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
    Sandpiper 120A

    Sandpiper 120A

    Princeville, HI

    Sandpiper 120A: Enjoy a quiet retreat in this attractively decorated, ground floor condo in Sandpiper Village. This Kauai vacation rental has a fully equipped kitchen for home cooked meals, a large tiled lanai to enjoy a cool drink amidst tropical...

    Pool Hot Tub
    FREE CANCELLATION

    $159 to $182/night

  2. CONDOMINIUM
    Palms at Wailea #1101

    Palms at Wailea #1101

    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

    $289 to $493/night

  3. CONDOMINIUM
    Maui Kamaole #B-206

    Maui Kamaole #B-206

    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

    $225 to $464/night

  4. CONDOMINIUM
    Kona Makai 3-302

    Kona Makai 3-302

    Kailua Kona, HI

    Kona Makai 3-302 is a gorgeous top floor, spacious condo that's been recently updated! Great showmanship of pride in property. Nice ocean view. Loft! Essentially a 2 bedroom for the price of 1!The Kona Makai is a beautiful sunny highly sought after...

    Pool Hot Tub
    FREE CANCELLATION

    $465 to $485/night

  5. CONDOMINIUM
    Maui Kamaole #I-109

    Maui Kamaole #I-109

    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

    $174 to $347/night

  6. 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

    $261 to $587/night

  7. 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

  8. CONDOMINIUM
    Maui Kamaole #J-219

    Maui Kamaole #J-219

    Kihei, HI

    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 and tennis...

    Pool Hot Tub
    FREE CANCELLATION

    $324 to $486/night

  9. CONDOMINIUM
    Wai'ula'ula A102

    Wai'ula'ula A102

    Kamuela, HI

    Your visit to our vacation home will capture the essence of Hawaii. We are located along the Big Island’s exclusive golden Kohala Coast. Play golf on the emerald fairways of the renowned Mauna Kea Resort courses. Experience Kauna’oa and Hapuna,...

    Pool Hot Tub
    FREE CANCELLATION

    $618 to $1,236/night

  10. CONDOMINIUM
    Maui Kamaole #K-108

    Maui Kamaole #K-108

    Kihei, HI

    Kamaole Beach #3 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 and tennis...

    Pool Hot Tub
    FREE CANCELLATION

    $204 to $413/night

  11. CONDOMINIUM
    Ke Nani Kai Condo 260

    Ke Nani Kai Condo 260

    Maunaloa, HI

    This bright and cheery 1 bedroom, 1 bath garden view condo is new to our rental pool and located on Molokai's West End. The condo has a brand new King size bed. Living room is equipped with couch, two chairs and flat screen TV.  This condo is...

    Pool Hot Tub
    FREE CANCELLATION

    $124 to $163/night

  12. CONDOMINIUM
    Maui Kamaole #A-203

    Maui Kamaole #A-203

    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 $458/night

  13. 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

  14. CONDOMINIUM
    Kamaole Sands #9-207

    Kamaole Sands #9-207

    Kihei, HI

    We welcome you to this beautiful condo at the Kamaole Sands #9-207 (second closest bldg to the BEACH) – Design by Jillian Harris (Designer from the famous Extreme Home Makeover Home Edition television series)Same day bookings (meaning arrival is...

    Pool Hot Tub
    FREE CANCELLATION

    $150 to $273/night

  15. CONDOMINIUM
    Palms at Wailea #603

    Palms at Wailea #603

    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 stretch of beach. The Palms at Wailea is a gorgeous property; lush with tropical landscaping. There...

    Pool Hot Tub
    FREE CANCELLATION

    $312 to $644/night

  16. CONDOMINIUM
    Kamaole Sands #7-408

    Kamaole Sands #7-408

    Kihei, HI

    Kamaole Sands is the premiere property in South Kihei. Kamaole Sands is located across the street from Kamaole Beach III. Whale watch, swim, snorkel, walk miles on the beach and watch the most amazing sunsets imaginable. There are 15 acres of lush...

    Pool Hot Tub
    FREE CANCELLATION

    $299 to $617/night

  17. CONDOMINIUM
    Palms at Wailea #1105

    Palms at Wailea #1105

    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

    $347 to $521/night

  18. CONDOMINIUM
    Palms at Wailea #1507

    Palms at Wailea #1507

    Wailea, HI

    Unit 1507 is a spacious, beautiful condo with a gorgeous ocean view located in the desirable inner courtyard just a short stroll to the picturesque pool, all without climbing steep stairs. Fully air conditioned with a 3 zone split system, this condo...

    Pool Hot Tub
    FREE CANCELLATION

    $405 to $579/night

  19. 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

  20. CONDOMINIUM
    Maui Kamaole #G-101

    Maui Kamaole #G-101

    Kihei, HI

    Kamaole Beach Park 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 and...

    Pool Hot Tub
    FREE CANCELLATION

    $197 to $412/night

  21. CONDOMINIUM
    Maui Kamaole #J-120

    Maui Kamaole #J-120

    Kihei, HI

    Kamaole Beach #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

    $191 to $347/night