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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Properties Available 82 properties available
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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
Wailea Beach Villas PH512 reserve-collection-logo
3 Bedroom Ocean View Condo - Diamond
Rating 5 (19)
3 bedrooms
3 baths
6 guests
Location Wailea, HI Icon of Ocean View Ocean View Icon of Complex Pool Complex Pool Icon of Private Outdoor space Private Outdoor space
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Let the sounds of palm fronds brushing against each other in the gentle trade winds sing you to sleep this vacation. With relaxing views of the ocean and the manicured tropical landscaping, Wailea Beach Villas Penthouse 411 leaves no stone unturned in the pursuit of your delight. Open up your lanai doors and head outside to look for whales or watch
Wailea Beach Villas PH411 reserve-collection-logo
2 Bedroom Ocean View Condo - Diamond
Rating 5 (3)
2 bedrooms
2 baths
6 guests
Location Wailea, HI Icon of Ocean View Ocean View Icon of Complex Pool Complex Pool Icon of Private Outdoor space Private Outdoor space
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Welcome to Wailea Beach Villas D302! Recently renovated, this residence features a custom gourmet kitchen and dining area, offering a luxurious and spacious retreat in one of Maui's premier locations. Spanning over 2,900 square feet of indoor and outdoor living, it comfortably accommodates families or groups of up to 8 guests.Located on the upper f
Wailea Beach Villas D302
3 Bedroom Ocean View Villa - Diamond
Rating 5 (10)
3 bedrooms
3.5 baths
8 guests
Location Wailea, HI Icon of Ocean View Ocean View Icon of Complex Pool Complex Pool Icon of Private Outdoor space Private Outdoor space
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CORALTREE RESIDENCE COLLECTION presents... Wailea Elua Village 1504Elua Village sits right on Ulua Beach and connects directly to the 3.2-mile Wailea Beach Walk. This recently remodeled 2nd-floor 2-bedroom condo sits elevated above the resort, with floor-to-ceiling glass on 2 walls framing panoramic ocean views from the living room and lanai. 2 oce
Wailea Elua Village 1504 reserve-collection-logo
2 Bedroom Ocean View Condo – Diamond
Rating 5 (18)
2 bedrooms
2 baths
4 guests
Location Wailea, HI Icon of Ocean View Ocean View Icon of Complex Pool Complex Pool Icon of Private Outdoor space Private Outdoor space
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CORALTREE RESIDENCE COLLECTION presents... Wailea Elua Village 2108This stunningly renovated 2nd-floor 1,528 sq.ft. 2-bedroom condo features 2 oceanside lanais with lovely views, access to 2 resort pools, a pickleball court, and a shared hot tub. Elua Village sits right on Ulua Beach and connects directly to the 3.2-mile Wailea Beach Walk, with the
Wailea Elua Village 2108 reserve-collection-logo
2 Bedroom Ocean View Condo – Diamond
Rating 5 (24)
2 bedrooms
2 baths
5 guests
Location Wailea, HI Icon of Ocean View Ocean View Icon of Complex Pool Complex Pool Icon of Private Outdoor space Private Outdoor space
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Marvel at the sophisticated style and decor of Wailea Beach Villas Penthouse 104, where a touch of Bali influence seamlessly merges with rustic undertones to create an unforgettable ambiance. The interior design captivates with elements like a textured wall-mounted matting behind the impressive 85'' living room TV and a charming wooden picnic-table
Wailea Beach Villas PH104
2 Bedroom Garden View Condo - Diamond
Rating 5 (10)
2 bedrooms
2 baths
6 guests
Location Wailea, HI Icon of Complex Pool Complex Pool Icon of Private Outdoor space Private Outdoor space Icon of Resort Golf Resort Golf
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CORALTREE RESIDENCE COLLECTION presents... Wailea Elua Village 1001This exquisitely designed ground-floor 1,259 sq. ft. residence sits steps from Ulua Beach and connects directly to the 3.2-mile Wailea Beach Walk. Walk straight from the extra-large patio to the backyard fronting the beach, explore 2 resort pools, and soothe your muscles in the hot
Wailea Elua Village 1001 reserve-collection-logo
2 Bedroom Oceanfront Condo - Diamond
Rating 5 (11)
2 bedrooms
2 baths
4 guests
Location Wailea, HI Icon of Oceanfront View Oceanfront View Icon of Complex Pool Complex Pool Icon of Private Outdoor space Private Outdoor space
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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
Wailea Beach Villas G302 reserve-collection-logo
3 Bedroom Ocean View Villa - Platinum
Rating 5 (5)
3 bedrooms
3.5 baths
8 guests
Location Wailea, HI Icon of Ocean View Ocean View Icon of Complex Pool Complex Pool Icon of Private Outdoor space Private Outdoor space
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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
Wailea Beach Villas PH111
2 Bedroom Garden View Condo - Platinum
Rating 5 (10)
2 bedrooms
2 baths
6 guests
Location Wailea, HI Icon of Complex Pool Complex Pool Icon of Private Outdoor space Private Outdoor space Icon of Resort Golf Resort Golf
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Penthouse 309 at Wailea Beach Villas offers a distinctive blend of luxury and cultural charm, making it an ideal vacation rental for families or groups of friends. This 2,520 square foot ocean view suite is located on the third floor and is accessible via a private elevator, ensuring privacy and exclusivity.The penthouse features three bedrooms and
Wailea Beach Villas PH309
3 Bedroom Ocean View Condo - Platinum
Rating 5 (12)
3 bedrooms
3 baths
8 guests
Location Wailea, HI Icon of Ocean View Ocean View Icon of Complex Pool Complex Pool Icon of Private Outdoor space Private Outdoor space
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Welcome to Wailea Beach Villas Penthouse 106, a luxurious ground-floor retreat in one of Maui's most prestigious beachfront communities. This stunning 1,899-square-foot villa offers the perfect blend of island elegance and modern comfort, making it an exceptional choice for families or small groups seeking a five-star getaway in Wailea.Inside, you'
Wailea Beach Villas PH106
2 Bedroom Garden View Condo - Platinum
Rating 5 (8)
2 bedrooms
2 baths
6 guests
Location Wailea, HI Icon of Complex Pool Complex Pool Icon of Private Outdoor space Private Outdoor space Icon of Resort Golf Resort Golf
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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 Beach Villas F201
3 Bedroom Ocean View Villa - Platinum
Rating 5 (4)
3 bedrooms
3.5 baths
8 guests
Location Wailea, HI Icon of Ocean View Ocean View Icon of Complex Pool Complex Pool Icon of Private Outdoor space Private Outdoor space
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