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
    B-109: Hale Nani Ikena Kai Ko Olina Beach Villa

    B-109: Hale Nani Ikena Kai Ko Olina Beach Villa

    Kapolei, HI

    The Hale Nani Ikena Kai beach villa at Ko Olina offers exactly what its name suggests; a home with a “Beautiful Ocean View”. Spectacular direct whitewater ocean and beach views will be what greets you at this upscale, luxurious ground floor...

    Pool Hot Tub

    $682 to $2,016/night

  2. CONDOMINIUM
    Wailea Elua #2303

    Wailea Elua #2303

    Kihei, HI

    Wailea Elua is the premier ocean front property in Wailea. A gated property situated right on picturesque 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...

    Pool Hot Tub
    FREE CANCELLATION

    $609 to $1,073/night

  3. CONDOMINIUM
    New! Updated! Modern, Maui Beachfront with Central A/C

    New! Updated! Modern, Maui Beachfront with Central A/C

    Lahaina, HI

    Most frequently asked questions re: payments, cancellations, our home, and the area, can be answered in the property info, guest reviews, and pictures, below. We kindly ask that you read all of these details, as we offer a lot of amenities that...

    Pool Hot Tub
    FREE CANCELLATION

    $561 to $731/night

  4. CONDOMINIUM
    Hale Ili Ili #D

    Hale Ili Ili #D

    Kihei, HI

    Hale Ili Ili is an oceanfront gated four-plex in Kihei Maui Hawaii. The property lends itself to a very private and relaxed atmosphere with breathtaking sunsets, sounds of the ocean and rustling palm trees. Many whales, turtles, dolphins and rays...

    Pool Hot Tub
    FREE CANCELLATION

    $556 to $927/night

  5. 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

  6. CONDOMINIUM
    Waterfall House

    Waterfall House

    Kailua-Kona, HI

    Beautiful high end home with views directly to the ocean below. Have your own private retreat within a secure, gated community in an expansive open home. Stay in perhaps one of the most unique homes in Hawaii where it rains into the house, filling...

    Pool Hot Tub

    $437 to $1,717/night

  7. CONDOMINIUM
    Honua Kai Konea 312

    Honua Kai Konea 312

    Kaanapali, HI

    UPGRADED 2 PLUS ONE!!! Two Bedroom One Bath! West Maui Mountain & Waterfall Views! 915 sq ft! Just renovated with new DESIGNER FURNISHINGS, new flooring and a brand new Queen Bed in the Private Den! New Flat screen 4K TV's with built in Netflix,...

    Pool Hot Tub
    FREE CANCELLATION

    $420 to $1,211/night

  8. CONDOMINIUM
    Honua Kai Konea 606

    Honua Kai Konea 606

    Kaanapali, HI

    NOTE: As of 2/6/18 construction of 72 Townhomes has commenced behind the Konea building at Honua kai. There may be noise and dust on work days during construction hours from 8am to 5pm. Konea 606 is a large 945 square foot (plus 180 sq ft Lanai)...

    Pool Hot Tub
    FREE CANCELLATION

    $378 to $1,211/night

  9. CONDOMINIUM
    Honua Kai #316

    Honua Kai #316

    Lahaina, HI

    This couples and family friendly resort is located on the exquisite Kaanapali Beach!  Enjoy  extraordinary dining, shopping, and top of the line amenities at our 4 diamond property. The resort has 3 large pools, 5 hot tubs and a spa! The FORMAL...

    Pool Hot Tub
    FREE CANCELLATION

    $359 to $474/night

  10. CONDOMINIUM
    Maui Hill #I-99

    Maui Hill #I-99

    Kihei, HI

    Maui Hill Resort is located minutes from the premier resort area of Wailea. Keawakapu and Kamaole beaches are within walking distance. The resort features a swimming pool, barbecue grills, tennis, a putting green, and shuffleboard. Enjoy free...

    Pool Hot Tub
    FREE CANCELLATION

    $347 to $695/night

  11. CONDOMINIUM
    Palms at Wailea #1507

    Palms at Wailea #1507

    Wailea, HI

    Unit 1507 is a beautifully renovated condo with a gorgeous ocean view. An end unit, located in the complex’s prime, inner courtyard; just a short stroll to the pool - all without climbing steep stairs. Unit 1507 features an impressive outdoor...

    Pool Hot Tub
    FREE CANCELLATION

    $324 to $521/night

  12. CONDOMINIUM
    Honua Kai Konea 314

    Honua Kai Konea 314

    Kaanapali, HI

    GREAT PRIVATE ONE BEDROOM!! NOTE: As of 2/6/18 construction of 72 Townhomes has commenced behind the Konea building at Honua kai. There may be noise and dust on work days during construction hours from 8am to 5pm. Best one bedroom plan available...

    Pool Hot Tub
    FREE CANCELLATION

    $315 to $1,003/night

  13. CONDOMINIUM
    Maui Kamaole #F-207

    Maui Kamaole #F-207

    Kihei, HI

    Kamaole Beach #3 is just across from the upscale Maui Kamaole. This property features lush tropical landscaping, two gorgeous pool areas with hot tubs and water features. There are gas grills peppered throughout the property and tennis courts...

    Pool Hot Tub
    FREE CANCELLATION

    $302 to $418/night

  14. CONDOMINIUM
    Hali'i Kai 19G Condominium

    Hali'i Kai 19G Condominium

    Waikoloa, HI

    Come and take a vacation in our new professionally designed townhome with everything you need to make your vacation the most memorable.. Hali'i Kai is located in the most famous Waikoloa Beach Resort nestled on the point with outstanding ocean views...

    Pool Hot Tub
    FREE CANCELLATION

    $295 to $741/night

  15. CONDOMINIUM
    Maui Kamaole #A-202

    Maui Kamaole #A-202

    Kihei, HI

    Unit A-202 has been completely renovated. This renovation includes: the kitchen cabinets, granite countertops, new kitchen appliances; lighting, carpeting and new tile everywhere; redesigned bathrooms with walk-in showers, new bathroom cabinets and...

    Pool Hot Tub
    FREE CANCELLATION

    $289 to $405/night

  16. CONDOMINIUM
    Honua Kai 224

    Honua Kai 224

    Lahaina, HI

    This luxury Honua Kai one bedroom located in the 'Konea Tower' features everything you need to make your Hawaiian vacation truly enjoyable! We provide you with those extra amenities that make a difference, including comfortable beach chairs, beach...

    Pool Hot Tub
    FREE CANCELLATION

    $270 to $401/night

  17. CABIN
    1075 Nanihoku Pl Cabin

    1075 Nanihoku Pl Cabin

    Haiku, HI

    Located in the lush rainforest in the upcountry of Haiku, this unique and luxurious 2BR Asian-style bamboo bungalow includes a private hot tub and a shared freshwater pool. Boasting a custom eco-design, this rental features 1,800 sq ft of covered...

    Pool Hot Tub
    FREE CANCELLATION

    $268 to $712/night

  18. CONDOMINIUM
    Palms at Wailea #1209

    Palms at Wailea #1209

    Wailea, HI

    The fabulous Keawakapu Beach is just a short 10 minute stroll from the Palms at Wailea. This beach is world famous for its great snorkeling and long walking beach. The Palms at Wailea is a gorgeous property; lush with tropical landscaping. There is...

    Pool Hot Tub
    FREE CANCELLATION

    $267 to $319/night

  19. CONDOMINIUM
    Honua Kai 322

    Honua Kai 322

    Lahaina, HI

    This luxury Honua Kai one bedroom located in the 'Konea Tower' features everything you need to make your Hawaiian vacation truly enjoyable! We provide you with those extra amenities that make a difference, including comfortable beach chairs, beach...

    Pool Hot Tub
    FREE CANCELLATION

    $263 to $370/night

  20. CONDOMINIUM
    Grand Champions #48

    Grand Champions #48

    Wailea, HI

    The nearby Ulua and Mokapu Beaches are a quick drive down the hill from the The Grand Champions Villas in Wailea. The complex is surrounded by lovely tropical gardens. It is located in the exclusive Wailea Resort. The complex offers two swimming...

    Pool Hot Tub
    FREE CANCELLATION

    $255 to $400/night

  21. CONDOMINIUM
    Honua Kai 506

    Honua Kai 506

    Lahaina, HI

    HONUA KAI RESORT AND SPA SUITE 506 Welcomes you... This spacious one bedroom one bath PLUS DEN can accommodate up to six (6) guests … Included in our fabulous price are many owner-supplied extras such as: • Beach chairs (2) • Beach...

    Pool Hot Tub
    FREE CANCELLATION

    $251 to $608/night

  22. CONDOMINIUM
    Grand Champions #51

    Grand Champions #51

    Wailea, HI

    The nearby Ulua and Mokapu Beaches are a quick drive down the hill from the Grand Champions Villas in Wailea. The complex is surrounded by lovely tropical gardens. It is located in the exclusive Wailea Resort. The complex offers two swimming pools,...

    Pool Hot Tub
    FREE CANCELLATION

    $244 to $358/night

  23. CONDOMINIUM
    Palms at Wailea #609

    Palms at Wailea #609

    Wailea, HI

    The fabulous Keawakapu Beach is just a short 10 minute stroll from the Palms at Wailea. This beach is world famous for its great snorkeling and long walking beach. This 1 bedroom / 2 bath unit offers privacy and comfort with over 1000 square feet of...

    Pool Hot Tub
    FREE CANCELLATION

    $232 to $376/night

  24. CONDOMINIUM
    Maui Kamaole #I-215

    Maui Kamaole #I-215

    Kihei, HI

    Kamaole Beach Park #3 is just across from the upscale Maui Kamaole. This property features lush tropical landscaping and beautiful ocean views, two gorgeous pool areas with hot tubs and water features. There are gas grills peppered throughout the...

    Pool Hot Tub
    FREE CANCELLATION

    $231 to $377/night

  25. CONDOMINIUM
    Grand Champions #86

    Grand Champions #86

    Kihei, HI

    The nearby Ulua and Mokapu Beaches are a quick drive down the hill from the The Grand Champions Villas in Wailea. The complex is surrounded by lovely tropical gardens. It is located in the exclusive Wailea Resort. The complex offers two swimming...

    Pool Hot Tub
    FREE CANCELLATION

    $203 to $313/night

  26. CONDOMINIUM
    Papakea E-306

    Papakea E-306

    Lahaina, HI

    One of the nicest ocean view units in Papakea. Highly upgraded with all the amenities you expect. Living room Air Conditioning, designer granite, Bosch dishwasher, GE washer/dryer, flat surface range/oven, LCD flat screen TV's in both living room...

    Pool Hot Tub

    $203 to $314/night

  27. CONDOMINIUM
    Maui Kamaole #L-105

    Maui Kamaole #L-105

    Kihei, HI

    The famous Kamaole Beach III is just across the street from the upscale Maui Kamaole. This property features lush tropical landscaping, two gorgeous pool areas with hot tubs and water features. There are gas grills peppered throughout the property...

    Pool Hot Tub
    FREE CANCELLATION

    $203 to $406/night

  28. CONDOMINIUM
    Maui Kamaole #A-102

    Maui Kamaole #A-102

    Kihei, HI

    Kamaole Beach #3 is just across from the upscale Maui Kamaole. This property features lush tropical landscaping, two gorgeous pool areas with hot tubs and water features. There are gas grills peppered throughout the property and tennis courts...

    Pool Hot Tub
    FREE CANCELLATION

    $186 to $360/night

  29. CONDOMINIUM
    Luana Kai #A-205

    Luana Kai #A-205

    Kihei, HI

    Luana Kai is a large oceanfront complex in Kihei. It is centrally located to shops, activities, and restaurants. It features a large oceanfront pool, hot tub, shuffleboard, and gas grills for your use. There is an expansive lawn between the...

    Pool Hot Tub
    FREE CANCELLATION

    $180 to $342/night

  30. CONDOMINIUM
    Pacific Shores #A-303

    Pacific Shores #A-303

    Kihei, HI

    Located in in the Heart of South Kihei, the Pacific Shores is central to the best activities South Maui has to offer. Just a quick stroll in any direction will take you to nearby shopping, popular restaurants, and world famous beaches. Take...

    Pool Hot Tub
    FREE CANCELLATION

    $173 to $300/night