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
    Maui Kamaole 2BR w/ Lanais & 2 Pools

    Maui Kamaole 2BR w/ Lanais & 2 Pools

    Kihei, HI

    Commanding a prime location in south Kihei, this 2BR condo offers a ground-level tropical retreat with two private lanais and upscale interior upgrades including a chef’s kitchen and stylish Hawaiian decor. Enjoy access to two pools, a hot tub,...

    Pool Hot Tub
    FREE CANCELLATION

    $193 to $556/night

  2. CONDOMINIUM
    Honua Kai- Hokulani 712- Romantic One Bedroom Ocean View!

    Honua Kai- Hokulani 712- Romantic One Bedroom Ocean View...

    Kanaanapali, 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.Located on the South side of the Hokulani tower, this top floor (7th floor)...

    Pool Hot Tub

    $299 to $1,033/night

  3. CONDOMINIUM
    Eldorado K102

    Eldorado K102

    Lahaina, HI

    Maui Eldorado located in the beautiful Kaanapali Resort is a Golf and beach lovers delight. If you like a quiet beach, go to The Maui Eldorado cabana which is to the right of Black Rock and is the only \"on the beach\" private cabana in Maui. The...

    Pool Hot Tub
    FREE CANCELLATION

    $171 to $725/night

  4. CONDOMINIUM
    Napili Shores C116

    Napili Shores C116

    Lahaina, HI

    Come Stay at the famous Napili Shores in this spacious garden view studio! The new owners are in the middle of updating and the unit with new decor! New photos to come soon!Beautiful Plumeria trees just off of your private lanai line the interior of...

    Pool Hot Tub
    FREE CANCELLATION

    $156 to $286/night

  5. CONDOMINIUM
    Kaanapali Shores 515

    Kaanapali Shores 515

    Lahaina, HI

    Relax on our 5th 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 515 lanai has views of the ocean, renovated garden pool and spa,...

    Pool Hot Tub
    FREE CANCELLATION

    $374 to $999/night

  6. CONDOMINIUM
    Sands of Kahana 354

    Sands of Kahana 354

    Lahaina, HI

    - Direct Oceanfront 2 BR/2 BA- Spectacular Views from unit- Long Sandy Beach- High Speed Internet in unit- Full Kitchen- Washer & Dryer in unitThis fully equipped condominium is beautifully maintained and decorated in island decor, totally remodeled...

    Pool Hot Tub
    FREE CANCELLATION

    $384 to $1,188/night

  7. CONDOMINIUM
    Honua kai- Konea 301 Frontline with BBQ!

    Honua kai- Konea 301 Frontline with BBQ!

    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.One of the MOST DESIRABLE 2 bedroom 2.5 bath condo in the entire complex.Konea...

    Pool Hot Tub

    $556 to $2,287/night

  8. CONDOMINIUM
    Honua Kai- Hokulani 108- Ground Floor & Huge Play Lawn! 1b/1b

    Honua Kai- Hokulani 108- Ground Floor & Huge Play 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.Beautiful Ground Floor One Bedroom at Honua Kai!This great Ground Floor unit...

    Pool Hot Tub

    $227 to $1,033/night

  9. CONDOMINIUM
    Honua Kai- Konea 606- Partial Ocean and Mountain Views! 2b/1b

    Honua Kai- Konea 606- Partial Ocean and Mountain Views! ...

    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.OCEAN VIEW 2 PLUS ONE!!NOTE: As of 2/6/18 construction of 72 Townhomes has...

    Pool Hot Tub

    $335 to $1,211/night

  10. CONDOMINIUM
    Aina Nalu C 203

    Aina Nalu C 203

    lahaina, HI

    AINA NALU C-203 Welcomes you with Aloha...C-203 is decorated with a touch of ALOHA! This is an amazing location and quality unit.Included in our fabulous price are many owner-supplied extras such as:• Beach chairs (2)• Beach umbrella• Beach...

    Pool Hot Tub
    FREE CANCELLATION

    $205 to $371/night

  11. CONDOMINIUM
    Aina Nalu G102

    Aina Nalu G102

    Lahaina, HI

    TROPICAL LUXURY, ELEGANCE AND CHARM best describe this splendid 2 bedroom / 2 bath 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 island...

    Pool Hot Tub
    FREE CANCELLATION

    $238 to $540/night

  12. CONDOMINIUM
    Honua Kai- Hokulani 709- Best Ocean Views! 2b/2.5b

    Honua Kai- Hokulani 709- Best Ocean Views! 2b/2.5b

    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.Honua Kai Hokulani 709 is clearly the best 2 bedroom condo available in the...

    Pool Hot Tub

    $501 to $2,020/night

  13. CONDOMINIUM
    Honua Kai Konea 508

    Honua Kai Konea 508

    Lahaina, HI

    HONUA KAI RESORT AND SPA SUITE 508 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 umbrella•...

    Pool Hot Tub
    FREE CANCELLATION

    $251 to $608/night

  14. CONDOMINIUM
    Hale Ikena Ko Olina Beach Villa (O1406)

    Hale Ikena Ko Olina Beach Villa (O1406)

    Kapolei, HI

    Book with confidence! This vacation rental is a LEGAL Oahu vacation rental operating in a Resort Zoned District and is not affected by the passage of Bill 89.LIVE CALENDAR: If the calendar shows as available, the property IS available and can be...

    Pool Hot Tub

    $432 to $1,384/night

  15. CONDOMINIUM
    Aina Nalu C201

    Aina Nalu C201

    Lahaina, HI

    The 2nd floor condos are desirable by guest as they offer a lanai. The condo offers a fully equipped kitchen as well as a washer and dryer for all the conveniences of home while you're on your Hawaiian Vacation. Beautiful tropical decore brings...

    Pool Hot Tub
    FREE CANCELLATION

    $188 to $658/night

  16. CONDOMINIUM
    3BR w/ Infinity Pool & Spa, Near Snorkeling Beach

    3BR w/ Infinity Pool & Spa, Near Snorkeling Beach

    Kailua Kona, HI

    Set right across the street from Kahalu’u Beach, this 3BR/2BA condo is within steps of one of the best beaches in Hawaii for surfing. Your prime locale is also close to Kona Town and Keauhou.Perched on the second-floor, this corner unit boasts...

    Pool Hot Tub
    FREE CANCELLATION

    $216 to $493/night

  17. CONDOMINIUM
    Honua kai- Luana Garden Villa 3C

    Honua kai- Luana Garden Villa 3C

    Kaanapali, HI

    Luana Garden Villas is the newest offering at the beautiful Honua kai Resort & Spa.  These spacious 3 bedroom Villas are located in 3 private enclaves and include large lanai's, private outdoor kitchens and a private garage. Each Enclave boasts a...

    Pool Hot Tub

    $844 to $2,843/night

  18. CONDOMINIUM
    Honua Kai- Konea 705- Amazing Sunset Views! 2b/2b

    Honua Kai- Konea 705- Amazing Sunset Views! 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! HUGE OCEAN VIEWS WITH SUNSETS ALL YEAR LONG!!!This spectacular 7th Floor...

    Pool Hot Tub

    $467 to $1,772/night

  19. CONDOMINIUM
    Honua Kai- Hokulani 409- Amazing Ocean Views! 2b/2b

    Honua Kai- Hokulani 409- Amazing Ocean Views! 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 AND GREAT OCEAN VIEWSThis Beautiful Condo is in the...

    Pool Hot Tub

    $495 to $1,694/night

  20. CONDOMINIUM
    Kaanapali Shores- 943- Panoramic Ocean View! 1b/1b

    Kaanapali Shores- 943- Panoramic Ocean View! 1b/1b

    Kaanapali, HI

    This beautiful 717 sq ft condo is on the 9th Floor with no one above you! Enjoy Sweeping Ocean Vistas, Sunsets and Whales leaping in Winter! The large 104 sq ft Lanai is perfect for enjoying your morning coffee or an afternoon cocktail as the sun...

    Pool Hot Tub

    $202 to $783/night

  21. CONDOMINIUM
    Waikoloa Beach Villas E33

    Waikoloa Beach Villas E33

    Waikoloa, HI

    This beautiful 2 bedroom, 2 bath villa has everything you need for a great vacation on The Big Island of Hawaii.Master bedroom has a king bed and on suite bath. Guest bedroom has 2 full size beds and the living room also has a queen size sofa...

    Pool Hot Tub
    FREE CANCELLATION

    $197 to $464/night

  22. CONDOMINIUM
    Colony Villas at Waikoloa Beach Resort #2204

    Colony Villas at Waikoloa Beach Resort #2204

    Waikoloa, HI

    Aloha and welcome to our Big Island getaway. Our Villa was purchased in March of 2011 and is a part of the Waikoloa Colony Villas located within the exclusive Waikoloa Beach Resort. Located just eighteen miles north of the Kona Airport, this...

    Pool Hot Tub
    FREE CANCELLATION

    $184 to $464/night

  23. CONDOMINIUM
    Sunny 1BR Condo- Across from Beach

    Sunny 1BR Condo- Across from Beach

    Kailua Kona, HI

    This delightful 1BR condo in the Kona Bali Kai Resort is the perfect home base for your time on the beautiful Big Island.Recent renovations include new hardwood and tile floors, kitchen upgrades, air-conditioning, and a fun tropical décor. This...

    Pool Hot Tub
    FREE CANCELLATION

    $113 to $289/night

  24. CONDOMINIUM
    Luxe 2BR/2BA- Infinity Pool & Spa- 1 Mile to Bay

    Luxe 2BR/2BA- Infinity Pool & Spa- 1 Mile to Bay

    Waikoloa Beach Resort, HI

    Nestled in an inclusive enclave on the Big Island's Kohala Coast, this ground-floor condo offers the ultimate home base for your island getaway. Take in sweeping golf course views from a private lanai with al fresco dining and lounge furniture.The...

    Pool Hot Tub
    FREE CANCELLATION

    $162 to $269/night

  25. CONDOMINIUM
    Hale Ka Wailele Malu Ko Olina Beach Villa (O226)

    Hale Ka Wailele Malu Ko Olina Beach Villa (O226)

    Kapolei, HI

    Book with confidence! This vacation rental is a LEGAL Oahu vacation rental operating in a Resort Zoned District and is not affected by the passage of Bill 89.LIVE CALENDAR: If the calendar shows as available, the property IS available and can be...

    Pool Hot Tub

    $508 to $1,668/night

  26. CONDOMINIUM
    Kahana Villa 2BR w/ Ocean-View Lanai, Pool & Spa

    Kahana Villa 2BR w/ Ocean-View Lanai, Pool & Spa

    Lahaina, HI

    Enjoy the island breeze and ocean views from your private lanai at this spacious two-level 2BR/2BA condo. Perched on the seventh floor (the top floor) at the Kahana Villa Resort, this dreamy getaway provides lavish amenities including a shared pool,...

    Pool Hot Tub
    FREE CANCELLATION

    $156 to $518/night

  27. HOUSE
    Junior Suite Oceanfront #303

    Junior Suite Oceanfront #303

    Lahaina, HI

    Jr. Suite - Bright and Easy Island Style. Queen bed (no sofa bed), tiled entryway, Flat Screen TV, light furnishings throughout. Put away your groceries and make yourself at home. Enjoy your private lanai with your favorite beverage. Watch the...

    Pool Hot Tub
    FREE CANCELLATION

    $278 to $341/night

  28. CONDOMINIUM
    Kolepa Aloha

    Kolepa Aloha

    Waikoloa, HI

    Description :Views of Mauna Kea and emerald fairways are yours at this two-bedroom, two-bath vacation rental at Fairway Villas, located within the prestigious Waikoloa Beach Resort. Step onto your private, covered lanai with the day's first cup of...

    Pool Hot Tub

    $162 to $401/night

  29. HOUSE
    Junior Suite Oceanfront #706

    Junior Suite Oceanfront #706

    Kaanapali, HI

    Our Junior Suite is spacious and well-appointed with a Queen Bed; as well as a sofa bed for the occasional guest. There are seating arrangements for relaxing and dining. You will find plenty of space to store your clothing and personal items. The...

    Pool Hot Tub
    FREE CANCELLATION

    $278 to $341/night

  30. CONDOMINIUM
    Leilani

    Leilani

    Waikoloa, HI

    Description for Beach Villas H4Flawless vacations start at Waikoloa Beach Resort, from its lush, palm-shaded grounds and lava rock swimming pool, to its gourmet kitchens and private lanais scented by tropical flowers.This coveted 3-bedroom, 3-bath...

    Pool Hot Tub

    $322 to $641/night