Vacation Rentals on Maui

Maui's Best Vacation Rentals to Rent or Own

From Maui’s incredible beauty and world-class beaches to its unforgettable sunsets and breathtaking scenery, it is the ultimate destination for a tropical island getaway.

When searching for a vacation rental on Maui, either to rent or to own, most people are looking for something that combines the comforts and luxuries of home with the authentic feel of the islands.  However, with numerous vacation rentals on Maui to choose from, identifying the property that’s the best fit for you can be a little overwhelming.

After 16 years of living and working on Maui, with intimate knowledge of these complexes, I’ve put together a short list of some of the best options Maui has to offer at a variety of price points.

The list is by no means fully comprehensive, and there are other great options out there, but whether you're looking for a property to rent or own, these are a few of my personal favorite vacation rental destinations broken down by the top areas for short-term vacation rentals: Wailea, Kapalua, Ka'anapali, and Kihei.

Best Vacation Rentals in Wailea, Maui

Wailea Beach Villas 

Wailea Beach Villas is among the top vacation rental destinations on Maui, offering the perfect balance of elite luxuries and relaxation in a majestic oceanfront setting.

Each individually decorated villa has beach or garden views as well as expansive indoor-outdoor living spaces. Both two- and three-bedroom villas are available in this gated community.

Resort amenities include a family game room, a business center, on-site concierge service, beach amenities, a pool and spa, and a fitness center. Nearby, you'll find Wailea Beach, Ulua Beach, and the Wailea golf courses, all in very close proximity.

Ho'olei Villas 

The Ho'olei Villas deliver an elite living experience with luxurious three-bedroom villas in the heart of the Wailea Resort. This gated community is perfectly situated on a tropical hillside, offering spectacular ocean and mountain views from various vantage points.

Each lavishly appointed villa includes a gourmet kitchen, a spacious lanai, and premium finishes throughout.

Owners at Ho'olei Villas, who also opt in to become members of the Kulana Club, have full access to the Grand Wailea resort’s top-rated amenities, including a spectacular pool featuring a children’s water feature, waterfalls, a sandy beach, and lagoon-like landscaping.

Other amenities include a spa, a fitness center, a business center, and childcare services. 

Wailea Ekahi 

Located on the northern edge of Wailea along Keawakapu Beach, Wailea Ekahi offers a different experience than other vacation rentals on Maui thanks to its sprawling gardens and low-rise buildings. In fact, there are only 10 buildings spread across 34 acres, which creates a garden-like atmosphere.

Most units offer views of the ocean, gardens, or four swimming pools. Many have been recently remodeled and include a full eat-in kitchen, a private lanai, air conditioning, and an in-unit washer and dryer.

From Ekahi, you'll be close to the Wailea Golf Course, Polo Beach Park, and Keawakapu Beach.

Polo Beach Club

Polo Beach Club is the southernmost condo complex in Wailea on the border of Makena next to the Fairmont Kea Lani. It is a picture-perfect beachfront destination with golden sandy shores and soft, gentle waves, making Polo Beach one of the best places for a beach day on Maui.

It is also right on the Wailea Beach Path and within walking distance to many great restaurants. Most of the units at Polo Beach Club feature incredible ocean views, with spacious lanais to enjoy those views for hours. 

View all of the Wailea Condos For Sale

Best Vacation Rentals in Kihei, Maui

Royal Mauian 

At the Royal Mauian, you will find quality accommodations nestled on a pristine beach just off of South Kihei Road. 

These one-, two-, and three-bedroom rentals offer individualized decor, private lanais, and in-unit washers and dryers. Most units feature beautiful ocean views, and the building stays cool with gentle ocean breezes and in-unit air conditioning. 

Residents and guests can use their unit’s full kitchen or the rooftop barbecue area to prepare meals. While this community is located close to many hotspots, the oceanfront pool and gardens are the ideal place to relax when you’re not exploring the island. 

Mana Kai 

Mana Kai is a premier condo community located directly along the sandy shoreline at the northern end of Keawakapu Beach. These vacation rentals on Maui include beautifully decorated one- and two-bedroom units overlooking the Pacific Ocean and the property’s lushly landscaped grounds.

Each condo is well-equipped with all of the comforts of home, including a full kitchen, a lanai, ceiling fans, and air conditioning. Property amenities at Mana Kai include a coin-operated laundry, a fitness room, an outdoor area with barbecue grills, and a lovely pool overlooking the beach. 

Menehune Shores 

Situated in the coveted Kihei area between Keaka Beach and Kalepolepo Beach Park, Menehune Shores offers a relaxed beachfront setting with incredible views and all of the amenities you need for a great island experience. There are 154 well-appointed condo units with 1 to 3 bedrooms.

On-site amenities include a rooftop deck and kitchen, a solar-heated pool, ample parking, and barbecue areas. The Maui Nui Golf Club, Kamaole beaches and Charley Young Beach are just minutes away.

Maui Banyan

Maui Banyan provides you with an incredible location in Kihei near Kamaole Beach II. These vacation rentals on Maui are ideally situated for making memories thanks to their proximity to world-class beaches, top-rated golf courses, and even Molokini snorkel tours.

Every condo unit at Maui Banyan has a spacious living area with a fully equipped kitchen, air conditioning, and ceiling fans.

The resort amenities available to all guests and residents are 24-hour security, two gated hot tubs and pools, outdoor dining areas with grills, an activity desk, and tennis courts. 

View all Kihei Condos For Sale

Best Vacation Rentals in Kapalua, Maui

Montage Kapalua (Soon to Be St. Regis Maui)

The Montage Residences at Kapalua Bay have recently undergone new management and will be getting rebranded and updated as a St. Regis property. Expect a continuation and expansion of the luxurious Montage tradition. The property is located on 24 lush acres along the gorgeous Kapalua Bay, placing you in close proximity to Kapalua Beach, Oneloa Beach, the Kapalua Coastal Trail, and the Kapalua golf courses.

This beachfront property in Kapalua has 50 beautifully decorated, larger 3-bedroom residences that embrace the island’s lifestyle while pampering visitors and residents with premium amenities. The property also features a variety of smaller hotel rooms that range from 1bd to 4bds. 

These units include a gourmet kitchen, incredible ocean views, a covered veranda or lanai, and a soaking tub. Property amenities include tennis courts, barbecue grills, several pools, and additional amenities. 

Kapalua Bay Villas 

Kapalua Bay Villas is unlike any of the other vacation rentals on Maui. Spread across 22 sprawling acres between a sandy beach and a lush hillside, the resort embraces the island’s natural coastal beauty. There are 141 premium condominium units offering one- and two-bedroom units.

The 12 buildings are adjacent to the Kapalua Coastal Trail and close to top-rated golf courses and dining options. On-site, you can enjoy three heated pools, tennis courts, gas barbecue grills, hiking trails, and gated access. Oneloa Beach is just steps away, and the magic of Kapalua is all around. 

View All Condos for Sale in Kapalua

Best Vacation Rentals in Ka'anapali, Maui

Honua Kai 

At the Honua Kai, you’ll enjoy the refinement and top-notch amenities of a five-star resort in a tropical paradise. The villas here are steps from Ka’anapali Beach and offer gracious indoor-outdoor living spaces.

The pool complex features multiple heated pools and hot tubs, a lazy river, waterslides, and other features. Additional on-site amenities are a fitness center, Duke’s Beach House, oceanfront patios with barbecue grills, and a general store. At this location, you'll be close to Kahekili Beach Park, Honokawai Beach Park, and the Ka'anapali golf courses.

Whaler Ka'anapali

When searching for the perfect vacation rentals on Maui, the generational favorite Whaler at Ka'anapali must be considered among the very best for location and views. This property is conveniently located near Whaler's Village, Black Rock Beach, and Kahekili Beach Park.

At Whaler Resort, you’ll find studio condos as well as one- and two-bedroom options. Many of the 360 condo units spread across several mid-rise buildings overlook the beach and pool. This 6.6-acre property offers fine amenities, including a jacuzzi, a pool and spa overlooking the beach, covered parking, and barbecue areas.

Sands of Kahana 

The Sands of Kahana is a little further north of Ka'anapali, in the small coastal community of Kahana, but is perfectly situated for both relaxation and fun, with a prime location on Lower Honoapi’ilani Road.

Each of the spacious condominium units at Sands of Kahana is appointed with one or more lanais overlooking the ocean, pool, or gardens. The two- and three-bedroom units feature premium finishes, a full kitchen, in-unit laundry, air conditioning, soaker tubs, soaring ceilings, and more.

Residents and guests of Sands of Kahana have on-site access to pickleball courts, tennis courts, Captain Jack’s restaurant, concierge service, a fitness center, and two pools.

View All Ka'anapali Condos for Sale

Learn More About Vacation Rental Opportunities on Maui

As you explore the top-rated communities for vacation rentals on Maui, be aware that the villas and condos at these properties are in high demand and typically don’t remain on the market for long.

By becoming fully acquainted with each community's features and benefits now, you’ll be able to make a better-informed decision about each complex you should be considering to own or rent.  

Get In Touch With Evan!

Evan Harlow ranks among the best real estate agents on Maui annually and is in the top 1% of Coldwell Banker agents worldwide in production. Evan has the expertise, experience, and work ethic to help you achieve your real estate buying and selling goals. We promise exceptional service and support from the beginning of the process through closing and beyond. See what Evan's clients are saying on Google.

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