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!
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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
Welcome to Wailea Beach Villas Penthouse 205, an elegant retreat that showcases sophisticated furnishings, vibrant colors, and striking artwork. This family-friendly penthouse features three bedrooms and three full baths, offering ample space for families or groups to relax and unwind.A private key-entry elevator transports you directly from your r
Wailea Beach Villas Penthouse 504 enjoys 180 degree views of the Pacific Ocean, Kaho‘olawe, Molokini crater, and Lanai. This generous two-bedroom, two-bathroom condo provides over 1900 sq. ft. of living space, outdoor lanai, entertaining space, plus a den. Located on the fifth floor, guests can take advantage of the elevated views! Lounge on the s
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
Welcome to your serene paradise at Wailea Ekahi Village 51D, a stunning 2-bedroom ocean view condo nestled in the heart of Wailea. This meticulously designed retreat offers a perfect blend of comfort and luxury, ideal for your next Hawaiian getaway. Step inside to discover a spacious, open-concept living area that seamlessly flows into the dining a
You will feel like a rock star in this oceanfront villa that even has a vinyl record Juke box with complimentary play! Villa B101 sits oceanfront within a secluded garden area surrounding a private plunge pool. A short stroll leads you to the oceanfront infinity pool where adults cool off in peace and tranquility. Cap off your full Maui day in para
Oceanfront View
Complex Pool
Private Outdoor space
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3 Bedroom Ocean Front Villa - Platinum
Oceanfront View
Complex Pool
Private Outdoor space
Call this private piece of paradise home, which features panoramic views of Maui and the ocean below as well as luxurious interior elements everywhere you look. This contemporary vacation residence spans 2,500 square feet and captures the true allure of vacationing in Hawaii while providing the ultimate in luxury, comfort, and convenience. Blending
Warm breezes and lush tropical gardens greet guests of Wailea Beach Villas E202 as the spacious and comfortably appointed interior blends seamlessly onto the private outdoor lanai. Contemporary neutral and earth-toned furnishings are complimented by splashes of color throughout, accentuating the natural light, swaying palms and fresh air of Maui.Tw
CORALTREE RESIDENCE COLLECTION presents... Wailea Elua Village 1703Elua Village sits right on Ulua Beach and connects directly to the 3.2-mile Wailea Beach Walk. This 1,336 sq.ft. ground-floor 2-bedroom sits directly oceanfront with only lawn between you and the water, and no neighboring condos in the view. A wrap-around lanai, 2 resort pools, a sh
Oceanfront View
Complex Pool
Private Outdoor space
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2 Bedroom Oceanfront Condo - Platinum
Oceanfront View
Complex Pool
Private Outdoor space
Discover for yourself why D301 is one of the most requested Villas in our vacation rental collection. Impressive artwork by internationally known Maui artist Elan Vital provides a fabulous backdrop to the welcoming great room in rich jewel colors of amethyst and jade furnishings. This three bedroom three and a half bath Villa features luxury appoin
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
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2 Bedroom Golf Course View Condo - Platinum
Golf View
Complex Pool
Private Outdoor space
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
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2 Bedroom Golf Course + Partial Ocean View - Gold
Golf View
Complex Pool
Private Outdoor space
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