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
    Kamaole Sands #10-205

    Kamaole Sands #10-205

    Kihei, HI

    Kamaole Sands is the premiere property in South Kihei. 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 tropical...

    Pool Hot Tub
    FREE CANCELLATION

    $191 to $383/night

  2. CONDOMINIUM
    Kamaole Sands #3-402

    Kamaole Sands #3-402

    Kihei, HI

    Unit 3-402 is a top floor two bedroom, Two bath condo in Kamaole Sands is located in Preferred Building 3. It has Ocean, Garden and Pool views. Tile flooring from the entry through the living room to the lanai gives a fresh feeling. The living room...

    Pool Hot Tub
    FREE CANCELLATION

    $219 to $347/night

  3. CONDOMINIUM
    Kamaole Sands #7-304

    Kamaole Sands #7-304

    Kihei, HI

    Kamaole Sands is the premiere property in South Kihei. 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 tropical...

    Pool Hot Tub
    FREE CANCELLATION

    $173 to $365/night

  4. CONDOMINIUM
    Honua Kai Konea 743 2BD 2BA

    Honua Kai Konea 743 2BD 2BA

    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 accommodate...

    Pool Hot Tub
    FREE CANCELLATION

    $513 to $988/night

  5. HOUSE
    Kauhale Pilialoha

    Kauhale Pilialoha

    Kamuela, HI

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

    Pool Hot Tub

    $17,975 to $27,561/night

  6. CONDOMINIUM
    Royal Kahana 106

    Royal Kahana 106

    Lahaina, HI

    Get ready for the trip of a lifetime! Royal Kahana 106 is a fantastic unit with tons of space and amazing ocean views! Equipped with cable, wifi, washer/dryer and more. You'll have all the comforts of home! Be sure to take full advantage of the...

    Pool Hot Tub
    FREE CANCELLATION

    $190 to $498/night

  7. HOUSE
    Papaua Paradise 43

    Papaua Paradise 43

    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

    $2,161 to $3,125/night

  8. 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

    $173 to $273/night

  9. CONDOMINIUM
    Kamaole Sands #1-406

    Kamaole Sands #1-406

    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

    $219 to $406/night

  10. CONDOMINIUM
    Kamaole Sands #5-103

    Kamaole Sands #5-103

    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

    $115 to $360/night

  11. CONDOMINIUM
    Kamaole Sands #6-408

    Kamaole Sands #6-408

    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

    $232 to $347/night

  12. CONDOMINIUM
    Kamaole Sands #10-312

    Kamaole Sands #10-312

    Kihei, HI

    Kamaole Sands is the premiere property in South Kihei. 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 tropical...

    Pool Hot Tub
    FREE CANCELLATION

    $174 to $348/night

  13. 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

    $244 to $537/night

  14. 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 Hot Tub

    $134 to $222/night

  15. 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...

    Pool

    $314 to $661/night

  16. CONDOMINIUM
    Kamaole Sands #8-310

    Kamaole Sands #8-310

    Kihei, HI

    Kamaole Sands is the premiere property in South Kihei. 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 tropical...

    Pool Hot Tub
    FREE CANCELLATION

    $157 to $289/night

  17. CONDOMINIUM
    Kamaole Sands #10-111

    Kamaole Sands #10-111

    Kihei, HI

    Kamaole Sands is the premiere property in South Kihei. 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 tropical...

    Pool Hot Tub
    FREE CANCELLATION

    $157 to $377/night

  18. 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

  19. CONDOMINIUM
    Kuleana 713 1 Bdrm

    Kuleana 713 1 Bdrm

    Lahaina, HI

    Kuleana 713 is the ultimate island home away from home! Here, you can relax and enjoy the beautiful Pacific Ocean and stunning West Maui sunsets from your living room and private lanai! You will find yourself staring at the hues of the ocean blues...

    Pool
    FREE CANCELLATION

    $230 to $346/night

  20. CONDOMINIUM
    Kanaloa at Kona 3304

    Kanaloa at Kona 3304

    Kailua Kona, HI

    Just a stone's throw from Heeia Bay, this private and spacious condo offers the ideal oceanfront setting for your Kona Resort getaway. Complete with huge ocean views, lovely Hawaiian décor, central air conditioning, wireless internet, cable, and a...

    Pool Hot Tub

    $423 to $1,223/night

  21. CONDOMINIUM
    Royal Kahana 202

    Royal Kahana 202

    Lahaina, HI

    SUMMER Special Prices! Ocean front studio with ocean views and central A/C to enjoy those hot summer days. Ready for an unforgettable vacation to Maui? Or is it time to just getaway for the weekend? This studio with a beautiful ocean view is the...

    Pool Hot Tub
    FREE CANCELLATION

    $166 to $373/night