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.

Filter by Region:


Filter by Amenities:


Filter by Entertainment:


Close Filters
  1. CONDOMINIUM
    Keauhou Kona Surf & Racquet Club 2103

    Keauhou Kona Surf & Racquet Club 2103

    Kailua Kona, HI

    Welcome to Paradise. You found the perfect condo for your Hawaiian Vacation. 2-103 at the Surf & Racquet Club is a gorgeous, 2 bedroom, 2 bath DIRECT oceanfront ground floor property. This property has EVERYTHING you'll need. Wifi, Tennis Racquets,...

    Pool
    FREE CANCELLATION
  2. CONDOMINIUM
    Cliffs 4205

    Cliffs 4205

    Princeville, HI

    This beautiful Kauai vacation rental is equipped with all of the modern luxury you’ll need, while also providing an easy, tranquil vacation-getaway on Kauai's paradisical north shore in Princeville. Stare into the expanse of the deep blue Pacific...

    Pool Hot Tub

    $235 to $301/night

  3. CONDOMINIUM
    Kaanapali Shores 422

    Kaanapali Shores 422

    Lahaina, HI

    Ka'anapali Shores is located on the most desired beach on Maui, perhaps even the world!  There is no greater place to unwind and relax than at this tropical oasis! Aside from the magnificent beach, the resort offers all the amenities of a AAA class...

    Pool Hot Tub
    FREE CANCELLATION

    $199 to $384/night

  4. VILLA
    Bay Villa 17B2 Gold Ocean View

    Bay Villa 17B2 Gold Ocean View

    Kapalua, HI

    Over $600K in recent upgrades! Even the best photos can not capture the true beauty of the high-end materials used, the designer furniture and accessories and the magnificent views that surround this 5 star property. If you have ever dreamed of...

    Pool

    $563 to $1,063/night

  5. CONDOMINIUM
    Maui Vista 1209

    Maui Vista 1209

    KIHEI, HI

    One bedroom condo with a partial ocean view. This unit sleeps up to four people with a queen bed in the bedroom and a pull out sofa bed in the living room. The kitchen opens up to the dining and living areas creating a wide open living space. The...

    Pool
    FREE CANCELLATION

    $242 to $294/night

  6. CONDOMINIUM
    Kamaole Beach Royale #612

    Kamaole Beach Royale #612

    Kihei, HI

    Kamaole Beach Royale is centrally located across the street from Kamaole Beach Park #1--a white sandy beach in South Kihei, Maui, Hawaii. It has lush tropical landscaping, a swimming pool, covered assigned parking, and a rooftop pavilion to barbecue...

    Pool
    FREE CANCELLATION

    $347 to $440/night

  7. CONDOMINIUM
    Maui Kamaole #D-107

    Maui Kamaole #D-107

    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

    $174 to $238/night

  8. CONDOMINIUM
    Wailea Ekolu #310

    Wailea Ekolu #310

    Kihei, HI

    Wailea Ekolu has several lovely pool areas as well as a large pavilion area for larger groups. There are also additional barbecue and picnic areas on the grounds with panoramic views of the ocean and the sunsets. The beautiful Mokapu and Ulua...

    Pool
    FREE CANCELLATION

    $302 to $534/night

  9. CONDOMINIUM
    Hale Kamaole #311

    Hale Kamaole #311

    Kihei, HI

    This two bedroom condo without a loft, has a good Ocean and Garden View. Master bedroom has king bed. Down stairs bedroom has king bed. Hide a bed couch in the living room. Spacious kitchen cabinets. Wood and tile floor including lanai no carpet....

    Pool
    FREE CANCELLATION

    $245 to $355/night

  10. TOWNHOUSE
    Puamana 52-3

    Puamana 52-3

    Lahaina, HI

    Come stay with us in Puamana, the best kept secret in West Maui!! This 30 acre ocean front town home community awaits you for a vacation full of relaxation and fun! 52-3 is a 2 BR with 2.5 baths and in unit laundry. There is a split AC unit in each...

    Pool
    FREE CANCELLATION

    $274 to $561/night

  11. HOUSE
    Ali'i Point 5

    Ali'i Point 5

    Kailua-Kona, HI

    Ali'i Point #5 is located at Ali'i Point, a private and gated community of 16 seaside homes with community pool and tennis court. Central A/C throughout. Main floor has living room, dining room, kitchen, half bath, and master king bedroom with en...

    Pool

    $668 to $846/night

  12. CONDOMINIUM
    Molokai Shores Condominium 121

    Molokai Shores Condominium 121

    Kaunakakai, HI

    Very nice one bedroom condo with views of the Pacific Ocean, and the island of Lanai from the lanai. Wintertime has the whales breaching in the channel and sunsetting over the ocean.  Kitchen has nice tiled countered and all the amenities you need...

    Pool
    FREE CANCELLATION

    $169 to $197/night

  13. HOUSE
    Sands Of Kahana 356

    Sands Of Kahana 356

    Kahana, HI

    Grasp the beautiful sunsets and rainbows from this very spacious three bedroom condominium This unit is one of the few 3 bedroom units at the Sands of Kahana that has air conditioning. Ocean views and vivid rainbow skies are visible from every...

    Pool Hot Tub

    $501 to $557/night

  14. HOUSE
    Kahana Sunset E6

    Kahana Sunset E6

    Kahana, HI

    Come enjoy paradise in this recently renovated two-bedroom, two and a half bath condominium in West Maui, Hawaii. With a panoramic view of the ocean, Kahana Sunset Condo, Unit E-6, is just steps away from a secluded beach. The two-level condo, which...

    Pool

    $276 to $332/night

  15. CONDOMINIUM
    Maui Kamaole #M-105

    Maui Kamaole #M-105

    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
    FREE CANCELLATION

    $211 to $339/night

  16. CONDOMINIUM
    Kona Plaza#220

    Kona Plaza#220

    Kailua Kona, HI

    Welcome to the listing page of Kona Plaza#220. It's amazing location puts you right in immediate walking distance to restaurants, beaches, shopping & entertainment right in the heart of Kailua Village. This comfortable 1 bedroom, 1 bath that sleeps...

    Pool
    FREE CANCELLATION
  17. HOUSE
    Mana Alana at Poipu

    Mana Alana at Poipu

    Koloa, HI

    This stunning Poipu home boasts over 3,300 square feet of elegant living space, along with sweeping views from the coastline up the sloping hills of Kalaheo. An open floor plan provides guests with the perfect setting for quality time together,...

    Pool Hot Tub

    $780 to $2,079/night

  18. CONDOMINIUM
    Wailea Ekolu #503

    Wailea Ekolu #503

    Kihei, HI

    Wailea Ekolu is one of most sought after properties in Wailea as it is nestled on the Wailea Golf Course. The property has a quiet and private atmosphere as the buildings are spread out across the lush tropical foliage. Wailea Ekolu has two lovely...

    Pool
    FREE CANCELLATION

    $261 to $521/night

  19. CONDOMINIUM
    Sugar Beach 308

    Sugar Beach 308

    Kihei, HI

    **The Pool will be CLOSED beginning September 10th, through September 17th, 2018. In 2019 the pool will be closed September 9th, through September 16th. Each year the pool will be closed for one week, starting on the second Monday of the month....

    Pool Hot Tub
    FREE CANCELLATION

    $299 to $465/night

  20. CONDOMINIUM
    Cliffs 8205

    Cliffs 8205

    Princeville, HI

    Located in Princeville on the lush north shore of Kauai, Cliffs 8205 is the perfect home away from home (up to 4). This luxury condo has spectacular unobstructed ocean views, pleasant trade winds and a front row seat for whale watching. Relax in...

    Pool Hot Tub

    $253 to $301/night

  21. HOUSE
    Bay Villa 30G1

    Bay Villa 30G1

    Kapalua, HI

    This is a beautifully remodeled unit decorated with the finest of furnishings. It is a one bedroom two bathroom oceanfront unit equipped with Air condition, King/Queen/sofa sleeper bedding, cable modem for computer access. It has granite counter...

    Pool

    $248 to $304/night

  22. CONDOMINIUM
    Hale Kamaole #326

    Hale Kamaole #326

    Kihei, HI

    Beautifully updated condo with partial Ocean View! Upstairs master bedroom has island style King bed and furniture. Remodeled master bath has walk-in tiled shower, new vanity and granite top. Downstairs bedroom has island style furniture with 2 Twin...

    Pool
    FREE CANCELLATION

    $269 to $379/night

  23. CONDOMINIUM
    Kuleana #305

    Kuleana #305

    Lahaina, HI

    Book today to see this beautiful Kuleana Unit 305. This one bed/one bath unit was very tastefully renovated just last year and it looks amazing. From new porcelain travertino tile flooring throughout, tumbled travertine shower floor, Moen fixtures...

    Pool
    FREE CANCELLATION

    $242 to $294/night

  24. CONDOMINIUM
    1 Bedroom Corner Oceanfront 908

    1 Bedroom Corner Oceanfront 908

    Kaanapali, HI

    This beautiful One Bedroom Corner unit was recently renovated and has a breathtaking view! Featuring a King Bed, Queen Sofa Sleeper, full kitchen, all done in the warm island style. Wake up and have breakfast on your spacious open lanai while you...

    Pool Hot Tub
    FREE CANCELLATION

    $372 to $444/night

  25. CONDOMINIUM
    Puu Poa 102

    Puu Poa 102

    Princeville, HI

    Pu’u Po’a 102 is located on the bluff of Princeville with spectacular ocean views. There are 2 tastefully decorated bedrooms and 2 bathrooms. Two private lanais for relaxing, dining, and barbequing. A large flat screen TV/DVD with a movie...

    Pool

    $362 to $512/night

  26. HOUSE
    Kahana Sunset A3

    Kahana Sunset A3

    Kahana, HI

    Our ocean front home sits on a cliff directly in front of and above the ocean and only a single flight of stairs separates you from a secluded bay with white pristine sands. You can hear and see the ocean from the Master bedroom and living room...

    Pool

    $326 to $383/night

  27. HOUSE
    Kahana Sunset E8

    Kahana Sunset E8

    Kahana, HI

    E8 is our 2 bedroom/2 bath condo and has been completely remodeled and redecorated.The furnishings are beautiful and comfortable. Kahana Sunset is a small oceanfront property offering an amazing private beach, beautiful pool and gorgeous grounds....

    Pool

    $276 to $332/night

  28. HOUSE
    Kahana Sunset F12

    Kahana Sunset F12

    Lahaina, HI

    This unit is an ocean front condo just right off the white sand beach and the Keonenui Bay that front Kahana Sunset. Two bedrooms two and a half bathrooms. No sofa sleeper. The kitchen and master bath have been recently remodeled. There is tile...

    Pool

    $371 to $428/night

  29. CONDOMINIUM
    Kaanapali Shores Studio #742

    Kaanapali Shores Studio #742

    Lahaina, HI

    Enjoy the luxuries of home with this upgraded, impeccably cared for studio unit.  You will enjoy spectacular ocean views from within the unit as well as from the lanai!  On clear days you will feel like you can touch the island of Molokai and also...

    Pool
    FREE CANCELLATION

    $186 to $359/night

  30. CONDOMINIUM
    Maui Kamaole #J-110

    Maui Kamaole #J-110

    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
    FREE CANCELLATION

    $204 to $327/night