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 a 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.

  • A Quiet Neighborhood In The Hill

    Aloha, come enjoy the beauty of Kailua Kona in Big Island. Our private rooms are cozy and comfortable. Less than 2 miles to Kailua Kona Pier and 1 mile to center of Kailua - Kona town on the beautiful Big Island of Hawaii. ハワイ島コナの街から近く、高台になる閑静な...

    1 Bedrooms, 1 Bathrooms, Sleeps 2

    HI>Kailua-Kona

    135 USD - 135 USD

    nightly

    900 USD - 900 USD

    weekly

    3,500 USD - 3,500 USD

    monthly

  • Ocean Front / Beach Front Penthouse Condominium

    If you enjoy beach front, ocean front with open seas, watching the beach fun, sea turtles, exotic fish, open skies and the most beautiful sunsets you've ever seen all from your lanai then this condo is just for you. Every view from this condo is i...

    0 Bedrooms, 1 Bathrooms, Sleeps 2

    HI>Kailua-Kona

    143 USD - 171 USD

    nightly

    1,000 USD - 1,200 USD

    weekly

  • Private 2008 Home 3bd/3ba - Koa/Tigerwood/Mahogany/SS - 2600 sq ft, new bath!

    This is it. Book it. You'll be the envy of your friends and family or bring em No booking or reservation fees required. This keeps rates as low as possible for you. Book with confidence as we have been renting homes for 11 years. A special...

    3 Bedrooms, 4 Bathrooms, Sleeps 15

    HI>Captain Cook

    199 USD - 209 USD

    nightly

    1,463 USD - 1,463 USD

    weekly

  • Beautiful Views, Beautiful Home, Beautiful Grounds! Hale Pu’ulani

    Hale Pu’ulani (Heavenly Hill Home) - A rare, fantastic property on the Kona Coast. It is in Holualoa, near the Village. A private road leads to a peaceful neighborhood. At a cool elevation, a gated entry opens revealing a fenced half-acre scene...

    3 Bedrooms, 3 Bathrooms, Sleeps 6

    HI>Holualoa

    1,463 USD - 2,268 USD

    weekly

    6,270 USD - 6,270 USD

    monthly

    209 USD - 209 USD

    nightly

  • Large 3 bedroom 2 bath home, cool elevation, Spectacular Ocean & Sunset Views

    Enjoy panoramic ocean and bay views, miles and miles of Pacific Ocean and unobstructed sunsets year-round. The main home consists of 3 bedrooms, a bonus room with 2 twins and 2 bathrooms.The home is located right above Kailua-Kona Village at about...

    3 Bedrooms, 2 Bathrooms, Sleeps 6

    HI>Kailua Kona

    3,150 USD - 3,990 USD

    weekly

    13,500 USD - 13,500 USD

    monthly

    450 USD - 450 USD

    nightly

  • Clean and comfortable, home away from home

    Brand new to the rental market, my home is unapologetically geared towards family's. It's set up with a master bed room for the parents and two separate bed rooms for the couple. It has a very large living room and dining area. The house is co...

    3 Bedrooms, 2 Bathrooms, Sleeps 5

    HI>Kailua-Kona

  • 180 degree Ocean View -Spring Special!!The Perfect Spot to Unwind and Relax!!

    Hale Maluhia Nestled near the top of the hill overlooking the ocean, this home is just a few minutes from Kailua Kona town center. Perched upon a knoll at the perfect elevation of 920' above sea level, it remains true to the Hawaiian word "Iolani...

    3 Bedrooms, 3 Bathrooms, Sleeps 8

    HI>Kailua Kona

  • Outstanding Views, Quiet Spot In The Best Area

    Leone Way is halfway between Kailua Kona town and Keahou on the Big Island. The 250 elevation gives you beautiful views of the ocean and Lymans Point. This can be viewed from the covered lanai which is across the front of the home. This is wher...

    2 Bedrooms, 2 Bathrooms, Sleeps 4

    HI>Kailua-Kona

  • KONA Hawaiian VILLAGE! Beautiful! OPEN for 2017 WEEK, ONE week open !

    High end Wyndham....Really great resort, Come enjoy our Week here we cant use.................ONE full week available- FRI, SAT , SUN check in. 7- nights ONLY Our timeshare week , we cant use; based on availability Reservation in you...

    2 Bedrooms, 2 Bathrooms, Sleeps 6

    HI>Kailua-Kona

  • Luxurious Designer Hawaiian Hale, Cool Upper Elevation With 180 Coastline Views

    Large King 4 Poster Bed with Luxurious Linens and Down Like Pillows has a view of the ocean. Beautifully Outfitted bottom half of home (900 square feet) was newly built in 2015. Walk in Shower in stone and tile in a Large Bathroom. Sofa Sectiona...

    1 Bedrooms, 1 Bathrooms, Sleeps 2

    HI>Kailua Kona

  • Keauhou Ocean View Condo

    Capture the essence of Hawaii with ever present ocean view, trade winds, palm trees, birds and lovely flowers. All things Hawaii. This condo is filled with natural light and always-present ocean breezes eliminate the need for air conditioning! ...

    2 Bedrooms, 2 Bathrooms, Sleeps 4

    HI>Kailua-Kona

    1,050 USD - 1,050 USD

    weekly

    3,500 USD - 3,500 USD

    monthly

  • Kona Coast Resort Dec 18-25, 2016 2br, 2 Bath

    In 21 acres of tropical gardens, this relaxed, beachfront resort is 6.5 miles from Hulihee Palace, a former vacation home for Hawaiian royaly, and 12.2 miles from Kealakekua Bay. Casual villas have traditional Hawaiian motifs and feature kitchen...

    2 Bedrooms, 2 Bathrooms, Sleeps 8

    HI>Kailua-Kona