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. CONDOMINIUM
    328

    328

    Kihei, HI

    Tennis court, garden and Ocean View. This condo has a king bed in master bedroom, queen hide-a-bed in loft area. Living room has nice, comfortable, rattan furniture. Downstairs bedroom has two twin beds. Very modern, new kitchen offers beautiful...

    Pool
    FREE CANCELLATION

    $258 to $366/night

  2. CONDOMINIUM
    329

    329

    Kihei, HI

    Garden, tennis court, and slight Ocean View. This two bedroom unit offers a king bed in the master bedroom and two twins in the downstairs bedroom. Very large flat screen in the living room, and 32 inch flat screens in each bedroom. Tile installed...

    Pool
    FREE CANCELLATION

    $235 to $346/night

  3. CONDOMINIUM
    330

    330

    Kihei, HI

    The main floor bedroom has a queen bed, air conditioner, and ceiling fan. The main floor bathroom has a walk-in tiled shower. The upper master bedroom has a beautiful king bed, wall mounted cable TV, air conditioning, and ceiling fan. The adjoining...

    Pool
    FREE CANCELLATION

    $258 to $366/night

  4. CONDOMINIUM
    333

    333

    Kihei, HI

    Extremely nice two bedroom Maui vacation condo with a slight Ocean, garden and pool views. Very modern and clean. Refurbished and modernized in 2014 with beautiful solid bamboo flooring installed throughout, completely repainted and the purchase of...

    Pool
    FREE CANCELLATION

    $235 to $363/night

  5. CONDOMINIUM
    336

    336

    Kihei, HI

    This beautiful Maui Vacation rental unit 336, has a fantastic view of both Haleakala and the Ocean. Living room has nice bamboo & rattan island style furniture, including a rattan queen hide a bed. Upstairs master bedroom has queen size bed rattan...

    Pool
    FREE CANCELLATION

    $258 to $366/night

  6. CONDOMINIUM
    338

    338

    Kihei, HI

    This Colorful two bedroom Maui condo features ocean, garden, and pool views!Kitchen has been remodeled with tile floors, new cabinets and is equip with all of your cooking essentials while visiting. Unit has a full washer/dryer.Living room has...

    Pool
    FREE CANCELLATION

    $235 to $346/night

  7. CONDOMINIUM
    340

    340

    Kihei, HI

    Ocean and Garden Views. This two bedroom with loft has been remodeled with tile installed from the entrance to the lanai. Tile walk-in shower in downstairs bathroom. Both Bathrooms’ cabinets and counter tops have been recently remodeled. Master...

    Pool
    FREE CANCELLATION

    $258 to $366/night

  8. CONDOMINIUM
    341

    341

    Kihei, HI

    Fabulous Ocean and Garden View – one the BEST views on the property. New wood flooring in living room! King bed in master bedroom, loft has hide a bed. Downstairs bedroom has new furniture with queen bed. No hide a bed in living room. Kitchen &...

    Pool
    FREE CANCELLATION

    $258 to $366/night

  9. CONDOMINIUM
    342

    342

    Kihei, HI

    Good Ocean and Garden Views. This two bedroom offers king beds in both the master and downstairs bedroom. Great for couples wanting to vacation together. Kitchen remodeled with an elongated larger kitchen area, very nice wood cabinets and granite...

    Pool
    FREE CANCELLATION

    $235 to $346/night

  10. CONDOMINIUM
    344

    344

    Kihei, HI

    Bright, airy corner unit with breathtaking ocean views and relaxing breezes –Enjoy an early morning cup of coffee with the native birds while overlooking the lush green vegetation of the Hale Kamaole complex and the sapphire ocean beyond.Our Maui...

    Pool
    FREE CANCELLATION

    $258 to $366/night

  11. HOUSE
    3BD Estate Home at Puako Bay (10D)

    3BD Estate Home at Puako Bay (10D)

    Kamuela, HI

    This oceanfront Kohala Coast home with breathtaking coastline views offers the ultimate setting for a once-in-a-lifetime escape to paradise. Decorated in a tranquil, elegant island style, it features two master suites, central air conditioning, and...

    $1,077 to $3,365/night

  12. 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 $2,858/night

  13. VILLA
    3BD Hali'ipua Villa (108) at Four Seasons Resort Hualalai

    3BD Hali'ipua Villa (108) at Four Seasons Resort Hu...

    Kailua Kona, HI

    Among the newest additions to the exclusive Four Seasons Resort Hualalai, this ocean-view villa provides the perfect setting for a romantic getaway for two or a relaxing retreat to paradise for two couples. The villa boasts over 2,600 square feet of...

    Pool Hot Tub

    $1,056 to $3,293/night

  14. HOUSE
    3BD Ke Kailani (1C) at Mauna Lani

    3BD Ke Kailani (1C) at Mauna Lani

    Kamuela, HI

    This golf course-adjacent luxury home in a gated oceanfront community is the premier destination for a once-in-a-lifetime Hawaiian getaway. Offering over 3,000 square feet of island elegance with stunning views, a private pool and hot tub, and...

    Pool Hot Tub

    $1,182 to $3,546/night

  15. VILLA
    3BD Villas at Mauna Kea #39

    3BD Villas at Mauna Kea #39

    Kamuela, HI

    Relax in your own private pool and waterfall spa on a spacious deck while enjoying some of the best panoramic ocean, coastline, sunset, and Maui views in the entire Mauna Kea Resort. This exquisite luxury property, recently renovated and refreshed...

    Pool Hot Tub

    $1,220 to $3,856/night

  16. TOWNHOUSE
    3BR Pacific Paradise w/ Pool- 5 Minutes to Beach

    3BR Pacific Paradise w/ Pool- 5 Minutes to Beach

    Kamuela, HI

    Located in the gated Kulalani community, this spacious 3BR/2.5BA is your Pacific paradise. Interiors include updated floors and towering ceilings throughout. Your rental offers prime outdoor living space with a lanai, as well as access to a shared...

    Pool Hot Tub
    FREE CANCELLATION

    $203 to $677/night

  17. CONDOMINIUM
    3BR w/ Infinity Pool & Spa, Near Snorkeling Beach

    3BR w/ Infinity Pool & Spa, Near Snorkeling Beach

    Kailua Kona, HI

    Set right across the street from Kahalu’u Beach, this 3BR/2BA condo is within steps of one of the best beaches in Hawaii for surfing. Your prime locale is also close to Kona Town and Keauhou.Perched on the second-floor, this corner unit boasts...

    Pool Hot Tub
    FREE CANCELLATION

    $188 to $493/night

  18. CONDOMINIUM
    401 Punahoa Condominium

    401 Punahoa Condominium

    Kihei, HI

    1 bedroom Penthouse unit! Since all Punahoa Beach condos are individually owned, each is decorated in its own island-style and all have an ocean front lanai perfect for your own outdoor dining above the Pacific. "All Units Are Non-smoking"...

    $240 to $411/night

  19. CONDOMINIUM
    402 Punahoa Condominium

    402 Punahoa Condominium

    Kihei, HI

    1 bedroom Penthouse condo. Since all Punahoa Beach condos are individually owned, each is decorated in its own island-style and all have an ocean front lanai perfect for your own outdoor dining above the Pacific. "All Units Are Non-smoking"...

    $198 to $411/night

  20. HOUSE
    4BD Estate Home at Puako Bay (74)

    4BD Estate Home at Puako Bay (74)

    Kamuela, HI

    This elegant and timeless oceanfront estate is situated on the scenic shores of beautiful Puako Bay. One of Hawaii's last remaining peaceful little beach communities, Puako is steeped in history from abundant fishing to sugar cane farming and epic...

    $1,160 to $3,653/night

  21. VILLA
    4BD Villas at Mauna Kea #21

    4BD Villas at Mauna Kea #21

    Kamuela, HI

    Relax and luxuriate in this spacious and bright four bedroom luxury property, newly renovated, redesigned and brand new to the rental market! Professional and cheerful Fine Design interior decor echoes tones of the nearby Pacific. Unwind on the...

    Pool Hot Tub

    $1,703 to $4,290/night

  22. HOUSE
    7 C's Kona (Big Island)

    7 C's Kona (Big Island)

    Kailua Kona, HI

    ***Please note there is a 7 night minimum during the holidays. Christmas reservations must check out by 10AM on Dec. 27 and New Year's reservations can check in on Dec. 27 or after for a week. There is a 14 night minimum to book both Christmas and...

    Pool

    $482 to $720/night

  23. HOUSE
    A'ala Hale (2-Bedroom Home)

    A'ala Hale (2-Bedroom Home)

    Kaunakakai, HI

    Our calendars on line are current and if you send an inquiry we will automatically respond and send you to a page where you can book on line. A'ala Hale is a licensed Vacation Rental on Molokai  A'ala in Hawaiian means fragrance.  The entrance to...

    FREE CANCELLATION

    $225 to $281/night

  24. CONDOMINIUM
    A1-2 Bedroom Beachfront

    A1-2 Bedroom Beachfront

    Kihei, HI

    Maalaea Surf, Unit A1 is a conveniently located ground floor unit, direct beachfront, just steps away from the beach. This unit features an updated kitchen with convection oven, dishwasher and large refrigerator. The master bedroom has twin beds....

    Pool
    FREE CANCELLATION

    $416 to $664/night

  25. CONDOMINIUM
    A2-1 Bedroom Beachfront

    A2-1 Bedroom Beachfront

    Kihei, HI

    Ma'alaea Surf, Unit A2 is a conveniently located ground floor condo, just steps from the beach. This luxurious unit features a full kitchen and dining table. The master bedroom has a king sized bed. The large living room has expansive views and a...

    Pool
    FREE CANCELLATION

    $304 to $467/night

  26. CONDOMINIUM
    A3-1 Bedroom Beachfront

    A3-1 Bedroom Beachfront

    Kihei, HI

    Ma'alaea Surf, Unit A3 is a conveniently located ground floor condo, just steps from Sugar beach. This condo features a full kitchen and dining table. The master bedroom has a king sized bed. The large living room has expansive views and a flat...

    Pool
    FREE CANCELLATION

    $304 to $467/night

  27. CONDOMINIUM
    A5-1 Beachfront Loft Suite

    A5-1 Beachfront Loft Suite

    Kihei, HI

    Maalaea Surf, Unit A5 is a townhouse unit on the second floor which offers our guest total privacy and is located beach front on the property. This loft suite with 2 baths is very well furnished.Enjoy ocean front outdoor living on your spacious...

    FREE CANCELLATION

    $304 to $467/night

  28. CONDOMINIUM
    Aina Nalu #A109

    Aina Nalu #A109

    Lahaina, HI

    Spacious Two Bedroom, Garden View Condo in Malia Tower. This end unit is located on the first floor of Aina Nalu, and right in the heart of Lahaina Town. Just a couple minutes walk from Front Street, this pirvate Maui boutique condo vacation rental...

    Pool
    FREE CANCELLATION

    $209 to $433/night

  29. CONDOMINIUM
    Aina Nalu #I109

    Aina Nalu #I109

    Lahaina, HI

    Spacious Two Bedroom, Garden View Condo in the Eucalyptus Bldg. Located on the ground floor, it is an end unit located in the heart of Lahaina Town. This quiet unit is only a couple minutes walk to historic Front Street with convenient access to...

    Pool
    FREE CANCELLATION

    $215 to $580/night

  30. CONDOMINIUM
    Aina Nalu 1BR w/ On-Site Pools, Spa & Cabanas

    Aina Nalu 1BR w/ On-Site Pools, Spa & Cabanas

    Lahaina, HI

    Enveloped by serene gardens and detailed with stylish Asian-inspired decor, your 1BR condo combines all the comforts of home with the luxe amenities of a boutique resort. As part of the small, exclusive community at Aina Nalu, you’ll enjoy access...

    Pool Hot Tub
    FREE CANCELLATION

    $135 to $502/night