Wine Country Villas - Vacation Rentals in South Maui

Villa Moana Maui From US $1,892
         

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New
Villa
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Spectacular 3rd Row Villa at Ho'olei with Ocean Views From US $1,465
         

10.0 (62 Reviews)
Villa
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5 Star Ocean View, Beach House Chic, Click the Video tour below! From US $382
         

Luxury Places to Stay in South Maui

Over 8109+ Luxury Places to Stay in or Near South Maui
Wailea Beach Villas Resort by KBM From US $9,660
         

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New
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South Maui's Best Family Reunion Spot From US $6,738
         

9.8 (44 Reviews)
Hotel
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  • TV
  • Balcony/Terrace
Polo Beach Club POL-109 by KBM From US $6,687
         

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8.0 (1 Review)
Condo
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FIVE BEDROOM BEACHFRONT HOME From US $5,824
         

9.8 (114 Reviews)
House
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Top-Rated Vacation Rentals with a Pool in South Maui

Over 7074+ Top-Rated Vacation Rentals with a Pool in or Near South Maui
Breathtaking ocean views! Steps to the beach! Recently remodeled! From US $422
         

Stunning Views from only double lanai Penthouse unit. From US $321
         

10.0 (266 Reviews)
Condo
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  • Pet Friendly

Pet-Friendly Vacation Rentals in South Maui

Over 49+ Pet-Friendly Vacation Rentals in or Near South Maui
Maui What a Wonderful World Bed & Breakfast From US $339
         

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9.4 (82 Reviews)
Bed & Breakfast
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  • Pet Friendly
The Ocean View Residence From US $526
         

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10.0 (1 Review)
Apartment
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Gated 2-story beach house with big yard From US $904
         

10.0 (79 Reviews)
Villa
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  • Pet Friendly
Dog-friendly condo with furnished lanai & washer/dryer plus pool & tennis From US $404
         

Maui Sunset Oasis- Top Unit w/AC, watch whales from from Lanai (Dec-Apr) From US $460
         

Large Vacation Homes & Villas in South Maui

Over 287+ Large Vacation Homes & Villas in or Near South Maui
Wailea Beach Villa H202 by Coldwell Banker Island Vacations From US $1,372
         

BEACHFRONT MAUI KIHEI HOUSE From US $1,437
         

9.8 (171 Reviews)
House
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  • TV
A 5-Star Estate, Large Groups, Luxury Living From US $1,469
         

10.0 (77 Reviews)
Condo
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Wheelchair Accessible Vacation Homes in South Maui

Over 2884+ Wheelchair Accessible Vacation Homes in or Near South Maui
Breathtaking Oceanfront Boutique From US $405
         

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8.5 (2 Reviews)
House
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Modern & Polished Oceanfront Vistas From US $524
         

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10.0 (18 Reviews)
Condo
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Corner Unit With Views From Every Window-Awesome Reviews From US $339
         

10.0 (202 Reviews)
Condo
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LOW JUNE RATES NOW ! RESERVE SOON ! From US $597
         

10.0 (149 Reviews)
Apartment
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South Maui Vacation Rentals and Airbnb Places to Stay Under $200

Over 248+ South Maui Vacation Rentals and Airbnb Places to Stay Under $200
Maui Vista 1207 From US $197
         

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7.8 (16 Reviews)
Apartment
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Kamaole Sands One Bedrooms by Coldwell Banker Island Vacations From US $88
         

Instantly Bookable Vacation Homes in South Maui

Over 5281+ Instantly Bookable Vacation Homes in or Near South Maui
Hawaiian Cottage and Personal Paradise/BBKM 2013/0004 From US $1,012
         

10.0 (206 Reviews)
Cottage
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Oceanfront, Million-Dollar-View, Newly renovated! B421 From US $725
         

10.0 (178 Reviews)
Condo
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Private 2BR Cottage House with Waterfall Pool Maui Meadows Permitted From US $546
         

Amazing view, Close to the beach, Wailea Ekahi Unit 20i From US $503
         

10.0 (136 Reviews)
Condo
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Direct Oceanfront/Beachfront Luxury! Recently Remodeled From US $700
         

10.0 (111 Reviews)
Condo
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Beachfront Condo B303 From US $1,088
         

10.0 (99 Reviews)
Condo
  • Air Conditioner
  • Parking
  • Pool

About South Maui Vacation Rentals

With more than 156 South Maui vacation rentals, we can help you find a place to stay. These rentals, including vacation rentals, Winecountryvillas and other short-term private accommodations, have top-notch amenities with the best value, providing you with comfort and luxury at the same time. Get more value and more room when you stay at a rental property in South Maui.

Looking for last-minute deals, or finding the best deals available for cottages, condos, private villas, and large vacation homes? With Winecountryvillas South Maui, you have the flexibility of comparing different options of various deals with a single click. Looking for a rental by owner with the best swimming pools, hot tubs, allows pets, or even those with huge master suite bedrooms and have large screen televisions? You can find vacation rentals by owner, and other popular Airbnb-style properties in South Maui. Places to stay near South Maui are 2174.47 ft² on average, with prices averaging US $1,934 a night.

Winecountryvillas makes it easy and safe to find and compare vacation rentals in South Maui with prices often at a 30-40% discount versus the price of a hotel. Just search for your destination and secure your reservation today.

Top Rental Accommodation Types in South Maui

Type Count
Villas 136
Vacation Homes 10
Holiday Apartments 9
Hotels 1

Use these Quick Filters to Find a Vacation Rental in South Maui

Pro Tip: Winecountryvillas makes it easy to compare the best listings on Winecountryvillas homes from online vacation rental OTAs, including Booking.com and more. Use the Advanced Filter feature at the top to easily flip between Winecountryvillas homes, vacation rentals, bed and breakfasts, private Airbnb-style rentals availability, eco-friendly properties, property type, cancellation policies, prices, and several different options. All these make it easier to find the perfect accommodation for your next vacation in South Maui.

Weather in South Maui

View the weather forecast for South Maui before booking your South Maui Vacation Rentals to confirm your best time to go.

December - February
High 60°F       Low 26°F
March - May
High 77°F       Low 40°F
June - August
High 91°F       Low 64°F
September - November
High 84°F       Low 38°F

South Maui Vacation Rental Frequently Asked Questions

What are the top vacation rentals in South Maui?
How many vacation rentals are available in South Maui?

Currently, the total number of properties listed in 2026 is over 156 in the South Maui area, and still counting. By aggregating listings from multiple websites, offers an immense amount of choice of the best properties in South Maui.