Winter Rentals in Maui

Stay in a Winter Rentals in Maui – Plan Your Next Vacation to Maui Today!

Find the Best Winter Rentals for Your Maui Trip

Smartours makes it easy to discover stays that match your style, budget, and location.

  • Winter Rentals
  • Luxury Winter Rentals
  • FAMILY FRIENDLY Winter Rentals
  • PET-FRIENDLY Winter Rentals
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10 (5 Reviews)
Resort
Ho'olei at Grand Wailea
  • Air Conditioner
  • Parking
  • Pool
US
View Availability
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9 (141 Reviews)
Resort
Four Seasons Resort Maui at Wailea
  • Air Conditioner
  • Parking
  • Pet Friendly
US
View Availability
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Top Rated Activities & Tours in Maui

Small-Group Road to Hana Adventure Tour with Pickup & Lunch
Small-Group Road to Hana Adventure Tour with Pickup & Lunch
10
Excellent
3446 Reviews
5 star rating Recommendation
From
US $210 Per Person
Reserve
Maui Pineapple Farm Tour in Haliimaile
Maui Pineapple Farm Tour in Haliimaile
10
Excellent
3057 Reviews
5 star rating Recommendation
From
US $99 Per Person
Reserve
Makawao Maui Pineapple Tour
Makawao Maui Pineapple Tour
10
Excellent
3057 Reviews
5 star rating Recommendation
From
US $99 Per Person
Reserve
Maui Eco-Raft Tour: Eye-Level Whale or Dolphin Watching - Lahaina
Maui Eco-Raft Tour: Eye-Level Whale or Dolphin Watching - Lahaina
10
Excellent
2777 Reviews
5 star rating Recommendation
From
US $85 Per Person
Reserve

Why Book Your Trip to Maui with Smartours?

Here’s why smart travelers plan travel with Smartours

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Smarter Stays

Winter Rentals selected for comfort, location and value – giving you the ideal base for your adventures.
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Smarter Itineraries

AI-powered trip plans that bundle accommodations, transport, and activities into flexible packages you can tailor to your style and budget.
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Smarter Exploration

Self-guided itineraries filled with local insights, hidden gems, and authentic experiences beyond the typical tourist trail.

How to Book Your Stay in Maui?

What’s the Smartours booking process?

Our platform connects you to a curated selection of Winter Rentals in Maui. Once you’ve found your ideal property, you’ll be redirected to our trusted booking partner to complete your reservation securely and with confidence.

Booking Steps

01

Search Stays

Use Smartours filters to find accommodations that match your style, location preferences, and budget.
02

View Details

Click on a listing to see photos, amenities, reviews, and pricing.
03

Book Securely

Follow the link to finalize your reservation directly with our verified booking partner.
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Indoor Features

  • Fully equipped kitchens or kitchenettes
  • Comfortable living areas with smart TVs
  • Free Wi-Fi for staying connected
  • Air conditioning and heating for year-round comfort
  • In-room coffee and tea facilities
  • Premium bedding for restful nights
  • Modern bathrooms with walk-in showers or soaking tubs

Outdoor Amenities

  • Balconies, terraces, or rooftop lounges with scenic views
  • Swimming pools, either private or shared
  • Outdoor dining spaces with BBQ or grill access
  • Gardens or courtyards for relaxing downtime
  • On-site parking or easy transport access
  • Proximity to key attractions, markets, or nature trails

Other Places to Stay in Maui

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Seasonal Weather in Maui

What’s the weather like in Maui throughout the year?

Maui’s climate varies by region, but most areas enjoy mild to warm weather year-round. Coastal cities benefit from ocean breezes, while inland areas and the desert see greater temperature swings between day and night.

Friday Aug 7

Maui, Hawaii

Fri
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23.2°C
Sat
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23.6°C
Sun
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23.7°C
Mon
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23.8°C
Tue
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23.3°C
Wed
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23.1°C
Thu
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23.6°C

Frequently Asked Questions

What are the top rated Winter Rentals in Maui?
How much does it cost to rent a place to stay near Maui in the wintertime?

The average cost for winter rentals in Maui is $1,095 per night. Smartours has a wide list of great winter places to stay near Maui that would suit your preferences. There are single and multiple rooms for solo trips or family vacations.

Are there any winter cottages/chalets in Maui that allow pets?
Do you have any winter rentals in Maui that are suitable for families?

Most of our rentals homes are suitable for families. Check out the complete list of places to stay in Maui to find what works for you.

Are there winter accommodations in Maui that have indoor swimming pools?

As of 2026, the data from Smartours shows that there are over 12651 private swimming pools or indoor pools accommodations near Maui along with other great amenities.

More Winter Rentals You May Like for Trips to Maui

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