South Maui Vacation Rentals - 362 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 6, $280 to $725/night

    City : Maui
    Bedrooms : 2
    Bathrooms : 2
    Pool

    This two-bedroom two-bathroom condo has been beautifully remodeled,...

  2. Sleeps 4, $255 to $670/night

    City : Maui
    Bedrooms : 2
    Bathrooms : 2
    Pool

    This two-bedroom condo is situated in the heart of the beautifully...

  3. Sleeps 6, $200 to $490/night

    City : Maui
    Bedrooms : 2
    Bathrooms : 2
    Pool

    This fully furnished 2 bedroom, 2 bathroom condo is perfect for...

  4. Sleeps 6, $385 to $470/night

    City : Kihei
    Bedrooms : 2
    Bathrooms : 2
    Pool

    Beautiful views of the Ocean, West Maui Mountains and the lush...

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

    City : KIHEI
    Bedrooms : 2
    Bathrooms : 2
    Pool

    Upgraded, Renovated and Remodeled two bedroom loft Condo. Beautiful...

  6. Sleeps 6, $310 to $370/night

    City : KIHEI
    Bedrooms : 2
    Bathroom : 1
    Pool

    Enjoy all the comforts of home in unit 405. Situated on the top...

  7. Sleeps 4, $285 to $330/night

    City : Kihei
    Bedrooms : 2
    Bathrooms : 2
    Pool

    Have fun in this two bedroom, two bath Ocean View condo....

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

    City : KIHEI
    Bedroom : 1
    Bathroom : 1
    Pool

    Walk out of this ocean front, ground floor unit and you are only a...

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

    City : KIHEI
    Bedroom : 1
    Bathroom : 1
    Pool

    Relax on your private lanai or take a step off your lanai onto the...

  10. Sleeps 6, $255 to $670/night

    City : Maui
    Bedrooms : 2
    Bathrooms : 2
    Pool

    Make yourself at home in our spacious and comfortable Wailea...

  11. Sleeps 4, $245 to $290/night

    City : KIHEI
    Bedroom : 1
    Bathroom : 1
    Pool

    Spacious and comfortable describe this ground floor condo with a...

  12. Sleeps 2, $290 to $385/night

    City : KIHEI
    Bedroom : 1
    Bathroom : 1
    Pool

    Make yourself at home in our Penthouse with amazing Ocean and...

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

    City : KIHEI
    Bedrooms : 2
    Bathrooms : 2
    Pool

    Beautiful Ocean Views from this two bedroom, two bathroom condo....

  14. Sleeps 6, $240 to $640/night

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

    This family-friendly condo is comfortable, clean, and in a fantastic...

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

    City : KIHEI
    Bedroom : 1
    Bathroom : 1.5
    Pool

    Kihei Surfside 210 is your home away from home. From the moment you...

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

    City : Kihei
    Bedroom : 1
    Bathroom : 1
    Pool

    Remodeled kitchen, bathroom and new flooring completed in Summer...

  17. Sleeps 4, $305 to $380/night

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

    Beautifully upgraded and renovated one bedroom condo. Renovated...

  18. Sleeps 5, $240 to $535/night

    City : Kihei
    Bedrooms : 2
    Bathrooms : 2
    Pool

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

  19. Sleeps 4, $240 to $445/night

    City : Kihei
    Bedroom : 1
    Bathroom : 1
    Pool

    Shores of Maui is a low density two-story property located across...

  20. Sleeps 4, $240 to $445/night

    City : Kihei
    Bedroom : 1
    Bathroom : 1
    Pool

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

  21. Sleeps 6, $285 to $345/night

    City : KIHEI
    Bedrooms : 2
    Bathrooms : 2
    Pool

    Enjoy Ocean views from this two bedroom two bathroom condo. The...

  22. Sleeps 4, $140 to $210/night

    City : Kihei
    Bedroom : 1
    Bathrooms : 2

    Welcome to NKH 301, a wonderful 1 bedroom 2 full bath condo right on...

  23. Sleeps 4, $185 to $460/night

    City : Maui
    Bedroom : 1
    Bathroom : 1
    Pool

    This premium renovated unit at Kauhale Makai is a guest favorite....

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

    City : KIHEI
    Bedroom : 1
    Bathroom : 1
    Pool

    Newly Renovated One bedroom Ocean View Condo. This unit has been...

  25. Sleeps 4, $175 to $400/night

    City : Maui
    Bedroom : 1
    Bathroom : 1
    Pool

    This open and spacious 1-bedroom condo is in an excellent location...

  26. Sleeps 6, $320 to $805/night

    City : Wailea
    Bedrooms : 3
    Bathrooms : 2
    Pool

    Grand Champions 134 is located in a quiet setting in Wailea. Large...

  27. Sleeps 2, $215 to $280/night

    City : Kihei
    Bedroom : 1
    Bathrooms : 2
    Pool

    308 is a luxurious 1 bedroom, 2 bath condo, steps from the beach,...

  28. Sleeps 2, $340 to $450/night

    City : KIHEI
    Bedroom : 1
    Bathroom : 1.5
    Pool

    Completely remodeled condo, from top to bottom. Nothing has been...

  29. Sleeps 6, $285 to $345/night

    City : Kihei
    Bedrooms : 2
    Bathrooms : 2
    Pool

    Relax in this spacious two bedroom, partial ocean view condo at the...

  30. Sleeps 6, $200 to $490/night

    City : Maui
    Bedrooms : 2
    Bathrooms : 2
    Pool

    This ground floor two-bedroom condo is located near the pool area in...