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
    Kauhale Pilialoha

    Kauhale Pilialoha

    Kamuela, HI

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

    Pool Hot Tub

    $18953 to $29061/night

  2. HOUSE
    Papaua Estate

    Papaua Estate

    Lahaina, HI

    APPROVED MAUI SHORT TERM RENTAL HOUSE #STWM 2104/0003. You and your family and friends will love your stay here for a vacation filled with Aloha! If you are looking for location, luxury and Hawaiian life style, you have found it. Perhaps the most...

    Hot Tub
    FREE CANCELLATION

    $1869 to $2874/night

  3. CONDOMINIUM
    Royal Kuhio 3802 Condo

    Royal Kuhio 3802 Condo

    Honolulu, HI

    Free Onsite Parking Included - Two levels, 3 Bedrooms & Bathrooms Three bedroom / Three Baths / Washer & Dryer / Full Kitchen / with Dishwasher / Free Parking. This condo has it all in the heart of waikiki! TOP FLOOR Penthouse on the 38th floor of...

    Pool
    FREE CANCELLATION

    $613 to $968/night

  4. CONDOMINIUM
    Honua Kai Konea 743

    Honua Kai Konea 743

    Lahaina, HI

    This rarely-available top-floor penthouse condominium is the ultimate in luxury living.  Konea 743 boasts amazing ocean views of Maui and the surrounding islands. This spacious suite includes two bedroom, two full baths and a sofa-bed to...

    Pool Hot Tub
    FREE CANCELLATION

    $577 to $944/night

  5. CONDOMINIUM
    Kaanapali Condominium 101

    Kaanapali Condominium 101

    Lahaina, HI

    This premium oceanfront Two Bedroom, Two Bath condo is conveniently located on the ground level. Master Bedroom has a King Bed with a private bathroom. Second Bedroom has a queen bed; and the living room has a queen sofa bed for the extra guests....

    Pool Hot Tub

    $516 to $620/night

  6. TOWNHOUSE
    Poipu Crater

    Poipu Crater

    Koloa, HI

    Tucked away in the heart of an extinct volcano, Poipu Crater Resort offers lush tropical gardens, privacy and comfort. Perched on the upper rim of the crater, perfectly situated to enjoy sunny mornings and cool tradewinds in the afternoon. This unit...

    Pool Hot Tub

    $374 to $814/night

  7. CONDOMINIUM
    1 Bedroom Corner Oceanfront 808

    1 Bedroom Corner Oceanfront 808

    Lahaina, HI

    Maui Kai unit #808 is a one Bedroom Corner - King bed; Flat screen TV; queen sofa sleeper; TV in bedroom. Beautiful one bedroom corner condo. The beach front location with its view of the ocean from our eighth floor lanai is very much like a cruise...

    Pool Hot Tub

    $372 to $444/night

  8. CONDOMINIUM
    Holualoa Bay Villas 102

    Holualoa Bay Villas 102

    Kailua Kona, HI

    Enjoy your Hawaiian vacation at this almost oceanfront complex. This fully equipped over 1200 square foot, A/C equipped 2 bedroom, 2 bath condo with oversized lanai is located in Holualoa Bay Villas. The master bedroom has a king size bed , the...

    Pool

    $368 to $550/night

  9. CONDOMINIUM
    1 Bedroom Corner Oceanfront 308

    1 Bedroom Corner Oceanfront 308

    Kaanapali, HI

    One Bedroom Corner - King Bed, NO sofa bed, Flat screen TV - hardwood floors; Livingroom is tiled in white. This condo will accommodate a maximum of two people. The unit has a fabulous panoramic view of the beach below and the neighboring islands....

    Pool Hot Tub

    $351 to $434/night

  10. CONDOMINIUM
    1 Bedroom Oceanfront 404

    1 Bedroom Oceanfront 404

    Kaanapali, HI

    One Bedroom - Flat screen TV ; King bed, 2 Twins on lanai. (No Sofa Bed) This unit located on the Kaanapali Beach less than one mile from the Kapalua West Maui Airport. This unit features an heated outdoor pool, a jacuzzi and free Wi-Fi. It...

    Pool

    $341 to $413/night

  11. CONDOMINIUM
    Royal Kuhio 3607 Condo

    Royal Kuhio 3607 Condo

    Honolulu, HI

    Spacious Bright And Modern 36th Floor Penthouse Suite In Central Waikiki Every detail has been carefully thought out during the full renovation of this 36th floor condominium. It turned out perfectly! The gorgeous fully equipped open plan kitchen,...

    Pool
    FREE CANCELLATION

    $326 to $557/night

  12. CONDOMINIUM
    Royal Kuhio 3501 Condo

    Royal Kuhio 3501 Condo

    Honolulu, HI

    Renovated / 2 Bedroom / 2bath / Full Kitchen/Washer&Dryer/Free Parking/Free Wifi Super Location, Ideal for Families & Awesome 2019 Rates! Free Onsite Parking Included This condo is a a perfect place for your family to enjoy all the comforts of...

    Pool
    FREE CANCELLATION

    $315 to $473/night

  13. CONDOMINIUM
    Kona Makai 6201

    Kona Makai 6201

    Kailua Kona, HI

    Kona Makai is an oceanfront condominium complex of about 100 one and two bedroom units located one mile from the beautiful town of Kailua-Kona. This absolute direct oceanfront unit has waves breaking right onto the lava below the lanai. This fully...

    Pool

    $298 to $409/night

  14. CONDOMINIUM
    Kona Makai 6301

    Kona Makai 6301

    Kailua Kona, HI

    One of the best ocean front locations along the Kona Coast; top level corner unit with panoramic ocean views. These oceanfront units are the most prized units in the complex. Completely remodeled 2 bedroom, 2 bath condo with an amazing wrap around...

    Pool

    $286 to $409/night

  15. CONDOMINIUM
    Maui Kaanapali Villas 501

    Maui Kaanapali Villas 501

    Lahaina, HI

    This 1 bedroom1 bath condo (provides everything you need for your vacation in paradise. Newly listed and fully furnished, this condo is a great deal. Equipped with air conditioning, wifi, a fully stocked kitchen and stainless steel grills outside,...

    Pool Hot Tub
    FREE CANCELLATION

    $211 to $563/night

  16. CONDOMINIUM
    Kamaole Sands #5-310

    Kamaole Sands #5-310

    Kihei, HI

    Kamaole Sands is the premiere property in South Kihei. It is located across the street from Kamaole Beach III. Have a picnic, whale watch, swim, snorkel, stand-up paddle board, walk miles on the beach and watch the most amazing sunsets imaginable....

    Pool Hot Tub
    FREE CANCELLATION

    $197 to $365/night

  17. CONDOMINIUM
    Kuleana 321

    Kuleana 321

    Lahaina, HI

    Beautifully landscaped grounds on the water. Hear the waves rolling in while you enjoy this upgraded unit with granite counter tops in the kitchen and bath and tile floors throughout. Cable TV in living room and bedroom.Master Bedroom has a king bed...

    Pool
    FREE CANCELLATION

    $174 to $638/night

  18. CONDOMINIUM
    Kanaloa 202 (2-Bedroom Condo)

    Kanaloa 202 (2-Bedroom Condo)

    Keauhou, HI

    Historic and Charming Keauhou Bay is just steps away from Kanaloa at Kona. The premier resort in Keauhou Resort area. The location is perfect. Close to supermarket, restaurants, shopping, golf, beaches, sport fishing, and other vacation activities....

    Pool

    $169 to $230/night

  19. CONDOMINIUM
    Kona Makai 2303

    Kona Makai 2303

    Kailua Kona, HI

    Unit is fully redecorated and updated in Hawaiian decor to enhance your vacation. This beautifully maintained complex is very quaint, peaceful and private in a gated community. The unit is on the top floor and you can hear the ocean waves from all...

    Pool

    $163 to $251/night

  20. CONDOMINIUM
    Kuleana 310

    Kuleana 310

    Lahaina, HI

    Enjoy Spectacular views as you relax on the lanai in this newly updated unit. Beautifully landscaped grounds on the water. Hear the waves rolling in while you enjoy this upgraded unit with granite counter tops in the kitchen and bath and tile floors...

    Pool
    FREE CANCELLATION

    $161 to $331/night

  21. CONDOMINIUM
    Royal Kahana 104

    Royal Kahana 104

    Lahaina, HI

    Only steps from the ocean on an incredible ocean front resort on the west Maui coast. This renovated studio with AC, Washer/Dryer, 1 King and 1 Twin bed comfortably sleeping three. Free wifi and parking, on resort fitness room, concierge desk, pool...

    Pool
    FREE CANCELLATION

    $149 to $336/night

  22. CONDOMINIUM
    Kona Makai 4104

    Kona Makai 4104

    Kailua Kona, HI

    Kona Makai is an oceanfront condominium complex of about 100 one and two bedroom units located one mile from the beautiful town of Kailua-Kona. This completely remodeled condo is open, airy and modern with amazing ocean views. Amenities include an...

    Pool

    $140 to $222/night