South Maui Vacation Rentals - 502 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, $315 to $380/night

    City : KIHEI
    Bedrooms : 2
    Bathrooms : 2
    Pool

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

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

    City : KIHEI
    Bedroom : 1
    Bathrooms : 2
    Pool

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

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

    City : KIHEI
    Bedroom : 1
    Bathrooms : 2
    Pool

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

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

    City : Kihei
    Bedroom : 1
    Bathrooms : 2
    Pool

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

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

    City : KIHEI
    Bedrooms : 2
    Bathrooms : 2
    Pool

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

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

    City : KIHEI
    Bedroom : 1
    Bathroom : 1
    Pool

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

  7. 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...

  8. 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...

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

    City : Kihei
    Bedrooms : 2
    Bathrooms : 2
    Pool

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

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

    City : KIHEI
    Bedroom : 1
    Bathroom : 1
    Pool

    Ocean Front Condo with one bedroom and one bathroom. The living area...

  11. 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...

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

    City : Kihei
    Bedroom : 1
    Bathroom : 1
    Pool

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

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

    City : Kihei
    Bedroom : 1
    Bathroom : 1
    Pool

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

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

    City : KIHEI
    Bedroom : 1
    Bathrooms : 2
    Pool

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

  15. Sleeps 2, $395 to $615/night

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

    ***Pool Closure Notice*** 9-11-17 to 9-25-17 Sugar Beach Resort will...

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

    City : KIHEI
    Bedroom : 1
    Bathroom : 1
    Pool

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

  17. Sleeps 4, $350 to $425/night

    City : KIHEI
    Bedroom : 1
    Bathrooms : 2
    Pool

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

  18. Sleeps 7, $210 to $340/night

    City : Kihei
    Bedrooms : 2
    Bathrooms : 2
    Pool

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

  19. Sleeps 4, $350 to $425/night

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

    Remodeled one (1) bedroom Ocean view Condo. The Kitchen has new...

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

    City : KIHEI
    Bedroom : 1
    Bathroom : 1
    Pool

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

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

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

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

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

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

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

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

    City : KIHEI
    Bedrooms : 3
    Bathrooms : 3
    Pool

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

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

    City : Kihei
    Bedroom : 1
    Bathroom : 1
    Pool

    This is a great unit that has recently been upgraded. Features a...

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

    City : KIHEI
    Bedroom : 1
    Bathroom : 1
    Pool

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

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

    City : Kihei
    Bedroom : 1
    Bathrooms : 2
    Pool

    Kamaole Sands is conveniently located across the street from the...

  27. Sleeps 4, $215 to $260/night

    City : KIHEI
    Bedroom : 1
    Bathroom : 1
    Pool

    One Bedroom Garden view unit at Kihei Bay Vista. This condo has many...

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

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

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

  29. Sleeps 2, $205 to $250/night

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

    TAT# 064-058-2656-01 This laid-back, beachside resort is 9 miles...

  30. 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...