Wailea Resorts
1500 ft²
4 Guests
2 Bathrooms
Ocean View
Resort
- Private Pool
- Pool
- Ocean View
US $839/Night
For 7 Nights US $5,876
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 $4,105/Night
For 7 Nights US $28,734
4 Guests
2 Bathrooms
Family Friendly
Resort
- Air Conditioner
- Child Friendly
- Laundry
US $313/Night
For 7 Nights US $2,191
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
US $1,364/Night
For 7 Nights US $9,545
4 Guests
1 Bathroom
Family Friendly
Resort
- Pool
- Balcony/Terrace
- Kitchen
US $275/Night
For 7 Nights US $1,925
US $617/Night
For 7 Nights US $4,322
US $1,003/Night
For 7 Nights US $7,022
US $1,168/Night
For 7 Nights US $8,178
553.51 ft²
104 Guests
29 Bathrooms
Ocean View
Resort
- Private Beach
- Oceanfront
- Hot Tub
US $641/Night
For 7 Nights US $4,487
1073.16 ft²
139 Guests
30 Bathrooms
Free Cancellation
Resort
- Oceanfront
- Hot Tub
- Spa
US $1,534/Night
For 7 Nights US $10,735
Why Choose Rent By Owner for your Wailea Resorts?
What makes our Resorts 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 Resorts stay?
Choosing the optimal time to vacation in Wailea, Kihei, Hawaii, USA can significantly enhance your experience by aligning your visit with the area's most favorable weather and fewer crowds, ensuring a memorable and relaxing stay at your preferred resorts.
Peak Season Highlights
Winter (December to February)
During winter months, you can enjoy ideal weather and vibrant local events, making this a popular time to visit the area. Expect lively atmosphere and perfect conditions for outdoor activities.
Average Temperature Daytime: 78°F (26°C) - Nighttime: 66°F (19°C)
Summer (June to August)
The summer season attracts visitors seeking warm, sunny days perfect for beach outings and water sports. This period offers a lively ambiance with longer daylight hours and warm ocean waters.
Average Temperature Daytime: 85°F (29°C) - Nighttime: 75°F (24°C)
Off-Season Highlights
Spring (March to May)
In spring, rates tend to be more affordable while the weather remains pleasant for outdoor exploration. It’s an ideal time if you prefer fewer crowds and peaceful surroundings.
Average Temperature Daytime: 79°F (26°C) - Nighttime: 65°F (18°C)
Fall (September to November)
Autumn offers mild temperatures and less tourist traffic, making it a tranquil period to enjoy the region’s natural beauty and serene beaches without the peak season rush.
Average Temperature Daytime: 81°F (27°C) - Nighttime: 68°F (20°C)
Weekly Weather Forecast for Wailea
How to Book Your Wailea Resorts
What's our booking process?
Our platform allows you to browse a curated selection of resorts. 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 Resorts Amenities
What amenities can you expect?
Our Resorts 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 stunning outdoor swimming pools that overlook the ocean or lush gardens.
- Relax on private or shared outdoor patios and lanais with scenic views of the surrounding landscape.
- Take advantage of well-maintained outdoor barbecue facilities for memorable cookouts in the sun.
- Explore beautifully landscaped gardens that offer peaceful walking paths and tropical scenery.
- Make the most of outdoor shower stations to rinse off after a day at the nearby beaches.
- Participate in organized outdoor activities such as yoga classes or fitness sessions amid the fresh air.
- Utilize outdoor lounge areas equipped with comfortable seating perfect for sunset viewing or relaxing with loved ones.
Top Attractions Around Wailea
What attractions are nearby?
When staying at one of the trustworthy resorts in the area, you can enjoy a variety of nearby activities including world-class beaches, scenic outdoor excursions, and vibrant local culture that showcase the best of this Hawaiian destination, ensuring your experience here is both memorable and enriching.
Family Activities
- Snorkeling at Molokini Crater: Discover vibrant marine life and clear waters just off the coast, perfect for family snorkeling adventures in this renowned regional attraction.
- Wailea Beach Activities: Enjoy relaxing days on the sandy shores with options for swimming, paddleboarding, and building sandcastles that cater to all ages here in the area’s popular beaches.
- Visit the Shops at Wailea: Explore a variety of family-friendly boutiques and eateries ideal for a leisurely day out while experiencing the local charm of this region.
- Attend a Luau Experience: Immerse your family in Hawaiian culture through authentic music, dance, and traditional feasts offered at resorts and cultural centers nearby.
Adult Activities
- Snorkeling and Beach Exploration: Discover the vibrant marine life and pristine sands along the coast, perfect for both relaxation and adventure.
- Golfing at World-Class Courses: Play a round on beautifully designed courses that offer stunning ocean views and challenging fairways.
- Spa and Wellness Treatments: Indulge in luxurious spa services to rejuvenate your body and mind amid this tropical paradise.
- Sunset Cruises and Marine Tours: Experience breathtaking sunsets and learn more about the region's diverse ecosystem through guided tours.
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?
- Explore the beaches early in the day: Take advantage of the calm mornings by visiting the renowned beaches to enjoy serene views and better swimming conditions.
- Utilize local transportation options: Consider renting bikes or taking shuttles to easily access popular spots around the area without the hassle of parking.
- Sample authentic local cuisine: Savor regional flavors at nearby eateries to enrich your experience here and gain insight into the area's culinary traditions.
- Plan outdoor activities during off-peak hours: Maximize your leisure time by scheduling snorkeling, hiking, or sightseeing excursions when crowds are typically smaller.
Transportation Options
- Rental Car Services: Renting a car gives you the flexibility to explore the area at your own pace, with numerous providers offering convenient pickup and drop-off options near popular resorts.
- Shuttle Services: Shuttle options are available for easy transportation between resorts, airports, and key attractions, ensuring a hassle-free journey around this tropical destination.
- Public Transit: Local bus services provide an affordable way to travel throughout the region, connecting you to various beaches, shopping centers, and dining spots.
- Taxi and Rideshare: Taxis and rideshare options offer a quick and reliable way to reach your resort or explore nearby sites without the need for personal vehicle ownership.
Local Customs Options
- Respect for Aloha Spirit: Embrace the local tradition of Aloha Spirit, which emphasizes kindness, respect, and harmony with others in the community here.
- Hula Traditions: Participating or observing hula performances is a cherished custom that reflects the area's rich cultural heritage and history.
- Kapu System: Recognizing and respecting the traditional Kapu system helps uphold the sacred customs and land boundaries important to locals here.
- Local Language Etiquette: Learning simple Hawaiian phrases can demonstrate respect and appreciation for the region's native language and customs during your stay.
Wailea Resorts Frequently Asked Questions
1. What are the top Resorts 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 Resorts in Wailea:
- Ho‘olei Villas at Grand Wailea
- Hotel Wailea, Relais & Chateaux - Adults Only
- Wailea Beach Resort - Marriott, Maui
- Andaz Maui at Wailea Resort - a concept by Hyatt
- Grand Champions
- Grand Wailea Maui, A Waldorf Astoria Resort
- Grand Wailea Resort Hotel & Spa, A Waldorf Astoria Resort
- Wailea Beach Villas Penthouse Panoramic Ocean Views KBM Resorts 2 Units 6 Bedrooms ML-3485
- KBM Resorts: Grand Champions GCH-42 Remodeled 2 Bd Villa in Heart of Wailea Includes Rental Car
- Grand Champions 2 Free Rental Cars KBM Resorts Extra Large Corner Suite 2 Units 5 Bedrooms ML-1149
2. How many Resorts are available in Wailea?
Currently, the total number of properties listed by RBO in 2026 is over 45 in the Wailea area, and still counting. By aggregating listings from multiple websites, RBO offers an immense amount of choice of the best Resorts in Wailea.
3. What is the cancellation policy for resorts in Wailea, Kihei?
Cancellation policies vary depending on the specific resort and booking terms. It is recommended to review the individual listing details or contact the property owner directly through the platform for precise information.
4. Are there any additional fees I should be aware of when booking a resort here?
Additional fees such as cleaning charges, resort fees, or taxes may apply. These details are usually outlined in the listing, so it's best to check the specifics before confirming your reservation.
5. Can I modify or cancel my booking if my plans change?
Yes, most reservations can be modified or canceled within the terms specified in the listing. To ensure smooth changes, contact the property owner or review the cancellation policy outlined in your booking confirmation.
6. What amenities are typically available at resorts in this area?
Resorts here generally offer amenities like swimming pools, fitness centers, beachfront access, and on-site dining. For detailed information about amenities included in your chosen property, refer to the listing details.
7. Is it possible to find pet-friendly resorts in the region?
Some resorts accommodate pets, but policies vary. Check each listing carefully to see if pet-friendly options are available and review any associated restrictions or fees.
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