Wailea Winter Rental
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
57 Bedrooms
1 Bathroom
Free Cancellation
Resort
- Private Beach
- Oceanfront
- Hot Tub
US $3,013/Night
For 7 Nights US $21,088
4 Guests
1 Bedroom
1 Bathroom
Ocean View
Condo
- Fireplace/Heating
- Pool
- Ocean View
US $2,359/Night
For 7 Nights US $16,513
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
1905.21 ft²
6 Guests
2 Bedrooms
2 Bathrooms
Free Cancellation
Villa
- Oceanfront
- Hot Tub
- Spa
US $1,372/Night
For 7 Nights US $9,607
1056 ft²
6 Guests
3 Bedrooms
2 Bathrooms
Ocean View
Condo
- Oceanfront
- Hot Tub
- Pool
US $392/Night
For 7 Nights US $2,741
1270.14 ft²
5 Guests
2 Bedrooms
2 Bathrooms
Apartment
- Oceanfront
- Hot Tub
- Pool
US $1,101/Night
For 7 Nights US $7,707
6 Guests
2 Bedrooms
2 Bathrooms
Family Friendly
Villa
- Hot Tub
- Fireplace/Heating
- Pool
US $370/Night
For 7 Nights US $2,591
1270.14 ft²
6 Guests
2 Bedrooms
2 Bathrooms
Ocean View
Apartment
- Oceanfront
- Hot Tub
- Pool
US $1,019/Night
For 7 Nights US $7,133
1012 ft²
2 Guests
1 Bedroom
2 Bathrooms
Ocean View
Condo
- Oceanfront
- Hot Tub
- Pool
US $670/Night
For 7 Nights US $4,693
1571.53 ft²
6 Guests
1 Bedroom
2 Bathrooms
Free Cancellation
Apartment
- Private Pool
- Oceanfront
- Hot Tub
US $902/Night
For 7 Nights US $6,312
700 ft²
4 Guests
2 Bedrooms
2 Bathrooms
Ocean View
Cottage
- Private Pool
- Oceanfront
- Hot Tub
US $1,012/Night
For 7 Nights US $7,087
Why Choose Rent By Owner for your Wailea Winter Rental?
What makes our Winter Rental 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 Winter Rental stay?
Choosing the optimal time to visit here ensures you enjoy the best weather and tranquility, making your winter rentals in this destination an ideal escape during Hawaii's cooler months.
Peak Season Highlights
Winter (December to February)
During this period, the region experiences its peak tourism season with ideal weather conditions, attracting visitors seeking warm winter escapes.
Average Temperature Daytime: 78°F - Nighttime: 65°F
Spring Break (March to April)
This time of year sees an influx of travelers enjoying spring holidays, making it a lively season for those looking to enjoy the area's renowned beaches and outdoor activities.
Average Temperature Daytime: 80°F - Nighttime: 66°F
Off-Season Highlights
Late Fall (October to November)
As the high season winds down, fewer visitors arrive, offering a more peaceful experience while still enjoying warm weather and scenic beauty.
Average Temperature Daytime: 81°F - Nighttime: 64°F
Early Summer (May to June)
Before the summer rush begins, this shoulder season provides quieter surroundings with pleasant temperatures perfect for exploring here without the crowds.
Average Temperature Daytime: 82°F - Nighttime: 67°F
Weekly Weather Forecast for Wailea
How to Book Your Wailea Winter Rental
What's our booking process?
Our platform allows you to browse a curated selection of winter rental. 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 Winter Rental Amenities
What amenities can you expect?
Our Winter Rental 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 lush outdoor swimming pools where you can relax and unwind amidst the tropical surroundings.
- Take advantage of beautifully landscaped gardens that offer tranquil spaces for strolling or picnicking.
- Make the most of private or shared outdoor barbecue areas perfect for enjoying local flavors with family or friends.
- Stay active with tennis courts available on the property, ideal for a friendly match in the warm climate.
- Discover outdoor lounge areas equipped with seating, allowing you to soak up the sun or admire scenic views.
- Utilize secure parking facilities with easy access to your rental, making day trips around the area convenient.
- Benefit from close proximity to beaches and outdoor water activities, enabling effortless exploration of the region’s coastline.
Top Attractions Around Wailea
What attractions are nearby?
Throughout your stay in this destination, you'll find a variety of nearby activities to enjoy, including stunning beaches ideal for sunbathing and water sports, scenic nature trails perfect for hiking and exploring local flora and fauna, and vibrant cultural sites that offer a glimpse into the region’s rich heritage-all conveniently accessible from your winter rentals.
Family Activities
- Beach Day at Wailea Beach: Spend a relaxing day with your family on the soft sands of this renowned beach, perfect for swimming, sunbathing, and building sandcastles.
- snorkeling Excursions: Explore vibrant marine life just off the coast with a family-friendly snorkeling tour in the clear waters of the region.
- Visit the Shops at Wailea: Enjoy a leisurely stroll through upscale boutiques and galleries, offering unique souvenirs and local crafts suitable for all ages.
- Attend a Cultural Luau: Immerse your family in Hawaiian traditions with an authentic luau experience featuring music, dance, and traditional cuisine in the area.
Adult Activities
- Snorkeling Tours: Explore the vibrant marine life and colorful coral reefs just off the coast, offering an immersive experience for underwater enthusiasts.
- Golfing on World-Class Courses: Play a round at championship golf courses with stunning ocean views, perfect for those looking to enjoy leisurely afternoons in this scenic region.
- Spa and Wellness Experiences: Indulge in luxurious spa treatments designed to rejuvenate your body and mind amidst the tranquil atmosphere of the area.
- Sunset Cruises: Embark on an evening cruise to witness breathtaking sunsets over the Pacific, creating unforgettable memories in this tropical paradise.
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 outdoor activities during the early morning or late afternoon: Take advantage of the region's pleasant climate by scheduling your outings to avoid the midday heat and enjoy the most comfortable weather.
- Explore local dining options for authentic Hawaiian cuisine: Sampling regional dishes enhances your stay and provides a taste of the area's rich culinary traditions.
- Utilize trusted transportation services to conveniently navigate between the various attractions and beaches in this destination, making your travel seamless and stress-free.
- Book your winter rentals well in advance: Securing accommodations early ensures you have the best selection and can fully enjoy the tranquility and beauty that this destination offers during peak season.
Transportation Options
- Rental Car Services: Local rental car agencies offer convenient options for exploring the area at your own pace, making it easy to reach your winter rentals and enjoy the scenic surroundings.
- Public Transportation: The region is served by reliable bus networks that provide affordable transportation, allowing you to travel comfortably between resorts, beaches, and shopping areas.
- Taxis and Rideshare Services: Taxis and rideshare providers like Uber and Lyft operate extensively here, offering flexible and quick transportation options for your vacation needs.
- Shuttle Services: Destination-specific shuttle services connect popular spots around this part of Hawaii, providing a hassle-free way to access local attractions from your winter rental.
Local Customs Options
- Respect for the Aina: It is customary to honor the land by practicing sustainable tourism and avoiding littering, ensuring the preservation of this beautiful destination for future visitors.
- Offering Lei: When greeting locals or participating in special occasions, offering a lei is a heartfelt tradition that symbolizes affection and aloha spirit here.
- Native Language Respect: Incorporating simple Hawaiian words like "Aloha" and "Mahalo" into your interactions exhibits cultural appreciation and enhances your experience in this area.
- Observing Local Etiquette: Removing shoes before entering homes and some businesses reflects respect for local customs, contributing to a harmonious visit in the region.
Wailea Winter Rental Frequently Asked Questions
1. What are the top Winter Rentals 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 Winter Rentals in Wailea:
- Aloha Kai Suite at Wailea Beach Villas. Penthouse 205. Ocean View. 3 BR/3 BA
- 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,
- Maui Luxury with Island Serenity - Wailea Beach Villas Penthouse K107
- 1br/1ba Condo Steps From The Pavilion pool, Mokapu Beach with beautiful views.
- Luxurious Tropical Retreat Wailea Ekahi Unit - 31 D
- Luxe Oceanview Hideaway on Wailea Old Blue Golf Course
- Ocean View, Double Lanai and a Quick Walk to the Beach
2. How many Winter Rentals are available in Wailea?
Currently, the total number of properties listed by RBO in 2026 is over 1237 in the Wailea area, and still counting. By aggregating listings from multiple websites, RBO offers an immense amount of choice of the best Winter Rentals in Wailea.
3. What is the cancellation policy for winter rentals in this area?
Cancellation policies can vary depending on the individual listing. It is recommended that you review the specific cancellation terms provided in the listing details or contact the property owner directly for clarification.
4. Are there any additional fees I should be aware of when booking a winter rental?
Additional fees such as cleaning, security deposits, or resort fees may apply and are detailed in each property’s listing. Be sure to read the full description or reach out to the owner for complete fee information before booking.
5. What amenities are typically included with winter rentals here?
Most properties offer amenities like fully equipped kitchens, Wi-Fi, air conditioning, and access to shared facilities. To confirm the amenities included in a particular rental, please review the listing details or contact the owner directly.
6. How do I know if a winter rental is available for my desired dates?
Availability is shown on each listing, but it is advisable to confirm by contacting the property owner or manager directly to ensure the dates are open and to secure your booking.
7. What is the check-in and check-out process for winter rentals in this region?
Check-in and check-out procedures vary by property. Specific instructions are usually provided by the owner upon booking confirmation. For detailed processes or special requests, reaching out to the host beforehand is recommended.
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