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!

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  1. CONDOMINIUM
    Wailea Ekolu Unit #312

    Wailea Ekolu Unit #312

    Wailea, HI

    Notes from the Owner: Come to relax in the luxury and tropical splendor of Maui's premier resort, Wailea. Featuring miles of pristine beaches, magnificent sunsets, and renowned cuisine, Wailea will surely be your ultimate vacation experience! The...

    Pool

    $212 to $382/night

  2. CONDOMINIUM
    Wailea Elua Unit #1503

    Wailea Elua Unit #1503

    Wailea, HI

    Wailea Elua Village is an exclusive beachfront property located in the heart of the resort community of Wailea. This relaxing low-density property consists of two-story buildings terraced over twenty-four acres of immaculate tropical landscaping....

    Pool

    $459 to $953/night

  3. CONDOMINIUM
    Makena Surf Resort, #G-304

    Makena Surf Resort, #G-304

    Makena, HI

    Makena Surf Resort is a luxurious secluded beachfront condominium located in exclusive Makena. This gated community was developed with six 2 & 3 story buildings each offering sweeping views of the Pacific. The pristine and picturesque beach and...

    Pool

    $898 to $1235/night

  4. CONDOMINIUM
    Kealia Resort Unit #304

    Kealia Resort Unit #304

    Kihei, HI

    Unit #304 at Kealia Resort is a nicely decorated third-floor oceanfront unit that comes equipped with a queen bed, 2 twin beds, sofa sleeper, DVD player, VCR and CD/Stereo. Kealia Resort is a tranquil beachfront condominium resort located in North...

    Pool

    $223 to $321/night

  5. CONDOMINIUM
    Kihei Beach Unit #508

    Kihei Beach Unit #508

    Kihei, Maui, HI

    Enjoy stunning views from this peaceful 5th floor condo - look out to over Sugar Beach to Maalaea Bay to views of Molokini, Lanai and Kahoolawe and regularly see whales from the lanai during whale season! This open-plan one bedroom, one bathroom...

    $212 to $309/night

  6. CONDOMINIUM
    Kihei Beach Unit #110

    Kihei Beach Unit #110

    Kihei, HI

    Kihei Beach is a moderately sized six story beachfront property located in North Kihei. It offers sweeping views of Kahoolawe, Molokini and the dazzling Pacific Ocean and a friendly casual atmosphere. Fronting the property is Sugar Beach, well known...

    Pool

    $263 to $421/night

  7. CONDOMINIUM
    Kihei Surfside, #411

    Kihei Surfside, #411

    Kihei, HI

    Kihei Surfside Resort is a unique six story oceanfront property located in South Kihei offering 180-degree views of the clear blue Pacific. The property and adjacent Keawekapu Beach together provide excellent locations for stunning sunsets,...

    Pool

    $208 to $448/night

  8. CONDOMINIUM
    Kihei Beach Unit #203

    Kihei Beach Unit #203

    Kihei, HI

    Our second floor, oceanfront unit has a picture perfect view including Kahoolawe island, Molokini Crater, the Southwestern shoreline of Maui, and is an ideal location for whale watching (seasonal). Sugar Beach, one of the longest continuous sand...

    Pool

    $212 to $309/night

  9. CONDOMINIUM
    203 Punahoa Condominium

    203 Punahoa Condominium

    Kihei, HI

    Oceanfront 1 bedroom condo! Since all Punahoa Beach condos are individually owned, each is decorated in its own island-style and all have an ocean front lanai perfect for your own outdoor dining above the Pacific. "All Units Are Non-smoking"...

    $165 to $382/night

  10. CONDOMINIUM
    401 Punahoa Condominium

    401 Punahoa Condominium

    Kihei, HI

    1 bedroom Penthouse unit! Since all Punahoa Beach condos are individually owned, each is decorated in its own island-style and all have an ocean front lanai perfect for your own outdoor dining above the Pacific. "All Units Are Non-smoking"...

    $165 to $411/night

  11. VILLA
    Ohana Hale (2-Bedroom Villa)

    Ohana Hale (2-Bedroom Villa)

    Kihei, HI

    Ohana Hale is a charming two bedroom, two bath ground floor condominium suite. Each bedroom has one full bathroom and its own private entrance to the pool. Each bedroom has your choice of a King bed or 2 Twin beds.  They also include two beach...

    Pool Hot Tub

    $463 to $786/night

  12. CONDOMINIUM
    Maui Banyan H-308

    Maui Banyan H-308

    Kihei, HI

    The Elevator for G & H building will be closed for Elevator Modernization starting at 10:00 am Monday September 10, 2018. We will have a bellman to help with luggage.  Bright and open Ocean View Condo. This unit has one bedroom with a queen bed...

    Pool
    FREE CANCELLATION

    $310 to $365/night

  13. CONDOMINIUM
    Maui Vista 1109

    Maui Vista 1109

    KIHEI, HI

    Beautifully Renovated one bedroom garden view condo. This unit sleeps up to four people with a queen bed in the bedroom and a pull out sofa bed in the living room, This unit offers Free WIFI and Free long distance phone calls to US and Canada....

    Pool
    FREE CANCELLATION

    $240 to $286/night

  14. CONDOMINIUM
    Kamaole Sands 07-206

    Kamaole Sands 07-206

    KIHEI, HI

    Recently renovated Garden view condo overlooking the center court! One bedroom unit with a fully equipped completely renovated kitchen and two bathrooms. With the ability to hold a maximum of 4 guests, there is a queen in the master bedroomand a...

    Pool
    FREE CANCELLATION

    $295 to $341/night

  15. CONDOMINIUM
    Maui Kamaole a-103

    Maui Kamaole a-103

    KIHEI, HI

    Spectacular ocean view one bedroom two full bath newly remodeled condo. Watch the sun set into the Pacific from your patio. Large lawn in front. Close to two of the most beautiful beaches on Maui. No steps to or in unit. Sleeps a maximum of 4 people...

    FREE CANCELLATION

    $357 to $446/night

  16. CONDOMINIUM
    Maui Vista 1220

    Maui Vista 1220

    KIHEI, HI

    One bedroom garden view condo located on the second floor. This unit sleeps up to four people with a queen bed in the bedroom and a pull out sofa bed in the living room. There are many tropical accents and upgrades throughout this unit. Enjoy the...

    Pool
    FREE CANCELLATION

    $240 to $286/night

  17. CONDOMINIUM
    Sugar Beach 223

    Sugar Beach 223

    KIHEI, HI

    **The Pool will be CLOSED beginning September 10th, through September 17th, 2018. In 2019 the pool will be closed September 9th, through September 16th. Each year the pool will be closed for one week, starting on the second Monday of the month....

    Pool
    FREE CANCELLATION

    $334 to $438/night

  18. CONDOMINIUM
    Sugar Beach 618

    Sugar Beach 618

    Kihei , HI

    **The Pool will be CLOSED beginning September 10th, through September 17th, 2018. In 2019 the pool will be closed September 9th, through September 16th. Each year the pool will be closed for one week, starting on the second Monday of the month....

    Pool
    FREE CANCELLATION

    $350 to $456/night

  19. CONDOMINIUM
    Sugar Beach 522

    Sugar Beach 522

    Kihei, HI

    **The Pool will be CLOSED beginning September 10th, through September 17th, 2018. In 2019 the pool will be closed September 9th, through September 16th. Each year the pool will be closed for one week, starting on the second Monday of the month....

    Pool Hot Tub
    FREE CANCELLATION

    $350 to $456/night

  20. CONDOMINIUM
    Leinaala 204

    Leinaala 204

    Kihei, HI

    Escape to this completely remodeled Ocean Front retreat. This condo has been remodeled with stylish finishing touches including crown moldings, a stunning backsplash, stainless steel appliances, colorful shower tile work and vintage Pan America...

    Pool
    FREE CANCELLATION

    $265 to $319/night

  21. CONDOMINIUM
    Hale Kamaole #333

    Hale Kamaole #333

    Kihei, HI

    Extremely nice two bedroom Maui vacation condo with a slight Ocean, garden and pool views. Very modern and clean. Refurbished and modernized in 2014 with beautiful solid bamboo flooring installed throughout, completely repainted and the purchase of...

    Pool
    FREE CANCELLATION

    $245 to $379/night

  22. CONDOMINIUM
    Maui Parkshore 105

    Maui Parkshore 105

    Kihei, HI

    Completely remodeled two bedroom condo with well-appointed furnishings and finishes. All rooms have been remodeled and furnished with tropical trendy style in mind. The stone counter tops in the beautifully remodeled kitchen capture your attention...

    Pool
    FREE CANCELLATION

    $273 to $335/night

  23. CONDOMINIUM
    Hale Kamaole #314

    Hale Kamaole #314

    Kihei, HI

    Great Ocean and Mountain View. Unit 314 was a Total remodel in the latter part of 2014. From the New walk in Tile showers, with beautiful Hawaiian style tile. Condo now has tile through out condo. The master bedroom has king bed, down stairs bedroom...

    Pool
    FREE CANCELLATION

    $245 to $379/night

  24. CONDOMINIUM
    Hale Kamaole #275

    Hale Kamaole #275

    Kihei, HI

    Look no further for your family beach getaway! This 2 story, 2 bedroom plus loft, beautiful beach front condo comes with all the comforts of home including WI-FI, three flat screen TV’s, a closet full of beach accessories, everything you will need...

    Pool
    FREE CANCELLATION

    $269 to $355/night

  25. CONDOMINIUM
    Hale Kamaole #203

    Hale Kamaole #203

    Kihei, HI

    Colorful condo with fantastic Ocean View. Kitchen has been remodeled, with floor tile installed from entrance to lanai. This spacious condo offers new bedroom furniture. There is a queen bed in the master bedroom, with 2 twins in the downstairs...

    Pool
    FREE CANCELLATION

    $245 to $330/night

  26. CONDOMINIUM
    Kihei Surfside 113

    Kihei Surfside 113

    KIHEI, HI

    Enjoy your stay on Maui in this ground floor, Ocean Front unit. This unit has recently added tile floors throughout. In 2012 kitchen was replaced with all new appliances, and in 2010 the fixtures, cabinetry, and countertops were replaced. You will...

    Pool
    FREE CANCELLATION

    $361 to $473/night

  27. CONDOMINIUM
    Maui Banyan T-304

    Maui Banyan T-304

    Kihei, HI

    Completely Refurnished three bedroom condo with renovations and many upgrades throughout. This garden view unit sleeps up to eight people with a king bed in 2 of the bedrooms and queen in one bedroom and a pull out sofa bed in the living room. This...

    Pool
    FREE CANCELLATION

    $509 to $568/night

  28. CONDOMINIUM
    Maui Kamaole h-212

    Maui Kamaole h-212

    KIHEI, HI

    Ocean View second floor condo. This is a two bedroom, two bath, unit that sleeps up to 4 people with a king bed in one bedroom and a queen bed in the other bedroom. Assorted rattan furniture and carpeting in the living room and bedrooms. The kitchen...

    Pool
    FREE CANCELLATION

    $433 to $542/night

  29. CONDOMINIUM
    Hale Kamaole #328

    Hale Kamaole #328

    Kihei, HI

    Tennis court, garden and Ocean View. This condo has a king bed in master bedroom, queen hide-a-bed in loft area. Living room has nice, comfortable, rattan furniture. Downstairs bedroom has two twin beds. Very modern, new kitchen offers beautiful...

    Pool
    FREE CANCELLATION

    $269 to $355/night

  30. CONDOMINIUM
    Hale Kamaole #327

    Hale Kamaole #327

    Kihei, HI

    Garden and tennis court View. Very nice two bedroom condo, newly updated. Comfortable and welcoming to any family. Queen bed in master bedroom, twin beds in the other room. Queen hide-a-bed and two recliners in living area. Rattan dining set with 6...

    Pool
    FREE CANCELLATION

    $245 to $379/night