South Maui Vacation Rentals - 486 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, $205 to $360/night

    City : Kihei
    Bedrooms : 2
    Bathrooms : 2
    Pool

    Waiohuli Beach Hale is a small oceanfront complex located in Kihei...

  2. Sleeps 4, $125 to $295/night

    City : Kihei
    Bedroom : 1
    Bathroom : 1
    Pool

    Kihei Kai Nani is located right across from the world renowned...

  3. Sleeps 4, $140 to $320/night

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

    Maui Sunset is a fabulous oceanfront property in Kihei that has lush...

  4. Sleeps 4, $125 to $325/night

    City : Kihei
    Bedroom : 1
    Bathroom : 1
    Pool

    Kihei Akahi has a great location as it is just a short walk to...

  5. Sleeps 6, $230 to $530/night

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

    The fabulous Keawakapu Beach is just a short 10 minute stroll from...

  6. Sleeps 4, $115 to $310/night

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

    Kamaole Sands is the premiere property in South Kihei. It is located...

  7. Sleeps 4, $220 to $285/night

    City : Kihei
    Bedrooms : 2
    Bathrooms : 2
    Pool

    Maui Vista is a lovely complex located across the street and...

  8. Sleeps 4, $125 to $310/night

    City : Kihei
    Bedroom : 1
    Bathroom : 1
    Pool

    Kihei Bay Vista is a wonderful property. It is located in Kihei...

  9. Sleeps 4, $320 to $350/night

    City : KIHEI
    Bedroom : 1
    Bathrooms : 2
    Pool

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

  10. Sleeps 4, $150 to $690/night

    City : Kihei
    Bedroom : 1
    Bathrooms : 2
    Pool

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

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

    City : Kihei
    Bedrooms : 2
    Bathrooms : 2
    Pool

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

  12. Sleeps 3, $100 to $165/night

    City : Kihei
    Bedroom :
    Bathroom : 1
    Pool Hot Tub

    Kihei Bay Surf unit 144 is a beautifully remodeled studio that can...

  13. Sleeps 6, $230 to $530/night

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

    Kamaole Sands is the premiere property in South Kihei. Kamaole Sands...

  14. Sleeps 4, $145 to $210/night

    City : Kihei
    Bedroom : 1
    Bathrooms : 2
    Pool

    507 is a 1 bedroom, 2 bath condo- steps from the beach. See and hear...

  15. Sleeps 4, $140 to $390/night

    City : Kihei
    Bedroom : 1
    Bathroom : 1
    Pool

    Waiohuli Beach Hale is a small oceanfront complex located in Kihei...

  16. Sleeps 2, $140 to $390/night

    City : Kihei
    Bedroom : 1
    Bathroom : 1
    Pool

    Waiohuli Beach Hale is a small oceanfront complex located in Kihei...

  17. Sleeps 4, $140 to $345/night

    City : Kihei
    Bedroom : 1
    Bathrooms : 2
    Pool

    Kamaole Sands is the premiere property in South Kihei. Located...

  18. Sleeps 3, $150 to $295/night

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

    Unit C403 at the Maui Beach Resort is an ocean view 1 Bedroom 1 Bath...

  19. Sleeps 4, $195 to $520/night

    City : Kihei
    Bedroom : 1
    Bathrooms : 2
    Pool

    Sleeps 4! Brand New furnishings! Kamaole Beach Park III is just...

  20. Sleeps 2, $190 to $390/night

    City : Kihei
    Bedroom : 1
    Bathroom : 1.5
    Pool

    Kihei Surfside is located on the ocean side of South Kihei Road at...

  21. Sleeps 6, $195 to $490/night

    City : Kihei
    Bedrooms : 2
    Bathrooms : 2
    Pool

    Kamaole III Beach Park is tropical paradise. The white sand, crystal...

  22. Sleeps 6, $260 to $395/night

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

    The fabulous Keawakapu Beach is just a short 10 minute stroll from...

  23. Sleeps 4, $300 to $650/night

    City : Kihei
    Bedroom : 1
    Bathroom : 1
    Pool

    Welcome to my sunny South Maui Paradise! Wailea Ekahi #45-F is a...

  24. Sleeps 6, $385 to $740/night

    City : Kihei
    Bedrooms : 2
    Bathrooms : 2
    Pool

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

  25. Sleeps 4, $130 to $320/night

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

    This is a beautiful ground floor spacious condo with a new king size...

  26. Sleeps 4, $430 to $1015/night

    City : Kihei
    Bedroom : 1
    Bathrooms : 2
    Pool

    The Wailea Elua is the premier ocean front property in Wailea....

  27. 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...

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

    City : KIHEI
    Bedroom : 1
    Bathroom : 1.5
    Pool

    Enjoy your stay on Maui in this ground floor, Ocean Front unit. This...

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

    City : KIHEI
    Bedroom : 1
    Bathroom : 1
    Pool

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

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

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

    Redesign in 2017!! This ocean view condo at Maui Kamaole will be...