Wailea Villa
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
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
6 Guests
2 Bedrooms
2 Bathrooms
Family Friendly
Villa
- Hot Tub
- Fireplace/Heating
- Pool
US $370/Night
For 7 Nights US $2,591
1388.54 ft²
8 Guests
3 Bedrooms
2 Bathrooms
Ocean View
House
- Oceanfront
- Ocean View
- View
US $744/Night
For 7 Nights US $5,208
1182 ft²
4 Guests
2 Bedrooms
2 Bathrooms
Ocean View
Villa
- Oceanfront
- Hot Tub
- Pool
US $380/Night
For 7 Nights US $2,659
8 Guests
1 Bedroom
4 Bathrooms
Villa
- Parking
- Internet
- Child Friendly
US $995/Night
For 7 Nights US $6,965
1371 ft²
5 Guests
2 Bedrooms
2 Bathrooms
Ocean View
Villa
- Oceanfront
- Hot Tub
- Pool
US $491/Night
For 7 Nights US $3,437
1151.74 ft²
8 Guests
2 Bedrooms
2 Bathrooms
Family Friendly
House
- View
- Breakfast
- Parking
US $633/Night
For 7 Nights US $4,431
906 ft²
2 Guests
1 Bedroom
2 Bathrooms
Ocean View
Villa
- Oceanfront
- Hot Tub
- Pool
US $350/Night
For 7 Nights US $2,451
1930.33 ft²
42 Guests
14 Bedrooms
9 Bathrooms
Villa
- Oceanfront
- Hot Tub
- Spa
US $3,289/Night
For 7 Nights US $23,023
908 ft²
4 Guests
1 Bedroom
2 Bathrooms
Ocean View
Villa
- Oceanfront
- Hot Tub
- Pool
US $425/Night
For 7 Nights US $2,978
1388.54 ft²
6 Guests
3 Bedrooms
2 Bathrooms
House
- View
- Breakfast
- Parking
US $979/Night
For 7 Nights US $6,853
Why Choose Rent By Owner for your Wailea Villa?
What makes our Villa 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 Villa stay?
To make the most of your stay in this beautiful part of Hawaii, consider planning your vacation during the shoulder seasons when the region enjoys pleasant weather and fewer crowds, ensuring a more relaxing experience whether you're seeking tranquility or adventure.
Peak Season Highlights
Winter (December to February)
During the winter months, you can enjoy warm weather and abundant sunshine here, making it a popular time for visitors seeking a tropical getaway.
Average Temperature Daytime: 78°F - Nighttime: 65°F
Summer (June to August)
The summer season attracts travelers looking for vibrant beach life and lively events, perfect for enjoying this destination’s scenic beauty.
Average Temperature Daytime: 85°F - Nighttime: 72°F
Off-Season Highlights
Spring (March to May)
In spring, the area experiences fewer crowds, providing a more relaxed environment while still offering pleasant weather for outdoor activities.
Average Temperature Daytime: 80°F - Nighttime: 66°F
Fall (September to November)
Autumn offers a quieter atmosphere with mild temperatures, making it an ideal time to book a villa and enjoy the region's natural serenity.
Average Temperature Daytime: 82°F - Nighttime: 68°F
Weekly Weather Forecast for Wailea
How to Book Your Wailea Villa
What's our booking process?
Our platform allows you to browse a curated selection of villa. 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 Villa Amenities
What amenities can you expect?
Our Villa 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 sparkling private or shared swimming pools, perfect for relaxation and unwinding in the warm Hawaiian sun.
- Take advantage of beautifully maintained outdoor lounging areas with comfortable seating, ideal for soaking up the coastal breezes.
- Many properties feature lush, tropical gardens that create a peaceful outdoor atmosphere reminiscent of this scenic destination.
- Utilize outdoor grilling stations and barbecue areas to savor delicious meals while enjoying the scenic surroundings.
- Explore nearby walking paths and scenic trails for outdoor activities and sightseeing within the region’s natural beauty.
- Some villas offer access to tennis courts or other sports facilities for active outdoor recreation.
- Many rentals have expansive lanais or verandas, providing perfect spaces for outdoor dining and entertaining while taking in views of the area’s stunning landscapes.
Top Attractions Around Wailea
What attractions are nearby?
In this beautiful destination, you can enjoy a variety of activities such as world-class beaches, scenic snorkeling spots, and stunning golf courses, all just moments away from your chosen Wailea accommodation, ensuring a memorable and relaxing Hawaiian getaway.
Family Activities
- Snorkeling at Molokini Crater: Experience vibrant marine life and clear waters just off the coast, perfect for family adventures in this renowned snorkeling destination.
- Visit the Maui Ocean Center: Discover Hawaii’s fascinating marine ecosystem through engaging exhibits and touch pools, making it a favorite family activity here.
- Attend a luau celebration: Immerse your family in Hawaiian culture with traditional dances, music, and cuisine at a lively luau hosted nearby.
- Relax on Wailea Beach: Enjoy the soft sands and gentle waves of this beautiful beach, ideal for sandcastle building and picnics with the entire family.
Adult Activities
- Golfing at Wailea Gold Course: Enjoy a round of world-class golf on this renowned course, offering stunning ocean views and a challenging layout perfect for enthusiasts seeking an exceptional golfing experience.
- Spa and Wellness Treatments: Indulge in relaxing spa services at local resorts, where you can unwind with massages, facials, and wellness therapies amid the tranquil surroundings of the area.
- Snorkeling and Marine Exploration: Discover vibrant marine life and coral reefs just off the coast, making snorkeling an ideal activity for those wanting to explore the underwater beauty of this tropical destination.
- Fine Dining Experiences: Savor delicious culinary offerings at upscale restaurants in the region, where you can enjoy fresh seafood and local Hawaiian cuisine in a sophisticated atmosphere.
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: Booking your excursions and dining reservations in advance will help you make the most of your time here and enjoy the best experiences the area has to offer.
- Choose a Prime Location for Your Villas: Selecting accommodations close to the beach and local attractions ensures easy access to the region's natural beauty and vibrant culture.
- Utilize Local Resources: Take advantage of the area's visitor centers and online guides to discover hidden gems and authentic experiences that enrich your stay.
- Respect the Environment and Community: Engage in eco-friendly practices and support local businesses to help preserve the region’s natural splendor and welcoming atmosphere.
Transportation Options
- Rental Car Services: You can easily rent a vehicle to explore this region at your own pace, with numerous rental agencies offering convenient pick-up and drop-off options nearby.
- Public Transportation: Local bus routes provide affordable transportation around the area, making it simple to access popular beaches and amenities in this destination.
- Shuttle Services: Many resorts and accommodations offer shuttle services that connect you to key locations, providing a hassle-free way to navigate here.
- Taxi and Rideshare: Taxis and rideshare options like Uber and Lyft are readily available, offering quick and reliable transportation throughout the region.
Local Customs Options
- Respect for Aloha Spirit: Embrace the local customs of hospitality and kindness that are central to the area’s welcoming atmosphere.
- Traditional Luaus: Participate in or observe luaus, which celebrate Hawaiian culture through dance, music, and storytelling.
- Ohana and Community Values: Prioritize family and community connections, reflecting the region's strong sense of togetherness.
- Environmental Respect: Practice sustainable and eco-friendly behaviors to honor the natural beauty of the destination.
Wailea Villa Frequently Asked Questions
1. What are the top Villas 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 Villas in Wailea:
- Exquisite Oceanview Villa with Resort Amenities in Gated Community
- Panoramic Ocean Views! - Luxury Villa! - Owner Direct!
- Spectacular 3rd Row Villa at Ho'olei with Ocean Views
- Breathtaking Ocean Views from 3rd Row Luxury Villa at Ho'olei
- Luxury Villa Steps from Wailea Beach with Resort Amenities and Stunning Upgrades
- Ho'olei 43-3; Hotel Privileges; Upgraded Internet!
- I.P.M PRESENTS: HOOLEI 69-2: GREAT LOCATION + STUNNING NEW REMODEL! WOW!
- I.P.M PRESENTS: HOOLEI 81-4: AMAZING NEW REMODEL! FLEXIBLE CANCELATION POLICY
- Maui escape with ocean views, lanai dining, poolside jacuzzis & gated community
- Private Ocean Front at Wailea Beach Villas B102
2. How many Villas are available in Wailea?
Currently, the total number of properties listed by RBO in 2026 is over 136 in the Wailea area, and still counting. By aggregating listings from multiple websites, RBO offers an immense amount of choice of the best Villas in Wailea.
3. What is the cancellation policy for villas in this area?
Cancellation policies vary by property; it's important to review the specific villa listing for detailed terms. Contact the property owner directly through the listing to clarify any questions about cancellations and refunds.
4. Are there any additional fees I should be aware of when booking a villa in this destination?
Additional fees such as cleaning charges, service fees, or taxes may apply and are detailed in each villa's listing. Always check the listing details or reach out to the owner to understand all costs involved before confirming your reservation.
5. How do I know if the villa has the amenities I need for my stay?
Each villa listing includes a comprehensive list of amenities. For specific requirements, contact the owner directly to confirm that the property meets your needs before booking.
6. Can I see photos of the villa before making a reservation?
Yes, all listings feature multiple high-quality photos of the villa interiors and exteriors. If you need more information or additional images, reach out to the owner to ensure the property matches your expectations.
7. What is the process for checking in and out at a villa here?
Check-in and check-out procedures are outlined in each villa's listing and may vary depending on the property. Contact the owner in advance to receive specific instructions and arrangements to ensure a smooth arrival and departure.
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