Wailea Rentals by Owner
1978 ft²
6 Guests
2 Bedrooms
2 Bathrooms
Ocean View
Villa
- Oceanfront
- Hot Tub
- Pool
US $1,370/Night
For 7 Nights US $9,590
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
1 Bedroom
1 Bathroom
Ocean View
Apartment
- Oceanfront
- Pool
- Ocean View
US $895/Night
For 7 Nights US $6,265
6 Guests
2 Bedrooms
2 Bathrooms
Family Friendly
Villa
- Hot Tub
- Fireplace/Heating
- Pool
US $370/Night
For 7 Nights US $2,591
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
1182 ft²
4 Guests
2 Bedrooms
2 Bathrooms
Ocean View
Villa
- Oceanfront
- Hot Tub
- Pool
US $380/Night
For 7 Nights US $2,659
1371 ft²
5 Guests
2 Bedrooms
2 Bathrooms
Ocean View
Villa
- Oceanfront
- Hot Tub
- Pool
US $491/Night
For 7 Nights US $3,437
1948.27 ft²
5 Guests
2 Bedrooms
3 Bathrooms
Apartment
- Oceanfront
- Pool
- Ocean View
US $618/Night
For 7 Nights US $4,326
906 ft²
2 Guests
1 Bedroom
2 Bathrooms
Ocean View
Villa
- Oceanfront
- Hot Tub
- Pool
US $350/Night
For 7 Nights US $2,451
1489 ft²
6 Guests
2 Bedrooms
2 Bathrooms
Ocean View
House
- Oceanfront
- Pool
- Ocean View
US $671/Night
For 7 Nights US $4,695
Why Choose Rent By Owner for your Wailea vacation rental?
What makes our Rentals by Owner 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 Rentals by Owner stay?
Choosing the optimal time to vacation here can enhance your experience, allowing you to enjoy the area's beautiful beaches and warm climate while making the most of your rental by owner in Wailea, Kihei, Hawaii, USA.
Peak Season Highlights
Winter (December to February)
During the winter months, you'll experience the highest influx of visitors seeking warm weather, making it an ideal time for enjoying the area's beaches and outdoor activities. Booking a rental by owner now ensures you secure a prime accommodation during this bustling peak season.
Average Temperature Daytime: around 80°F - Nighttime: approximately 65°F
Summer (June to August)
The summer months attract travelers eager to enjoy the sunny climate and lively atmosphere. This is when demand for vacation rentals peaks, so reserving early through Rent By Owner helps you find the best options in this popular destination.
Average Temperature Daytime: about 85°F - Nighttime: roughly 70°F
Off-Season Highlights
Spring (March to May)
In spring, the area offers pleasant weather with fewer crowds, making it a perfect time for a more relaxed stay. Securing your vacation rental during this period allows you to enjoy the tranquility of this destination without the high-season prices.
Average Temperature Daytime: around 78°F - Nighttime: approximately 60°F
Fall (September to November)
During fall, visitor numbers decrease, providing a peaceful retreat in this region. Booking through Rent By Owner in advance helps you take advantage of lower rates while still enjoying comfortable weather.
Average Temperature Daytime: about 82°F - Nighttime: roughly 65°F
Weekly Weather Forecast for Wailea
How to Book Your Wailea vacation rental
What's our booking process?
Our platform allows you to browse a curated selection of rentals by owner. 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 Rentals by Owner Amenities
What amenities can you expect?
Our Rentals by Owner 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 scenic outdoor swimming pools, perfect for relaxing under the Hawaiian sun.
- Take advantage of lush landscaped gardens or private yards for outdoor leisure and gatherings.
- Make the most of beach access or nearby shoreline for sunbathing, swimming, or water activities.
- Utilize outdoor grilling areas or BBQ stations to savor meals with a view of the ocean or garden scenery.
- Benefit from well-maintained tennis courts or other sports facilities available on the property.
- Relax in outdoor lounge areas designed for enjoying panoramic views here in this tropical destination.
- Participate in outdoor fitness or yoga sessions to start your day amidst the natural beauty of the region.
Top Attractions Around Wailea
What attractions are nearby?
In this beautiful area, you can enjoy a variety of activities such as relaxing on pristine beaches, exploring scenic coastal walks, and experiencing water sports like snorkeling and paddleboarding, all conveniently nearby when you choose your rental by owner in Wailea, Kihei, Hawaii, USA.
Family Activities
- Snorkeling at Molokini Crater: Experience the vibrant marine life and clear waters just off this destination, perfect for family adventures in Hawaii.
- Visit the Maui Ocean Center: Discover fascinating Hawaiian sea creatures and interactive exhibits that engage children and adults alike, making it an educational family outing.
- Relaxing on Wailea Beach: Enjoy sunbathing, swimming, and building sandcastles on the pristine shores that are ideal for families seeking a peaceful day by the water.
- Exploring Kealia Pond National Wildlife Refuge: Observe native bird species and partake in gentle walks along scenic trails, offering a natural escape for families in this region.
Adult Activities
- Snorkeling at Molokini Crater: Explore the vibrant marine life just off the coast, offering an unforgettable underwater experience in this renowned snorkeling site near the region.
- Golfing on Wailea Gold Course: Tee off at one of the area’s premier golf courses, where stunning ocean views and lush fairways create a perfect setting for a relaxing day on the greens.
- Sunset Coastline Walks: Enjoy scenic strolls along the picturesque coastline, taking in breathtaking views of the Pacific as you explore the area's natural beauty.
- Luxury Spa Experiences: Indulge in rejuvenating treatments at high-end spas nearby, designed to provide relaxation and pampering amidst the stunning surroundings.
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 local beaches: Take advantage of the region's renowned beaches to enjoy relaxing days by the ocean, making your stay truly memorable.
- Book activities in advance: Secure popular tours and excursions early to ensure you experience the best of this destination without last-minute surprises.
- Choose a rental by owner: Opt for vacation rentals managed directly by owners to enjoy personalized service and a more authentic local experience.
- Visit local markets: Immerse yourself in the area's culture by shopping at nearby farmers' markets and sampling fresh regional produce.
Transportation Options
- Rental Car Services: You can easily explore the area at your own pace by renting a vehicle from local providers that operate conveniently near rental properties.
- Public Transit Options: The region is served by bus lines offering affordable and reliable transportation, making it simple to get around here without needing a car.
- Shared Shuttle Services: Several shuttle companies provide door-to-door service between major hotels, popular attractions, and rental homes, ensuring a stress-free experience during your stay.
- Bicycle Rentals: For an eco-friendly way to see the surrounding scenery, bike rentals are available locally, giving you the flexibility to enjoy the area's natural beauty at your leisure.
Local Customs Options
- Respect for Hawaiian Culture: It is customary to honor local traditions and practices, especially when participating in community events or visiting cultural sites in the area.
- Greeting with Aloha: When meeting locals or engaging in activities, a warm "Aloha" is appreciated and reflects the friendly spirit of the region.
- Environmental Respect: You are encouraged to practice responsible tourism by conserving water, reducing waste, and protecting the natural beauty of this destination.
- Sun Protection and Attire: Wearing appropriate clothing and sun protection demonstrates respect for the climate while enjoying outdoor experiences here.
Wailea Rentals by Owner Frequently Asked Questions
1. What are the top Vacation 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 Vacation Rentals in Wailea:
- Wailea Custom Home, Pool, Panoramic Ocean View, Waterfalls - Maui Ocean Palms
- Walk to Beach, Ocean Views, Relax by the Pool
- 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,
- Oceanfront Private Home
- Stunning Ocean View Wailea Beach Villa- Book & Save
- Direct Beach Access - Best Location - Wailea Beach Villas H101 - Walk Everywhere
- Amazing House with Pool, Spa, Cabana & More Kihei Wailea Area
- Hoolei Uni 31-2 Ocean view- ideal Wailea location walking to beaches and shops
2. How many Vacation Rentals are available in Wailea?
Currently, the total number of properties listed by RBO in 2026 is over 565 in the Wailea area, and still counting. By aggregating listings from multiple websites, RBO offers an immense amount of choice of the best Vacation Rentals in Wailea.
3. What is the cancellation policy for rentals by owner in this area?
Cancellation policies vary by individual property listing. It’s important to review the specific cancellation terms provided on the rental’s page or contact the owner directly for details.
4. How do I ensure my booking with a private owner is secure?
When booking through Rent By Owner, your reservation is protected by our secure platform. Confirm all details with the owner and use the website’s messaging system for communication to ensure safety and transparency.
5. Are there any additional fees beyond the listed nightly rate?
Additional fees such as cleaning, service charges, or taxes are typically outlined in the listing. Check the final price breakdown before confirming your reservation to understand all costs involved.
6. What amenities are usually included in a rental by owner here?
Most private rentals offer amenities like fully equipped kitchens, Wi-Fi, parking, and often access to shared facilities or outdoor spaces. For specific amenities, refer to each listing's description or contact the owner directly.
7. How far in advance should I book my stay in this destination during peak seasons?
To secure the best options during busy times, it’s recommended to book several months ahead. Availability can be limited during high-demand seasons, so early planning ensures you get the ideal rental.
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