Winter Rentals in Wailea:【 GREAT PRICES 】Rent By Owner

Wailea Winter Rental

Lavish Premier Beachfront Townhouse W/Unrivaled Views Wailea Elua 1305

New

Condo

Lavish Premier Beachfront Townhouse W/Unrivaled Views Wailea Elua 1305

10.0

Exceptional

(5 Reviews)

3 Bedrooms 3 Baths 8 Guests 1749 ft²

R58,936/Night 7 Nights - R412,559

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Frequently Viewed

Resort

Ho'olei at Grand Wailea

10.0

Exceptional

(5 Reviews)

1 Bath 24 Guests 3196.88 ft²

R49,533/Night 7 Nights - R346,739

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Condo

Grand Champions by KBM

10.0

Exceptional

(4 Reviews)

1 Bedroom 1 Bath 4 Guests

R73,724/Night 7 Nights - R516,064

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Condo

Wailea Elua 808 - Scenic Ocean Views, Classic Wailea Charm, Central AC, Wi-Fi

10.0

Exceptional

(5 Reviews)

2 Bedrooms 2 Baths 6 Guests 1259 ft²

R14,031/Night 7 Nights - R98,211

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Villa

Wailea Beach Villa H202 by Coldwell Banker Island Vacations

10.0

Exceptional

(1 Review)

2 Bedrooms 2 Baths 6 Guests 1905.21 ft²

R22,566/Night 7 Nights - R157,963

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New

Condo

Luxurious Beachfront Condo with Modern Amenities - Makena Surf Resort #E-203

10.0

Exceptional

(3 Reviews)

2 Bedrooms 2 Baths 6 Guests 1564 ft²

R22,779/Night 7 Nights - R159,459

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Polo Beach Club 604 by Coldwell Banker Island Vacations

Apartment

Polo Beach Club 604 by Coldwell Banker Island Vacations

10.0

Exceptional

(1 Review)

2 Bedrooms 2 Baths 6 Guests 1237.85 ft²

R21,970/Night 7 Nights - R153,787

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Cozy Treasure Nestled on a Lush Oceanfront Property - Wailea Elua 1508

New

Condo

Cozy Treasure Nestled on a Lush Oceanfront Property - Wailea Elua 1508

10.0

Exceptional

(3 Reviews)

3 Bedrooms 2 Baths 6 Guests 1363 ft²

R17,032/Night 7 Nights - R119,225

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Apartment

Wailea Elua, #0908

10.0

Exceptional

(1 Review)

2 Bedrooms 2 Baths 5 Guests 1270.14 ft²

R18,103/Night 7 Nights - R126,722

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New

Condo

Luxurious Oceanfront Condo at Wailea Elua Village - Unit 1201, Central AC, Wi-Fi

9.8

Exceptional

(31 Reviews)

1 Bedroom 1 Bath 4 Guests 891 ft²

R16,711/Night 7 Nights - R116,972

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Apartment

WAILEA ELUA, #2501

10.0

Exceptional

(1 Review)

2 Bedrooms 2 Baths 6 Guests 1270.14 ft²

R16,755/Night 7 Nights - R117,284

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Amazing Remodeled Oceanfront Escape – Makena Surf F-202 with Spectacular Views!

New

Condo

Amazing Remodeled Oceanfront Escape – Makena Surf F-202 with Spectacular Views!

9.8

Exceptional

(25 Reviews)

2 Bedrooms 2 Baths 6 Guests 1564 ft²

R14,538/Night 7 Nights - R101,763

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More Top-Rated Winter Rental in Wailea Area

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

Search Properties

Use our filters to find the right property that fits your needs.

Select a Rental

Click on your preferred listing to view details, amenities, and pricing.

Book Online

Follow the link to finalize your reservation directly on the partner’s website.

Explore and book the perfect rental in Wailea

More Top-Rated Winter Rental in Wailea Area

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

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.

Frequently Asked Questions About Wailea Winter Rentals

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:

2. How many Winter Rentals are available in Wailea?

Currently, the total number of properties listed by RBO in 2026 is over 1185 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.