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  2. Hawaii
  3. Kihei
  4. Wailea Beach
  5. Rentals by Owner

Discover Your Perfect Wailea Beach Rentals by Owner

Wailea Beach Rentals by Owner

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10.0 (4 Reviews)
Apartment
Wailea Ekahi 21F
  • Pool
  • Security/Safety
  • Guest Services
View Availability
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10.0 (4 Reviews)
House
Kamaole Sands 3-303
  • Parking
  • Pool
  • Accessibility
View Availability
More Top-Rated Rentals by Owner in Wailea Beach Area

Why Choose Rent By Owner for your Wailea Beach vacation rental?

What makes our Rentals by Owner 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 Beach Rentals by Owner

Where are the best neighborhoods to stay in Wailea Beach?

If you're considering a stay in the beautiful area of Wailea Beach, Kihei, Hawaii, you'll find that each neighborhood offers a unique charm and convenient access to stunning coastal views. Whether you prefer the upscale atmosphere near Wailea Beach or the relaxed vibe of Kihei’s vibrant streets, there are plenty of rental options by owner through Rent By Owner to suit your needs. Exploring this region means immersing yourself in a picturesque setting with easy access to pristine beaches, ensuring a memorable Hawaiian vacation. Trust in Rent By Owner to help you find reliable vacation rental accommodations that make your stay in this renowned Hawaiian location seamless and enjoyable.

Wailea

In this upscale area, you'll find luxurious vacation rentals nestled along pristine beaches, offering you a relaxing and elegant stay. The region is renowned for its world-class resorts and stunning ocean views, making it an ideal choice for travelers seeking comfort and exclusivity.

View 1583+ Rentals in Wailea

Halama Street

Located in a serene part of the region, this neighborhood offers charming rental options perfect for visitors looking for a peaceful retreat. Its convenient proximity to local beaches and amenities makes it a favored spot for those wanting easy access to outdoor activities and dining.

View 5623+ Rentals in Halama Street

Ukumehame Ahupuaa

This coastal community provides an authentic Hawaiian experience with cozy rental homes near the water's edge. Staying here allows you to enjoy the tranquility of the area while still being close to the vibrant attractions of Kihei and the surrounding region.

View 490+ Rentals in Ukumehame Ahupuaa

Best Times to Visit Wailea Beach

When should you plan your Rentals by Owner stay?

Choosing the optimal time to vacation here can enhance your experience, as the region offers ideal conditions for relaxing on the beach and exploring local surroundings throughout the year, making it essential to consider seasonal patterns and weather trends when booking your rental by owner in Wailea Beach, Kihei, Hawaii, USA.

Peak Season Highlights

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Winter (December to February)

During the winter months, the region experiences peak visitor interest due to its warm climate and holiday season appeal, making it an ideal time for you to explore this destination’s beaches.

Average Temperature Daytime: Around 78°F (26°C) - Nighttime: About 65°F (18°C)
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Summer (June to August)

The summer period sees high activity levels, as travelers flock here to enjoy the sunny weather and vibrant atmosphere, perfect for a memorable getaway by owner in this area.

Average Temperature Daytime: Approximately 85°F (29°C) - Nighttime: Roughly 75°F (24°C)

Off-Season Highlights

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Spring (March to May)

In spring, the region experiences a quieter atmosphere, offering a peaceful environment for your vacation rental stay amid pleasant weather conditions.

Average Temperature Daytime: Between 76°F and 81°F (24°C - 27°C) - Nighttime: Around 64°F to 68°F (18°C - 20°C)
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Fall (September to November)

Fall brings a slower pace with fewer visitors, giving you a perfect opportunity to enjoy the area’s tranquil beauty while booking a rental here without the crowds.

Average Temperature Daytime: Approximately 80°F (27°C) - Nighttime: About 70°F (21°C)

Weekly Weather Forecast for Wailea Beach

How to Book Your Wailea Beach 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 Beach

More Top-Rated Rentals by Owner in Wailea Beach Area

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

  • Access to scenic outdoor swimming pools with views of the ocean or lush gardens
  • Private or shared beachfront patios ideal for relaxing and enjoying the ocean breeze
  • Outdoor grills and barbecue areas perfect for family cookouts in the warm Hawaiian sun
  • Well-maintained walking paths and gardens to explore the natural beauty of the region
  • Convenient outdoor showers for rinsing off after a day at the beach
  • Lounging furniture on terraces or lanais to soak in the stunning coastal vistas
  • Community tennis courts or fitness areas set amidst the area's tropical landscape

Top Attractions Around Wailea Beach

What attractions are nearby?

Within this vibrant region, you can enjoy a variety of nearby activities such as relaxing on beautiful beaches, exploring scenic outdoor trails, or engaging in water sports—all just moments from your Rent By Owner rental in Wailea Beach, Kihei, Hawaii.

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Family Activities

  • Snorkeling at Wailea Beach: Discover the vibrant underwater world just offshore, perfect for family fun and educational adventures in the region.
  • Beach picnics and sunbathing: Enjoy relaxing days on the soft sands of Wailea Beach, where you can have a delicious picnic while soaking up the Hawaiian sun with your loved ones.
  • Exploring nearby tide pools: Venture along the shoreline to observe fascinating tide pools that are fun and engaging for children and adults alike in this scenic area.
  • Family-friendly water activities: Rent kayaks or paddleboards locally to make the most of your visit, creating memorable moments here on Hawaii’s beautiful coast.
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Adult Activities

  • Snorkeling Adventures: Discover vibrant marine life just off the coast, where clear waters and coral reefs offer an exceptional snorkeling experience unique to this part of Hawaii.
  • Golfing at Local Courses: Tee off at world-class golf courses nearby that provide stunning ocean views and challenging fairways for enthusiasts seeking a relaxing day on the greens.
  • Luxury Spa Treatments: Indulge in rejuvenating spa experiences available in the region that use native ingredients and expert techniques to enhance your relaxation.
  • Sunset Ocean Cruises: Embark on a scenic cruise from here to witness breathtaking sunsets over the Pacific, creating memorable moments during your stay.

Wailea Beach Travel Tips

How Can You Make the Most of Your Stay?

  • Plan Your Activities Early: To fully enjoy this tropical paradise, book your preferred excursions and rentals in advance to secure the best options available locally.
  • Choose a Convenient Location: Selecting a vacation rental close to beaches and amenities allows you to maximize relaxation and explore the region effortlessly.
  • Embrace the Local Culture: Engage with the area's unique traditions and cuisines to enrich your experience while respecting the local community’s customs.
  • Utilize Trusted Accommodation Platforms: Book through reputable services offering owner-direct rentals here to ensure a seamless, trustworthy stay in this sought-after destination.

Transportation Options

  • Rental Car Services: Renting a car is one of the most flexible options for exploring this area, offering convenience and independence during your stay.
  • Airport Shuttle: Many hotels and rental services provide shuttle transportation to and from the nearby airport, simplifying your arrival and departure experience.
  • Public Transportation: Local bus services connect this destination with surrounding towns and attractions, providing an affordable way to get around.
  • Ride-Sharing Apps: Popular ride-sharing platforms are readily available here, allowing you to quickly and safely navigate the region at your convenience.

Local Customs Options

  • Respect for the Aloha Spirit: Embracing the welcoming and harmonious attitude of the locals fosters positive interactions in this coastal community.
  • Honoring Hawaiian Sacred Sites: When visiting beaches or inland areas, it’s customary to show reverence by following posted guidelines and refraining from disruptive behavior.
  • Practicing Malama Aina: Taking care of the land and ocean through responsible tourism helps preserve the natural beauty that makes this region special.
  • Participating in Local Cultural Events: Engaging respectfully in traditional ceremonies or festivals enhances your experience while honoring local customs here.

Frequently Asked Questions About Wailea Beach Rentals by Owner

1. What are the top vacation rentals in Wailea Beach?

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

2. How many Rentbyowner vacation rentals are available in Wailea Beach?

Currently, the total number of properties listed by Rent By Owner in 2025 is over 1482 in the Wailea Beach 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 Beach. 

3. What is the cancellation policy for a rental by owner in this area?

Cancellation policies vary depending on the individual host and listing. You should review the specific cancellation terms detailed on the rental's listing page or contact the property owner directly for clarification.

4. How do I confirm availability and book a rental by owner here?

Availability can be checked through the listing details, and you can proceed with booking by following the reservation instructions provided. For any questions, reaching out directly to the owner ensures a smooth booking process.

5. Are there any additional fees or charges for rentals by owner in this destination?

Additional fees such as cleaning, service charges, or taxes are typically outlined on the listing. It’s recommended to read the full details of the listing or communicate with the owner to understand all costs involved.

6. What amenities are usually included in a rental by owner in this region?

Amenities vary between listings but commonly include essentials like Wi-Fi, fully equipped kitchens, and laundry facilities. Check the specific listing for a complete list of amenities offered by the owner.

7. Is there a minimum stay requirement for booking a rental by owner here?

Minimum stay requirements depend on the individual property and its host. These details are provided on the listing, and you can also inquire directly with the owner to confirm any stay restrictions.

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More Top-Rated Rentals by Owner in Wailea Beach Area