South Maui Vacation Rentals - 300 Properties

RedAwning has 100 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 4, $205 to $245/night

    City : Kihei
    Bedroom : 1
    Bathroom : 1

    This sixth floor condo features a full kitchen, large master bedroom...

  2. Sleeps 4, $185 to $205/night

    City : Kihei
    Bedroom : 1
    Bathroom : 1

    This lovely fourth floor condo features a full kitchen and large...

  3. Sleeps 2, $125 to $200/night

    City : Kihei
    Bedroom : 1
    Bathroom : 1

    Relax in this beautiful remodelled ground floor unit located on a...

  4. Sleeps 4, $165 to $240/night

    City : Kihei
    Bedroom : 1
    Bathrooms : 2

    Relax in this comfy second floor unit located on a peaceful and...

  5. Sleeps 7, $135 to $340/night

    City : Kihei
    Bedrooms : 2
    Bathrooms : 2

    This top floor condo is a gem in South Kihei! Enjoy panoramic views...

  6. Sleeps 4, $125 to $190/night

    City : Kiehi
    Bedroom : 1
    Bathroom : 1

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

  7. Sleeps 2, $205 to $245/night

    City : Kihei
    Bedroom : 1
    Bathroom : 1

    This contemporary fifth floor condo features a beautifully remodeled...

  8. Sleeps 4, $205 to $245/night

    City : Kihei
    Bedroom : 1
    Bathroom : 1

    Enjoy the huge ocean views and Maui's colorful sunsets from your...

  9. Sleeps 2, $145 to $165/night

    City : Kihei
    Bedroom : 1
    Bathroom : 1

    This beautiful studio condo has beach views, and views of the lush...

  10. Sleeps 2, $205 to $245/night

    City : Kihei
    Bedroom : 1
    Bathroom : 1

    This sixth floor, corner unit features breathtaking ocean front...

  11. Sleeps 6, $290 to $330/night

    City : Kihei
    Bedrooms : 3
    Bathrooms : 2

    Large swimming pool and hot tub.Cabana with BBQ, lots of grassy...

  12. Sleeps 2, $185 to $205/night

    City : Kihei
    Bedroom : 1
    Bathroom : 1

    This recently remodeled sixth floor condo features a full kitchen...

  13. Sleeps 2, $260 to $305/night

    City : KIHEI
    Bedroom : 1
    Bathroom : 1

    Enjoy stunning Ocean views from this top floor, One bedroom, Ocean...

  14. Sleeps 4, $355 to $450/night

    City : KIHEI
    Bedroom : 1
    Bathroom : 1

    Ocean front views take you across the Pacific and allow you to see...

  15. Sleeps 4, $260 to $305/night

    City : Kihei
    Bedroom : 1
    Bathroom : 1

    Escape to this completely remodeled Ocean Front retreat. This condo...

  16. Sleeps 4, $425 to $515/night

    City : KIHEI
    Bedrooms : 2
    Bathrooms : 2

    This condo is ocated in Kihei, Hawaii. Second floor Ocean Views in...

  17. Sleeps 6, $395 to $475/night

    City : KIHEI
    Bedroom : 1
    Bathrooms : 2

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

  18. Sleeps 6, $315 to $380/night

    City : KIHEI
    Bedrooms : 2
    Bathrooms : 2

    Remodeled two bedroom garden view condo with brand new Split AC...

  19. Sleeps 2, $230 to $290/night

    City : KIHEI
    Bedroom : 1
    Bathroom : 1

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

  20. Sleeps 6, $315 to $380/night

    City : KIHEI
    Bedrooms : 2
    Bathrooms : 2

    Beautifully renovated and refurnished two bedroom garden view unit...

  21. Sleeps 2, $230 to $290/night

    City : KIHEI
    Bedroom : 1
    Bathroom : 1

    This one bedroom garden view condo has peaking ocean views in the...

  22. Sleeps 4, $305 to $350/night

    City : KIHEI
    Bedroom : 1
    Bathrooms : 2

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

  23. Sleeps 4, $315 to $350/night

    City : KIHEI
    Bedroom : 1
    Bathrooms : 2

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

  24. Sleeps 4, $285 to $325/night

    City : KIHEI
    Bedroom : 1
    Bathrooms : 2

    Fully remodeled and upgraded ground floor condo. This One bedroom,...

  25. Sleeps 4, $285 to $325/night

    City : KIHEI
    Bedroom : 1
    Bathrooms : 2

    Recently renovated Garden view condo overlooking the center court!...

  26. Sleeps 4, $255 to $305/night

    City : Kihei
    Bedroom : 1
    Bathrooms : 2

    Escape to paradise and call this condo home! With partial Ocean...

  27. Sleeps 6, $345 to $410/night

    City : KIHEI
    Bedrooms : 2
    Bathrooms : 2

    Book Now and receive our Beat Available rate for this two bedroom...

  28. Sleeps 6, $355 to $420/night

    City : KIHEI
    Bedrooms : 2
    Bathrooms : 2

    Large two bedroom Ocean Front condo located on the ground floor....

  29. Sleeps 6, $355 to $420/night

    City : KIHEI
    Bedrooms : 2
    Bathrooms : 2

    Stunning panoramic ocean views are seen from every room of this...

  30. Sleeps 4, $275 to $320/night

    City : KIHEI
    Bedroom : 1
    Bathroom : 1

    This condo is located in Kihei, Hawaii. One Bedroom Ocean View...