Wailea Family Friendly Stays

This collection of Wailea residences is ideal for families of all sizes in Maui's premier Resort location.  Find your perfect stay! 

Sort by
  • Random
  • Name
  • Bedrooms
  • Sleeps
  • Price
  • Quality
Map View
Favorites
Compare Favorites
Viewed
viewed
You have not recently viewed any properties.
Properties Available 907 properties available
Sort by:
Random
Sort Random Down
  • Random
  • Bedrooms
  • Sleeps
  • Price
  • Quality
Tamarack Townhomes 28, a 840 square-foot townhome, features two bedrooms and two bathrooms. The master bedroom includes a king bed and a gas fireplace, while the guest bedroom offers a queen bed. The living room is equipped with a sleeper sofa and another gas fireplace. The fully equipped kitchen boasts granite countertops and stainless steel appli
Tamarack 28
Tamarack 2 Bedroom Platinum
Rating 5 (21)
2 bedrooms
2 baths
6 guests
Location Snowmass Village, CO Icon of Resort View Resort View Icon of Complex Pool Complex Pool Icon of Airport Transportation Airport Transportation
View Details
Port O’Call A303 by Wild Dunes1 Bedroom | 1 Bathroom | Sleeps 2 | Ocean View________________________________________Enjoy beachfront living at this 800 Sq. Ft. Port O’ Call unit, where a complex pool and easy beach access await. This well-appointed condo neighborhood is just moments from the Links Golf Course clubhouse, making it an ideal base for
Port O'Call A303 by Wild Dunes, Ocean View
Port O'Call A303 by Wild Dunes, Ocean View Condo
Rating 5 (14)
1 bedrooms
1 baths
2 guests
Location Isle Of Palms, SC Icon of Steps to Beach Steps to Beach Icon of Complex Pool Complex Pool Icon of Private Outdoor space Private Outdoor space
View Details
Kaanapali Alii 1722 Bedrooms | 2 Bathrooms | Sleeps 4 | Ocean View________________________________________Welcome to Kaanapali Alii 172, a beautiful one-bedroom ocean-view condo with a fully enclosed den that comfortably serves as a second bedroom. Filled with natural light and framed by large windows, the space captures the gentle trade winds and
Kaanapali Alii 172
2 Bedroom Ocean View
2 bedrooms
2 baths
4 guests
Location Kaanapali, HI Icon of Ocean View Ocean View Icon of Complex Pool Complex Pool Icon of Private Outdoor space Private Outdoor space
View Details
Kaanapali Alii 1362 Bedrooms | 2 Bathrooms | Sleeps 6 | Ocean Front________________________________________This two-bedroom oceanfront condo offers beautiful ocean views from all rooms! Enjoy an unobstructed look at the gleaming pacific and the golden Kaanapali Beach, plus a peek at the neighboring islands of Lana'i and Molokai. Because this condo
Kaanapali Alii 136
2 Bedroom Ocean Front
2 bedrooms
2 baths
6 guests
Location Kaanapali, HI Icon of Oceanfront View Oceanfront View Icon of Complex Pool Complex Pool Icon of Private Outdoor space Private Outdoor space
View Details
Montaneros 408 is an elegant 1,375 sq ft platinum-rated three-bedroom, three-bath condominium located on the 4th floor of Montaneros in Vail, offering partial views of Vail Mountain. The spacious layout is perfect for groups or families, providing a luxurious and comfortable retreat. The master bedroom, situated on the second floor, features a king
Montaneros (31)
Montaneros 408
Montaneros 3 Bedroom Platinum
Rating 5 (21)
3 bedrooms
3 baths
8 guests
Location Vail, CO Icon of Steps to Slopes Steps to Slopes Icon of Complex Pool Complex Pool Icon of Private Outdoor space Private Outdoor space
View Details
Grand Pavilion 24 by Wild Dunes3 Bedrooms | 3 Bathrooms | Sleeps 8 | Resort View________________________________________This 1880 Sq. Ft. Grand Pavilion Home is located within the heart of the resort being just steps away from the main beach entrance, pools, dining, curated shopping, and a full suite of resort activities.___________________________
Grand Pavilion 24 by Wild Dunes
Grand Pavilion 24 by Wild Dunes, Resort View Home
Rating 5 (1)
3 bedrooms
3 baths
8 guests
Location Isle Of Palms, SC Icon of Resort View Resort View Icon of Complex Pool Complex Pool Icon of Private Outdoor space Private Outdoor space
View Details
Kaanapali Alii 1622 Bedrooms | 2 Bathrooms | Sleeps 4 | Ocean View________________________________________Welcome to Kaanapali Alii 162, a gorgeous one-bedroom condo, with a fully enclosed den that comfortably serves as a second bedroom. Featuring gleaming hardwood floors, bold artwork, and vibrant coastal accents, this spacious residence exudes bo
Kaanapali Alii 162
2 Bedroom Ocean View
Rating 5 (1)
2 bedrooms
2 baths
4 guests
Location Kaanapali, HI Icon of Ocean View Ocean View Icon of Complex Pool Complex Pool Icon of Private Outdoor space Private Outdoor space
View Details
Welcome to the serene and luxurious Wailea Elua Village 2502, a stunning 2-bedroom ocean view condo nestled in the heart of Wailea, Hawaii. This meticulously designed 1,336 sq. ft. property offers a perfect blend of comfort and elegance, ideal for a memorable family getaway.Step inside to discover a thoughtfully laid-out living space featuring a co
Wailea Elua Village 2502
2 Bedroom Ocean View Condo - Platinum
Rating 5 (17)
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
View Details
Kaanapali Alii 3612 Bedrooms | 2 Bathrooms | Sleeps 4 | Ocean View________________________________________This beautiful platinum-rated sixth-floor Maui condo is a serene escape, featuring one-bedroom with a fully enclosed den that comfortably serves as a second bedroom. Guests can unwind on the large, private lanai while soaking in the gorgeous oc
Kaanapali Alii 361
2 Bedroom Ocean View
Rating 5 (2)
2 bedrooms
2 baths
4 guests
Location Kaanapali, HI Icon of Ocean View Ocean View Icon of Complex Pool Complex Pool Icon of Private Outdoor space Private Outdoor space
View Details
Sandcrab Court 18 by Wild Dunes4 Bedrooms | 2 Bathrooms | Sleeps 10 ________________________________________Welcome to Sandcrab Court 10, a stunning retreat on Isle of Palms’ exclusive Wild Dunes Resort. This spacious island retreat is great for accommodations up to 10 guests. Located in a peaceful cul-de-sac just a short walk from the beach, this
Sandcrab Court 18 by Wild Dunes
Sandcrab Court 18 by Wild Dunes, Resort View Home
Rating 5 (4)
4 bedrooms
2 baths
10 guests
Location Isle Of Palms, SC Icon of Resort View Resort View Icon of Complex Pool Complex Pool Icon of Private Outdoor space Private Outdoor space
View Details
Montaneros in Vail 202 is a spacious 1,500 sq ft platinum-rated three-bedroom, two-bath condominium located on the 2nd floor, offering partial Vail Mountain views. This well-appointed condo comfortably sleeps up to eight guests. The master bedroom features a king bed and an en-suite bathroom with a bidet. The second and third bedrooms both offer tw
Montaneros (31)
Montaneros 202
Montaneros 3 Bedroom Platinum
Rating 5 (14)
3 bedrooms
2 baths
8 guests
Location Vail, CO Icon of Steps to Slopes Steps to Slopes Icon of Complex Pool Complex Pool Icon of Private Outdoor space Private Outdoor space
View Details
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
2 Bedroom Ocean View Condo - Diamond
Rating 5 (4)
3 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
View Details

Tell us what you're looking for and someone will contact you with available options.

I agree