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

    $18,953 to $29,061/night

  2. VILLA
    Hale Waiulu #150470

    Hale Waiulu #150470

    Kailua Kona, HI

    Our well-appointed home has everything you could possible need. Fresh, home grown mango, guava and finger lime for our guests to feast on . Enjoy the relaxing sound of the cascading rush of your private pool's waterfall. The lush golf green views of...

    Pool Hot Tub

    $2,022 to $6,318/night

  3. HOUSE
    Hale Keanu- Waimea Home

    Hale Keanu- Waimea Home

    Waimea, HI

    Sweeping Ocean Views & Separate Ohana. Rare 4 bedroom - Wai'ula'ula at Mauna Kea Step into a dream at an exceptional four-bedroom ocean-view rental at Wai'ula'ula within the Mauna Kea Resort. At this single level brand-new home, you will find a...

    Pool Hot Tub

    $1,390 to $3,032/night

  4. HOUSE
    Alii Point

    Alii Point

    Kailua Kona, HI

    Experience a vacation of a lifetime in this massive oceanfront custom home tucked away in an exclusive and quiet gated community along the Kona coast. A pond with a waterfall, filled with flowers welcomes you upon entering this beautiful custom...

    Pool Hot Tub

    $1,150 to $1,605/night

  5. CONDOMINIUM
    Ocean View Beachfront Beach Level 4-Bed Turtle Bay Villa 104

    Ocean View Beachfront Beach Level 4-Bed Turtle Bay Villa...

    Kahuku, HI

    Ocean View & Beachfront Beach Level 4-Bedroom (2 Masters) Turtle Bay Villa 104 At Ocean Villa 104 you have dramatic ocean views from just about everywhere! My 4-bedroom villa is located on the beach level so you can walk right out your living room...

    Pool Hot Tub

    $1,037 to $3,517/night

  6. CONDOMINIUM
    Hale Lelea Ko Olina Beach Villa (B310)

    Hale Lelea Ko Olina Beach Villa (B310)

    Kapolei, HI

    This vacation home has been registered as a Transient Accommodation with the State of Hawaii – HAWAII TAX ID TA-083-717-4272-01 #groundfloor #view #oceanview #whitewater #group  #wedding #KoOlina #resort #luxury #villa #Kapolei #Oahu #Hawaii...

    Pool Hot Tub

    $856 to $2,016/night

  7. CONDOMINIUM
    Villa 316

    Villa 316

    Kahuku, HI

    This penthouse villa is located in the most desirable location in the complex, on the third level just steps from the sandy beach with panoramic ocean views and a private serene lanai. This villa is only about 20 yards from the ocean! Photographs...

    Pool Hot Tub

    $808 to $2,609/night

  8. VILLA
    Villa Cinco Resort at Kona Plantation Estates

    Villa Cinco Resort at Kona Plantation Estates

    Kailua Kona, HI

    This beautiful custom home, built in 2007, boasts 5 buildings totaling interior 3,829 sq. feet; including main house, and a private master suite situated at each of 4 corners. Main house has a private study converted to bedroom with a sink, a half...

    Pool Hot Tub
    FREE CANCELLATION

    $759 to $1,540/night

  9. CONDOMINIUM
    Direct Ocean & Beach View 2nd Level 3Bd Villa 203

    Direct Ocean & Beach View 2nd Level 3Bd Villa 203

    Kahuku, HI

    Direct Ocean & Beach View 2nd Level 3Bd (or 4bd w/adjoin studio) Villa 203This villa is located on the second floor in the most desirable location in the complex, just 20 yards from the sandy beach with direct ocean and beach views from just about...

    Pool Hot Tub

    $756 to $2,478/night

  10. CONDOMINIUM
    Beach Level 3 Bed Direct Ocean Views Villa 106 Turtle Bay

    Beach Level 3 Bed Direct Ocean Views Villa 106 Turtle Ba...

    Kahuku, HI

    This beach level villa has beach and ocean views and is located just steps from the sandy beach with a lawn area before the sand starts. The Ocean Villas pool, jaccuzzi and BBQs are all just 20 yards to your right! It has a serene lanai where you...

    Pool Hot Tub

    $756 to $2,478/night

  11. CONDOMINIUM
    Ko Olina Beach Villa (O121)

    Ko Olina Beach Villa (O121)

    Kapolei, HI

    Celebrities want privacy and quick exit routes, but so does everyone else! You deserve this one-of-a-kind Ko Olina Beach Villa, unlike any other located within the resort. It boasts over 1600 sq.ft of living space, 3 ground floor private lanais, no...

    Pool Hot Tub

    $682 to $1,668/night

  12. CONDOMINIUM
    Ocean and Pool View Beachfront 2nd Floor Villa 208

    Ocean and Pool View Beachfront 2nd Floor Villa 208

    Kahuku, HI

    This villa is located on the second level with Spectacular Ocean and pool views from the lanai, the living room, the dining room, and the master bedroom! This villa is just 35 yards from the sandy beach and 10 yards to the Pool and BBQs. It has...

    Pool Hot Tub

    $677 to $2,217/night

  13. CONDOMINIUM
    Direct Ocean View Beach Level 3Bed Villa 103

    Direct Ocean View Beach Level 3Bed Villa 103

    Kahuku, HI

    Direct Ocean View Beach Level 3Bed (or 4Bed w/Adjoin Studio) Villa 103 This villa is in the most desirable location in the complex. It has just 20 yards of lawn before the sandy beach and the pool and BBQs are just 50 yards to the right!  It has...

    Pool Hot Tub

    $677 to $2,609/night

  14. CONDOMINIUM
    Ocean & Pool View Beachfront 3rd Floor Penthouse Villa 309

    Ocean & Pool View Beachfront 3rd Floor Penthouse Vil...

    Kahuku, HI

    Ocean & Pool View Beachfront 3rd Floor (top) Penthouse Villa 309 This penthouse villa is located on the third level just steps from the sandy beach with beautiful ocean and pool views from the lanai, living room and master bedroom. It has a serene...

    Pool Hot Tub

    $651 to $2,217/night

  15. CONDOMINIUM
    Ocean View and Beachfront Beach Level 3 Bedroom Villa 110

    Ocean View and Beachfront Beach Level 3 Bedroom Villa 11...

    Kahuku, HI

    This beach level villa is located just steps from the pool, BBQs, and the sandy beach! It has partial ocean views from the dining room, kitchen, living room, master bedroom and lanai. It has a serene lanai with Tiki torches lighting the grounds at...

    Pool Hot Tub

    $651 to $2,217/night

  16. CONDOMINIUM
    Honua Kai Konea 301

    Honua Kai Konea 301

    Kaanapali, HI

    One of the MOST DESIRABLE 2 bedroom 2.5 bath condo in the entire complex. Konea 301 is one of only 5 Two Bedroom Ali'I Suites with Direct Ocean Views and private Outdoor Kitchens. At 1620 sq ft with a HUGE 415 sq ft lanai this gorgeous home has 180...

    Pool Hot Tub
    FREE CANCELLATION

    $645 to $2,287/night

  17. CONDOMINIUM
    Mahana 501

    Mahana 501

    LAHAINA, HI

    This brand-new beautiful new 5th floor listing at the Mahana at Kaanapali boasts gorgeous views of both the tranquil blue Pacific Ocean AND the lush West Maui Mountains. This property is extremely close to the water, you can literally sit in the 5th...

    Pool Hot Tub
    FREE CANCELLATION

    $583 to $1,861/night

  18. 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 $950/night

  19. CONDOMINIUM
    Ocean & Garden View Beach Level 3-Bed Villa 115

    Ocean & Garden View Beach Level 3-Bed Villa 115

    Kahuku, HI

    Beachfront Ocean & Garden View Beach Level by Pool & BBQs 3-Bed Villa 115 This beach level villa is just 20 yards from the sandy beach and 10 yards from the pool and BBQs! It has all new, top of the line, furniture including a sleeper sofa with a...

    Pool Hot Tub

    $573 to $2,348/night

  20. CONDOMINIUM
    Hale Ko Olina Beach Villa Penthouse (O-1602)

    Hale Ko Olina Beach Villa Penthouse (O-1602)

    Kapolei, HI

    Enjoy panoramic ocean views from this incredible 16th floor, 3 bedroom, 2.5 bathroom penthouse at the Beach Villas at Ko'Olina! This one of a kind villa features two lanais, a gourmet kitchen with Sub-Zero fridge, Wolf oven & glass top range....

    Pool Hot Tub

    $566 to $1,668/night

  21. 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

  22. HOUSE
    Aniani Hale

    Aniani Hale

    Kailua Kona, HI

    Known as ‘Aniani Hale,’ or Glass House, this stunning 4BR/4.5BA home is situated just above the heart of Kailua-Kona. Elevated 700 feet above sea level, your beautiful island getaway boasts refreshing trade winds from the west and mountain...

    Pool Hot Tub
    FREE CANCELLATION

    $534 to $986/night

  23. CONDOMINIUM
    Hanalei Bay Resort 52012

    Hanalei Bay Resort 52012

    Princeville, HI

    Hanalei Bay Resort 52012: Includes both of the elegant, recently updated, air-conditioned suites below, at a savings compared to renting separately. Close the connecting door for complete privacy, or open for a large shared apartment. Combined, the...

    Pool Hot Tub

    $520 to $581/night

  24. CONDOMINIUM
    Ko Olina Beach Villa (O1105)

    Ko Olina Beach Villa (O1105)

    Kapolei, HI

    This 3BD Penthouse Beach Villa is located on the 11th floor of the Ocean Tower and is 1,734 sq ft of luxury. It features ocean views the kitchen and living/dining area. The master bedroom has a private lanai with views of the golf course and...

    Pool Hot Tub

    $520 to $1,668/night

  25. CONDOMINIUM
    Sands of Kahana 316

    Sands of Kahana 316

    Lahaina, HI

    The Sands of Kahana has something for everyone! With an ocean front pool that the whole family will love and a pool just for children where the little ones can enjoy. After a adventuring Maui, make your way and relax in the Jacuzzi. There is a sand...

    Pool Hot Tub
    FREE CANCELLATION

    $519 to $1,249/night

  26. 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
    FREE CANCELLATION

    $516 to $620/night

  27. CONDOMINIUM
    Whaler 859

    Whaler 859

    Lahaina, HI

    Spend your dream vacation on Maui at The Whaler on Kaanapali Beach.  Watch sunsets with colors so beautiful you will wish you were an artist to capture it on canvas.  Relax on the lanai with a cup of coffee or cocktail where you can see Mauka to...

    Pool Hot Tub
    FREE CANCELLATION

    $473 to $1,561/night

  28. CONDOMINIUM
    Honua Kai Konea 1026

    Honua Kai Konea 1026

    Lahaina, HI

    NOTE: As of 2/6/18 construction of 72 Townhomes has commenced behind the Konea building at Honua kai. This condo overlooks the construction site. There may be noise and dust on work days during construction hours from 8am to 5pm. This beautiful...

    Pool Hot Tub
    FREE CANCELLATION

    $469 to $1,436/night

  29. CONDOMINIUM
    Whaler 206/208

    Whaler 206/208

    Lahaina, HI

    Spend your dream vacation on Maui at The Whaler on Kaanapali Beach.  Watch sunsets with colors so beautiful you will wish you were an artist to capture it on canvas.  Relax on the lanai with a cup of coffee or cocktail where you can see Mauka to...

    Pool Hot Tub
    FREE CANCELLATION

    $469 to $719/night

  30. CONDOMINIUM
    O-1406: Hale Ikena Ko Olina Beach Villa

    O-1406: Hale Ikena Ko Olina Beach Villa

    Kapolei, HI

    Leave the world behind as you’re greeted by the warm blue expansive ocean views from the living area and spacious lanai (balcony) of Hale Ikena Ko Olina Beach Villa. This incredible 2 bedroom, 2 bathroom Penthouse condo in the Ocean Tower has...

    Pool Hot Tub

    $462 to $1,384/night