Maui Dream Wedding - Vacation Rentals in South Maui

Breathtaking Oceanfront Boutique From US $405
         

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8.5 (2 Reviews)
House
  • Air Conditioner
  • Parking
  • Pool
Modern & Polished Oceanfront Vistas From US $524
         

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10.0 (17 Reviews)
Condo
  • Air Conditioner
  • Parking
  • Pool
Hawaiian Cottage and Personal Paradise/BBKM 2013/0004 From US $1,012
         

10.0 (204 Reviews)
Cottage
  • Air Conditioner
  • Parking
  • Pool
Corner Unit With Views From Every Window-Awesome Reviews From US $344
         

10.0 (201 Reviews)
Condo
  • Air Conditioner
  • Parking
  • Pool

Luxury Places to Stay in South Maui

Over 8028+ Luxury Places to Stay in or Near South Maui
Wailea Beach Villas Resort by KBM From US $9,660
         

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New
Apartment
  • Air Conditioner
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  • Pool
Polo Beach Club POL-109 by KBM From US $8,784
         

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8.0 (1 Review)
Condo
  • Air Conditioner
  • Parking
  • Pool

Top-Rated Vacation Rentals with a Pool in South Maui

Over 6893+ Top-Rated Vacation Rentals with a Pool in or Near South Maui
Breathtaking ocean views! Steps to the beach! Recently remodeled! From US $485
         

Stunning Views from only double lanai Penthouse unit. From US $311
         

10.0 (261 Reviews)
Condo
  • Air Conditioner
  • Parking
  • Pet Friendly

Pet-Friendly Vacation Rentals in South Maui

Over 57+ 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
  • Air Conditioner
  • Parking
  • Pet Friendly
The Ocean View Residence From US $648
         

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10.0 (1 Review)
Apartment
  • Air Conditioner
  • Parking
  • Pet Friendly
Gated 2-story beach house with big yard From US $904
         

10.0 (77 Reviews)
Villa
  • Air Conditioner
  • Parking
  • Pet Friendly
Maui Sunset Oasis- Top Unit w/AC From US $516
         

10.0 (6 Reviews)
Condo
  • Air Conditioner
  • Parking
  • Pet Friendly

Large Vacation Homes & Villas in South Maui

Over 297+ Large Vacation Homes & Villas in or Near South Maui
Villa Moana Maui From US $1,892
         

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New
Villa
  • Air Conditioner
  • Parking
  • View
BEACHFRONT MAUI KIHEI HOUSE From US $1,270
         

9.8 (169 Reviews)
House
  • Air Conditioner
  • Parking
  • TV
Spectacular 3rd Row Villa at Ho'olei with Ocean Views From US $1,595
         

10.0 (61 Reviews)
Villa
  • Air Conditioner
  • Parking
  • Pool
FIVE BEDROOM BEACHFRONT SOUTH MAUI HOME - MODERN! From US $5,011
         

9.8 (114 Reviews)
House
  • Air Conditioner
  • Parking
  • Pool

Wheelchair Accessible Vacation Homes in South Maui

Over 2842+ Wheelchair Accessible Vacation Homes in or Near South Maui
March dates available NOW ! RESERVE SOON ! From US $660
         

10.0 (149 Reviews)
Apartment
  • Air Conditioner
  • Parking
  • Pool
Hale Hui Kai #112 From US $420
         

10.0 (1 Review)
House
  • Pool
  • View
  • Wheelchair Accessible
Calming Coastal Vistas From US $460
         

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10.0 (9 Reviews)
Condo
  • Air Conditioner
  • Parking
  • Pool
Direct Oceanfront/Beachfront Luxury! Recently Remodeled From US $704
         

10.0 (111 Reviews)
Condo
  • Air Conditioner
  • Parking
  • Pool

South Maui Vacation Rentals and Airbnb Places to Stay Under $200

Over 209+ South Maui Vacation Rentals and Airbnb Places to Stay Under $200
A Piece Of Paradise! From US $190
         

9.8 (99 Reviews)
Condo
  • Air Conditioner
  • Parking
  • Pool
Maui Vista 1207 From US $197
         

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7.8 (16 Reviews)
Apartment
  • Air Conditioner
  • Parking
  • View
Kamaole Sands One Bedrooms by Coldwell Banker Island Vacations From US $88
         

Deluxe Camper Van on the island of Maui + Freebies! From US $172
         

10.0 (2 Reviews)
House
  • Air Conditioner
  • Parking
  • Balcony/Terrace
Remodeled Ground floor studio, AC, across from beach From US $200
         

10.0 (1 Review)
Apartment
  • Air Conditioner
  • Parking
  • Pool

Instantly Bookable Vacation Homes in South Maui

Over 5232+ Instantly Bookable Vacation Homes in or Near South Maui
Amazing view, Close to the beach, Wailea Ekahi Unit 20i From US $522
         

10.0 (134 Reviews)
Condo
  • Air Conditioner
  • Parking
  • Pool
Oceanfront, Million-Dollar-View, Newly renovated! B421 From US $725
         

10.0 (178 Reviews)
Condo
  • Air Conditioner
  • Parking
  • Pool
1BA/1 BA BEACHFRONT-PRIVATE-GREAT LOCATION-5 STAR REVIEWS! From US $383
         

10.0 (73 Reviews)
Apartment
  • Air Conditioner
  • Parking
  • TV
Maui Family Owned & Managed - Wailea Grand Champions Villa From US $449
         

2BR/1BA BEACHFRONT - GREAT LOCATION- EXCEPTIONAL REVIEWS From US $505
         

10.0 (52 Reviews)
Apartment
  • Air Conditioner
  • Parking
  • TV

About South Maui Vacation Rentals

With more than 8037 South Maui vacation rentals, we can help you find a place to stay. These rentals, including vacation rentals, Mauidreamwedding 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 Mauidreamwedding 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 768.67 ft² on average, with prices averaging $586 a night.

Mauidreamwedding 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
Holiday Apartments 1375
Vacation Homes 798
Villas 136
Resorts 132
Hotels with Suites 64
Cottages 17
B&B 8
Cabin Rentals 1
Others 1

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

Pro Tip: Mauidreamwedding makes it easy to compare the best listings on Mauidreamwedding homes from online vacation rental OTAs, including Booking.com and more. Use the Advanced Filter feature at the top to easily flip between Mauidreamwedding 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 8037 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.