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
    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
    FREE CANCELLATION

    $126 to $231/night

  2. 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

  3. CONDOMINIUM
    Kihei Beach Unit #203

    Kihei Beach Unit #203

    Kihei, HI

    Our second floor, oceanfront unit has a picture perfect view including Kahoolawe island, Molokini Crater, the Southwestern shoreline of Maui, and is an ideal location for whale watching (seasonal). Sugar Beach, one of the longest continuous sand...

    Pool

    $212 to $309/night

  4. CONDOMINIUM
    Sugar Beach Resort, #121

    Sugar Beach Resort, #121

    Kihei, HI

    Unit #121 at Sugar Beach Resort is a ground floor oceanfront unit that comes equipped with a king bed, queen size sofa sleeper, DVD/VCR and CD player. Sugar Beach Resort is a tranquil beachfront condominium resort located in North Kihei offering...

    Pool Hot Tub

    $202 to $387/night

  5. CONDOMINIUM
    Kealia Resort Unit #304

    Kealia Resort Unit #304

    Kihei, HI

    Unit #304 at Kealia Resort is a nicely decorated third-floor oceanfront unit that comes equipped with a queen bed, 2 twin beds, sofa sleeper, DVD player, VCR and CD/Stereo. Kealia Resort is a tranquil beachfront condominium resort located in North...

    Pool

    $223 to $321/night

  6. CONDOMINIUM
    Sugar Beach Resort, #330

    Sugar Beach Resort, #330

    Kihei, HI

    Unit #330 at Sugar Beach Resort is a nicely decorated third floor oceanfront unit that comes equipped with a king bed, queen sofa sleeper, 2 TV's, each with it's own DVD player, 2 cordless phones, wireless Internet, CD player, all new furniture,...

    Pool Hot Tub

    $202 to $387/night

  7. CONDOMINIUM
    Hale Pau Hana Unit #11

    Hale Pau Hana Unit #11

    Maui, HI

    Hale Pau Hana is a combination of high rise and low rise beachfront property located in South Kihei. Fronting the property is Kamaole Beach II, well known for it's romantic sunsets, great swimming, and seasonal whale watching. Hale Pau Hana offers...

    Pool

    $387 to $477/night

  8. CONDOMINIUM
    Wailea Ekolu Unit #312

    Wailea Ekolu Unit #312

    Wailea, HI

    Notes from the Owner: Come to relax in the luxury and tropical splendor of Maui's premier resort, Wailea. Featuring miles of pristine beaches, magnificent sunsets, and renowned cuisine, Wailea will surely be your ultimate vacation experience! The...

    Pool

    $222 to $382/night

  9. 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 upgraded condo. This lovely third floor one bedroom, one bath...

    Pool
    FREE CANCELLATION

    $148 to $276/night

  10. 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

    $139 to $277/night

  11. 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

  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

    $161 to $328/night

  13. 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

  14. 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

  15. 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

  16. CONDOMINIUM
    Palms at Wailea #702

    Palms at Wailea #702

    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, whale watching and strolling. The Palms at Wailea is a gorgeous property; lush with tropical landscaping....

    Pool Hot Tub
    FREE CANCELLATION

    $196 to $347/night

  17. CONDOMINIUM
    Waiohuli Beach Hale #B-107

    Waiohuli Beach Hale #B-107

    Kihei, HI

    Waiohuli Beach Hale #B-107 is a 1 Bd that sleeps 4. 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...

    Pool
    FREE CANCELLATION

    $139 to $277/night

  18. 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

    $186 to $374/night

  19. 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

  20. 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

  21. CONDOMINIUM
    Kihei Beach Unit #402

    Kihei Beach Unit #402

    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

  22. 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

  23. 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

  24. 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

    $139 to $277/night

  25. 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

  26. CONDOMINIUM
    Maui Sunset #A-103

    Maui Sunset #A-103

    Kihei, HI

    Maui Sunset is a fabulous oceanfront property in Kihei that has lush tropical landscaping, large pool which is heated during the winter months, hot tub, gas grills, work out room and tennis courts out on the beach for your use. Guests return here...

    Pool Hot Tub
    FREE CANCELLATION

    $162 to $232/night

  27. CONDOMINIUM
    Maui Parkshore #204

    Maui Parkshore #204

    Kihei, HI

    Maui Parkshore features expansive two bedroom, two bathroom condos located in the heart of Kihei, across the street from the beach at Kamaole Park III. Easy walking to all of the Kamaole beaches, the shops at Kihei, and the renowned Keawakapu Beach....

    Pool
    FREE CANCELLATION

    $179 to $354/night

  28. 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

  29. 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
    FREE CANCELLATION

    $208 to $255/night

  30. 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