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South Maui Vacation Rentals - 647 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, $227 to $369/night

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

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

  2. Sleeps 6, $328 to $391/night

    City : KIHEI
    Bedrooms : 2
    Bathrooms : 2
    Pool

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

  3. Sleeps 6, $328 to $391/night

    City : Kihei
    Bedrooms : 2
    Bathrooms : 2
    Pool

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

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

    City : KIHEI
    Bedroom : 1
    Bathroom : 1
    Pool

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

  5. Sleeps 4, $312 to $373/night

    City : KIHEI
    Bedrooms : 2
    Bathrooms : 2
    Pool

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

  6. Sleeps 4, $302 to $357/night

    City : Kihei
    Bedroom : 1
    Bathrooms : 2
    Pool

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

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

    City : Kihei
    Bedrooms : 3
    Bathrooms : 3
    Pool

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

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

    City : Kihei
    Bedroom : 1
    Bathrooms : 2
    Pool

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

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

    City : Kihei
    Bedroom : 1
    Bathrooms : 2
    Pool

    Book now for the best available rate on this Garden view Condo with...

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

    City : Kihei
    Bedroom : 1
    Bathrooms : 2
    Pool

    Book now to get our best available rate for this one bedroom,...

  11. Sleeps 6, $347 to $419/night

    City : KIHEI
    Bedrooms : 2
    Bathrooms : 2
    Pool

    Vaulted open beam ceilings make the living area a bright and open...

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

    City : KIHEI
    Bedroom : 1
    Bathrooms : 2
    Pool

    Sleep up to four (4) people in this one bedroom condo at the Kamaole...

  13. Sleeps 6, $354 to $428/night

    City : KIHEI
    Bedrooms : 2
    Bathrooms : 2
    Pool

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

  14. Sleeps 6, $354 to $428/night

    City : KIHEI
    Bedrooms : 2
    Bathrooms : 2
    Pool

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

  15. Sleeps 4, $273 to $327/night

    City : KIHEI
    Bedroom : 1
    Bathroom : 1
    Pool

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

  16. Sleeps 2, $259 to $312/night

    City : Kihei
    Bedroom : 1
    Bathroom : 1
    Pool

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

  17. Sleeps 4, $352 to $461/night

    City : Kihei
    Bedroom : 1
    Bathroom : 1
    Pool

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

  18. Sleeps 4, $259 to $312/night

    City : Kihei
    Bedroom : 1
    Bathroom : 1
    Pool

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

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

    City : KIHEI
    Bedrooms : 2
    Bathrooms : 2
    Pool

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

  20. Sleeps 6, $392 to $489/night

    City : KIHEI
    Bedrooms : 2
    Bathrooms : 2
    Pool

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

  21. Sleeps 4, $304 to $391/night

    City : Kihei
    Bedroom : 1
    Bathrooms : 2
    Pool

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

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

    City : KIHEI
    Bedroom : 1
    Bathroom : 1
    Pool

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

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

    City : KIHEI
    Bedroom : 1
    Bathroom : 1
    Pool

    Enjoy spectacular Ocean Front views from the private lanai and...

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

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

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

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

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

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

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

    City : KIHEI
    Bedroom : 1
    Bathroom : 1
    Pool

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

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

    City : KIHEI
    Bedroom : 1
    Bathroom : 1
    Pool

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

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

    City : Kihei
    Bedroom : 1
    Bathrooms : 2
    Pool

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

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

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

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

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

    City : Kihei
    Bedrooms : 2
    Bathrooms : 2
    Pool

    This two bedroom, two bath, condo sleeps up to six people. The...