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
    Honua Kai- Konea 501- OCEAN FRONT with private BBQ! 2b/2b

    Honua Kai- Konea 501- OCEAN FRONT with private BBQ! 2b/2...

    Kaanapali, HI

    HAPPY HOUR ON US! FREE $25 Dukes gift card for stays between 7/11/19-12/19/19. 5-night minimum, for bookings made after 7/9/19, may not be combined with any promo pricing. Absolutely the MOST DESIRABLE 2 bedroom 2.5 bath condo in the entire...

    Pool Hot Tub

    $622 to $2,134/night

  2. CONDOMINIUM
    Maui Kamaole #K-209

    Maui Kamaole #K-209

    Kihei, HI

    Aloha and welcome to Maui Kamaole K-209 where vacationing is all about location, location, location… and comfort, of course! Maui Kamaole condominium complex is strategically positioned on the sunny side of the island of Maui. The south side...

    Pool Hot Tub
    FREE CANCELLATION

    $173 to $347/night

  3. CONDOMINIUM
    Kaanapali Shores Studio 642

    Kaanapali Shores Studio 642

    Lahaina, HI

    Relax and enjoy the serenity at Ka'anapali Shores Resort! Our adorable studio suite has been beautifully remodeled to sleep four guests comfortably with a king size bed and a full size sofa pull out for a second bed. The fully appointed kitchen is...

    Pool Hot Tub
    FREE CANCELLATION

    $186 to $359/night

  4. CONDOMINIUM
    2BR/2BA at Kahalu’u Beach w/ Pool, Spa, Ocean View

    2BR/2BA at Kahalu’u Beach w/ Pool, Spa, Ocean View

    Kailua Kona, HI

    PROPERTY OVERVIEWPrime surfing and snorkeling are within steps of this 2BR/2BA condo, situated right across the street from Kahalu’u Beach. The ultra-convenient location is also close to Kona Town and Keauhou.Boasting beautiful ocean views from...

    Pool Hot Tub
    FREE CANCELLATION

    $171 to $437/night

  5. 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

    $162 to $480/night

  6. DUPLEX
    Manoa Valley 3BR w/ Hot Tub & Lanai w/ Ocean View

    Manoa Valley 3BR w/ Hot Tub & Lanai w/ Ocean View

    Honolulu, HI

    Perched on a hill overlooking Honolulu City and the majestic Diamond Head volcano, this 3BR/2.5BA Manoa Valley duplex features gorgeous Craftsman touches and an expansive lanai that’s perfect for a barbecue.Striking stained glass and teak accents...

    Hot Tub Pets OK
    FREE CANCELLATION

    $568 to $1,420/night

  7. HOUSE
    Diamond Head Hillside Retreat

    Diamond Head Hillside Retreat

    Honolulu, HI

    Welcome to our serene Diamond Head Hillside Estate, where you can rest and relax in a tranquil Bali inspired villa.Located on a secluded cul-de-sac just on the cusp of Diamond Head and Kahala, nestled right below the idyllic landmark and hiking...

    Pool Hot Tub

    $1,428 to $2,484/night

  8. 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 $1,225/night

  9. 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 $2,899/night

  10. HOUSE
    Hale Keanu

    Hale Keanu

    Kamuela, 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

    $1,168 to $2,876/night

  11. CONDOMINIUM
    Hale Ohana Aloha

    Hale Ohana Aloha

    Waikoloa, HI

    Big Island dreams begin at Hali'i Kai 7D, an ocean-view vacation condominium at renowned Waikoloa Beach Resort. Ideal for group getaways of up to six people, this 2-bedroom, 2-bath condo features an updated interior, access to impeccable resort...

    Pool Hot Tub

    $286 to $478/night

  12. CONDOMINIUM
    Aina Nalu I104

    Aina Nalu I104

    Lahaina, HI

    TROPICIAL LUXURY, ELEGANCE AND CHARM best describe this splendid 2 bedroom / 2 bath at Aina Nalu condominium. Abundant comforts await your arrival at this award winning and highly sought after Lahaina resort. You will be greeted to this 9 acre...

    Pool Hot Tub
    FREE CANCELLATION

    $194 to $651/night

  13. CONDOMINIUM
    Maui Kai 108

    Maui Kai 108

    Lahaina, HI

    Enjoy unbeatable panoramic views from this coveted first floor oceanfront unit on the Kaanapali coast. This very special unit is one of only 2 that have a door on your lanai to access the ocean side of the condo directly! You can’t get any closer...

    Pool Hot Tub
    FREE CANCELLATION

    $211 to $563/night

  14. CONDOMINIUM
    Maui Kai 601

    Maui Kai 601

    Lahaina, HI

    Beautiful remodel just completed May 2019! Enjoy the brand new lanai, with incredible views to enjoy from the comfort of chaise chairs or the dining set. Luxurious tile throughout the condo, gorgeous granite counters and all new appliances in the...

    Pool Hot Tub
    FREE CANCELLATION

    $301 to $688/night

  15. CONDOMINIUM
    Kamaole Sands 8-203

    Kamaole Sands 8-203

    Kihei, HI

    Your dream Maui vacation awaits! Kamaole Sands 8-203 is on the second floor of building 8 in one of the most sought-after complexes in South Maui. This unit has been newly updated and has a brand new sofa sleeper in the living area and King mattress...

    Pool Hot Tub
    FREE CANCELLATION

    $149 to $374/night

  16. CONDOMINIUM
    Whaler 859

    Whaler 859

    Lahaina, HI

    Spend your dream vacation on Maui at the Whaler on beautiful Kaanapali beach! Enjoy stunning West Maui sunsets and gorgeously landscaped grounds! Relax on the lanai with a cup of coffee or a cocktail where you can see from Mauka to Makai (from...

    Pool Hot Tub
    FREE CANCELLATION

    $503 to $1,564/night

  17. CONDOMINIUM
    Mahana 713

    Mahana 713

    Lahaina, HI

    Beautiful 7th floor studio condominium at The Mahana at Kaanapali provides everything you need for your vacation in paradise. Equipped with granite counter tops, beautiful tile floors, central A/C, WiFi, flat screen TV, stocked kitchen, and...

    Pool Hot Tub
    FREE CANCELLATION

    $236 to $738/night

  18. CONDOMINIUM
    Kaanapali Royal B303

    Kaanapali Royal B303

    Lahaina, HI

    Come and enjoy the Kaanapali Royal B303 2 bedroom, 2 bath condo! This beautiful and very spacious 2-bedroom condo, located in the famous Kaanapali Beach Resort area is the perfect getaway for your next Maui vacation! Just walking distance to the...

    Pool Hot Tub
    FREE CANCELLATION

    $264 to $576/night

  19. CONDOMINIUM
    Papakea B405

    Papakea B405

    Lahaina, HI

    Papakea resort is perfectly located right on the ocean in West Maui. Winter visitors have a special treat as this location is a favorite for the Humpback whales! They love to put on a show just for you, breaching and frolicking! Long walks down to...

    Pool Hot Tub
    FREE CANCELLATION

    $449 to $1,478/night

  20. CONDOMINIUM
    Kaanapali Shores 936

    Kaanapali Shores 936

    Lahaina, HI

    Wonderful ocean views from this spacious penthouse level studio. The owners have completed a beautiful remodel featuring tile floors and a new sofa-sleeper. The full kitchen was recently re-done with new appliances, granite counter tops, new...

    Pool Hot Tub
    FREE CANCELLATION

    $185 to $636/night

  21. CONDOMINIUM
    Maui Kai 206

    Maui Kai 206

    Lahaina, HI

    Enjoy unbeatable panoramic views from this highly desirable 2nd floor oceanfront unit on the Kaanapali coast. You can’t get any closer to the ocean than this resort! Watch gorgeous sunsets over Molokai & Lanai every day from the comfort of your...

    Pool Hot Tub
    FREE CANCELLATION

    $189 to $500/night

  22. CONDOMINIUM
    Maui Kai 602

    Maui Kai 602

    Lahaina, HI

    Enjoy unbeatable panoramic views from this highly desirable 6th floor oceanfront unit on the Kaanapali coast. You can’t get any closer to the ocean than this resort! Watch gorgeous sunsets over Molokai and Lanai every day from the comfort of your...

    Pool Hot Tub
    FREE CANCELLATION

    $193 to $630/night

  23. CONDOMINIUM
    Kaanapali Royal J202

    Kaanapali Royal J202

    Lahaina, HI

    A luxury condo in the heart of the Kaanapali Beach Resort. This beautiful two bedroom two bathroom condominium, surrounded by lush, tropical landscaping makes Kaanapali Royal a beautiful retreat in paradise. It is located in a gated community for...

    Pool Hot Tub
    FREE CANCELLATION

    $335 to $1,105/night

  24. CONDOMINIUM
    Kaanapali Shores 403

    Kaanapali Shores 403

    Lahaina, HI

    Relax on our 4th floor lanai, overlooking the ocean, well-kept grounds and pool at Kaanapali Shores! Kaanapali Shores resort is located on the beach in North Kaanapali. Unit 403 lanai has views of the ocean,spectacular sunsets, and whales in...

    Pool Hot Tub
    FREE CANCELLATION

    $366 to $1,188/night

  25. CONDOMINIUM
    Papakea L108

    Papakea L108

    Lahaina, HI

    The condo is totally renovated and updated. From your private lanai you have a lovely area to sit and dine or just relax with nothing but the crystal blue ocean and the famous Maui sunsets in front, FRONT SEAT WHALE WATCHING from the lanai. Tile...

    Pool Hot Tub
    FREE CANCELLATION

    $251 to $844/night

  26. CONDOMINIUM
    Ocean View from Lanai, Walk to Beach- 2BR w/ Pool

    Ocean View from Lanai, Walk to Beach- 2BR w/ Pool

    Lahaina, HI

    This all-suite 2BR condo boasts the ultimate backdrop for a dream Maui vacation. Relax on a huge covered lanai with sweeping views that stretch out from the Royal Kaanapali Golf Course to the sparkling blue Pacific Ocean.Nestled in the gated...

    Pool Hot Tub
    FREE CANCELLATION

    $296 to $665/night

  27. CONDOMINIUM
    Honua Kai- Konea 924- One Bedroom Ocean View! Renovated!

    Honua Kai- Konea 924- One Bedroom Ocean View! Renovated!...

    Kaanapali, HI

    HAPPY HOUR ON US! FREE $25 Dukes gift card for stays between 7/11/19-12/19/19. 5-night minimum, for bookings made after 7/9/19, may not be combined with any promo pricing. NOTE: As of 2/6/18 construction of 72 Townhomes has commenced behind the...

    Pool Hot Tub

    $316 to $1,003/night

  28. CONDOMINIUM
    Honua Kai- Hokulani 841- Ocean View! 2b/2b

    Honua Kai- Hokulani 841- Ocean View! 2b/2b

    Kaanapali, HI

    HAPPY HOUR ON US! FREE $25 Dukes gift card for stays between 7/11/19-12/19/19. 5-night minimum, for bookings made after 7/9/19, may not be combined with any promo pricing. WOW! WRAP AROUND LANAI TOP OF THE STACK!!! TOP FLOOR - UNMATCHED OCEAN...

    Pool Hot Tub

    $592 to $1,912/night

  29. CONDOMINIUM
    Ohana Hale 2 bed/2bath w/ Pool & Hot Tub- Steps To Beach

    Ohana Hale 2 bed/2bath w/ Pool & Hot Tub- Steps To B...

    Kihei, HI

    Ohana Hale is a charming two bedroom, two bath ground floor condominium suite. Each bedroom has one full bathroom and its own private entrance to the pool. Each bedroom has your choice of a King bed or 2 Twin beds. They also include two beach...

    Pool Hot Tub

    $347 to $786/night

  30. CONDOMINIUM
    Honua Kai- Hokulani 836- Ocean Views & Huge Party Lanai! 2b/2b

    Honua Kai- Hokulani 836- Ocean Views & Huge Party La...

    Kaanapali, HI

    HAPPY HOUR ON US! FREE $25 Dukes gift card for stays between 7/11/19-12/19/19. 5-night minimum, for bookings made after 7/9/19, may not be combined with any promo pricing. GREAT OCEAN & MOUNTAIN VIEWS FROM 8TH FLOOR WITH HUGE PARTY LANAI! Unit...

    Pool Hot Tub

    $526 to $1,607/night