Welcome to Hawaii! Paradise on earth! RedAwning has the perfect vacation rental for your island adventures. Beach bungalows, resort condos, and sun-kissed ocean-front villas await. Browse your island destination using the blue location links below or filter your preferences using the panel to the side. RedAwning offers easy, instant, hotel-style reservations and a simplified booking process so you can have your vacation plans covered in no time.

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  1. HOUSE
    Hale Ke Aluala

    Hale Ke Aluala

    Waimea, HI

    This large 2 bedroom/ 2 bath home has enormous square footage, vaulted bamboo ceilings and a huge wrap around deck. New furnishings, top of the line appliances, gourmet kitchen and so much more… Newly installed A/C and many ceiling fans make it a...

    FREE CANCELLATION

    $471 to $683/night

  2. CONDOMINIUM
    Villa 317

    Villa 317

    Kahuku, HI

    This villa is in a private location on the third floor with dramatic panoramic ocean views, just 20 yards from the ocean and just 80 yards from the sandy beach! Watch the whales swim past while in your living room during migration season! The Pool...

    Pool Hot Tub

    $515 to $920/night

  3. HOUSE
    O'oma Plantation

    O'oma Plantation

    Kailua Kona, HI

    Why book individual resorts or condos when your whole group can enjoy a mansion in paradise? Enjoy exceptional panoramic coastal views from the private and quiet custom home at the O’oma Plantation.This large home is the perfect escape for a large...

    Pool Hot Tub

    $1,179 to $1,664/night

  4. CONDOMINIUM
    Kona Alii 304

    Kona Alii 304

    Kailua-Kona, HI

    Upgraded one bedroom oasis looking right over the ocean. You will love the unit, you will love the location, walking distance to everywhere in town.Stroll down Alii Drive and you will find a variety of shops and restaurants. Nearby restaurants...

    Pool

    $181 to $309/night

  5. CONDOMINIUM
    Pikake A-4

    Pikake A-4

    Lahaina, HI

    An incredibly comfortable unit! This renovated one bedroom unit fronts directly on a beautiful white sand beach. You'll have just enough lawn area to stretch out and shake the sand off before stepping directly into your beautiful ocean side living...

    FREE CANCELLATION

    $195 to $324/night

  6. CONDOMINIUM
    Wai'ula'ula A202

    Wai'ula'ula A202

    Kamuela, HI

    Welcome to Wai'ula'ula at the Mauna Kea Resort! Your vacation will truly be one to remember in this beautifully decorated condominium in the gated community of Wai'ula'ula is located on the Hapuna Golf Course. This recently built luxury development...

    Pool Hot Tub
    FREE CANCELLATION

    $525 to $1,205/night

  7. CONDOMINIUM
    Kahana Sunset E 11

    Kahana Sunset E 11

    Lahaina, HI

    The Kahana Sunset Welcomes you withThis unique condo is a beachfront property on the world famous West Coast of Maui between Kaanapali and Kapalua.Included in our fabulous price are many owner-supplied extras such as:• Beach chairs (2)• Beach...

    Pool
    FREE CANCELLATION

    $223 to $389/night

  8. CONDOMINIUM
    Hale Kalena (Kanaloa 701)

    Hale Kalena (Kanaloa 701)

    Kailua Kona, HI

    Tropical gardens and oceanfront views surround this 1800sqft peaceful 2 bedroom centrally air conditioned condo. With 3 pools facing the ocean, 2 resurfaced tennis courts, and a relaxing BBQ area, this condominium complex provides wonderful...

    Pool Hot Tub

    $204 to $304/night

  9. CONDOMINIUM
    Casa De Emdeko 204

    Casa De Emdeko 204

    Kailua Kona, HI

    Casa 204 is an excellent, affordable 2nd floor property that you will certainly love. Unit#204 has been NEWLY REMODELED IN APRIL 2019! All new flooring, furniture, kitchen, bathrooms, paint, appliances!Central AC, WIFI, Elevators, Beach gear! Look...

    Pool
    FREE CANCELLATION

    $165 to $186/night

  10. CONDOMINIUM
    Casa De Emdeko 111

    Casa De Emdeko 111

    Kailua Kona, HI

    Casa#111 is an excellent ground floor unit, that's VERY spacious! Nearly 1300 square feet! Close to the pool for easy access. There are new owners who own the property! Wifi!Casa De Emdeko offers owners and guests the perfect blend of Hawaiian...

    Pool
    FREE CANCELLATION

    $309 to $323/night

  11. CONDOMINIUM
    Kona Isle B31

    Kona Isle B31

    Kailua Kona, HI

    B31 at the Kona Isle is an amazing top floor condo in building B at the Kona Isle.Comfortable Queen Sized bed, and pull out sofa that can sleep 2! Comfortably sleep 4 in the property.Being on the top floor gives you a beautiful view of the grounds....

    Pool
    FREE CANCELLATION

    $152 to $280/night

  12. CONDOMINIUM
    Waikoloa Beach Villas J32

    Waikoloa Beach Villas J32

    Waikoloa, HI

    This brand new upscale luxury condo is located in the privately gated new Waikoloa Beach Villas Complex, close to the activity center with two pools, fitness workout room and spa areas. Unit includes discounted GOLD GOLF KINGS' CLUB MEMBERSHIP....

    Pool Hot Tub
    FREE CANCELLATION

    $258 to $506/night

  13. CONDOMINIUM
    Kaleialoha #115

    Kaleialoha #115

    Lahaina, HI

    Lovely corner unit with all one side louvered windows to let the outside in!Recently upgraded with gorgeous granite counter, all new appliances and tile through out! Unit has unique four poster bed, walk in tiled shower, AC in living area, in suite...

    Pool
    FREE CANCELLATION

    $207 to $384/night

  14. CONDOMINIUM
    Sealodge D1

    Sealodge D1

    Princeville, HI

    Sealodge D1: With a private oceanfront lanai and spacious expanse of lawn in front, you'll enjoy sitting outside admiring the view and the passing chickens and nene. Take along the provided binoculars and get an up close view of the surfers, or...

    Pool
    FREE CANCELLATION

    $238 to $275/night

  15. CONDOMINIUM
    Sea Village 4-205

    Sea Village 4-205

    Kailua Kona, HI

    This amazing 2 bedroom direct oceanfront condo is the PERFECT spot for your Vacation. Completely remodeled, extremely clean, the owners have done a beautiful job with this property. Wifi, Direct oceanfront views, excellent complex, close to town,...

    Pool Hot Tub
    FREE CANCELLATION

    $421 to $467/night

  16. HOUSE
    Kauhale Pilialoha

    Kauhale Pilialoha

    Kamuela, HI

    Indulge yourself in the ultimate island style luxury at the Big Island of Hawaii’s most exclusive retreat, Kauhale Pilialoha. Experience breathtaking sunsets, enjoy the natural beauty of Hawaii from the ultimate poolside lanai perched on the...

    Pool Hot Tub

    $17,975 to $27,561/night

  17. CONDOMINIUM
    Oceanfront 1BR w/ Lanai & Pool

    Oceanfront 1BR w/ Lanai & Pool

    Kihei, HI

    Book a memorable Maui vacation at this third-floor 1BR condo in central Kihei. With open-concept living and an additional sleeper sofa, there’s plenty of room for four people. Step out to your private lanai with retractable net enclosure and take...

    Pool
    FREE CANCELLATION

    $131 to $326/night

  18. CONDOMINIUM
    Honua Kai Konea 215

    Honua Kai Konea 215

    Lahaina, HI

    HONUA KAI RESORT AND SPA SUITE 215 welcomes you with so muchThis spacious studio, 1 bath can accommodate up to 4 guests.Included in our fabulous price are many owner-supplied extras such as:• Beach chairs (2)• Beach umbrella• Beach towels•...

    Pool Hot Tub
    FREE CANCELLATION

    $275 to $413/night

  19. CONDOMINIUM
    Kapalua Bay Villa 33B1 Gold Ocean View

    Kapalua Bay Villa 33B1 Gold Ocean View

    Kapalua, HI

    Paint to exterior of building scheduled between Aug 5th to Oct 15th. This is a rare opportunity to experience this 5 star property for a fraction of the cost!! Contact manager for special rates and details!Recently and fully upgraded, this lovely...

    Pool

    $436 to $631/night

  20. CONDOMINIUM
    Ocean-View 2BR Kamaole Beach Royale

    Ocean-View 2BR Kamaole Beach Royale

    Kihei, HI

    Discover the meaning of true relaxation at this fourth-floor 2BR/2BA Kamaole Beach Royale Resort condo. Your spacious island getaway boasts incredible indoor/outdoor living space with an ocean-view lanai, as well as upscale finishes including...

    Pool
    FREE CANCELLATION

    $165 to $392/night

  21. CONDOMINIUM
    Kolepa Aloha

    Kolepa Aloha

    Waikoloa, HI

    Description :Views of Mauna Kea and emerald fairways are yours at this two-bedroom, two-bath vacation rental at Fairway Villas, located within the prestigious Waikoloa Beach Resort. Step onto your private, covered lanai with the day's first cup of...

    Pool Hot Tub

    $162 to $401/night

  22. CONDOMINIUM
    Hali'i Kai at Waikoloa Beach Resort 9F

    Hali'i Kai at Waikoloa Beach Resort 9F

    Waikoloa, HI

    On the sun-drenched Kohala coast on the Big Island of Hawaii, the elements have come together to create a place like no other. It is at this point of convergence that we have chosen to situate our residential community Hali’i Kai at Waikoloa....

    Pool Hot Tub

    $409 to $689/night

  23. CONDOMINIUM
    Turtle Bay Hale Lilly**NUC 90-TVU-0350

    Turtle Bay Hale Lilly**NUC 90-TVU-0350

    Kahuku, HI

    This 2 bedroom + loft unit is located on the first fairway of the Fazio golf course. Window A/C's in both bedrooms. Trundle bed on the loft. Flat screen TV/VCR/DVD/CD player. New couch and dining room furniture. Refurbished bath tub and marble...

    Pool
    FREE CANCELLATION

    $266 to $283/night

  24. CONDOMINIUM
    Villas on the Prince 34

    Villas on the Prince 34

    Princeville, HI

    NOTE: 30-DAY MINIMUM STAY AT THIS LOCATION. Villas on the Prince 34 is a spacious luxury town house with pool and easy walking distance to Anini Beach and Princeville shopping. This beautifully cared for villa has 3 bedrooms and 2 1/2 baths. Two...

    Pool Hot Tub
    FREE CANCELLATION

    $175 to $183/night

  25. CONDOMINIUM
    Kaleialoha #208

    Kaleialoha #208

    Lahaina, HI

    Near Shopping, Restaurants and all beach activities. Farmer's Market, coffee shop and beach park 3 blks away. Swim and snorkel right in front of property within our protected outer reef. Observe a myriad of sea life including, sea turtles, dolphins...

    Pool
    FREE CANCELLATION

    $207 to $384/night

  26. CONDOMINIUM
    Keauhou Kona Surf and Racquet Club 2-204

    Keauhou Kona Surf and Racquet Club 2-204

    Kailua Kona, HI

    Welcome to the page of our gorgeous Keauhou Kona Surf & Racquet Club#2-204! DIRECT OCEANFRONT CORNER units are extra special here. The lanai is extended for extra space. 2nd floor, so only 1 flight of stairs! This property is absolutely spectacular....

    Pool
    FREE CANCELLATION

    $311 to $350/night

  27. CONDOMINIUM
    Casa de Emdeko 337

    Casa de Emdeko 337

    Kailua-Kona, HI

    This perfectly located deluxe one bedroom unit with amazing ocean views from the lanai, has been fully redecorated and upgraded. All new appliances and tasteful appointments placed throughout with your peace and comfort in mind. The mirrors in the...

    Pool

    $140 to $257/night

  28. CONDOMINIUM
    Keauhou Kona Surf and Racquet Club 5-304

    Keauhou Kona Surf and Racquet Club 5-304

    Kailua Kona, HI

    5-304 is by far arguably one of the BEST properties in the entire complex. Being in building 5, the top floor corner, the location is undeniably too perfect. Private, direct oceanfront penthouse living at its finest.BRAND NEW REMODELED KITCHEN...

    Pool
    FREE CANCELLATION

    $717 to $748/night

  29. CONDOMINIUM
    Kaleialoha #304

    Kaleialoha #304

    Lahaina, HI

    Third floor corner unit with one side all windows! View the ocean from your new queen size bed. Lovely upgrades include new furnishings, carpet and kitchen with all stainless steel appliances!Near Shopping, Restaurants and all beach activities....

    Pool
    FREE CANCELLATION

    $207 to $384/night

  30. CONDOMINIUM
    Keauhou Kona Surf & Racquet Club 3202

    Keauhou Kona Surf & Racquet Club 3202

    Kailua Kona, HI

    Welcome to Keauhou Kona Surf & Racquet Club, Unit #3-202! This beautiful, DIRECT oceanfront condo is Hawaiian Living at it's finest! Hear the ocean directly from the living room, lanai, and master bedroom. This condo is located on the 2nd floor of...

    Pool
    FREE CANCELLATION

    $350/night