Hotel Bookings Ai - Vacation Rentals in South Maui

South Maui's Best Family Reunion Spot From US $6,620
         

9.8 (44 Reviews)
Hotel
  • Air Conditioner
  • TV
  • Balcony/Terrace
Island Surf 508 From US $188
         

9.4 (5 Reviews)
Hotel
  • Air Conditioner
  • Parking
  • Pool
Maui Coast Hotel From US $376
         

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9.6 (2543 Reviews)
Hotel
  • Air Conditioner
  • Parking
  • Pool
Hotel Wailea, Relais & Châteaux - Adults Only From US $988
         

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9.3 (145 Reviews)
Hotel
  • Air Conditioner
  • Parking
  • Pool
Residence Inn by Marriott Maui Wailea From US $652
         

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9.2 (1003 Reviews)
Hotel
  • Air Conditioner
  • Parking
  • Pool
Hilton Grand Vacations Club Maui Bay Villas From US $498
         

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9.2 (288 Reviews)
Hotel
  • Air Conditioner
  • Parking
  • Pool

Luxury Places to Stay in South Maui

Over 8055+ 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
ICONIC OCEANFRONT ESTATE IN WONDERFUL WAILEA, MAUI! From US $7,208
         

10.0 (6 Reviews)
House
  • Air Conditioner
  • Parking
  • Pool

Top-Rated Vacation Rentals with a Pool in South Maui

Over 6963+ 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 56+ 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 (78 Reviews)
Villa
  • Air Conditioner
  • Parking
  • Pet Friendly
Maui Sunset Oasis- Top Unit w/AC From US $472
         

9.8 (8 Reviews)
Condo
  • Air Conditioner
  • Parking
  • Pet Friendly

Large Vacation Homes & Villas in South Maui

Over 300+ 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 (170 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 $4,084
         

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

Wheelchair Accessible Vacation Homes in South Maui

Over 2856+ Wheelchair Accessible Vacation Homes in or Near 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
Corner Unit With Views From Every Window-Awesome Reviews From US $343
         

10.0 (201 Reviews)
Condo
  • Air Conditioner
  • Parking
  • Pool
March dates available NOW ! RESERVE SOON ! From US $660
         

10.0 (149 Reviews)
Apartment
  • Air Conditioner
  • Parking
  • Pool

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

Over 215+ 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
  • Air Conditioner
  • Parking
  • View
A Piece Of Paradise! From US $190
         

9.8 (99 Reviews)
Condo
  • Air Conditioner
  • Parking
  • Pool
Kamaole Sands One Bedrooms by Coldwell Banker Island Vacations From US $88
         

Instantly Bookable Vacation Homes in South Maui

Over 5238+ Instantly Bookable Vacation Homes in or Near South Maui
Hawaiian Cottage and Personal Paradise/BBKM 2013/0004 From US $1,012
         

10.0 (204 Reviews)
Cottage
  • Air Conditioner
  • Parking
  • Pool
Oceanfront, Million-Dollar-View, Newly renovated! B421 From US $725
         

10.0 (178 Reviews)
Condo
  • Air Conditioner
  • Parking
  • Pool
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 $522
         

10.0 (134 Reviews)
Condo
  • Air Conditioner
  • Parking
  • Pool

About South Maui Vacation Rentals

With more than 66 South Maui vacation rentals, we can help you find a place to stay. These rentals, including vacation rentals, Hotelbookings 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 Hotelbookings 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 299.02 ft² on average, with prices averaging US $783 a night.

Hotelbookings 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
Hotels 64
Holiday Apartments 1
Resorts 1

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

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

There are a lot of options in South Maui. If you plan on staying in the South Maui area, consider making a reservation for a few nights at one of these properties as these have been rated 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 66 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.