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
    Kihei Akahi #D-412

    Kihei Akahi #D-412

    Kihei, HI

    Kihei Akahi has a great location as it is just a short walk to Kamaole Beach II and it is moderately priced. Each unit has a private lanai, washer and dryer, AC in the living room and ceiling fans throughout. It also has cable TV and high speed...

    Pool
    FREE CANCELLATION

    $133 to $231/night

  2. CONDOMINIUM
    Kihei Kai Nani #2-210

    Kihei Kai Nani #2-210

    Kihei, HI

    Kihei Kai Nani is located right across from the world renowned Kamaole Beach #2. This gorgeous beach is famous for its long sandy shoreline, clean clear water for snorkeling, and great body surfing. Whale watch, paddle board, walk the beach and...

    Pool
    FREE CANCELLATION

    $128 to $208/night

  3. CONDOMINIUM
    Waiohuli Beach Hale #D-119

    Waiohuli Beach Hale #D-119

    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
    FREE CANCELLATION

    $157 to $277/night

  4. CONDOMINIUM
    Maui Kamaole #D-109

    Maui Kamaole #D-109

    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

    $168 to $354/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
    FREE CANCELLATION

    $128 to $208/night

  6. CONDOMINIUM
    Grand Champions #50

    Grand Champions #50

    Wailea, HI

    The nearby Ulua and Mokapu Beaches are a quick drive down the hill from 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 pools,...

    Pool
    FREE CANCELLATION

    $231 to $347/night

  7. CONDOMINIUM
    Waiohuli Beach Hale #D-118

    Waiohuli Beach Hale #D-118

    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
    FREE CANCELLATION

    $157 to $277/night

  8. CONDOMINIUM
    Wailea Ekolu #406

    Wailea Ekolu #406

    Wailea, HI

    If you love sitting on a large, comfortable lanai and luxuriating in multi-million dollar views with the most amazing sunsets imaginable, there is no better place for you than Wailea Ekolu 406! This unit offers one of the best views in the entire...

    Pool
    FREE CANCELLATION

    $296 to $521/night

  9. 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...

    Pool
    FREE CANCELLATION

    $133 to $226/night

  10. CONDOMINIUM
    Palms at Wailea #1902

    Palms at Wailea #1902

    Wailea, HI

    Enjoy your stay in paradise at The Palms at Wailea, a gorgeous property with lush, tropical landscaping and expansive lawn areas. The complex is conveniently located within short walking distance of popular restaurants, shops, and a spectacular...

    Pool Hot Tub
    FREE CANCELLATION

    $284 to $458/night

  11. CONDOMINIUM
    Kamaole Sands #7-408

    Kamaole Sands #7-408

    Kihei, HI

    Kamaole Sands is the premiere property in South Kihei. Kamaole Sands is located across the street from Kamaole Beach III. Whale watch, swim, snorkel, walk miles on the beach and watch the most amazing sunsets imaginable. There are 15 acres of lush...

    Pool Hot Tub
    FREE CANCELLATION

    $231 to $429/night

  12. CONDOMINIUM
    Waiohuli Beach Hale #D-225

    Waiohuli Beach Hale #D-225

    Kihei, HI

    Waiohuli Beach Hale #D-225 is a completely remodeled second floor oceanfront, ocean view 1 bedroom, 1 bath condo. It is just steps from the ocean. It has a full kitchen, window unit air conditioning in the bedroom only, 2 flat screen TVs, DVD, high...

    Pool
    FREE CANCELLATION

    $162 to $289/night

  13. CONDOMINIUM
    Wailea Elua #207

    Wailea Elua #207

    Kihei, HI

    The Wailea Elua is the premier ocean front property in Wailea. Situated right on Ulua Beach, it has one of the best locations in Wailea. There are miles of spectacular walking paths that follow the ocean In addition the property has two swimming...

    Pool Hot Tub
    FREE CANCELLATION

    $464 to $725/night

  14. 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...

    Pool Hot Tub
    FREE CANCELLATION

    $231 to $563/night

  15. CONDOMINIUM
    Kamaole Sands #10-312

    Kamaole Sands #10-312

    Kihei, HI

    Kamaole Sands is the premiere property in South Kihei. Located across the street from Kamaole Beach 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 Hot Tub
    FREE CANCELLATION

    $174 to $348/night

  16. 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
    FREE CANCELLATION

    $244 to $441/night

  17. CONDOMINIUM
    Luana Kai #B-203

    Luana Kai #B-203

    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...

    Pool Hot Tub
    FREE CANCELLATION

    $173 to $324/night

  18. 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

    $186 to $494/night

  19. HOUSE
    Ocean Tree House w/ Lanai & Yard- Walk to Beach

    Ocean Tree House w/ Lanai & Yard- Walk to Beach

    Kailua, HI

    Located in the upscale neighborhood of Lanikai, this 3BR/2BA is affectionately named Ocean Tree House and is within strolling distance to Lanikai Beach — regarded as one of the world's most beautiful top beaches, with its flour-soft white sands,...

    FREE CANCELLATION

    $485 to $803/night

  20. CONDOMINIUM
    Keauhou Kona Surf & Racquet Club #5-104

    Keauhou Kona Surf & Racquet Club #5-104

    Kailua Kona, HI

    Keauhou Kona Surf & Racquet Club#5-104 DIRECT OCEANFRONT, BEST GROUND FLOOR CORNER! REMODELED! AMAZING PROPERTY AIR CONDITIONING INSTALLED AS OF NOVEMBER 2017!! BRAND NEW SPLIT AC UNITS INSTALLED IN LIVING ROOM, & BOTH BEDROOMS!! RARE & PHENOMENAL...

    Pool
    FREE CANCELLATION

    $453 to $467/night

  21. CONDOMINIUM
    Waikoloa Beach Villas O2

    Waikoloa Beach Villas O2

    Waikoloa, HI

    Come enjoy the beauty of Hawaii in our perfectly located condo at Waikoloa Beach Villas. Just 20 minutes north of the Kona airport you will find yourself in paradise! Our property is perfect for 2 couples or a family of four. Decorated to honour...

    Pool Hot Tub
    FREE CANCELLATION

    $234 to $478/night

  22. CONDOMINIUM
    Kamaole Sands #4-201

    Kamaole Sands #4-201

    Kihei, HI

    Kamaole Sands is the premiere property in South Kihei. Located across the street from Kamaole Beach 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 Hot Tub
    FREE CANCELLATION

    $197 to $406/night

  23. 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
    FREE CANCELLATION

    $197 to $377/night

  24. CONDOMINIUM
    Villas on the Prince 34

    Villas on the Prince 34

    Princeville, HI

    NOTE: 30-DAY MINIMUM STAY AT THIS LOCATION. Villas on the Prince 34 is a spacious luxury town house with pool and easy walking distance to Anini Beach and Princeville shopping. This beautifully cared for villa has 3 bedrooms and 2 1/2 baths. Two...

    Pool Hot Tub
    FREE CANCELLATION

    $164 to $183/night

  25. CONDOMINIUM
    Hale Mahina Unit #A-201

    Hale Mahina Unit #A-201

    Lahaina, HI

    Hale Mahina Beach Resort, West Maui Hale Mahina (House of the Moon) is located on the world famous West Coast of Maui adjacent to the West Maui Mountains, nestled between Kaanapali and Kapalua in the charming oceanfront town of Honokowai. Hale...

    $302 to $560/night

  26. CONDOMINIUM
    Kihei Beach Unit #508

    Kihei Beach Unit #508

    Kihei, Maui, HI

    Enjoy stunning views from this peaceful 5th floor condo - look out to over Sugar Beach to Maalaea Bay to views of Molokini, Lanai and Kahoolawe and regularly see whales from the lanai during whale season! This open-plan one bedroom, one bathroom...

    $185 to $309/night

  27. CONDOMINIUM
    Lower Honoapiilani Condo 1 Bedroom Sleeps 2

    Lower Honoapiilani Condo 1 Bedroom Sleeps 2

    Lahaina, HI

    Oceanfront! Awesome oceanfront views from this paradise condo. Just feet away from swimming with sea turtles or snorkeling. Heated saline pool right outside your private lanai surrounded by tropical grounds and gardens. The community is a low...

    Pool
    FREE CANCELLATION

    $280 to $330/night

  28. CONDOMINIUM
    Hale Kamaole #201

    Hale Kamaole #201

    Kihei, HI

    Kamaole Beach #3 is just across the street from Hale Kamaole. This beach is one of the best beaches in the world. Whale watch, snorkel, walk the beach and witness the most amazing sunsets imaginable. Hale Kamaole features two pool areas, charcoal...

    Pool
    FREE CANCELLATION

    $277 to $335/night

  29. CONDOMINIUM
    Waiohuli Beach Hale #D-114

    Waiohuli Beach Hale #D-114

    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
    FREE CANCELLATION

    $151 to $277/night

  30. CONDOMINIUM
    Wailea Ekolu #105

    Wailea Ekolu #105

    Wailea, 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

    $307 to $534/night