South Maui Vacation Rentals - 359 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 4, $250 to $460/night

    City : Kihei
    Bedroom : 1
    Bathroom : 1
    Pool

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

  2. Sleeps 4, $205 to $220/night

    City : Kihei
    Bedroom : 1
    Bathroom : 1
    Pool

    Close to the beach, this first floor, garden-level condo features a...

  3. Sleeps 4, $210 to $240/night

    City : Kihei
    Bedroom : 1
    Bathroom : 1
    Pool

    This luxurious third floor condo features a full kitchen, large...

  4. Sleeps 4, $205 to $220/night

    City : Kihei
    Bedroom : 1
    Bathroom : 1
    Pool

    Close to the beach, this second floor condo features a queen bed in...

  5. Sleeps 4, $210 to $240/night

    City : Kihei
    Bedroom : 1
    Bathroom : 1
    Pool

    This luxurious garden level condo features a full kitchen, large...

  6. Sleeps 4, $195 to $200/night

    City : Kihei
    Bedroom : 1
    Bathroom : 1
    Pool

    This nicely remodeled third floor condo features a full kitchen and...

  7. Sleeps 4, $195 to $200/night

    City : Kihei
    Bedroom : 1
    Bathroom : 1
    Pool

    This luxurious condo features a large master bedroom with a king...

  8. Sleeps 4, $210 to $240/night

    City : Kihei
    Bedroom : 1
    Bathroom : 1
    Pool

    This luxurious fourth floor condo features a full kitchen, large...

  9. Sleeps 4, $205 to $220/night

    City : Kihei
    Bedroom : 1
    Bathroom : 1
    Pool

    Beautifully remodeled condo on the second floor. Features a full...

  10. Sleeps 2, $210 to $240/night

    City : Kihei
    Bedroom : 1
    Bathroom : 1
    Pool

    This luxurious fourth floor condo features a full kitchen, large...

  11. Sleeps 4, $210 to $240/night

    City : Kihei
    Bedroom : 1
    Bathroom : 1
    Pool

    This ground floor garden level condo features a full kitchen, large...

  12. Sleeps 4, $210 to $240/night

    City : Kihei
    Bedroom : 1
    Bathroom : 1
    Pool

    This newly remodeled condo features a full kitchen with oceanfront...

  13. Sleeps 8, $280 to $435/night

    City : Kihei
    Bedrooms : 3
    Bathrooms : 2
    Pool

    This completely remodeled 3 bedroom and 2 bath second-floor condo is...

  14. Sleeps 6, $175 to $235/night

    City : Kihei
    Bedrooms : 2
    Bathrooms : 2
    Pool

    Spend your perfect beach vacation at this 2 bedroom, 2 bathroom,...

  15. Sleeps 8, $235 to $340/night

    City : Kihei
    Bedrooms : 2
    Bathrooms : 2
    Pool

    Spend your perfect beach vacation at this 2 bedroom, 2 bathroom,...

  16. Sleeps 8, $285 to $435/night

    City : Kihei
    Bedrooms : 3
    Bathrooms : 3
    Pool

    New Inventory! This beautifully decorated 3 bedroom condo is located...

  17. Sleeps 5, $245 to $555/night

    City : Kihei
    Bedrooms : 2
    Bathrooms : 2
    Pool

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

  18. Sleeps 3, ~$285/night

    City : Kihei
    Bedroom : studio
    Bathroom : 1
    Pool

    Chilledcoconut Kihei is a 500 square feet studio unit on the top...

  19. Sleeps 4, $150 to $220/night

    City : Kihei
    Bedroom : 1
    Bathrooms : 2
    Pool

    Ocean and garden views close to the pool. Enjoy beautiful sunsets...

  20. Sleeps 4, $205 to $220/night

    City : Kihei
    Bedroom : 1
    Bathroom : 1
    Pool

    This unit has been beautifully remodeled. Luxurious condo features...

  21. Sleeps 6, $240 to $705/night

    City : Maui
    Bedrooms : 2
    Bathrooms : 2
    Pool

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

  22. Sleeps 6, $195 to $515/night

    City : Maui
    Bedrooms : 2
    Bathrooms : 2
    Pool

    This condo shows beautifully, with newer upgrades and renovations...

  23. Sleeps 6, $205 to $580/night

    City : Maui
    Bedrooms : 2
    Bathrooms : 2
    Pool

    This condo is amazingly comfortable for families! Well-kept, clean,...

  24. Sleeps 6, $175 to $445/night

    City : Maui
    Bedrooms : 2
    Bathrooms : 2
    Pool

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

  25. Sleeps 6, $240 to $705/night

    City : Maui
    Bedrooms : 2
    Bathrooms : 2
    Pool

    The owners of this two-bedroom Maui Kamaole condo take great care to...

  26. Sleeps 4, $220 to $640/night

    City : Maui
    Bedrooms : 2
    Bathrooms : 2
    Pool

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

  27. Sleeps 6, $295 to $795/night

    City : Maui
    Bedrooms : 2
    Bathrooms : 2
    Pool

    This 2-Bedroom 2-Bathroom air-conditioned condo features a fantastic...

  28. Sleeps 6, $180 to $455/night

    City : Maui
    Bedrooms : 2
    Bathrooms : 2
    Pool

    This two-bedroom two-bathroom works well for two traveling couples,...

  29. Sleeps 4, $215 to $605/night

    City : Maui
    Bedrooms : 2
    Bathrooms : 2
    Pool

    With major renovations in 2013 and 2014, this two-bedroom condo at...

  30. Sleeps 6, $200 to $545/night

    City : Maui
    Bedrooms : 2
    Bathrooms : 2
    Pool

    This two-bedroom two-bathroom condo is clean, comfortable, and...