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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. Hale Kamaole #111

    Hale Kamaole #111

    Kihei, HI

    One bedroom condo with Garden View, located near pool & office. Very Hawaiian rattan furniture in front room & bedroom. Kitchen has granite counter tops with new wood kitchen cabinets. Large flat screen TV in front room, and 32 inch flat screen in...

    Pool
    FREE CANCELLATION

    $190 to $261/night

  2. Hale Kamaole #241

    Hale Kamaole #241

    Kihei, HI

    Fantastic Ocean/Garden View. Just remodeled and includes new furnishings. Sleep well on the new Tempurpedic King size bed in the master bedroom. The TEMPUR-Breeze® mattresse responds to body temperature in three ways to transfer heat and humidity,...

    Pool
    FREE CANCELLATION

    $190 to $300/night

  3. 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

    $237 to $320/night

  4. Kauhale Makai 607

    Kauhale Makai 607

    Kihei, HI

    Please note: Kauhale Makai is undergoing exterior building maintenance. Enjoy stunning Ocean views from this top floor, Penthouse unit. Recently upgraded, including a complete kitchen remodel, this unit sleeps up to two people in a Cal-King bed....

    Pool

    $259 to $312/night

  5. Maui Sunset A-408

    Maui Sunset A-408

    Kihei, HI

    Enjoy Ocean views from this two bedroom, two bathroom condo at the popular, Maui Sunset Resort. This large condo can accommodate up to six guests. The master bedroom has a King bed and en-suite. The second bedroom has a queen bed and twin bunk-beds....

    Pool Hot Tub

    $312 to $391/night

  6. Kihei Kai Nani #113

    Kihei Kai Nani #113

    Kihei, HI

    Kihei Kai Nani #113 is a beautiful South Maui getaway apart of the Kihei Kai Nani Rentals complex. This tropical home has 1 bedroom and 1 bathroom, spacious enough to accommodate 4 guests. Family and friends will love the prime location this...

    $124 to $233/night

  7. Nani Kai Hale # 507

    Nani Kai Hale # 507

    Kihei, HI

    507 is a 1 bedroom, 2 bath condo- steps from the beach. See and hear the ocean waves from the living room, bedoom and private lana. Enjoy sunsets and views of the beautiful West Maui mountains. The apartment has custom tile throughout and island...

    Pool

    $142 to $210/night

  8. Hale Kamaole #315

    Hale Kamaole #315

    Kihei, HI

    Two bedroom condo with loft has Ocean and Garden View. Newly remodeled kitchen with stone counter top, and new walk-in showers with etched designer tile. King bed in master bedroom. Queen bed in loft area. Open feel. An additional door from the loft...

    Pool

    $261 to $344/night

  9. Hale Kamaole #341

    Hale Kamaole #341

    Kihei, HI

    Fabulous Ocean and Garden View – one the BEST views on the property. New wood flooring in living room! King bed in master bedroom, loft has hide a bed. Downstairs bedroom has new furniture with queen bed. No hide a bed in living room. Kitchen &...

    Pool

    $261 to $344/night

  10. 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

    $237 to $367/night

  11. Hale Kamaole #245

    Hale Kamaole #245

    Kihei, HI

    This two bedroom corner unit with loft has an Ocean View from the living room & kitchen. Additional side window provides extra light. There is a King bed located in the master bedroom, the loft is enclosed with a queen bed. The downstairs bedroom...

    Pool

    $261 to $344/night

  12. Maui Parkshore 114

    Maui Parkshore 114

    Kihei, HI

    Two bedroom ground floor Condo. This unit has seen a complete renovation as it sleeps up to six people with a queen bed in the master bedroom, two twins in the second bedroom and a pull out sofa bed in the living room. The kitchen is open to the...

    Pool

    $267 to $327/night

  13. Sugar Beach 127

    Sugar Beach 127

    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. You...

    Pool

    $342 to $445/night

  14. 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

    $237 to $367/night

  15. Kamaole Sands 04-312

    Kamaole Sands 04-312

    Kihei, HI

    One bedroom condo at the Kamaole Sands in South Kihei. This unit has a Queen bed in the bedroom and a sofa bed in the living room, allowing this unit to accommodate up to four (4) people. There is a fully equipped kitchen and a dining and living...

    Pool

    $258 to $312/night

  16. 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

    $267 to $327/night

  17. Kihei Akahi D-415

    Kihei Akahi D-415

    KIHEI, HI

    This two bedroom garden view condo has peaking Ocean Views. This unit will accommodate up to four (4) people with a queen bed in the master bedroom and two twin beds in the second bedroom. The furnishings are a mixture of rattan with tropical...

    Pool

    $312 to $391/night

  18. Maui Parkshore 401

    Maui Parkshore 401

    KIHEI, HI

    Entire condo renovation completed January 2015! Enjoy Ocean views and views of South Maui from this top floor condo. This unit features two bedrooms and two full bathrooms. The master bedroom has a king bed and a full bathroom ensuite. The second...

    Pool

    $296 to $351/night

  19. Maui Kamaole a-204

    Maui Kamaole a-204

    KIHEI, HI

    Ocean View Condo at the popular Maui Kamaole in south Kihei. This condo is located on the second floor in building A, at the front of the property and boasts the best ocean views on the property. This condo has two bedrooms, one on the main level...

    Pool

    $422 to $529/night

  20. Sugar Beach 217

    Sugar Beach 217

    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

    $342 to $445/night

  21. Kauhale Makai 411

    Kauhale Makai 411

    KIHEI, HI

    Please note: Kauhale Makai is undergoing exterior building maintenance. Stunning panoramic ocean views are seen from every room of this ocean front condo. This unit is great for two couples or a family of six as it accommodates up to six people....

    Pool

    $354 to $428/night

  22. Kihei Surfside 307

    Kihei Surfside 307

    Kihei, HI

    Ocean front views take you across the Pacific and allow you to see the West Maui Mountains and the island of Lanai. This third floor 1 bedroom, 1 bath unit has new tile floors in the entryway, kitchen, and bathroom. There is carpet in the living and...

    Pool

    $352 to $461/night

  23. Maui Kamaole h-106

    Maui Kamaole h-106

    KIHEI, HI

    Remodeled one (1) bedroom Ocean view Condo. The Kitchen has new cabinetry, fixtures, granite counter tops, and white appliances. This one bedroom and two bath unit sleeps up to 4 people with a king bed in the bedroom and a pull out sofa bed in the...

    Pool Hot Tub

    $348 to $435/night

  24. 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

    $342 to $445/night

  25. 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

    $302 to $357/night

  26. Hale Kamaole #163

    Hale Kamaole #163

    Kihei, HI

    This beautiful one bedroom ground floor unit has tile installed throughout the entire condo, lanai tile has turtles crossing as an accent tile. King bed in bedroom and queen hide a bed in living room. Walk-in simulated marble shower enclosure, and...

    Pool

    $190 to $261/night

  27. Kihei Akahi Resort- Unit D605

    Kihei Akahi Resort- Unit D605

    Kihei, HI

    Panoramic ocean views! Top Floor Luxury Pent House - Building D. Penthouse Suite D605 - Luxury One Bedroom One Bath 655 sq. ft. located on the top floor, the 6th floor, in building D. Enjoy spectacular PANORAMIC views from your living room,...

    Pool

    $196 to $327/night

  28. Kihei Akahi Resort- Unit C618

    Kihei Akahi Resort- Unit C618

    Kihei, HI

    Charming ocean and garden view top floor upgraded artist home. Kathy McCartney owns popular C618 located on the top floor of building C at the Kihei Akahi Resort. Enjoy spectacular views of the Pacific Ocean, Mount Haleakala, Kaho'olawe Island,...

    Pool

    $142 to $303/night

  29. Hale Kamaole #258

    Hale Kamaole #258

    Kihei, HI

    Nice garden and tennis court view, slight Ocean view. This two bedroom with loft has a new king bed in the master bedroom also small flat screen TV. Queen bed in loft making this condo comfortable for 3 couples, or large family. The new queen Hide a...

    Pool

    $261 to $344/night

  30. Kihei Akahi #C-202

    Kihei Akahi #C-202

    Kihei, HI

    New to the Market! A spacious Ocean View condo with two bedrooms and two bathrooms. The accommodations are for up to four people with a Queen bed in the Master bedroom and two twin beds in the second bedroom. This condo is located at the Kihei...

    Pool

    $312 to $373/night