Hotel Wailea was once a budget hotel in upscale Wailea, but a complete renovation in 2014 turned this property into a luxury stunner with all the trimmings of a stylish boutique hotel. Each of the rooms are one-bedroom suites with private outdoor spaces; some have distant ocean views. Guests can eat Mediterranean food at Capische?, which has a chef's table and uses organic ingredients, or The Cabanas, a poolside bar. Kids under the age of 16 aren't allowed here, making for a peaceful and romantic property that appeals to honeymooners. One caveat -- Hotel Wailea isn't directly on the beach but a Mercedes-Benz limo brings guests to a nearby beach club with free chairs and bottled water. The nearby Four Seasons Maui is a good bet for families with kids. 

The Ho’olei at Grand Wailea offers luxury condos on a beautiful, relaxed property connected to the Grand Wailea, one of Maui’s most impressive mega-resorts. In huge villas that average 3,500 square feet, families will find all the comforts of a luxury home, including a decked-out kitchen, walk-in closets, a spacious lanai, a garage, and an elevator. While the property has its own lovely pool and fitness room, guests can access the main resort’s elaborate maze of pools and waterslides, enormous fitness center, and other activities. It’s perfect for visitors who want all the features of the Grand Wailea, but with a more peaceful atmosphere and more spacious accommodations.

The Four Seasons Resort Maui at Wailea established itself as one of Hawaii’s premier luxury resorts when it opened its oceanfront doors in 1990. Today, after a multi-million dollar renovation in 2016, the 383-room beachfront stunner still maintains its elite status and doesn't charge a resort fee. Renovated guest rooms are spacious and sumptuously outfitted with marble bathrooms and luxe amenities. Three restaurants provide varied dining options, and Wolfgang Puck’s acclaimed Spago is one of Maui’s best eateries. Families and couples are equally catered to here with: two family-friendly pools, a game room, free kids' club, secluded adult-only oasis pool, and world class spa. However, some couples may find the hotel to be a bit too family-friendly. Travelers looking for a more hip, adult-centric property may prefer the Andaz Maui at Wailea Hotel.

Wailea's aptly named Fairmont Kea Lani is a "white heaven" indeed -- its 450 units sit on a 22-acre beachfront property that includes three pools, four restaurants, a luxurious spa, and access to world-class golf. Unlike its competitors, this property does an excellent job of keeping both couples and families happy without the long lines and battles for sun loungers by the pool. Oceanfront villas and suites are some of the largest in Maui, though a pesky resort fee applies to anyone who doesn't book a villa.

After a top-to-bottom $100 million renovation in 2016, the four-pearl Wailea Beach Resort - Marriott, Maui feels like a new property. The hotel’s 547 guest rooms are housed in low-rise buildings spread across the well manicured property. They’re decorated with sleek furnishings and are stocked with nice amenities like Nespresso machines and flat-screen TVs. Four pools and a water park cater to all kinds of travelers, and varied dining options keep the food scene interesting. Additional amenities include a spa, fitness center, family game room, and a small movie theater, but the biggest disappointment is the resort’s indirect access to Wailea Beach. Though it’s an oceanfront property, there is, ironically, no beach in front of the Wailea Beach Resort. Guests must walk to the nearby Grand Wailea in order to access the sand. Travelers looking for a truly beachfront property may prefer Marriott’s Maui Ocean Club, though it isn’t as upscale. 

Four-and-a-half pearl Andaz Maui at Wailea was built in 2013 and has been popular with the jet set since its opening. The combination of Mokapu Beach access, personalized attention at ‘Āwili Spa and Salon, and a multi-tiered infinity pool draws honeymooners and couples for Hawaiian-style romance. There's a Japanese restaurant and a farm-to-table style restaurant for breakfast. Artisan cocktails are the norm at two lounges. Minimalist rooms are built with the bathroom in the center and some balconies overlook the beach. There isn't a resort fee but valet parking and breakfast cost extra. Kids are welcome, though the hip scene and concept bathrooms may not be the best fit for families. Check rates next door at Four Seasons Maui which often has comparable prices and a slightly more luxe, yet family-friendly, vibe.

The Polo Beach Club is an eight-story, oceanfront condominium resort located directly on a secluded beach in the Wailea/Makena area. The quiet location makes it ideal for families and couples looking for an affordable Hawaiian vacation. The condo units are spacious and all come with fully equipped kitchens offering microwaves, refrigerators, and coffeemakers. Units are individually owned, so they differ in size and decor. As such, it's a good idea to look at the floor plans on the hotel website before deciding which unit to book. The property features an outdoor pool and hot tub, as well as easy beach access. However, some guests have complained that the beach is small and can seem too crowded at times. The property offers thoughtful amenities, such as in-room massages, chefs, and pre-stock grocery services (all for a fee). The outdoor grill station and herb garden is an enticing option for guests to cook a relaxing dinner on their own.

Makena Beach and Golf Resort is an upscale property with a laid-back vibe on family friendly Maluaka Beach. Rooms have (some) private lanais overlooking the ocean, cherry wood furniture, and granite vanities in the bathrooms. The rates here are lower than what you'll find at nearby luxury resorts, but the swimming pool is much smaller. Still, there's off-the-beach snorkeling, three restaurants, free oceanfront yoga, and a spacious fitness center. The Hawaiian Rain Forest spa helps make this hotel an attractive option for honeymooners and couples. There's no resort fee and lots of free extras like parking, Wi-Fi, and resort activities, so guests won't feel nickel and dimed. It may be worth comparing rates at nearby four-pearl Wailea Beach Marriott Resort & Spa for many of the same features, though you'll pay for parking and Wi-Fi there.