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
    Wailea Grand Champion, #148

    Wailea Grand Champion, #148

    Wailea, HI

    Wailea Grand Champions Golf Villas is a modern property located between the Wailea Blue Golf Course and the Wailea Tennis Club. This quiet low density development consists of twenty mostly two-story buildings set amongst lush tropical landscaping...

    Pool Hot Tub

    $201 to $549/night

  2. CONDOMINIUM
    WAILEA ELUA, #1402^

    WAILEA ELUA, #1402^

    Wailea, HI

    Wailea Elua Village is an exclusive beachfront property located in the heart of the resort community of Wailea. This relaxing low-density property consists of two-story buildings terraced over twenty-four acres of immaculate tropical landscaping....

    Pool

    $448 to $896/night

  3. CONDOMINIUM
    Palms at Wailea #2205

    Palms at Wailea #2205

    Kihei, HI

    We are pleased that our properties at the Palms at Wailea have been chosen to be featured in the number 1 selling book "Maui Revealed" and their website. These properties were chosen because of their superior quality and great rates! The fabulous...

    Pool Hot Tub
    FREE CANCELLATION

    $363 to $747/night

  4. CONDOMINIUM
    Kamaole Sands #10-205

    Kamaole Sands #10-205

    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

    $213 to $383/night

  5. CONDOMINIUM
    Maui Kamaole #A-102

    Maui Kamaole #A-102

    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

    $237 to $490/night

  6. CONDOMINIUM
    Mahana Resort #1017

    Mahana Resort #1017

    Lahaina, HI

    Outstanding ocean front views on North Ka'anapali beach. Enjoy heavenly sunsets from your living room AND bedroom. This condo has been totally remodeled and is tastefully decorated with an island style theme. The kitchen has granite counter tops and...

    Pool
    FREE CANCELLATION

    $290 to $606/night

  7. HOUSE
    1 Bedroom Corner Oceanfront #701

    1 Bedroom Corner Oceanfront #701

    Kaanapali, HI

    Our One Bedroom Corner unit is spacious and well-appointed with a King Bed in the bedroom and a Queen sofa bed in the living room. There is seating arrangements for relaxing and dining. You will find plenty of space to store your clothing and...

    Pool Hot Tub
    FREE CANCELLATION

    $372 to $444/night

  8. HOUSE
    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

  9. HOUSE
    Best Rate- 1 Bedroom Corner Oceanfront 12

    Best Rate- 1 Bedroom Corner Oceanfront 12

    Kaanapali, HI

    One Bedroom Corner - King Bed, NO sofa bed, enclosed lanai which makes the unit , Flat screen TV - hardwood floors; Livingroom is tiled in white. This condo will accommodate a maximum of two people, four with queen areo bed as extra bedding. The...

    Pool Hot Tub
    FREE CANCELLATION

    $351 to $423/night

  10. CONDOMINIUM
    Wailea Ekolu #310

    Wailea Ekolu #310

    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

    $302 to $534/night

  11. HOUSE
    1 Bedroom Oceanfront #404

    1 Bedroom Oceanfront #404

    Kaanapali, HI

    One Bedroom - Flat screen TV ; King bed, 2 Twins on lanai. (NO SOFA BED) This unit is part of the Maui Kai Condos a Lahaina hotel located on the Kaanapali Beach less than one mile from the Kapalua West Maui Airport. This unit features an heated...

    Pool Hot Tub
    FREE CANCELLATION

    $341 to $413/night

  12. CONDOMINIUM
    Maui Kamaole #G-101

    Maui Kamaole #G-101

    Kihei, HI

    Kamaole Beach Park 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 and...

    Pool Hot Tub
    FREE CANCELLATION

    $197 to $412/night

  13. CONDOMINIUM
    Maui Kamaole #G-107

    Maui Kamaole #G-107

    Kihei, HI

    Kamaole Beach Park 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 and...

    Pool Hot Tub
    FREE CANCELLATION

    $249 to $515/night

  14. CONDOMINIUM
    Kaanapali Royal #C101

    Kaanapali Royal #C101

    Lahaina, HI

    Golf course views on the Ka'anapali Golf course. There are stairs only to this entrance-no elevators. 3 stairs lead down to living room and to master bedroom. In addition to the TV in the living room there is also a TV, DVD player and VCR in the...

    Pool
    FREE CANCELLATION

    $284 to $600/night

  15. CONDOMINIUM
    Maui Kamaole #J-120

    Maui Kamaole #J-120

    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 Hot Tub
    FREE CANCELLATION

    $191 to $347/night

  16. HOUSE
    Junior Suite Oceanfront #1006

    Junior Suite Oceanfront #1006

    Lahaina, HI

    {Jr. Suite (Studio) - King bed; Flat screen TV; extended lanai} MAUI KAI 1006 This oceanfront junior suite is a bright, airy unit decorated in light tones, pale off-white tile in the kitchen and bath, with carpet in the center living area of the...

    Pool Hot Tub
    FREE CANCELLATION

    $278 to $341/night

  17. CONDOMINIUM
    Papakea #H103

    Papakea #H103

    Lahaina, HI

    Welcome to: "Tranquility Maui Condo" This charming 2 bedroom Papakea condominium is located in "H" building near ponds and gardens. Great views from the beach and off to the neighbor islands of Lanai and Molokai. Tastefully decorated with Hawaiian...

    Pool
    FREE CANCELLATION

    $278 to $580/night

  18. CONDOMINIUM
    Maui Kaanapali Villas #B233

    Maui Kaanapali Villas #B233

    Lahaina, HI

    Remodeled! Garden and resort views at this 1 bedroom-loft style condo in the Banyan Building at the beautiful Ocean front resort of Maui Kaanapali Villas. Our condo is nicely updated and furnished. Watch your favorite DVD on the 42 flat screen TV...

    Pool
    FREE CANCELLATION

    $296 to $447/night

  19. CONDOMINIUM
    Kaanapali Shores #916

    Kaanapali Shores #916

    Lahaina, HI

    Remodeled with ocean views in Ka'anapali, this condo is well equipped, thoughtfully decorated and a perfect place for a family. Bring your DVD's from home and watch them in the living room and guest bedroom. There's also a TV in the master bedroom....

    Pool
    FREE CANCELLATION

    $284 to $706/night

  20. CONDOMINIUM
    Lahaina Shores #531

    Lahaina Shores #531

    Lahaina, HI

    5th floor direct ocean front views from our studio unit #531 at the Beach Front Resort: Lahaina Shores. Brand new to our program! Full size kitchen, tiled walk-in shower and a cozy king size bed. Did I mention the views? Breathtaking! Central AC...

    Pool
    FREE CANCELLATION

    $273 to $447/night

  21. CONDOMINIUM
    Kaanapali Royal #A303

    Kaanapali Royal #A303

    Lahaina, HI

    Kaanapali Royal #A303: Fully remodeled (as of 2015) included tile floors throughout, new furniture, new kitchen with bright and shiny new appliances including washer and dryer. Large lanai features wet bar with sink. Master suite upstairs features a...

    Pool
    FREE CANCELLATION

    $267 to $600/night

  22. CONDOMINIUM
    Papakea #A105

    Papakea #A105

    Lahaina, HI

    Remodeled with ocean front views on the ground floor in North Ka'anapali. Sleeping accommodations will allow for a maximum of two people only. A window air conditioner in the living room cools the entire condo. The bathroom features a walk-in...

    Pool
    FREE CANCELLATION

    $186 to $459/night

  23. CONDOMINIUM
    Maui Kaanapali Villas #C152

    Maui Kaanapali Villas #C152

    Lahaina, HI

    Garden views from the ground floor in North Ka'anapali. The condo has a cool tropical theme with tile throughout. A fully equipped galley kitchen. Bring your laptop and surf free wireless internet access from anywhere in the condo. Listen to your...

    Pool
    FREE CANCELLATION

    $191 to $331/night

  24. CONDOMINIUM
    Maui Kaanapali Villas #B242

    Maui Kaanapali Villas #B242

    Lahaina, HI

    Garden views in North Ka'anapali. This remodeled second floor condo has stairs to its entrance, no elevators. Bring your laptop and enjoy free wireless internet access from anywhere in the condo. Bring your CD's from home and listen on the player...

    Pool
    FREE CANCELLATION

    $215 to $331/night

  25. CONDOMINIUM
    Valley Isle #1209

    Valley Isle #1209

    Lahaina, HI

    Enjoy this relaxed ocean front Hawaiian style condo on Kahana Bay. Watch spectacular views of both Molokai , Lanai & Sunsets. Feel the tropical breezes off of the ocean. Smell the fragrant flowers, dip your toes in the warm island waters. Now...

    FREE CANCELLATION

    $232 to $669/night

  26. CONDOMINIUM
    Maui Kaanapali Villas #B133

    Maui Kaanapali Villas #B133

    Lahaina, HI

    Garden and resort views at this studio condo in the Banyan Building at the beautiful Ocean front resort of Maui Kaanapali Villas. Our condo is nicely updated and furnished. Watch your favorite DVD on the 42" flat screen TV. Beach chairs, boogie...

    Pool
    FREE CANCELLATION

    $232 to $406/night

  27. CONDOMINIUM
    Maui Kaanapali Villas #C255

    Maui Kaanapali Villas #C255

    Lahaina, HI

    Partial Ocean View 2nd floor studio condo in the Coconut Bldg in the beautiful Maui Kaanapali Villas. Tastefully furnished with remodeled kitchen and bathroom include custom cabinetry and granite and wall mounted hair dryer. Stairs to entrance, no...

    Pool
    FREE CANCELLATION

    $209 to $354/night

  28. CONDOMINIUM
    Royal Kahana #319

    Royal Kahana #319

    Lahaina, HI

    3rd floor vacation rental on Kahana Bay with ocean views at The Royal Kahana Resort. This condo has a king size bed and twin sofa sleeper for your comfort. It is a fully equipped condo with a complete kitchen. Enjoy a new flat screen LCD TV and DVD...

    Pool
    FREE CANCELLATION

    $122 to $406/night

  29. CONDOMINIUM
    Kamaole Sands #2-306

    Kamaole Sands #2-306

    Kihei, HI

    Kamaole Sands is the premiere property in South Kihei, located across the street from Kamaole Beach Park III. Whale watch, swim and 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

    $196 to $347/night

  30. CONDOMINIUM
    Grand Champions #143

    Grand Champions #143

    Wailea, HI

    Unit 143 at the Wailea Grand Champions is a RARE 3 bedroom 2 bath unit with magnificent golf course views. It has a fully equipped kitchen, washer and dryer, room air conditioning in each room as well as ceiling fans throughout.Same day bookings...

    Pool Hot Tub
    FREE CANCELLATION

    $458 to $748/night