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
    Holua Kai #34

    Holua Kai #34

    Kailua Kona, HI

    Situated in the exclusive, gated oceanfront community of Holua Kai, this luxurious and inviting home provides the perfect setting for your Hawaiian getaway. The home comfortably accommodates six and is just a 10-minute walk from Keauhou Bay, the...

    Pool

    $493 to $909/night

  2. CONDOMINIUM
    Honua Kai-Konea #539

    Honua Kai-Konea #539

    Lahaina, HI

    Ocean views from the Konea tower in North Ka'anapali with a wrap-around corner Lanai. The stainless steel appliances, granite counter tops and modern decor compliment this brand new 2 bedroom condo at a brand new resort. In addition to the flat...

    Pool
    FREE CANCELLATION

    $493 to $1,467/night

  3. CONDOMINIUM
    Wailea Elua #701

    Wailea Elua #701

    Kihei, HI

    The Wailea Elua is the premier ocean front property in Wailea. Situated right on Ulua Beach, it has one of the best locations in Wailea. There are miles of spectacular walking paths that follow the ocean  In addition the property has two swimming...

    Pool
    FREE CANCELLATION

    $493 to $922/night

  4. CONDOMINIUM
    Kaanapali Shores #255

    Kaanapali Shores #255

    Lahaina, HI

    This Hawaiian themed condo has ocean views from the lanai and both bedrooms in Ka'anapali. Remodeled and updated. The guest bathroom has a glass block walk-in shower only-no tub. Bring your DVD's from home and watch them on the flat screen TV in the...

    Pool
    FREE CANCELLATION

    $493 to $800/night

  5. CONDOMINIUM
    Kapalua Golf Villas 12T5

    Kapalua Golf Villas 12T5

    Kapalua, HI

    Relax and enjoy the tranquil setting of this luxurious Kapalua Golf Villa. Let the gorgeous greenery captivate and soothe your soul. This unit has been remodeled with only top of the line materials and furnishings and is well apointed. Spend your...

    Pool
    FREE CANCELLATION

    $493 to $626/night

  6. CONDOMINIUM
    Kaanapali Royal #A201 (MAUI)

    Kaanapali Royal #A201 (MAUI)

    Lahaina, HI

    FALL SPECIAL! 10% off until the end of November! Experience five-star Maui luxury at an affordable price! This modern ground-floor unit at Kaanapali Royal features a spacious floor plan that opens to sweeping golf course views. Extensively...

    Pool Hot Tub

    $491 to $1,256/night

  7. CONDOMINIUM
    Papakea A404

    Papakea A404

    Lahaina, HI

    One of the nicest penthouse units at Papakea Resort. From your lanai and the master bedroom, watch the whales play and the honu (turtles) swim. The KING bed in master bedroom allows you to sleep to the sounds of the ocean just 25 feet away. The...

    Pool Hot Tub

    $491 to $707/night

  8. CONDOMINIUM
    Sands of Kahana #292

    Sands of Kahana #292

    Kahana, HI

    9th Floor Ocean Front 3 bedroom, 3 bath Penthouse at the beautiful Sands of Kahana with exquisite views of the neighboring islands. This spacious 3 bedroom condo allows for plenty of room and seating areas for the entire family. A fully equipped...

    Pool
    FREE CANCELLATION

    $487 to $1,183/night

  9. 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 $547/night

  10. CONDOMINIUM
    O-805: Hale Makai Ko Olina Beach Villa

    O-805: Hale Makai Ko Olina Beach Villa

    Kapolei, HI

    Overview: This 3 BD, 2.5 BA luxury villa on the 8th floor of the Ocean Tower has stunning direct ocean views and is conveniently located just 20 miles from Honolulu International Airport on the beautiful southwestern shores of Oahu. The four...

    Pool Hot Tub

    $485 to $1,668/night

  11. CONDOMINIUM
    B-903 Beach Villa

    B-903 Beach Villa

    Kapolei, HI

    Beachfront Living at its finest! This 3 bedroom, 3 bath Villa is located in the beautiful Ko Olina Resort on the quiet West side of Oahu. The Beach Villas are the newest, and only, beachfront condominiums available on the island in 25 years....

    Pool

    $485 to $1,784/night

  12. HOUSE
    Hale Ulu'wehi

    Hale Ulu'wehi

    Waimea, HI

    Experience beach living in this beautiful vacation home on Puako Beach. This private residence is located right across the street from the ocean. Great place to kayak and snorkel in one of the best snorkeling spots on the Big Island. Or bask with...

    $485 to $652/night

  13. CONDOMINIUM
    Ko Olina Beach Villa B806

    Ko Olina Beach Villa B806

    Kapolei, HI

    Beachfront Living at its finest! This 2 bedroom, 2 bath Villa is located in the beautiful Ko Olina Resort on the quiet West side of Oahu. The Beach Villas are the newest, and only, beachfront condominiums available on the island in 25 years. You...

    Pool Hot Tub

    $485 to $1,500/night

  14. CONDOMINIUM
    Maui Kaanapali Villas #A101

    Maui Kaanapali Villas #A101

    Kaanapali, HI

    Luxury + Privacy = Our Maui Kaanapali Villa Vacation Rental Home. Our Villa, located on the ocean side ground level of Aloha Tower, represents the finest in gracious Hawaiian living. Featuring soaring ceilings and fine Asian art throughout, this 2...

    Pool
    FREE CANCELLATION

    $481 to $1,167/night

  15. CONDOMINIUM
    Wai'ula'ula D201 Condominium

    Wai'ula'ula D201 Condominium

    Waimea, 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, located on the Hapuna Golf Course. This recently built luxury development...

    Pool
    FREE CANCELLATION

    $481 to $1,174/night

  16. CONDOMINIUM
    Honua Kai Konea 643

    Honua Kai Konea 643

    Kaanapali, HI

    This great sixth floor 1315 square foot condo is in the interior courtyard of the Konea building with wonderful ocean views from the spacious lanai. Enjoy your morning coffee while watching the whales play in winter and the tours boats passing by...

    Pool Hot Tub
    FREE CANCELLATION

    $480 to $1,603/night

  17. CONDOMINIUM
    Hale Kai O'Kona

    Hale Kai O'Kona

    Kailua Kona, HI

    Hale Kai O'Kona is an exclusive oceanfront Hawaii vacation home one mile south of the town of Kailua-Kona, on the Big Island of Hawaii. Our home is a 2400 Sq. Ft. end property with no connecting walls. The beauty and privacy of this 4 bedroom, 3...

    Pool

    $479 to $642/night

  18. HOUSE
    Sands Of Kahana 315

    Sands Of Kahana 315

    Kahana, HI

    Take advantage of this opportunity to stay and indulge at a beachfront, luxury condominium with 100% ocean views from the living room, bedroom and lanai. Beautiful 2 bedroom, 2 bathroom, ocean front corner unit that provides stunning ocean views...

    Pool Hot Tub

    $478 to $531/night

  19. HOUSE
    Sands Of Kahana 234

    Sands Of Kahana 234

    Kahana, HI

    Enjoy views of Molokai and Lanai in one of nicest remodeled corner units in the Sands of Kahana. This air conditioned 2 bedroom 2 bath unit with two lanais is one of the most spacious waterfront units in Maui. From the front Lanai you’re so close...

    Pool Hot Tub

    $478 to $531/night

  20. HOUSE
    Sands Of Kahana 215

    Sands Of Kahana 215

    Kahana, HI

    A newly remodeled corner unit that is beautifully decorated and includes central air-conditioning. Relish and take in an amazing 180 degree view of the ocean stretching from Molokai to Lanai. With this condominium, you are steps from the sandy beach...

    Pool Hot Tub

    $478 to $531/night

  21. HOUSE
    Sands Of Kahana 272

    Sands Of Kahana 272

    Kahana, HI

    This luxurious two bedroom, two bathroom is one of the best-remodeled units at the Sands of Kahana. This ocean front corner unit on the seventh floor has stunning panoramic views of Molokai and Lanai. There is a king bed in the master bedroom, two...

    Pool Hot Tub

    $478 to $531/night

  22. CONDOMINIUM
    Menehune Shores Unit #218

    Menehune Shores Unit #218

    Maui, HI

    A note from the owner: Unit 218 has been completely remodeled in 2006. It is a spacious 3 bedroom condo and is great for larger families or couples traveling together. This ocean front condo has spectacular outer island views. The condo is well...

    Pool

    $477 to $533/night

  23. CONDOMINIUM
    Menehune Shores Unit #515

    Menehune Shores Unit #515

    Maui, HI

    This center unit, ideally situated, offers unsurpassed, panoramic views of the ocean and neighboring islands. Step onto the lanai, experience the soft sea breeze and rejoice in your arrival! Sit, relax, and watch paddlers in outriggers glide across...

    Pool

    $477 to $533/night

  24. VILLA
    Bay Villa 19G4 Gold Beach Front

    Bay Villa 19G4 Gold Beach Front

    Kapalua, HI

    This lovely ocean front beauty will make you feel like you are on top of the world! Too many upgrades to list. Beautiful new kitchen, granite, and brushed stainless; new furniture, 60" flat screen and central AC throughout. Inside, the king size...

    Pool

    $475 to $780/night

  25. HOUSE
    Sands of Kahana 366

    Sands of Kahana 366

    Kahana, HI

    Sit on your lanai in the morning with your beverage of choice and watch the sea turtles feeding on the reef. This unit was enriched with new furniture and central air conditioning in June 2015. When in season, watch the whales in the channel between...

    Pool Hot Tub

    $473 to $584/night

  26. HOUSE
    Sands Of Kahana 356

    Sands Of Kahana 356

    Kahana, HI

    Grasp the beautiful sunsets and rainbows from this very spacious three bedroom condominium This unit is one of the few 3 bedroom units at the Sands of Kahana that has air conditioning. Ocean views and vivid rainbow skies are visible from every...

    Pool Hot Tub

    $473 to $526/night

  27. CONDOMINIUM
    Whaler 859

    Whaler 859

    Lahaina, HI

    Spend your dream vacation on Maui at The Whaler on Kaanapali Beach.  Watch sunsets with colors so beautiful you will wish you were an artist to capture it on canvas.  Relax on the lanai with a cup of coffee or cocktail where you can see Mauka to...

    Pool Hot Tub
    FREE CANCELLATION

    $473 to $1,561/night

  28. 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...

    $471 to $683/night

  29. CONDOMINIUM
    Wailea Elua, #1601

    Wailea Elua, #1601

    Wailea, HI

    About this condo: Wailea Elua Village #1601 is an inviting ground floor one bedroom, two bath oceanfront condo plus sofa sleeper with a large wrap-around lanai: the perfect location for watching stunning Maui sunsets and enjoying the lush tropical...

    Pool Hot Tub

    $471 to $896/night

  30. CONDOMINIUM
    Whaler 206/208

    Whaler 206/208

    Lahaina, HI

    Spend your dream vacation on Maui at The Whaler on Kaanapali Beach.  Watch sunsets with colors so beautiful you will wish you were an artist to capture it on canvas.  Relax on the lanai with a cup of coffee or cocktail where you can see Mauka to...

    Pool Hot Tub
    FREE CANCELLATION

    $469 to $719/night