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
    Mahina Surf 205 Condo

    Mahina Surf 205 Condo

    Lahaina, HI

    We welcome you to come and enjoy the pristine Pacific Ocean views that warmly greet you from our Mahina Surf 205 lanai.  This unit has a private bedroom, a loft, 2 full bathrooms, a queen sofa sleeper in the living room, and is conveniently cooled...

    Pool

    $274 to $649/night

  2. CONDOMINIUM
    Honua Kai 224

    Honua Kai 224

    Lahaina, HI

    This luxury Honua Kai one bedroom located in the 'Konea Tower' features everything you need to make your Hawaiian vacation truly enjoyable! We provide you with those extra amenities that make a difference, including comfortable beach chairs, beach...

    Pool Hot Tub

    $299 to $401/night

  3. VILLA
    Kahana Villa E614

    Kahana Villa E614

    Lahaina, HI

    We invite you to experience our wonderful 2 bedroom (*second bedroom is an open loft)/1 bathroom ocean view Kahana Villa! This condo includes a queen-sized bed in the bedroom, a queen-sized sleeper sofa in the living room, and a queen-sized bed in...

    Pool

    $248 to $641/night

  4. CONDOMINIUM
    Kihei Bay Vista #C-106

    Kihei Bay Vista #C-106

    Kihei, HI

    Kihei Bay Vista is a wonderful property. It is located in Kihei Maui, just steps from the ocean. It has a pool and hot tub, gas grills for your use as well as an outdoor dining area. This property is one of the great finds for the price in Kihei....

    Pool

    $126 to $231/night

  5. CONDOMINIUM
    Kihei Alii Kai #A-305

    Kihei Alii Kai #A-305

    Kihei, HI

    The Kihei Ali'i Kai is a wonderful property located just across the street from the best beach in Kihei; Kamaole Beach #1. This property is in walking distance to shops, activities and restaurants and is a short drive from the championship golf...

    Pool Hot Tub

    $128 to $208/night

  6. CONDOMINIUM
    O-226: Hale Ka Wailele Malu Ko Olina Beach Villa

    O-226: Hale Ka Wailele Malu Ko Olina Beach Villa

    Kapolei, HI

    Hale Ka Wailele Malu is one of the most unique and desirable Beach Villas in all of Ko'Olina. The large (1,650 sq ft) 3 bedroom, 3 bathroom, 2nd floor, ocean-facing Beach Villa is one of only four Villas (out of the 247) that fronts the soothing and...

    Pool Hot Tub

    $636 to $1,668/night

  7. CONDOMINIUM
    Kihei Bay Vista #A-102

    Kihei Bay Vista #A-102

    Kihei, HI

    Kihei Bay Vista #A-102 is a ground floor unit that is just across the street from the beach. This unit has a fully equipped kitchen, washer and dryer, There is a king bed in the bedroom and a queen sofa bed in the living room. This unit is...

    Pool Hot Tub

    $126 to $231/night

  8. CONDOMINIUM
    Grand Champions #86

    Grand Champions #86

    Kihei, HI

    The nearby Ulua and Mokapu Beaches are a quick drive down the hill from the The Grand Champions Villas in Wailea. The complex is surrounded by lovely tropical gardens. It is located in the exclusive Wailea Resort. The complex offers two swimming...

    Pool Hot Tub

    $215 to $325/night

  9. CONDOMINIUM
    Maalaea Surf Resort #C-3

    Maalaea Surf Resort #C-3

    Kihei, HI

    Maalaea Surf Resort is an oceanfront property in North Kihei near the beautiful white sand beach known as Sugar Beach. Centrally located, it features eight two-story buildings on five acres, two pools, a barbecue area, an on-site tennis court, and...

    Pool

    $244 to $418/night

  10. CONDOMINIUM
    Kamaole Sands #10-313

    Kamaole Sands #10-313

    Kihei, HI

    Kamaole Sands is the premiere property in South Kihei. Located across the street from Kamaole Beach Park 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

    $197 to $377/night

  11. CONDOMINIUM
    Puamana 9C

    Puamana 9C

    Princeville, HI

    Puamana 9C: AC in the master bedroom, and so many extras provided for your comfort and convenience! A spacious 1550sf of living space surrounded by the open green spaces of the Robert Trent Jones Jr designed Makai golf course, ocean views, and a...

    Pool

    $214 to $238/night

  12. CONDOMINIUM
    Palms at Wailea #1209

    Palms at Wailea #1209

    Wailea, HI

    The fabulous Keawakapu Beach is just a short 10 minute stroll from the Palms at Wailea. This beach is world famous for its great snorkeling and long walking beach. The Palms at Wailea is a gorgeous property; lush with tropical landscaping. There is...

    Pool Hot Tub

    $267 to $365/night

  13. CONDOMINIUM
    Waiohuli Beach Hale #C-211

    Waiohuli Beach Hale #C-211

    Kihei, HI

    Waiohuli Beach Hale is a small oceanfront complex located in Kihei Maui Hawaii. This property has a great aloha feeling with a relaxed and quiet atmosphere. Each unit is steps from the ocean and is centrally located to great shopping, restaurants,...

    Pool

    $208 to $347/night

  14. CONDOMINIUM
    Maui Kamaole #A-202

    Maui Kamaole #A-202

    Kihei, HI

    Unit A-202 has been completely renovated. This renovation includes: the kitchen cabinets, granite countertops, new kitchen appliances; lighting, carpeting and new tile everywhere; redesigned bathrooms with walk-in showers, new bathroom cabinets and...

    Pool Hot Tub

    $289 to $405/night

  15. CONDOMINIUM
    Maui Kamaole #L-205

    Maui Kamaole #L-205

    Kihei, HI

    The famous Kamaole Beach III is just across the street 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...

    $231 to $563/night

  16. CONDOMINIUM
    Kihei Garden Estates #G-103

    Kihei Garden Estates #G-103

    Kihei, HI

    Kihei Garden Estates is a lovely property right across the street from Waiohuli Beach. Kihei Garden Estates boasts a family friendly gathering area, seating up to 25 people to your barbecue feast under the covered pavilion. Enjoy this full outdoor...

    Pool Hot Tub

    $145 to $244/night

  17. CONDOMINIUM
    Waiohuli Beach Hale #A-203

    Waiohuli Beach Hale #A-203

    Kihei, HI

    Waiohuli Beach Hale is a small oceanfront complex located in Kihei Maui Hawaii. This property has a great aloha feeling with a relaxed and quiet atmosphere. Each unit is steps from the ocean and is centrally located to great shopping, restaurants,...

    Pool

    $208 to $255/night

  18. CONDOMINIUM
    Kamaole Sands #2-301

    Kamaole Sands #2-301

    Kihei, HI

    Unit #2-301 is a large 1,036 sq ft. two-bedroom two-bath single-level end unit on the third floor. There is A/C in the living room and ceiling fans throughout, a fully-equipped kitchen with all new appliances and counter top, washer/dryer,...

    Pool

    $244 to $441/night

  19. CONDOMINIUM
    Kihei Alii Kai #C-306

    Kihei Alii Kai #C-306

    Kihei, HI

    The Kihei Alii Kai complex is across South Kihei Road from Kamaole Beach Park I, right in the heart of Kihei. From the complex, you're just a quick stroll from favorite restaurants, shopping, and world class beaches. On the grounds there is a large...

    Pool

    $133 to $226/night

  20. CONDOMINIUM
    Honua Kai #316

    Honua Kai #316

    Lahaina, HI

    This couples and family friendly resort is located on the exquisite Kaanapali Beach!  Enjoy  extraordinary dining, shopping, and top of the line amenities at our 4 diamond property. The resort has 3 large pools, 5 hot tubs and a spa! The FORMAL...

    Pool Hot Tub

    $328 to $474/night

  21. CONDOMINIUM
    B-109: Hale Nani Ikena Kai Ko Olina Beach Villa

    B-109: Hale Nani Ikena Kai Ko Olina Beach Villa

    Kapolei, HI

    The Hale Nani Ikena Kai beach villa at Ko Olina offers exactly what its name suggests; a home with a “Beautiful Ocean View”. Spectacular direct whitewater ocean and beach views will be what greets you at this upscale, luxurious ground floor...

    Pool Hot Tub

    $856 to $2,016/night

  22. HOUSE
    Rainbow Hale Estate

    Rainbow Hale Estate

    Lahaina, HI

    Maui's Premier Vacation Home! Rainbow Hale Estate Kaanapali! Family Retreat, Private Honeymoon Retreat! Surrounded by 5 acres of Maui tropical plantation, lies a BRAND NEW spectacular estate you've always dreamed of, with the lifestyle you've always...

    Pool

    $1,661 to $2,429/night

  23. CONDOMINIUM
    Papakea E304

    Papakea E304

    Lahaina, HI

    Highly upgraded West Maui Ka’anapali Papakea Studio, 1 full bathroom, third floor condo, with fantastic ocean, sunset, pool and garden views. SLEEPS 4! Watch the whales, sunsets, and the ocean from the kitchen, living room and lanai. Sleep to the...

    Pool

    $166 to $252/night

  24. CONDOMINIUM
    Papakea G206

    Papakea G206

    Lahaina, HI

    Brand new washer and dryer. Brand new refrigerator. Brand new living room carpet. Enjoy the ocean view from this cozy condo. It has a remodeled kitchen with granite counter tops. Fully stocked with dishes, glassware, small appliances, and...

    Pool

    $252 to $387/night

  25. CONDOMINIUM
    Milowai 303 (1-Bedroom Condo)

    Milowai 303 (1-Bedroom Condo)

    Maalaea, HI

    Milowai #303 is registered as a Transient Accommodation Owner Registration I.D. GE/TA114-450-0224-02 Exceptional brand new remodel! Prime Ocean Front at the Milowai Complex in the quaint harbor village of Maalaea (the most central location to all...

    Pool

    $260/night

  26. CONDOMINIUM
    Kihei Bay Vista #D-202

    Kihei Bay Vista #D-202

    Kihei, HI

    Located across the street from Kalepolepo Beach and the Pacific Whale Sanctuary in Kihei Maui, the Kihei Bay Vista is a great property. It is just steps from a long sandy walking beach. It has a pool and hot tub, gas grills for your use as well as...

    Pool

    $126 to $231/night

  27. CONDOMINIUM
    Wailea Ekolu #105

    Wailea Ekolu #105

    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

    $307 to $534/night

  28. CONDOMINIUM
    Wailea Ekolu #501

    Wailea Ekolu #501

    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

    $261 to $521/night

  29. CONDOMINIUM
    Kamaole Sands #8-104

    Kamaole Sands #8-104

    Kihei, HI

    Kamaole Sands is the premiere property in South Kihei. Located across the street from Kamaole Beach Park III.  A 2 minute walk from the beach park and a 2 minute drive to  the Shops at Wailea, golf courses, and dining makes Kamaole Sands a great...

    Pool

    $150 to $289/night

  30. CONDOMINIUM
    Luana Kai #C-103

    Luana Kai #C-103

    Kihei, HI

    Luana Kai is a large oceanfront complex in Kihei. It is centrally located to shops, activities and restaurants. It features a large oceanfront pool, hot tub, shuffleboard and gas grills for your use. There is an expansive lawn between the buildings...

    Pool

    $157 to $203/night