South Maui Vacation Rentals - 451 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 10, $3470 to $6330/night

    City : Kihei
    Bedrooms : 4
    Bathrooms : 5.5
    Pool

    The Wailea Sunset Estate is a legal hotel-zoned ocean front vacation...

  2. 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...

  3. Sleeps 4, $185 to $260/night

    City : Kihei
    Bedroom : 1
    Bathrooms : 2
    Pool

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

  4. Sleeps 2, $145 to $220/night

    City : Kihei
    Bedroom : 1
    Bathroom : 1
    Pool

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

  5. Sleeps 6, $370 to $655/night

    City : Kihei
    Bedrooms : 2
    Bathrooms : 2
    Pool

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

  6. 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...

  7. Sleeps 6, $380 to $455/night

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

    Escape to Maui and relax in this clean and comfortable home away...

  8. Sleeps 4, $175 to $350/night

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

    Comfortable and clean condo located in building Q, near the upper...

  9. Sleeps 8, $500 to $540/night

    City : KIHEI
    Bedrooms : 3
    Bathrooms : 3
    Pool

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

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

    City : KIHEI
    Bedroom : 1
    Bathrooms : 2
    Pool

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

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

    City : KIHEI
    Bedroom : 1
    Bathrooms : 2
    Pool

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

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

    City : Kihei
    Bedroom : 1
    Bathrooms : 2
    Pool

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

  13. Sleeps 4, $230 to $290/night

    City : KIHEI
    Bedroom : 1
    Bathroom : 1
    Pool

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

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

    City : KIHEI
    Bedroom : 1
    Bathroom : 1
    Pool

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

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

    City : KIHEI
    Bedroom : 1
    Bathroom : 1
    Pool

    Enjoy beautiful Ocean views from this one bedroom condo. The kitchen...

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

    City : KIHEI
    Bedroom : 1
    Bathroom : 1
    Pool

    Enjoy Ocean Views from this one (1) bedroom condo. This unit has a...

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

    City : KIHEI
    Bedroom : 1
    Bathroom : 1
    Pool

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

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

    City : Kihei
    Bedroom : 1
    Bathroom : 1
    Pool

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

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

    City : KIHEI
    Bedrooms : 2
    Bathrooms : 2
    Pool

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

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

    City : KIHEI
    Bedroom : 1
    Bathrooms : 2
    Pool

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

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

    City : KIHEI
    Bedrooms : 2
    Bathrooms : 2
    Pool

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

  22. Sleeps 2, $335 to $410/night

    City : KIHEI
    Bedroom : 1
    Bathrooms : 2
    Pool

    This unit is located in ground floor. It has one bedroom and two...

  23. Sleeps 6, $270 to $320/night

    City : Kihei
    Bedrooms : 2
    Bathrooms : 2
    Pool

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

  24. Sleeps 4, $345 to $435/night

    City : KIHEI
    Bedroom : 1
    Bathroom : 1
    Pool

    Great value on an Ocean Front condo located on the Ground Floor,...

  25. Sleeps 4, $345 to $435/night

    City : KIHEI
    Bedroom : 1
    Bathroom : 1
    Pool

    Ocean Front Condo located on the second floor of the Sugar Beach...

  26. Sleeps 2, $330 to $420/night

    City : KIHEI
    Bedroom : 1
    Bathroom : 1
    Pool

    Ocean Front Condo with one bedroom and one bath. This Unit has a...

  27. Sleeps 4, $225 to $270/night

    City : KIHEI
    Bedroom : 1
    Bathroom : 1
    Pool

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

  28. Sleeps 2, $225 to $270/night

    City : KIHEI
    Bedroom : 1
    Bathroom : 1
    Pool

    Beautifully remodeled one bedroom garden view condo. Enjoy a...

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

    City : Kihei
    Bedroom : 1
    Bathrooms : 2
    Pool

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

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

    City : KIHEI
    Bedroom : 1
    Bathrooms : 2
    Pool

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