Explore Your Dream Wailea Vacation Rentals

Handpicked homes, condos, and villas designed for comfort and aloha living.

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RECENTLY BOOKED ACCOMMODATIONS

EXPERIENCE THE MAGIC OF WAILEA

Looking for Vacation Rentals in Wailea, Maui?

Welcome to Wailea Vacation Rentals, your gateway to Maui’s most beautiful stays. From luxurious oceanfront villas to peaceful resort condos, every space is handpicked for comfort, style, and aloha living. Unwind on golden beaches, explore coastal trails, and make lasting memories in Wailea’s serene paradise.

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Why Choose Wailea Vacation Rentals

Wailea Vacation Rentals offers a curated collection of upscale accommodations in one of Maui’s most coveted coastal regions. Whether you're seeking peaceful oceanfront relaxation, family-friendly comfort, or luxury amenities with a tropical touch, our rentals deliver the ideal blend of privacy, convenience, and island elegance. With access to world-class beaches, golf, dining, and wellness experiences, every stay feels effortless and unforgettable.

  • Prime locations near Wailea Beach, golf courses, and top resorts

  • Handpicked properties with upscale features and private lanais

  • Ideal for families, couples, or groups seeking space and comfort

  • Local support and seamless booking for a stress-free stay

Where the Best Wailea Vacation Rentals Are

The best vacation rentals in Wailea are nestled along the sun-drenched coastline, within exclusive resort communities and near some of Maui’s most iconic beaches. Whether you want direct beach access, golf course views, or a quiet hillside retreat, Wailea offers a range of luxurious and serene spots to call home during your stay.

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Frequently Asked Questions

Learn more about Wailea Vacation Rentals

We want your journey to Hammamet to be effortless. Below, we've answered some of the most common questions about our accommodations, booking process, and services to help you prepare for a seamless stay. If you need further assistance, feel free to contact us—we're here to ensure your experience is exceptional.

We offer a range of properties including oceanfront villas, resort-style condos, private homes, and golf course accommodations — all designed for comfort, style, and convenience.

Many of our rentals are beachfront or within walking distance to Wailea’s most popular beaches like Wailea Beach, Mokapu Beach, and Polo Beach.

Yes, we have a wide selection of family-friendly properties with spacious layouts, full kitchens, multiple bedrooms, and easy access to parks, pools, and beaches.

Minimum stay requirements vary by property and season, but most rentals require at least 3 to 5 nights. Longer minimums may apply during peak holiday periods.

Wailea enjoys sunny weather year-round, but the most popular months are December through April for winter sun and whale watching, and June through August for summer vacations.

Cancellation policies may vary depending on the property. Each listing includesdetailed information about the cancellation terms, so you can plan with peace of mind. If you needany clarification, feel free to reach out to us.