RedAwning’s Big Island vacation homes both include instant online booking and no security deposits, to make your trip easy and stress-free. The youngest and largest of the Hawaiian islands, the Big Island is home to an active volcano, the tallest sea mountain in the world, and countless beautiful beaches. Book your stay today!

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  1. CONDOMINIUM
    Kona 2 Bedroom

    Kona 2 Bedroom

    Kailua-Kona, HI

    Kona Aloha! Relax in a true Hawaiian paradise. Welcome to abundant Pacific beach access and topical relaxation, for your group, couples, or family stay. The Kona Coast Resort on Hawaii's Big Island offers a tropical vacation backdrop of Hawaii's...

    Pool Hot Tub
  2. HOUSE
    Home of the Hula Moon

    Home of the Hula Moon

    Waimea, HI

    Stately and serene, Hula Moon sits on one of the most beautiful properties in Puako. Located at the quiet end of the road, you will enjoy year-round sunsets and privacy. As you enter through the gates, lush tropical plantings enhance the large...

    Pool

    $1,876 to $2,662/night

  3. CONDOMINIUM
    Casa De Emdeko 317

    Casa De Emdeko 317

    Kailua Kona, HI

    Casa#317 is an amazing addition to our Vacation Rental Inventory that Knutson & Associates is proud to be newly representing. **Hard Wood Floors And Kitchen Remodel Completed In May 2018. Living room & Bedrooms have gorgeous brand new hard wood...

    Pool
    FREE CANCELLATION

    $158 to $337/night

  4. CONDOMINIUM
    Kona Makai 2-102

    Kona Makai 2-102

    Kailua Kona, HI

    Kona Makai#2-102 is an excellant option for your Hawaiian Vacation. The owners have put BRAND NEW CARPET in the Property as of June 2018! This spectacular ground floor unit is a true gem at the Kona Makai. The owners keep their property maintained...

    Pool Hot Tub
    FREE CANCELLATION

    $116 to $326/night

  5. CONDOMINIUM
    Kona Pacific D623

    Kona Pacific D623

    Kailua Kona, HI

    The stylish condo accommodates 4 people with 1 king bed, 1 sofa bed and 2 bathrooms. The kitchen is fully equipped with stainless steel appliances and Hawaiian touches that will make you feel right at home. Inside this Big Island Property, you'll...

    Pool

    $268 to $399/night

  6. VILLA
    Vista Waikoloa Vila G104

    Vista Waikoloa Vila G104

    Waikoloa Village, HI

    Aloha! Welcome to our 2 bedroom, 2.5 bathroom cozy Hawaiian retreat at the beautifully landscaped Vista Waikoloa. Conveniently located in a relaxing and peaceful gated community, our condo is situated on the ground floor near the 4th green of the...

    Pool
    FREE CANCELLATION

    $184 to $464/night

  7. CONDOMINIUM
    Waikoloa Beach Villas B2

    Waikoloa Beach Villas B2

    Waikoloa, HI

    Come share the enjoyment of our home away from home in Hawaii! We fell in love with the Big Island 30 plus years ago on our honeymoon and have been vacationing here ever since. We love bringing our children and grandchildren because this island...

    Pool
    FREE CANCELLATION

    $209 to $431/night

  8. CONDOMINIUM
    Keauhou Kona Surf & Racquet Club #5-202

    Keauhou Kona Surf & Racquet Club #5-202

    Kailua Kona, HI

    Brand New Vacation Rental With Brand New Ownership. Welcome to #5-202 at the Keauhou Kona Surf & Racquet Club. The new owners are excited to have their new property that's never been rented before be placed as a new Vacation Rental. Direct...

    Pool
    FREE CANCELLATION

    $181 to $459/night

  9. VILLA
    Hualalai Resort Hillside 4102

    Hualalai Resort Hillside 4102

    Kailua-Kona, HI

    Location-Location-Location! This spectacular 2 bedroom, 2 bath luxury villa is a short distance to the Four Seasons Resort Hualalai - truly one of the worlds' great resorts. Enjoy the soothing sounds of gentle waves on the shoreline from this ground...

    Pool
    FREE CANCELLATION

    $1,109 to $3,736/night

  10. CONDOMINIUM
    Kona Coast Resort at Keauhou Gardens 8204

    Kona Coast Resort at Keauhou Gardens 8204

    Kailua Kona, HI

    Kona Coast Resort #8-204 is a beautifully maintained 2 bedroom, 2 bath condo that has all of the amazing amenities of a 5-Star Resort. You are able to enjoy the two Swimming Pools (one “family” pool with a children's pool and one quiet spa...

    Pool Hot Tub
    FREE CANCELLATION

    $190 to $518/night

  11. HOUSE
    Hale Keanu- Waimea Home

    Hale Keanu- Waimea Home

    Waimea, HI

    Sweeping Ocean Views & Separate Ohana. Rare 4 bedroom - Wai'ula'ula at Mauna Kea Step into a dream at an exceptional four-bedroom ocean-view rental at Wai'ula'ula within the Mauna Kea Resort. At this single level brand-new home, you will find a...

    Pool Hot Tub

    $1,264 to $3,032/night

  12. CONDOMINIUM
    78-6721 ALii Dr Condo Unit 1-203

    78-6721 ALii Dr Condo Unit 1-203

    Kailua Kona, HI

    The Beach Villas represent the first new beachfront condo construction on Alii Drive in the last 20 years. This two bedroom, two bath villa is large, luxurious, designer decorated and has all the amenities you desire. You'll find ocean front views...

    Pool
    FREE CANCELLATION

    $191 to $485/night

  13. CONDOMINIUM
    Keauhou Kona Surf and Racquet Club Townhouse #185

    Keauhou Kona Surf and Racquet Club Townhouse #185

    Kailua Kona, HI

    Townhome#185 is an amazing DIRECT oceanfront property at a amazing value. Enjoy the privacy of a townhome. Living area & Kitchen downstairs, bedrooms upstairs. Wifi, Beachgear available to you for your convenience. The Keauhou Surf and Racquet Club...

    Pool
    FREE CANCELLATION

    $176 to $444/night

  14. TOWNHOUSE
    Keauhou Kona Surf & Racket Club Townhouse #3

    Keauhou Kona Surf & Racket Club Townhouse #3

    Kailua Kona, HI

    This oceanfront townhouse is beautifullly furnished, very clean, and cozy. It has Wifi, HD Television & DVR. Have a bigger group? We manage Townhome#4 right next door. This property sleeps 4, and next door sleeps 6. A great option for 10 to be right...

    Pool
    FREE CANCELLATION

    $165 to $411/night

  15. ESTATE
    Mauna Kea Bluffs #5: La Ikena O Komohana

    Mauna Kea Bluffs #5: La Ikena O Komohana

    Kamuela, HI

    Found on the sunny Kohala Coast of the Big Island of Hawaii, the Mauna Kea Bluffs #5 estate is conveniently located within an exclusive gated community. This magnificent estate home boasts 11,500 square feet of interior space. Every detail has been...

    Pool Hot Tub

    $10,240 to $12,620/night

  16. CONDOMINIUM
    Vistas'S B302 Condominium

    Vistas'S B302 Condominium

    Waikoloa, HI

    Newly remodeled unit, master bedroom has a king bed, guest bedroom has 2 twins beds that can be converted to a king upon request. Master bath and a guest full bathroom. Queen size sleeper sofa. Fully stocked kitchen with a convection microwave oven...

    Pool
    FREE CANCELLATION

    $184 to $464/night

  17. HOUSE
    Aniani Hale

    Aniani Hale

    Kailua Kona, HI

    Known as ‘Aniani Hale,’ or Glass House, this stunning 4BR/4.5BA home is situated just above the heart of Kailua-Kona. Elevated 700 feet above sea level, your beautiful island getaway boasts refreshing trade winds from the west and mountain...

    Pool Hot Tub
    FREE CANCELLATION

    $534 to $986/night

  18. CONDOMINIUM
    Kona Pacific D623

    Kona Pacific D623

    Kailua Kona, HI

    The stylish condo accommodates 4 people with 1 king bed, 1 sofa bed and 2 bathrooms. The kitchen is fully equipped with stainless steel appliances and Hawaiian touches that will make you feel right at home. Inside this Big Island Property, you'll...

    Pool

    $140 to $269/night

  19. HOUSE
    Kahalu'u Hale

    Kahalu'u Hale

    Kailua-Kona, HI

    This beautiful, hand-crafted, custom home, with open-beam, cedar ceilings, and air-conditioned bedrooms, is the perfect getaway vacation site. The home is located just minutes from famous Kahalu’u Beach State Park. Kahalu’u provides access to...

    Pool

    $350 to $467/night

  20. VILLA
    Hualalai Resort Ke Alaula Villa 210A

    Hualalai Resort Ke Alaula Villa 210A

    Kailua-Kona, HI

    Spectacular three bedroom three bath villa centrally located within the Hualalai Resort. Two story townhome style in the exclusive Ke Alaula neighborhood, just a 3-4 minute cart ride to the Four Seasons Hotel. Fully receding pocket glass, screen and...

    FREE CANCELLATION

    $1,109 to $3,736/night

  21. HOUSE
    Hoku'Ea Hale

    Hoku'Ea Hale

    Kailua Kona, HI

    All Rooms open to the ocean to fully enjoy spectacular oceanfront living in the Kahalu’u Bay. Enter the beautiful Hoku' Ea Hale named for the beautiful turtle gate that provides complete privacy from the outside. You will immediately be drawn to...

    $566 to $846/night

  22. COTTAGE
    The Cottage

    The Cottage

    Kailua-Kona, HI

    "The Cottage", Mahina Meli Makai (Oceanside Honey Moon) This truly oceanfront Cottage, captures spectacular coastline views as well as the captivating ocean right in front of you. The "Honeymoon Getaway" begins the moment you arrive and step...

    $239 to $379/night

  23. HOUSE
    Piko Nani

    Piko Nani

    Kailua Kona, HI

    Piko Nani “Hilltop Beauty” sits high on a knoll at the very top of O'oma Plantation, a newer subdivision of 19 estate-sized, 2-acre parcels. This quiet, supremely private home is perfect for a serene getaway. The elegantly finished interior of...

    Pool

    $555 to $759/night

  24. HOUSE
    Magic Sands Retreat

    Magic Sands Retreat

    Kailua Kona, HI

    With it’s ideal location just 5 minutes walking distance from the famous Magic Sands Beach park, 7-minutes walking to Pahoeoe Park, and less than a mile to Kahaluu Beach Park this cozy, private cottage is what vacation dreams are made of. Our...

    $309 to $473/night

  25. CONDOMINIUM
    Kalanikai 306

    Kalanikai 306

    Kailua Kona, HI

    This beautifully remodeled 1 bedroom 1 bathroom unit makes for the perfect retreat for a Big Island Vacation. Enjoy breath taking views from the spacious Lanai, while simultaneously luxuriate in the comforts of home with the well equipped newly...

    Pool

    $123 to $257/night

  26. CONDOMINIUM
    Casa De Emdeko 222

    Casa De Emdeko 222

    Kailua-Kona, HI

    Casa De Emdeko, an oceanfront condominium complex, is located on famous Alii Drive just 1.5 miles south of Kailua Kona Village. This is a no-smoking property. This deluxe one bedroom unit with garden, fountain and partial ocean views from the lanai...

    Pool

    $128 to $210/night

  27. HOUSE
    Leilani Hale

    Leilani Hale

    Kailua Kona, HI

    Tucked into the side of the mountain just above Kona at a cooler 600 ft. elevation Happy Leilani Hale has a zen feel to it as you look out over the blue pacific and feel the Soft ocean breezes take you away from it all. Enter through the Asian...

    Pool

    $425 to $729/night

  28. HOUSE
    Kona Bay Hale

    Kona Bay Hale

    Kailua Kona, HI

    Watch the Dolphins frolic and the whales in season from your own private lanai where the soft ocean breezes and the gentle waves lapping against the shoreline will relax your mind and body. Kona Bay Hale consists of a 2BR / 2 BA home with additional...

    $522 to $668/night

  29. CONDOMINIUM
    Kona Bali Kai 317- Oceanfront

    Kona Bali Kai 317- Oceanfront

    Kailua Kona, HI

    Lovely Oceanfront 3rd floor 2bd/2bth Beautifully maintained unit in Kona Bali Kai, one of Kona's most popular oceanfront destinations. Watch the dolphins, whales (during winter season) surfers, and those magnificent Kona Sunsets right from your own...

    Pool

    $181 to $213/night

  30. HOUSE
    Hale Nui Ohana

    Hale Nui Ohana

    Kailua-Kona, HI

    If you have a large group or extended family this is the home for you. Hale Nui Ohana (Large family home) is a large 2 story home with panoramic ocean views. Both upper and lower areas have separate entrances. Main upper floor has a full kitchen,...

    $364 to $608/night