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. CONDOMINIUM
    Puako Beach Penthouse 405

    Puako Beach Penthouse 405

    Waimea, HI

    Fantastic panoramic ocean views. You can see the whales splashing their tales in the winter from the lanai! You can see the white sand at Hapuna Beach! Gorgeous sunsets, too! Watch the sunset while you BBQ and dine outdoors. This fabulous 3...

    Pool
    FREE CANCELLATION

    $273 to $435/night

  3. CONDOMINIUM
    Kanaloa at Kona 3304

    Kanaloa at Kona 3304

    Kailua Kona, HI

    Just a stone's throw from Heeia Bay, this private and spacious condo offers the ideal oceanfront setting for your Kona Resort getaway. Complete with huge ocean views, lovely Hawaiian décor, central air conditioning, wireless internet, cable, and a...

    Pool Hot Tub

    $423 to $1,084/night

  4. CONDOMINIUM
    Palm Villas (H23) at Mauna Lani 2 Bedrooms + Loft

    Palm Villas (H23) at Mauna Lani 2 Bedrooms + Loft

    Kamuela, HI

    This beautifully decorated 2 bedroom, 2 bath, plus large spacious loft property is located in Palm Villas, a privately gated, small group of condominium homes, centrally located in the heart of the fabulous Mauna Lani Resort. This exceptional unit...

    Pool Hot Tub

    $393 to $897/night

  5. 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

  6. 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

  7. HOUSE
    Pacific Edge Kona

    Pacific Edge Kona

    Kailua Kona, HI

    Pacific Edge Kona, a gracious oceanfront island style beach home! From the lanai of this waterfront vintage Hawaiian home see breaching humpback whales (when in season) and spinner dolphins frolic by day, spectacular sunsets at twilight and watch...

    $309 to $438/night

  8. CONDOMINIUM
    Hale Ohana Aloha

    Hale Ohana Aloha

    Waikoloa, HI

    Big Island dreams begin at Hali'i Kai 7D, an ocean-view vacation condominium at renowned Waikoloa Beach Resort. Ideal for group getaways of up to six people, this 2-bedroom, 2-bath condo features an updated interior, access to impeccable resort...

    Pool Hot Tub

    $286 to $478/night

  9. HOUSE
    Kilohana Vista

    Kilohana Vista

    Kailua Kona, HI

    Settle in at Kilohana Vista and let the warm gentle trade wind breeze envelope you as you view an unmatched spectacular view of the harbor and Cruise Ships from your Lanai, Spa or Pool provided by the perfect 500 foot elevation. Close to the center...

    Pool

    $555 to $771/night

  10. CONDOMINIUM
    Kahaluu Bay Villas #304

    Kahaluu Bay Villas #304

    Kailua Kona, HI

    This beautiful, private top floor condo at Kahaluu Bay Villas is quite the gem. The unit has a well equipped kitchen and all the rooms are spacious with a balcony overlooking the pool and the ocean. The bedrooms and baths are wonderfully appointed....

    Pool
    FREE CANCELLATION
  11. 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

  12. CONDOMINIUM
    Casa De Emdeko 336

    Casa De Emdeko 336

    Kailua Kona, HI

    Let the stresses of life drift away when you stay in this 2 bedroom, 2 bath condo in Kona Hawaii. Included are a king sized bed in the master bedroom, 2 Twin beds in the guest bedroom, Queen sleeper sofa in the living room, central air conditioning,...

    Pool

    $216 to $333/night

  13. 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

  14. VILLA
    3BD Fairways Villa (116C) at Four Seasons Resort Hualalai

    3BD Fairways Villa (116C) at Four Seasons Resort Hualala...

    Kailua Kona, HI

    Make memories with family and friends in this spacious Waiulu Street ground floor villa, overlooking the 15th hole of the Jack Nicklaus Hualalai Golf Course with the Pacific Ocean and Mount Hualalai beyond. The home features an open floor plan, high...

    Pool Hot Tub

    $970 to $3,353/night

  15. COTTAGE
    Honl's Beach Hale (Big Island)

    Honl's Beach Hale (Big Island)

    Kailua Kona, HI

    Location, location, location!!! HONLS BEACH HALE is located in the heart of the Kona Coast on the famous Ali'i Dr. This fantastic ocean front property offers unsurpassed, stunning sunset views. Hear the waves crashing and smell the sea spray as...

    Hot Tub

    $443 to $1,039/night

  16. CONDOMINIUM
    Kona Pacific B409

    Kona Pacific B409

    Kailua Kona, HI

    Kona Pacific B-409 is a newly remodeled upper floor condo with breathtaking ocean views. The owners have extensively made changes that every guest will absolutely love. All completed in April of 2017. The entire condo has been freshly painted,...

    Pool
    FREE CANCELLATION
  17. CONDOMINIUM
    Kona Plaza#402

    Kona Plaza#402

    Kailua Kona, HI

    ***New Property In Vacation Rental Inventory As Of June 2018.*** Knutson & Associates Property Management is proud to be newly representing Kona Plaza#402. Welcome to the listing page of Kona Plaza#402. It's amazing location puts you right in...

    Pool
    FREE CANCELLATION
  18. 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
  19. CONDOMINIUM
    Kona Isle D4

    Kona Isle D4

    Kailua Kona, HI

    Kona Isle D4 is a lovely, ground floor unit featuring a direct oceanfront view from the living room, kitchen, and bedroom. Brand new mattress purchased as of november 2018. This unit is located in the best building in the complex. No stairs, since...

    Pool
    FREE CANCELLATION
  20. CONDOMINIUM
    Kona Magic Sands 313

    Kona Magic Sands 313

    Kailua Kona, HI

    Kona Magic Sands#313 is a direct oceanfront, top floor condo that is meticulously maintained, beautifully furnished, and has absolutely anything any guest could dream of. Wifi, Air Conditioning, beach gear, you name it, the condo most likely has it!...

    FREE CANCELLATION
  21. 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

  22. HOUSE
    Kona Bay Seaclusion-Oceanfront

    Kona Bay Seaclusion-Oceanfront

    Kailua Kona, HI

    Beautifully appointed "like new" 2 bedroom 2.5 bath oceanfront home with pool. Gourmet kitchen and huge deck for tanning, dining & sunset cocktails. Upstairs master has shower & hot tub. Sliding doors disappear into walls for the ultimate "on the...

    Pool

    $486 to $608/night

  23. VILLA
    Waikoloa Beach Villas B22

    Waikoloa Beach Villas B22

    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

    $234 to $464/night

  24. VILLA
    Villa Cinco Resort at Kona Plantation Estates

    Villa Cinco Resort at Kona Plantation Estates

    Kailua Kona, HI

    This beautiful custom home, built in 2007, boasts 5 buildings totaling interior 3,829 sq. feet; including main house, and a private master suite situated at each of 4 corners. Main house has a private study converted to bedroom with a sink, a half...

    Pool Hot Tub
    FREE CANCELLATION
  25. HOUSE
    Hale Pahukoa

    Hale Pahukoa

    Kailua Kona, HI

    This vintage Hawaiian beach house is nestled in a private gated community of Kona Bay Estates. The simple seaside style will melt all of your cares away as you sip on your Mai Tai in the cool shade of the deep, covered lanai. Experience the feel of...

    Pool
    FREE CANCELLATION
  26. VILLA
    Waikoloa Beach Villas H32

    Waikoloa Beach Villas H32

    Waikoloa, HI

    New Listing - Our unit is across from the Queens’ Market Place shopping village and has views of the golf course & lake. It is an elegant 2 bedroom, 2 bath top floor vacation retreat with all the comforts of your own home, including...

    Pool Hot Tub
    FREE CANCELLATION

    $234 to $476/night

  27. 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 $242/night

  28. CONDOMINIUM
    2BD Hainoa Villa (2901B) at Four Seasons Resort Hualalai

    2BD Hainoa Villa (2901B) at Four Seasons Resort Hualalai...

    Kailua Kona, HI

    An upstairs residence at Four Seasons Resort Hualalai, 2901B offers the ultimate in Big Island luxury. With amazing ocean and sunset views, central air conditioning, stylish décor, and use of a golf cart included in every rental, this villa...

    Pool

    $720 to $2,118/night

  29. CONDOMINIUM
    Kona Pacific D623

    Kona Pacific D623

    Kailua Kona, HI

    Please note that this property was previously managed by Boundless Hawaii. In the interest of providing our guests with the highest level of service, we at Boundless Hawaii have joined the team at Elite Pacific Vacations. Although we “lost” our...

    Pool

    $268 to $720/night

  30. 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