Wailea Ski Chalets
1978 ft²
6 Guests
2 Bedrooms
2 Bathrooms
Ocean View
Villa
- Oceanfront
- Hot Tub
- Pool
US $1,345/Night
For 7 Nights US $9,414
3196.88 ft²
24 Guests
1 Bathroom
Free Cancellation
Resort
- Private Beach
- Oceanfront
- Hot Tub
US $3,013/Night
For 7 Nights US $21,088
US $1,151/Night
For 7 Nights US $8,057
1186 ft²
4 Guests
2 Bedrooms
2 Bathrooms
Ocean View
Condo
- Oceanfront
- Hot Tub
- Pool
US $1,171/Night
For 7 Nights US $8,200
796.53 ft²
3 Guests
1 Bedroom
1 Bathroom
Family Friendly
Apartment
- Pool
- Internet
- Child Friendly
US $571/Night
For 7 Nights US $3,998
960 ft²
4 Guests
1 Bedroom
2 Bathrooms
Family Friendly
Condo
- Pool
- Kitchen
- Parking
US $560/Night
For 7 Nights US $3,922
1571.53 ft²
6 Guests
3 Bedrooms
2 Bathrooms
Free Cancellation
Apartment
- Oceanfront
- Spa
- Pool
US $2,601/Night
For 7 Nights US $18,205
1056 ft²
6 Guests
3 Bedrooms
2 Bathrooms
Ocean View
Condo
- Oceanfront
- Hot Tub
- Pool
US $392/Night
For 7 Nights US $2,741
6 Guests
2 Bedrooms
2 Bathrooms
Family Friendly
Villa
- Hot Tub
- Fireplace/Heating
- Pool
US $370/Night
For 7 Nights US $2,591
1948.27 ft²
5 Guests
2 Bedrooms
3 Bathrooms
Apartment
- Oceanfront
- Pool
- Ocean View
US $618/Night
For 7 Nights US $4,326
1012 ft²
2 Guests
1 Bedroom
2 Bathrooms
Ocean View
Condo
- Oceanfront
- Hot Tub
- Pool
US $687/Night
For 7 Nights US $4,811
Why Choose Rent By Owner for your Wailea Ski Chalets?
What makes our Ski Chalets special?
Verified Listings
Book with confidence knowing every property meets our quality and safety standards.
Unbeatable Value
Enjoy competitive pricing with no hidden fees, providing exceptional value for every stay.
Diverse Options
From cozy cabins to luxurious villas, find a rental that suits your style and needs.
Best Times to Visit Wailea
When should you plan your Ski Chalets stay?
Timing your visit to this sought-after region ensures you enjoy optimal weather and fewer crowds, making it the ideal choice for booking your ski chalets in Wailea, Kihei, Hawaii, USA, through a reliable platform that guarantees a seamless vacation experience.
Peak Season Highlights
Winter (December to February)
During this peak season, you can enjoy warm, sunny days perfect for outdoor activities in the area’s inviting climate.
Average Temperature Daytime: Highs around 80°F (27°C) - Nighttime: Lows around 65°F (18°C)
Summer (June to August)
The summer months bring the busiest period with ideal weather for exploring and relaxing on the beaches of this tropical destination.
Average Temperature Daytime: Highs around 85°F (29°C) - Nighttime: Lows around 70°F (21°C)
Off-Season Highlights
Spring (March to May)
In the spring, fewer visitors mean a more tranquil experience while still enjoying pleasant weather in this region.
Average Temperature Daytime: Highs around 78°F (26°C) - Nighttime: Lows around 62°F (17°C)
Fall (September to November)
During fall, the area sees less tourist traffic, offering an excellent opportunity for peaceful stays amidst mild temperatures.
Average Temperature Daytime: Highs around 81°F (27°C) - Nighttime: Lows around 64°F (18°C)
Weekly Weather Forecast for Wailea
How to Book Your Wailea Ski Chalets
What's our booking process?
Our platform allows you to browse a curated selection of ski chalets. Once you find the ideal property, you’ll be redirected to a trusted booking partner to complete your reservation securely.
Booking Steps
01
Search Properties
Use our filters to find the right property that fits your needs.
02
Select a Rental
Click on your preferred listing to view details, amenities, and pricing.
03
Book Online
Follow the link to finalize your reservation directly on the partner’s website.
Explore and book the perfect rental in Wailea
Common Ski Chalets Amenities
What amenities can you expect?
Our Ski Chalets are designed to offer all the comforts of home, often with added perks to make your stay unforgettable. Here’s some common amenities to look forward to:
Indoor Features
- Fully-equipped kitchens with modern appliances
- Comfortable living areas with flat-screen TVs
- Free Wi-Fi for staying connected
- Air conditioning and heating for year-round comfort
- In-unit washers and dryers for convenience
- Luxurious bedrooms with premium bedding
- Spa-like bathrooms with soaking tubs or walk-in showers
Outdoor Amenities
- Enjoy access to private outdoor pools or community swimming areas designed for relaxation and leisure.
- Relax on spacious balconies or lanais with stunning views of the ocean or lush landscapes typical of the area.
- Take advantage of beautifully maintained gardens and outdoor pathways perfect for leisurely strolls.
- Make use of barbecue grills and picnic areas ideal for outdoor dining experiences under the Hawaiian sun.
- Benefit from outdoor fitness amenities such as tennis courts or yoga decks to maintain your wellness routine.
- Experience the convenience of shaded outdoor lounging spaces equipped with comfortable seating.
- Participate in organized outdoor activities or water sports facilities that cater to guests seeking adventure or tranquility here.
Top Attractions Around Wailea
What attractions are nearby?
In this vibrant area, you can enjoy a variety of outdoor activities such as snorkeling, whale watching, and scenic coastal walks that showcase the stunning natural beauty of Wailea. Whether you're exploring nearby beaches or engaging in water sports, you'll find plenty to do just moments from your cozy ski chalet, allowing for a perfect blend of relaxation and adventure in this captivating destination.
Family Activities
- Snorkeling at Molokini Crater: Discover vibrant marine life and crystal-clear waters just off the coast, offering an unforgettable family adventure in the region.
- Visit the Maui Ocean Center: Explore Hawaii’s largest tropical reef aquarium, providing educational fun and close-up encounters with native sea creatures for all ages.
- Enjoy a Beach Day at Wailea Beach: Relax on the soft sands and swim in the calm, warm waters, making it a perfect spot for family-friendly sunbathing and water activities.
- Take a Family Road Trip Along the Road to Hana: Experience lush scenery, waterfalls, and scenic stops along this iconic route that offers an engaging day trip for families here.
Adult Activities
- Snorkeling and Diving: Discover vibrant marine life by exploring the clear waters and coral reefs that surround this destination, offering memorable underwater experiences.
- Golfing: Tee off at world-class golf courses in the area, where scenic ocean views and lush fairways provide an ideal setting for a relaxing round of golf.
- Spa and Wellness Treatments: Indulge in luxurious spa services and wellness therapies designed to rejuvenate your body and mind amidst this tranquil region.
- Dining Experiences: Savor a variety of gourmet restaurants and local eateries, showcasing fresh seafood and Hawaiian cuisine that capture the essence of here.
Other Places to Stay in Wailea, HI
South Maui
Keawakapu Beach
Mokapu Beach
Ulua Beach
Ulua Beach Park
Wailea Shopping Village Shopping Center
Shops at Wailea
Wailea Beach
Polo Beach
Wailea Blue Golf Course
Palauea Beach
Makena
Wailea Travel Tips
How Can You Make the Most of Your Stay?
- Plan your activities early: Take advantage of the region's stunning beaches and outdoor adventures by booking excursions in advance to ensure availability and convenience.
- Choose an ideal location: Opt for accommodations close to popular amenities and scenic spots to maximize your time enjoying the natural beauty here.
- Explore local dining options: Sample authentic flavors by visiting nearby restaurants, but consider staying in a property with a fully equipped kitchen for flexible meal planning.
- Respect the environment: Preserve this destination’s natural charm by following eco-friendly practices and adhering to local conservation guidelines during your stay.
Transportation Options
- Rental Car Services: Major rental companies operate here, offering flexible transportation options to explore the region at your own pace.
- Public Transit: Local bus systems provide economical and convenient routes throughout the area, making it easy to get around without a private vehicle.
- Taxi and Ride-Sharing: Taxis and ride-sharing services are readily available for quick transfers to beaches, shopping centers, and other popular destinations.
- Bike Rentals: Biking is a popular way to enjoy the scenic surroundings while accessing nearby attractions and accommodations with ease.
Local Customs Options
- Respect for Aloha Spirit: Embracing the local value of aloha, which emphasizes kindness and harmony, is essential during your stay in this welcoming destination.
- Traditional Hawaiian Greetings: Using a simple hui hou (until we meet again) or mahalo (thank you) shows appreciation for the warm, friendly culture here.
- Environmental Respect: Participating in sustainable practices, such as avoiding plastic waste and respecting natural sites, aligns with the area's deep connection to nature.
- Community Participation: Engaging respectfully with local customs and events helps you immerse yourself in the region’s authentic traditions and way of life.
Wailea Ski Chalets Frequently Asked Questions
1. What are the top Ski Chalets in Wailea?
There are a lot of options in Wailea. If you plan on staying in the Wailea area, consider making a reservation for a few nights at one of these properties as these have been rated the Top Ski Chalets in Wailea:
- Wailea Custom Home, Pool, Panoramic Ocean View, Waterfalls - Maui Ocean Palms
- Aloha Kai Suite at Wailea Beach Villas. Penthouse 205. Ocean View. 3 BR/3 BA
- Walk to Beach, Ocean Views, Relax by the Pool
- The Maui Escape - Spectacular 2.5 Bdr Penthouse -Oceanfront Resort-Owner Direct!
- Very Best Deluxe Ocean View.Panoramic View.First Class!
- Maui Breeze Retreat at Ho'olei! Available April 9-17, April 24-May 1 & May 8-20!
- Paradise is calling, views, pool, hot tub,
- ~ BOOK WITH WITH US AND WITH CONFIDENCE THOUGH 2031 ~
- BEACH LUX VILLA with AWESOME VIEW! CLICK on “About this Property” for a TOUR!
- Hula On In to Beach House Chic Style, Click the Video tour below!
2. How many Ski Chalets are available in Wailea?
Currently, the total number of properties listed by RBO in 2026 is over 1879 in the Wailea area, and still counting. By aggregating listings from multiple websites, RBO offers an immense amount of choice of the best Ski Chalets in Wailea.
3. What is the cancellation policy for booking a ski chalet in this destination?
Cancellation policies vary depending on the property listing. You should review the specific terms and conditions provided in the property details or contact the owner directly for precise information.
4. Are there any additional fees or charges when booking a ski chalet here?
Additional fees such as cleaning, service charges, or taxes are typically outlined in the listing details. It’s recommended to read the full description or reach out to the owner for clarification before booking.
5. How do I ensure my booking for a ski chalet in this area is secure?
All bookings are processed through a secure platform that prioritizes your payment safety. Confirm your reservation details and communicate through the official channels to ensure a smooth booking experience.
6. Is it possible to make special requests or accommodations when reserving a ski chalet?
Yes, many property owners accept special requests such as early check-in, late check-out, or specific amenities. Contact the owner directly through the booking platform to discuss any particular needs.
7. What amenities are typically included with a ski chalet stay in this region?
Most chalets offer essential amenities like Wi-Fi, television, kitchen facilities, and outdoor spaces. For specific features, refer to the detailed listing or contact the owner directly.
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