Family Friendly Vacation Rentals in Wailea
This collection of Wailea residences features two- to four-bedroom homes, making it ideal for families of all sizes in Maui’s premier resort destination. With full kitchens, spacious living areas, and multiple bedrooms, there’s room for everyone to relax and enjoy time together. Find your perfect stay in Wailea, and be sure to inquire about our family-friendly board game library during your stay—we’d be happy to include a selection of games for added enjoyment. Full-size washers and dryers make it easy to pack less and travel more!
travel dates
82 properties available
Sort by:
Random
-
Random
-
Bedrooms
-
Sleeps
-
Price
-
Quality
Welcome to Villa F201, an expansive vacation retreat that embodies upscale relaxation. Spanning a generous 3,676 square feet, this luxurious 3-bedroom, 3.5-bath villa is perfect for families or couples seeking a serene getaway.Villa F201 is a decorator's dream, harmoniously blending Hawaiiana art, modern furnishings, and Asian accents. Enjoy breath
Wailea Grand Champions 159 is a beautifully updated three-bedroom vacation rental located along the fairway of the Wailea Blue Golf Course. This ground-floor condo offers a spacious layout with three bedrooms and two bathrooms, making it ideal for families or groups seeking a luxurious and convenient retreat.As you step into the condo, you are gree
Wailea Beach Villas Penthouse 403 offers a luxurious escape with stunning ocean views and ample space for the whole family. Spanning 2,000 square feet, this penthouse features three bedrooms and three full bathrooms, making it an ideal holiday retreat. Guests can enjoy breathtaking Maui sunsets from the expansive 375-square-foot covered lanai, perf
Indulge in entertainment abound when vacationing in Wailea Beach Villas Penthouse 211. After you've spent an action-packed day at the beach or hiking one of Maui’s scenic trails, return to your vacation residence and discover some more relaxing entertainment options that will bring a smile to your face. Whether you choose to put in your favorite mo
Experience the beauty of Maui in the luxurious Penthouse 210 at Wailea Beach Villas, a stunning retreat featuring two bedrooms and two bathrooms designed with tropical island elegance. This vacation rental welcomes families with its spacious layout, offering stylish overstuffed Tommy Bahama furniture in a soothing color palette of caramel, cherry,
Welcome to Villa G302, your luxurious Hawaiian escape where relaxation meets elegance. This stunning ocean view villa features two walls of retractable sliding doors that seamlessly blend the open living area with a spacious corner lanai, complete with a built-in Viking grill-perfect for sunset barbecues in a tranquil island atmosphere.Designed wit
Curated with our guests in mind, Wailea Beach Villas PH111's outdoor elements are just as immaculate as the home’s interiors. Unwind and enjoy peekaboo views of the ocean along with tropical greenery from your private lanai. The pristine Wailea Beach is located nearby for additional endless entertainment and relaxation.Step inside to discover seren
Nestled in the heart of Wailea, this charming Grand Champions residence offers a tranquil retreat that feels like your own private Hawaiian sanctuary. As you step through the door, you\'re immediately embraced by the warmth of island living and the thoughtful design that sets this two-bedroom rental apart.Grand Champions 27 features a large, privat
Golf View
Complex Pool
Private Outdoor space
View Details
2 Bedroom Golf Course View Condo - Platinum
Golf View
Complex Pool
Private Outdoor space
Welcome to Wailea Beach Villas Penthouse 105, where luxury living meets the breathtaking beauty of Maui. This elegant ocean view penthouse spans 2,500 square feet and features a spacious floor plan that flows seamlessly onto a generous lanai, providing the perfect backdrop for enjoying the island's tropical splendor.Located in a prime position with
Wailea Grand Champions 75 is an exceptional vacation rental situated in the picturesque Wailea region of Maui. This luxurious property promises an unforgettable escape with its blend of elegance, comfort, and stunning natural beauty. Upon entering Wailea Grand Champions 75, you'll immediately notice the spacious and inviting atmosphere. The open
Golf View
Complex Pool
Private Outdoor space
View Details
2 Bedroom Golf Course + Partial Ocean View - Gold
Golf View
Complex Pool
Private Outdoor space
Welcome to your serene oasis at Wailea Elua Village 1509, a luxurious 2-bedroom garden view condo nestled in the heart of Wailea. This meticulously designed retreat offers a perfect blend of comfort and elegance, ideal for your next Hawaiian getaway. Step inside to discover a spacious, open-concept living area adorned with modern furnishings and a
Penthouse 512 at Wailea Beach Villas offers an unparalleled top-floor experience with expansive ocean and island views, ideal for a Hawaiian dream vacation. This 2,300-square-foot home features a wrap-around lanai, providing one of the most breathtaking views in the Wailea Beach resort area. Just a short five-minute walk immerses you in the Pacific
Tell us what you're looking for and someone will contact you with available options.