2 bathroom
    • Sleeps 5
    Hawaii> Kailua-Kona
    202  reviews
    from $350 
      View Property   Book Now
  • Kailua-Kona Cottage < 1 Mile to Magic Sands Beach!

    Clear the calendar and say 'Aloha' to your next tropical getaway at this 1-bed, 1-bath vacation rental cottage in Kailua-Kona. Perched on the west coast of the Big Island, this quaint getaway showcases Hawaii's best snorkeling, surfing, diving ...

    • 1 bedroom
    • 1 bathroom
    • Sleeps 2
    Hawaii> Kailua-Kona
    53  reviews
    from $131 
      View Property   Book Now