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
    Kamaole Sands 06-405

    Kamaole Sands 06-405

    KIHEI, HI

    You will not be disappointed! This well-appointed two bedroom garden view condo has been remodeled and has new furnishings throughout. The main floor bedroom has two twin beds and there is a full bath located just outside the bedroom. The loft...

    Pool
    FREE CANCELLATION

    $377 to $470/night

  2. CONDOMINIUM
    Maui Kamaole i-111

    Maui Kamaole i-111

    KIHEI, HI

    Ground floor condo with one (1) bedroom and two (2) bathrooms. There is a king bed in the bedroom and a full bathroom ensuite and a pull out sofa bed in the living room, which allows this condo to accommodate up to four (4) people. The kitchen...

    Pool
    FREE CANCELLATION

    $311 to $401/night

  3. CONDOMINIUM
    Kamaole Sands 08-411

    Kamaole Sands 08-411

    KIHEI, HI

    Beautiful Ocean View Unit in Building 8! With recent updates and renovations to the fully equipped kitchen, this unit is our ideal vacation rental condo. The unit allows for 6 guests with a King bed in the upstairs loft, 2 twins in the main level...

    Pool
    FREE CANCELLATION

    $400 to $494/night

  4. CONDOMINIUM
    Kauhale Makai 605

    Kauhale Makai 605

    Kihei , HI

    Please note: Kauhale Makai is undergoing exterior building maintenance. Newly Renovated One bedroom Ocean View Condo. This unit has been completely renovated from the ground up. The kitchen and bathroom have both been renovated. The kitchen features...

    Pool
    FREE CANCELLATION

    $265 to $319/night

  5. CONDOMINIUM
    Sugar Beach 605

    Sugar Beach 605

    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
    FREE CANCELLATION

    $297 to $402/night

  6. CONDOMINIUM
    Kamaole Sands 10-410

    Kamaole Sands 10-410

    KIHEI, HI

    Enjoy ocean views from this fourth floor, two bedroom condo. This unit sleeps up to six (6) people with a King Bed with a Simmons Beauty Rest mattress in the master bedroom loft, two twins that can convert into a King in the second bedroom and a...

    Pool
    FREE CANCELLATION

    $400 to $494/night

  7. CONDOMINIUM
    Maui Kamaole i-212

    Maui Kamaole i-212

    Kihei, HI

    Enjoy Ocean Views from this second floor condo featuring two bedrooms and two bathrooms. The master bedroom is located in the loft and has a king bed and a full bathroom ensuite. The second bedroom is located on the main floor and has two (2) twin...

    Pool
    FREE CANCELLATION

    $448 to $560/night

  8. CONDOMINIUM
    Nani Kai Hale 208

    Nani Kai Hale 208

    KIHEI, HI

    Enjoy Ocean views in this large one bedroom condo located at the Nani Kai Hale in North Kihei. The fully equipped kitchen is open to the living area creating a large open living space. The bedroom has a king bed and the living room has a sofa bed,...

    Pool
    FREE CANCELLATION

    $250 to $335/night

  9. CONDOMINIUM
    Kihei Akahi C-109

    Kihei Akahi C-109

    KIHEI, HI

    Bright and open One bedroom garden view condo located on the ground floor. This unit sleeps up to four people with a king bed in the bedroom and a pull out sofa bed in the living room. There is a fully equipped kitchen, perfect for enjoying meals in...

    Pool
    FREE CANCELLATION

    $246 to $304/night

  10. CONDOMINIUM
    Kamaole Sands 03-407

    Kamaole Sands 03-407

    Kihei, HI

    Large two bedroom loft, Garden view Condo. Feel right at home in this spacious condo overlooking the pool and beautifully manicured green way. There is a King bed in the loft bedroom, two twins in the second bedroom, and a sofa bed in the living...

    Pool
    FREE CANCELLATION

    $377 to $470/night

  11. CONDOMINIUM
    Kihei Akahi C-401

    Kihei Akahi C-401

    KIHEI, HI

    Welcome cool ocean breezes and incredible ocean views from this newly renovated studio condo. Astonishing sunset views from the lanai. Enjoy all the comforts and amenities of home, including a full kitchen and bath with washer and dryer. Your condo...

    Pool
    FREE CANCELLATION

    $216 to $273/night

  12. CONDOMINIUM
    Kauhale Makai 312

    Kauhale Makai 312

    KIHEI, HI

    Please note: Kauhale Makai is undergoing exterior building maintenance. Enjoy Ocean Views from the living room and master bedroom in this two bedroom condo. Relax on the lanai each evening and watch the Maui sun set over the Pacific Ocean. The...

    Pool
    FREE CANCELLATION

    $304 to $382/night

  13. CONDOMINIUM
    Kahana Reef 314

    Kahana Reef 314

    LAHAINA, HI

    **Kahana Reef is currently undergoing construction to the South-end of the Seawall, now through November 2018.The seawall construction is not taking place in front of this unit, but there will be residual noise. This unit is available to rent, but...

    Pool
    FREE CANCELLATION

    $289 to $335/night

  14. 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 been recently renovated with all new furnishings. It has a fully equipped kitchen, washer and dryer, room AC in each room as well as...

    Pool Hot Tub
    FREE CANCELLATION

    $377 to $725/night

  15. CONDOMINIUM
    Kauhale Makai 122

    Kauhale Makai 122

    Kihei, HI

    Please note: Kauhale Makai is undergoing exterior building maintenance. Spacious and comfortable describe this ground floor condo with a beautiful garden view and partial ocean/mountain views. This unit, which sleeps 4, boasts a fully equipped...

    Pool
    FREE CANCELLATION

    $250 to $304/night

  16. CONDOMINIUM
    Kihei Surfside 412

    Kihei Surfside 412

    Kihei, HI

    Completely remodeled condo, from top to bottom. Nothing has been overlooked in this beautifully appointed one bedroom Ocean Front condo. This stunning renovation, features top of the line materials including granite counter tops in kitchen and...

    Pool
    FREE CANCELLATION

    $361 to $473/night

  17. CONDOMINIUM
    Sugar Beach 133

    Sugar Beach 133

    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
    FREE CANCELLATION

    $334 to $438/night

  18. HOUSE
    Hale Ola Kai

    Hale Ola Kai

    Hanalei, HI

    Hale Ola Kai is a three bedroom, two and a half bath home located near world famous Hanalei Bay. The house is a comfortable family-style home. Casual, yet equipped with anything you need to make your stay in Hanalei perfect. Two of the bedrooms have...

    $613 to $842/night

  19. HOUSE
    525 Emmalani Court

    525 Emmalani Court

    Princeville, HI

    Emmalani Court #525 Walk to the Princeville St Regis!  Beautiful Ocean View Air-Conditioned unit and just a short walk to the beach. Emmalani Court is a small, quiet condominium complex located near the St Regis Hotel in Princeville and the...

    Pool Hot Tub

    $268 to $345/night

  20. CONDOMINIUM
    Grand Champions 089

    Grand Champions 089

    Wailea, HI

    Remodeled two bedroom condo at Wailea Grand Champions with fabulous views of the golf course. This condo completed renovations in November 2016 and features a completely renovated Kitchen and bathrooms and new furnishings. The Kitchen has new...

    Pool Hot Tub
    FREE CANCELLATION

    $448 to $559/night

  21. CONDOMINIUM
    Royal Mauian 204

    Royal Mauian 204

    KIHEI, HI

    This is the condo you have been looking for. Completely remodeled condo with incredible ocean views. From the flooring to the ceiling and everything in between, this remodeled condo is truly paradise. The new granite counter tops complement the new...

    Pool
    FREE CANCELLATION

    $417 to $519/night

  22. CONDOMINIUM
    Maui Parkshore #303

    Maui Parkshore #303

    Kihei, HI

    Open air living at it's finest! The living area completely opens up to the lanai and offers views of the Pacific Ocean and the center courtyard of the property. The breakfast bar provides additional eating space. The fully equipped kitchen is...

    Pool
    FREE CANCELLATION

    $289 to $343/night

  23. CONDOMINIUM
    Maui Sunset B402

    Maui Sunset B402

    Kihei, HI

    Gorgeously updated 1 bedroom with AC- right on the beach! This unit has 2 full bathrooms, a great kitchen, a lanai with ocean view, and it sleeps 4. Imagine taking a stroll down the beach, drink in hand, and soaking up the warm Hawaiian sun. This is...

    Pool
    FREE CANCELLATION

    $186 to $374/night

  24. CONDOMINIUM
    O-805: Hale Makai Ko Olina Beach Villa

    O-805: Hale Makai Ko Olina Beach Villa

    Kapolei, HI

    Overview: This 3 BD, 2.5 BA luxury villa on the 8th floor of the Ocean Tower has stunning direct ocean views and is conveniently located just 20 miles from Honolulu International Airport on the beautiful southwestern shores of Oahu. The four...

    Pool Hot Tub

    $473 to $768/night

  25. CONDOMINIUM
    B-708: Hale Leilani Ko Olina Beach Villa

    B-708: Hale Leilani Ko Olina Beach Villa

    Kapolei, HI

    This 2bd, 2ba luxury oceanfront villa sleeps 4-6 and is located steps away from the pristine and relaxing beaches, lagoons, pools and jacuzzis. Close to shops, dining, golf and a variety of outdoor activities. Why ko olina? If you haven't been to...

    Pool

    $485 to $710/night

  26. CONDOMINIUM
    O-704 Hale Lau Wai Ko Olina Beach Villa

    O-704 Hale Lau Wai Ko Olina Beach Villa

    Kapolei, HI

    Enjoy direct ocean-facing views and beautiful garden and pool area views from this luxury Beach Villa at Ko'Olina. This well-appointed 1,171 square foot 2 bedroom 2 bathroom 7th floor Beach Villa has direct ocean views overlooking the lap pool and...

    Pool

    $427 to $664/night

  27. CONDOMINIUM
    Maui Kamaole #J-103

    Maui Kamaole #J-103

    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

    $196 to $342/night

  28. CONDOMINIUM
    Kamaole Sands #3-402

    Kamaole Sands #3-402

    Kihei, HI

    Unit 3-402 is a top floor Two bedroom, Two bath condo in Kamaole Sands is located in Preferred Building 3. It has Ocean, Garden and Pool views. Tile flooring from the entry through the living room to the lanai gives a fresh feeling. The Living room...

    Pool Hot Tub
    FREE CANCELLATION

    $219 to $347/night

  29. CONDOMINIUM
    Kamaole Sands #7-304

    Kamaole Sands #7-304

    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

    $347 to $347/night

  30. 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
    FREE CANCELLATION

    $162 to $365/night