RedAwning has 300 South Maui vacation rentals which all include instant online booking and no security deposits, to make your trip easy and stress-free! On this beautiful region of the island, in addition to relaxing on the pristine beaches, such as Wailea, there are plenty of fun activities to partake in, such as surfing in Makena State Park, snorkeling at Maalaea Harbor, joining the Maui Sun Divers to learn how to scuba dive, or going on a Blue Water Rafting snorkel cruise. Book your stay today!

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  1. CONDOMINIUM
    401 Punahoa Condominium

    401 Punahoa Condominium

    Kihei, HI

    1 bedroom Penthouse unit! Since all Punahoa Beach condos are individually owned, each is decorated in its own island-style and all have an ocean front lanai perfect for your own outdoor dining above the Pacific. "All Units Are Non-smoking"...

    $198 to $411/night

  2. CONDOMINIUM
    402 Punahoa Condominium

    402 Punahoa Condominium

    Kihei, HI

    1 bedroom Penthouse condo. Since all Punahoa Beach condos are individually owned, each is decorated in its own island-style and all have an ocean front lanai perfect for your own outdoor dining above the Pacific. "All Units Are Non-smoking"...

    $198 to $411/night

  3. CONDOMINIUM
    204 Punahoa Condominium

    204 Punahoa Condominium

    Kihei, HI

    Oceanfront studio! Since all Punahoa Beach condos are individually owned, each is decorated in its own island-style and all have an ocean front lanai perfect for your own outdoor dining above the Pacific. Our studios feature a real pull down Queen...

    $114 to $287/night

  4. CONDOMINIUM
    302 Punahoa Condominium

    302 Punahoa Condominium

    Kihei, HI

    Oceanfront 1 bedroom condo! Since all Punahoa Beach condos are individually owned, each is decorated in its own island-style and all have an ocean front lanai perfect for your own outdoor dining above the Pacific. "All Units Are Non-smoking"...

    $144 to $382/night

  5. CONDOMINIUM
    Kihei Akahi C-616

    Kihei Akahi C-616

    Kiehi, HI

    Imagine yourself sitting on the lanai with a drink in hand, watching the gorgeous colors of the Hawaiian sunset! This is a perfect budget getaway. Come explore the island! See gorgeous beaches, taste the island cuisine, shop the local businesses and...

    Pool
    FREE CANCELLATION

    $173 to $603/night

  6. VILLA
    Luxury 3bed/3bath Hideaway

    Luxury 3bed/3bath Hideaway

    Kihei, HI

    Lele Hideaway is a three bedroom, 3 bath two-level condominium suite. Two bedrooms each have a full bathroom and are located on the ground floor. The third bedroom is located below ground level, down a spiral staircase from the living room. The...

    Pool Hot Tub

    $579 to $984/night

  7. 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, air conditioning in the bedroom only, 2 flat screen TVs, DVD, high speed...

    Pool
    FREE CANCELLATION

    $162 to $289/night

  8. 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
    FREE CANCELLATION

    $150 to $289/night

  9. CONDOMINIUM
    Waiohuli Beach Hale #C-111

    Waiohuli Beach Hale #C-111

    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

    $232 to $394/night

  10. CONDOMINIUM
    Hale Kamaole #341

    Hale Kamaole #341

    Kihei, HI

    Fabulous Ocean and Garden View – one the BEST views on the property. New wood flooring in living room! King bed in master bedroom, loft has hide a bed. Downstairs bedroom has new furniture with queen bed. No hide a bed in living room. Kitchen &...

    Pool
    FREE CANCELLATION

    $269 to $379/night

  11. CONDOMINIUM
    Kihei Kai Nani- Unit 341

    Kihei Kai Nani- Unit 341

    Kihei, HI

    Beautiful garden and partial ocean view upgraded condo. Clean, comfortable and plenty of natural light. Property Info 1 Br/1 Ba | Sleeps 4 | 621 SF Garden and partial ocean view. pgraded condo with window AC in the livng room This lovely third...

    Pool
    FREE CANCELLATION

    $127 to $276/night

  12. CONDOMINIUM
    Kihei Akahi Resort- Unit C618

    Kihei Akahi Resort- Unit C618

    Kihei, HI

    Charming ocean and garden view top floor upgraded artist home. Kathy McCartney owns popular C618 located on the top floor of building C at the Kihei Akahi Resort. Enjoy spectacular views of the Pacific Ocean, Mount Haleakala, Kaho'olawe Island,...

    FREE CANCELLATION

    $127 to $328/night

  13. CONDOMINIUM
    Kihei Akahi Resort- Unit D605

    Kihei Akahi Resort- Unit D605

    Kihei, HI

    Panoramic ocean views! Top Floor Luxury Pent House - Building D. Penthouse Suite D605 - Luxury One Bedroom One Bath 655 sq. ft. located on the top floor, the 6th floor, in building D. Enjoy spectacular PANORAMIC views from your living room,...

    FREE CANCELLATION

    $186 to $353/night

  14. 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
    FREE CANCELLATION

    $261 to $521/night

  15. CONDOMINIUM
    Kihei Beach Unit #110

    Kihei Beach Unit #110

    Kihei, HI

    Kihei Beach is a moderately sized six story beachfront property located in North Kihei. It offers sweeping views of Kahoolawe, Molokini and the dazzling Pacific Ocean and a friendly casual atmosphere. Fronting the property is Sugar Beach, well known...

    Pool

    $263 to $421/night

  16. 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
    FREE CANCELLATION

    $133 to $226/night

  17. CONDOMINIUM
    Maui Vista 1417

    Maui Vista 1417

    Kihei, HI

    This top floor condo is a gem in South Kihei! Enjoy panoramic views of the ocean while sipping your morning coffee on the spacious lanai. This beautiful 2 bedroom, 2 bathroom condo has a king size bed in the master bedroom, a queen and a twin in the...

    Pool
    FREE CANCELLATION

    $249 to $563/night

  18. CONDOMINIUM
    Maui Parkshore #215

    Maui Parkshore #215

    Kihei, HI

    Kamaole III Beach Park is tropical paradise. The white sand, crystal clear water, grass park, and snorkeling make this beach experience unique and exciting. The complex is centrally located and within walking distance to nearby shopping,...

    Pool
    FREE CANCELLATION

    $196 to $354/night

  19. CONDOMINIUM
    Maui Parkshore #304

    Maui Parkshore #304

    Kihei, HI

    Expansive two bedroom, two bathroom condo located in the heart of Kihei, across the street from the beach at Kamaole Park lll. Easy walking to all the Kamaole beaches, the shops in Kihei, and the renowned Keawakapu Beach. This complex has a heated...

    Pool
    FREE CANCELLATION

    $191 to $354/night

  20. 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

    $197 to $406/night

  21. CONDOMINIUM
    Maui Vista #1-206

    Maui Vista #1-206

    Kihei, HI

    Maui Vista is a lovely complex located across the street and literally a 3-minute walk from this unit to Charley Young Beach - voted one of the most beautiful beaches in the world. Connected to Charlie Young Beach is the famous Kamaole Beach #1....

    Pool
    FREE CANCELLATION

    $161 to $219/night

  22. 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

  23. 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
    FREE CANCELLATION

    $126 to $231/night

  24. CONDOMINIUM
    Kihei Kai Nani #3-116

    Kihei Kai Nani #3-116

    Kihei, HI

    Kihei Kai Nani is located right across from the world renowned Kamaole Beach Park #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 $244/night

  25. CONDOMINIUM
    Hale Kamaole #315

    Hale Kamaole #315

    Kihei, HI

    Two bedroom condo with loft has Ocean and Garden View. Newly remodeled kitchen with stone counter top, and new walk-in showers with etched designer tile. King bed in master bedroom. Queen bed in loft area. Open feel. An additional door from the loft...

    Pool
    FREE CANCELLATION

    $269 to $379/night

  26. CONDOMINIUM
    Hale Kamaole #327

    Hale Kamaole #327

    Kihei, HI

    Garden and tennis court View. Very nice two bedroom condo, newly updated. Comfortable and welcoming to any family. Queen bed in master bedroom, twin beds in the other room. Queen hide-a-bed and two recliners in living area. Rattan dining set with 6...

    Pool
    FREE CANCELLATION

    $245 to $379/night

  27. CONDOMINIUM
    Hale Kamaole #275

    Hale Kamaole #275

    Kihei, HI

    Look no further for your family beach getaway! This 2 story, 2 bedroom plus loft, beautiful beach front condo comes with all the comforts of home including WI-FI, three flat screen TV’s, a closet full of beach accessories, everything you will need...

    Pool
    FREE CANCELLATION

    $269 to $379/night

  28. CONDOMINIUM
    Sugar Beach #124

    Sugar Beach #124

    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

    $352 to $468/night

  29. 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
    FREE CANCELLATION

    $126 to $231/night

  30. 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, two hot...

    Pool
    FREE CANCELLATION

    $277 to $335/night