South Maui Vacation Rentals - 579 Properties

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!

Search results

  1. Sleeps 6, $385 to $740/night

    City : Kihei
    Bedrooms : 2
    Bathrooms : 2
    Pool

    Mana Kai Maui is a popular eight story beachfront property located...

  2. Sleeps 4, $230 to $370/night

    City : Kihei
    Bedroom : 1
    Bathroom : 1
    Pool Hot Tub

    Kauhale Makai is Hawaiian for "Village by the Sea" Kauhale Makai is...

  3. Sleeps 4, ~$320/night

    City : KIHEI
    Bedroom : 1
    Bathrooms : 2
    Pool

    Beautiful Ocean View condo with many upgrades throughout. This unit...

  4. Sleeps 2, ~$245/night

    City : Kihei
    Bedroom : 1
    Bathroom : 1
    Pool

    Quiet and charming one bedroom condo located on the ground level....

  5. Sleeps 4, ~$315/night

    City : KIHEI
    Bedrooms : 2
    Bathrooms : 2
    Pool

    This two bedroom garden view condo has peaking Ocean Views. This...

  6. Sleeps 4, ~$350/night

    City : Kihei
    Bedroom : 1
    Bathrooms : 2
    Pool

    Beautifully Renovated Kitchen and bathrooms adorn in this one...

  7. Sleeps 4, $235 to $250/night

    City : KIHEI
    Bedroom : 1
    Bathroom : 1
    Pool

    One bedroom garden view condo located on the second floor. This unit...

  8. Sleeps 2, ~$335/night

    City : Kihei
    Bedroom : 1
    Bathrooms : 2
    Pool Hot Tub

    Redesign in 2017!! This ocean view condo at Maui Kamaole will be...

  9. Sleeps 4, ~$305/night

    City : Kihei
    Bedroom : 1
    Bathrooms : 2
    Pool

    Bright and open Ocean View Condo. This unit has one bedroom with a...

  10. Sleeps 4, $260 to $270/night

    City : Kihei
    Bedroom : 1
    Bathrooms : 2
    Pool

    One bedroom condo at the Kamaole Sands in South Kihei. This unit has...

  11. Sleeps 4, ~$345/night

    City : KIHEI
    Bedroom : 1
    Bathroom : 1
    Pool Hot Tub

    Beautifully renovated Ocean Front Condo located on the fourth floor....

  12. Sleeps 4, ~$345/night

    City : Kihei
    Bedroom : 1
    Bathroom : 1
    Pool Hot Tub

    Located Ocean Front on the Fifth floor of the Sugar Beach Resort on...

  13. Sleeps 4, $235 to $250/night

    City : KIHEI
    Bedroom : 1
    Bathroom : 1
    Pool

    Beautifully Renovated one bedroom garden view condo. This unit...

  14. Sleeps 4, ~$305/night

    City : Kihei
    Bedroom : 1
    Bathrooms : 2
    Pool

    Remodeled one bedroom and two bathroom condo. This unit sleeps up to...

  15. Sleeps 4, $245 to $260/night

    City : KIHEI
    Bedroom : 1
    Bathroom : 1
    Pool

    Welcoming one bedroom condo located across the beach from Kihei's...

  16. Sleeps 2, ~$330/night

    City : Kihei
    Bedroom : 1
    Bathroom : 1
    Pool

    The pool, jacuzzi, sauna, kitchen, and the entire deck will be...

  17. Sleeps 4, $235 to $250/night

    City : KIHEI
    Bedroom : 1
    Bathroom : 1
    Pool

    Enjoy Maui while staying in this one bedroom and one bath garden...

  18. Sleeps 2, $260 to $280/night

    City : Kihei
    Bedroom : 1
    Bathrooms : 2

    409 is a 1 bedroom, 2 bath condo offering beachfront living at its...

  19. Sleeps 4, ~$275/night

    City : KIHEI
    Bedroom : 1
    Bathroom : 1
    Pool

    One Bedroom Ocean View Condo at the Kauhale Makai. The fully...

  20. Sleeps 4, $260 to $270/night

    City : Kihei
    Bedroom : 1
    Bathrooms : 2
    Pool

    Located in building nine at the Kamaole Sands, this ground floor...

  21. Sleeps 4, ~$345/night

    City : KIHEI
    Bedroom : 1
    Bathroom : 1
    Pool

    Renovated and refurnished Ocean Front condo located on the Ground...

  22. Sleeps 4, $290 to $300/night

    City : Kihei
    Bedroom : 1
    Bathrooms : 2
    Pool

    Escape to Maui and find your piece of paradise at this one bedroom...

  23. Sleeps 6, ~$315/night

    City : Kihei
    Bedrooms : 2
    Bathrooms : 2
    Pool Hot Tub

    Enjoy Ocean views from this two bedroom, two bathroom condo at the...

  24. Sleeps 6, ~$270/night

    City : Kihei
    Bedrooms : 2
    Bathrooms : 2
    Pool

    Completely remodeled two bedroom condo with well-appointed...

  25. Sleeps 4, $145 to $210/night

    City : Kihei
    Bedroom : 1
    Bathrooms : 2
    Pool

    507 is a 1 bedroom, 2 bath condo- steps from the beach. See and hear...

  26. Sleeps 6, ~$395/night

    City : KIHEI
    Bedrooms : 2
    Bathrooms : 2
    Pool

    Beautifully remodeled Two bedroom and two baths Garden View Condo....

  27. Sleeps 4, ~$425/night

    City : KIHEI
    Bedrooms : 2
    Bathrooms : 2
    Pool

    Ocean View second floor condo. This is a two bedroom, two bath, unit...

  28. Sleeps 4, $145 to $250/night

    City : Kiehi
    Bedroom : 1
    Bathroom : 1
    Pool

    Imagine yourself sitting on the lanai with a drink in hand, watching...

  29. Sleeps 4, $260 to $570/night

    City : Wailea
    Bedroom : 1
    Bathrooms : 2
    Pool Hot Tub

    The fabulous Keawakapu Beach is just a short 10 minute stroll from...

  30. Sleeps 4, $140 to $390/night

    City : Kihei
    Bedroom : 1
    Bathroom : 1
    Pool

    Waiohuli Beach Hale is a small oceanfront complex located in Kihei...