Discover Your Perfect Wailea-Makena Vacation Homes

Best Vacation Homes in Wailea-Makena

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10.0 (4 Reviews)
Apartment
Wailea Ekahi 21F
  • Pool
  • Security/Safety
  • Guest Services
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Wailea-Makena Luxury Rentals

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Wailea-Makena Pet Friendly Vacation Rentals

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Why Choose Rent By Owner for your Wailea-Makena Vacation Rental Homes?

What makes our Vacation Rentals special?

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Verified Listings
Book with confidence knowing every property meets our quality and safety standards.
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Unbeatable Value
Enjoy competitive pricing with no hidden fees, providing exceptional value for every stay.
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Diverse Options
From cozy cabins to luxurious villas, find a rental that suits your style and needs.

Popular Areas for Wailea-Makena Vacation Rentals

Where are the best neighborhoods to stay in Wailea-Makena?

When exploring the beautiful Wailea-Makena area in Hawaii, selecting the right neighborhood to stay in can greatly enhance your vacation experience. Wailea offers a range of upscale communities known for their stunning beaches, luxurious amenities, and picturesque surroundings, making it an ideal choice for those seeking comfort and tranquility. Makena, on the other hand, provides a more secluded atmosphere with pristine natural beauty and exclusivity. Whether you prefer the vibrant energy of Wailea or the peaceful ambiance of Makena, both neighborhoods offer exceptional places to stay that showcase the best of Hawaii’s stunning landscape and warm hospitality. Booking your vacation rentals in these neighborhoods ensures easy access to scenic views and a relaxing getaway tailored to your preferences."

Wailea

In this area, you will find a selection of vacation rentals that offer easy access to stunning beaches and scenic golf courses. Staying here provides a perfect balance of luxury and relaxation, ideal for exploring the natural beauty and tranquil ambiance of the region.

View 1292+ Rentals in Wailea

Best Times to Visit Wailea-Makena

When should you plan your Vacation Rentals stay?

Choosing the ideal time to visit this destination can enhance your experience, as understanding seasonal trends in the region allows you to plan your stay when weather conditions and local events align perfectly with your vacation goals.

Peak Season Highlights

spring
December to April

During these months, the area experiences its peak tourist season, attracting visitors for ideal beach weather and outdoor activities. You can enjoy warm daytime temperatures that are perfect for exploring and relaxing.

Average Temperature Daytime: 75°F to 80°F - Nighttime: 65°F to 70°F
spring
June to August

Summer brings high visitor influx, with the region buzzing with activity and vibrant events. These months offer consistently warm weather, making it an excellent time for outdoor pursuits and enjoying the scenic coastlines.

Average Temperature Daytime: 85°F to 88°F - Nighttime: 70°F to 74°F

Off-Season Highlights

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May and November

These shoulder months provide a quieter atmosphere, ideal for travelers seeking less crowded vacation rentals while still enjoying warm weather and pleasant ocean breezes.

Average Temperature Daytime: 78°F to 82°F - Nighttime: 63°F to 67°F
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September to October

This period is considered off-peak, offering more affordable vacation rentals and a peaceful setting. The weather remains warm, and you can experience the region's natural beauty without the peak-season crowds.

Average Temperature Daytime: 80°F to 84°F - Nighttime: 66°F to 70°F

Weekly Weather Forecast for Wailea-Makena

How to Book Your Wailea-Makena Vacation Rental Home

What's our booking process?

Our platform allows you to browse a curated selection of vacation rentals. 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-Makena

More Top-Rated Vacation Rentals in Wailea-Makena Area

Common Vacation Rentals Amenities

What amenities can you expect?

Our Vacation Rentals 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 private outdoor pools or community swimming areas for a refreshing dip under the Hawaiian sun.
  • Relax on spacious lanais or decks that offer stunning views of the region’s natural beauty.
  • Make use of well-maintained outdoor grilling stations, perfect for preparing local cuisine while enjoying the tropical air.
  • Take advantage of lush gardens and landscaped grounds that create a serene environment right outside your door.
  • Participate in outdoor activities such as tennis or pickleball, often available at many properties here.
  • Utilize dedicated outdoor dining spaces that allow you to enjoy meals al fresco with scenic surroundings.
  • Access to nearby beaches or shoreline amenities, providing opportunities for sunbathing, swimming, and water sports within easy reach.

Top Attractions Around Wailea-Makena

What attractions are nearby?

In this vibrant area, you can enjoy an array of outdoor activities such as snorkeling, golfing, and relaxing on pristine beaches just moments from your vacation rental, offering the perfect setting for an unforgettable Hawaiian escape.

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Family Activities

  • Snorkeling at Molokini Crater: Discover vibrant marine life just off the coast, ideal for family adventures in this renowned snorkeling spot near here.
  • Wailea Beach Activities: Enjoy a relaxing day on the golden sands of Wailea Beach, perfect for building sandcastles or swimming with your loved ones.
  • Maui Ocean Center: Explore Hawaii’s unique marine ecosystem through interactive exhibits, providing an educational and entertaining experience for all ages.
  • Family Hiking Trails: Embark on scenic hikes along the area’s well-maintained trails, offering breathtaking views and opportunities to observe local wildlife.
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Adult Activities

  • Snorkeling at Molokini Crater: Explore vibrant underwater life in a protected volcanic caldera just off the coast, perfect for an unforgettable aquatic adventure.
  • Golfing on world-class courses: Tee off at premier golf courses in the area that offer stunning ocean views and challenging fairways for enthusiasts of all skill levels.
  • Luxury spa experiences: Indulge in rejuvenating treatments at top-tier spas that utilize locally sourced ingredients, providing the ultimate relaxation.
  • Sunset sailing cruises: Enjoy breathtaking sunsets aboard private or group sails that showcase the region’s scenic coastline and tranquil waters.

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Wailea-Makena Travel Tips

How Can You Make the Most of Your Stay?

  • Explore the beaches early in the morning: Enjoy the serene beauty and less crowded shores by visiting during sunrise, making the most of your time on this pristine coastline.
  • Take advantage of the local culinary scene: Savor authentic flavors by dining at nearby eateries or preparing fresh seafood and tropical fruits in your vacation rentals here.
  • Participate in outdoor activities: Whether it’s snorkeling, paddleboarding, or golf, engaging in these pursuits allows you to experience the region’s natural beauty fully.
  • Plan scenic drives along the coast: Discover breathtaking views and hidden spots by exploring the area's scenic routes at your own pace for an unforgettable adventure.

Transportation Options

  • Rental Car Services: Opt for rental cars to explore the area at your own pace, with numerous providers offering convenient options near this popular Hawaiian destination.
  • Shared Shuttle Services: Shared shuttles provide affordable and reliable transportation between the region's major airports and your vacation rental in Wailea-Makena.
  • Taxis and Ride-Sharing: Taxis and ride-sharing apps like Uber and Lyft are readily available for quick, hassle-free trips around here’s scenic coastlines and local attractions.
  • Bicycle Rentals: Biking is an eco-friendly way to enjoy the region’s beautiful scenery while getting around comfortably from your vacation rental.

Local Customs Options

  • Respect for Aloha Spirit: In this region, embracing the Aloha Spirit by greeting others with warmth and kindness is a cherished tradition that enhances your experience here.
  • Hula Dancing Etiquette: Participating in or observing hula performances involves respectful listening and appreciation for its cultural significance to local customs.
  • Traditional Hawaiian Blessings: Many gatherings and ceremonies are preceded by blessings, emphasizing respect for nature and community that you should honor during your stay.
  • Environmental Stewardship: Protecting the pristine beaches and natural surroundings through responsible behavior aligns with the local commitment to sustainability and conservation practices here.

Frequently Asked Questions About Wailea-Makena?

1. What are the top vacation rentals in Wailea-Makena?

There are a lot of options in Wailea-Makena. If you plan on staying in the Wailea-Makena 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-Makena:

2. How many vacation rentals have private pools in Wailea-Makena?

There are 81 vacation rentals with private pools near Wailea-Makena. Top-rated RBO homes that have access to a swimming pool include:

3. Which vacation homes in Wailea-Makena are best for families?

If you are looking for a family-friendly vacation home in Wailea-Makena, check out one of the following properties as all are highly-rated places to stay with excellent review for families or groups staying in Wailea-Makena:

4. How many Rentbyowner vacation rentals are available in Wailea-Makena?

Currently, the total number of properties listed by Rent By Owner in 2025 is over 1602 in the Wailea-Makena area, and still counting. By aggregating listings from multiple websites, Rent By Owner offers an immense amount of choice of the best RBO properties in Wailea-Makena. 

5. What is the cancellation policy for vacation rentals in Wailea-Makena?

Cancellation policies vary by property owner, so it’s important to review the specific listing details. You can find this information on the property page or contact the host directly for clarification.

6. Are there any additional fees or charges when booking a vacation rental in Wailea-Makena?

Additional fees such as cleaning, service charges, or taxes are typically outlined in the listing details. Be sure to read the full description and contact the host if you have questions about potential extra costs.

7. How do I know if a vacation rental in Wailea-Makena is available for my travel dates?

Availability is shown on each property’s calendar. If your preferred dates are not available, you can contact the owner for alternative options or explore similar listings in the area.

8. What amenities can I expect from vacation rentals here in Wailea-Makena?

Amenities vary by property but often include features like kitchens, Wi-Fi, pools, and outdoor spaces. To ensure the rental meets your needs, review the amenities listed on the property profile or reach out to the host.

9. Is it necessary to contact the property owner before booking a vacation rental in Wailea-Makena?

While most listings allow direct booking, contacting the owner beforehand can help clarify any questions about the property, rules, or special requests, ensuring a smooth stay.

Wailea-Makena Top Rated Vacation Rentals

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