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South Maui Vacation Rentals - 646 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 4, $302 to $357/night

    City : Kihei
    Bedroom : 1
    Bathrooms : 2
    Pool
    FREE CANCELLATION

    Weekday Weekend Weekly Bright and open Ocean View Condo. This unit...

  2. Sleeps 4, $348 to $435/night

    City : Kihei
    Bedroom : 1
    Bathrooms : 2
    Pool
    FREE CANCELLATION

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

  3. Sleeps 4, $258 to $302/night

    City : KIHEI
    Bedroom : 1
    Bathrooms : 2
    Pool Hot Tub
    FREE CANCELLATION

    Weekday Weekend Weekly Ground floor unit! Walk out onto the...

  4. Sleeps 4, $342 to $445/night

    City : Kihei
    Bedroom : 1
    Bathroom : 1
    Pool
    FREE CANCELLATION

    Weekday Weekend Weekly Modern designs and contemporary furnishings...

  5. Sleeps 6, $312 to $391/night

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

    Weekday Weekend Weekly Weekday Weekend Weekly Enjoy Ocean views from...

  6. Sleeps 6, $228 to $467/night

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

    Weekday Weekend Weekly Escape to Maui and relax in this clean and...

  7. Sleeps 2, $325 to $428/night

    City : Kihei
    Bedroom : 1
    Bathroom : 1
    Pool
    FREE CANCELLATION

    Weekday Weekend Weekly Weekday Weekend Weekly The pool, jacuzzi,...

  8. Sleeps 4, $190 to $261/night

    City : Kihei
    Bedroom : 1
    Bathroom : 1
    Pool
    FREE CANCELLATION

    Weekday Weekend Weekly Weekday Weekend Weekly Ocean View from the...

  9. Sleeps 4, $190 to $261/night

    City : Kihei
    Bedroom : 1
    Bathroom : 1
    Pool
    FREE CANCELLATION

    Weekday Weekend Weekly Weekday Weekend Weekly One bedroom condo with...

  10. Sleeps 4, $190 to $261/night

    City : Kihei
    Bedroom : 1
    Bathroom : 1
    Pool
    FREE CANCELLATION

    Weekday Weekend Weekly Weekday Weekend Weekly Ocean View from the...

  11. Sleeps 6, $237 to $367/night

    City : Kihei
    Bedrooms : 2
    Bathrooms : 2
    Pool
    FREE CANCELLATION

    Weekday Weekend Weekly Weekday Weekend Weekly Garden and tennis...

  12. Sleeps 6, $261 to $344/night

    City : Kihei
    Bedrooms : 2
    Bathrooms : 2
    Pool
    FREE CANCELLATION

    Weekday Weekend Weekly Weekday Weekend Weekly This two bedroom...

  13. Sleeps 4, $271 to $390/night

    City : Kihei
    Bedroom : 1
    Bathroom : 1

    Weekday Weekend Weekly Weekday Weekend Weekly 1 bedroom Penthouse...

  14. Sleeps 3, $201 to $217/night

    City : Kihei
    Bedroom : 1
    Bathroom : 1
    Pool

    Comfortable 1 bedroom condo on the sixth floor. Bedroom has queen...

  15. Sleeps 6, $261 to $344/night

    City : Kihei
    Bedrooms : 2
    Bathrooms : 2
    Pool
    FREE CANCELLATION

    Weekday Weekend Weekly Weekday Weekend Weekly Tennis court, garden...

  16. Sleeps 4, $190 to $300/night

    City : Kihei
    Bedroom : 1
    Bathroom : 1
    Pool
    FREE CANCELLATION

    Weekday Weekend Weekly Weekday Weekend Weekly Fantastic Ocean/Garden...

  17. Sleeps 4, $146 to $303/night

    City : Kihei
    Bedroom : 1
    Bathroom : 1
    Pool

    Weekday Weekend Weekly Charming ocean and garden view top floor...

  18. Sleeps 4, $422 to $529/night

    City : KIHEI
    Bedrooms : 2
    Bathrooms : 2
    Pool
    FREE CANCELLATION

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

  19. Sleeps 6, $378 to $467/night

    City : Kihei
    Bedrooms : 2
    Bathrooms : 2
    Pool
    FREE CANCELLATION

    Weekday Weekend Weekly This two bedroom, two bath, condo sleeps up...

  20. Sleeps 8, $497 to $554/night

    City : Kihei
    Bedrooms : 3
    Bathrooms : 3
    Pool
    FREE CANCELLATION

    Completely Refurnished three bedroom condo with renovations and many...

  21. Sleeps 6, $237 to $367/night

    City : Kihei
    Bedrooms : 2
    Bathrooms : 2
    Pool
    FREE CANCELLATION

    Weekday Weekend Weekly Weekday Weekend Weekly Extremely nice two...

  22. Sleeps 2, $332 to $419/night

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

    Weekday Weekend Weekly Weekday Weekend Weekly Redesign in 2017!!...

  23. Sleeps 4, $342 to $445/night

    City : Kihei
    Bedroom : 1
    Bathroom : 1
    Pool
    FREE CANCELLATION

    Weekday Weekend Weekly Ocean Front Condo with one bedroom and one...

  24. Sleeps 4, $258 to $312/night

    City : Kihei
    Bedroom : 1
    Bathrooms : 2
    Pool
    FREE CANCELLATION

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

  25. Sleeps 4, $258 to $312/night

    City : Kihei
    Bedroom : 1
    Bathrooms : 2
    Pool
    FREE CANCELLATION

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

  26. Sleeps 4, $288 to $332/night

    City : KIHEI
    Bedroom : 1
    Bathrooms : 2
    Pool
    FREE CANCELLATION

    Weekday Weekend Weekly Recently renovated Garden view condo...

  27. Sleeps 2, $240 to $297/night

    City : KIHEI
    Bedroom : 1
    Bathroom : 1
    Pool
    FREE CANCELLATION

    Weekday Weekend Weekly This one bedroom garden view condo has...

  28. Sleeps 4, $235 to $279/night

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

    New to the vacation rental market! This renovated one bedroom condo,...

  29. Sleeps 6, $261 to $344/night

    City : Kihei
    Bedrooms : 2
    Bathrooms : 2
    Pool
    FREE CANCELLATION

    Weekday Weekend Weekly Weekday Weekend Weekly Nice garden and tennis...

  30. Sleeps 4, $342 to $445/night

    City : KIHEI
    Bedroom : 1
    Bathroom : 1
    Pool
    FREE CANCELLATION

    Weekday Weekend Weekly Ocean Front Condo located on the second floor...