Fabulous luxury vacation rentals in Maui

Are you looking to splurge on your next vacation? Then this selection of amazing luxury vacation rentals in Maui is for you. It includes some of the most luxurious residential and resort villas in Maui. Some come with an incredible ocean view, others with direct beach access or a spectacular pool.

Luxury home rentals in Maui can be found in several areas, from the outskirts of Kaanapali in West Maui to the resort grounds of Wailea in South Maui and even the rolling hills of Kula in Upcountry Maui.

So, are you ready to discover the most fabulous luxury home rentals in Maui? Then let’s dive in!

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My selection of luxury vacation rentals in Maui

For every luxury home rental in Maui in this list, I include the number of rooms, the number of persons it sleeps, the license number, the average cost per night, and extra fees (if any). That way you can see at a glance if the home is spacious enough and if it fits within your budget.

Every Maui vacation rental in this list links out to the corresponding listing on VRBO. Simply read through the details, check the reviews, and set your preferred dates to get an exact breakdown of the costs. If you still like what you see, you can go ahead and make your booking.

Now, without further ado, here’s my personal selection of the best luxury home rentals in Maui.

1. Beachfront luxury rental in Kihei

• Specifications: 3 bedrooms, 3 bathrooms, sleeps 6 people.
• Location: In a quiet, residential neighborhood of Kihei (South Maui).
• Registration: TAT #TA-080-834-5600-01 | TMK #390100170000 | License #STKM 2016/0005.
• Average rate per night: $2,995 plus taxes and fees.

If you’re looking for a family getaway in a recently updated luxury beach villa in Maui, then look no further than the Mango Surf Beachfront Villa. This gorgeous old-Hawaii-style home has everything you could wish for and more.

Three cheerful bedrooms accommodate up to 6 guests. The interior is colorful yet stylish and features top-quality furnishings and premium amenities throughout.

The lanai is equipped with a large heated swimming pool with a waterfall feature, a panoramic hot tub, a comfy hammock, and a pavilion with a Weber grill, fridge, and ice maker. Waving palms, a mature mango tree, and a collection of fragrant flowers complete the outdoor decor.

The garden connects to a quiet beach. It’s a sheltered coastal lagoon with shallow waters thanks to the presence of an off-shore reef. Beach gear is provided.

This stunning home is located in the residential beach community of Waimahaihai, making it one of the most peacefully located villa rentals in Maui. Yet, everything you need – grocery stores, gyms, outdoor sports facilities, surf shops, bars, and restaurants – can be found within walking distance. Even Kalama Park is just around the corner.

Guests of the Mango Surf Beachfront Villa enjoy concierge services and the assistance of a property manager.

VRBO

2. Luxury resort condo in Wailea

• Specifications: 3 bedrooms, 3.5 bathrooms, sleeps 8 people (all in beds, no futons).
• Location: In the prestigious, gated Ho’olei resort, located uphill from the Grand Wailea Resort (South Maui).
• Registration: TAT #TA-064-937-3696-01 | TMK #210081190082 | License n/a due to zoning.
• Average rate per night: $3,050 plus taxes and fees.

Next on our list is one of the best luxury resort rentals in Maui. This beautiful vacation home is located in the Ho’olei Resort, a gated luxury villa complex across the street and uphill from the Grand Wailea Resort. The villa complex comes with its own pool and restaurant.

But this villa’s service goes beyond these facilities: It also includes access to the spectacular pool complex of the Grand Wailea Resort. Your travel company can enjoy the pool slides, swim-in-grotto, whirlpools, lazy river, and waterfall at no extra cost. The villa also comes with daily housekeeping and on-site concierge services.

So, at this luxury Maui home, you get to enjoy the best of both worlds: The tranquil setting of the prestigious Ho’olei Resort and the lively water paradise at the Grand Wailea Resort.

This gorgeous luxury villa features 3 bedrooms and a total of 4 beds, sleeping up to 8 people. There are 3.5 baths. The indoor area has been tastefully decorated. Sliding glass doors connect the state-of-the-art kitchen and elegant dining area to a spacious lanai with a panoramic dining area and a built-in Wolf grill. You can enjoy unobstructed views of the resort area and Wailea Beach.

An elevator connects the one-car private garage and laundry room to the main floor.

Note that not all Ho’olei Maui villas offer Grand Wailea Resort privileges. So, if this particular listing isn’t the right fit for you and you decide to browse through more Ho’olei listings on VRBO, then be sure to read the fine print. The price point can be an indication.

VRBO

3. Luxury oceanfront penthouse in Lahaina

• Specifications: 2 bedrooms and a queen sleeper sofa, 2 bathrooms, sleeps 6 people.
• Location: In Lahaina town and within walking distance from Baby Beach (West Maui).
• Registration: TAT #TA-003-358-1056-01 | TMK #450130270042 | License n/a due to zoning.
• Average rate per night: $1,325 plus taxes and fees.

UPDATE OCTOBER 2023:
Most of Lahaina town has been destroyed in the 2023 wildfires. Miraculously, the Lahaina Roads complex managed to escape the flames. However, do note that this luxury vacation rental might not immediately resume operations.

If endless ocean views are what you’re looking for, then this luxury Maui vacation rental is for you! It’s the most gorgeous penthouse located on the 5th floor of the Lahaina Roads complex and offers complete privacy.

The wraparound lanai is huge and offers plenty of seating arrangements, a Sonos music system, a BBQ grill, and even an outdoor shower. Watch the honu swim over the reef, the whales passing by, and the sailboats cruising the water.

The state-of-the-art kitchen and neutral-toned living area are equipped with sliding doors, resulting in a seamless indoor-outdoor living concept. There are 2 bedrooms – one with a king bed and one with a queen bed – as well as a queen sleeper sofa.

Guests can enjoy the communal pool and the covered ground-floor parking. This luxury home is located on Front Street, with several restaurants and a lively Lahaina atmosphere down the street. Baby Beach is a ten-minute walk away but you might just as well rent bikes and head directly for Kaanapali Beach.

VRBO

4. Huge luxury home in Napili

• Specifications: 7 bedrooms, 7 bathrooms, sleeps 26 people.
• Location: Steps away from Napili Bay Beach (West Maui).
• Registration: TAT #TA-111-969-6896-01 | TMK #430020450000 | License n/a due to zoning.
• Average rate per night: $2,195 plus taxes and fees.

This spectacular gated home is one of the most luxurious Maui vacation rentals for large groups and family reunions. It’s spacious enough to comfortably accommodate up to 26 persons (although 24 seems more appropriate).

There are 7 bedrooms, 5 of which have their ensuite bathroom. In addition, there’s 1 bunk room that fits up to 10 people. It’s the perfect sleeping area for kids. In the hallway, you’ll find a pull-out sofa that sleeps an additional 2 people.

The open floor plan with a chef’s kitchen and large living and dining room gives out to the backyard. That’s where you’ll find the fabulous pool with a rock waterfall, twisting water slide, and in-water lounge chairs that sit on a shallow shelf. Note that the pool can be heated on request but this does involve an extra fee.

On the third floor of this luxury vacation home, there’s a rooftop lounge with ocean views. This gorgeous property is located on the access trail leading to the family-friendly Napili Bay Beach.

Note that this rental is located in a hotel zone so expect lively surroundings.

VRBO

5. Luxurious beachfront home in Kaanapali

• Specifications: 5 bedrooms, 5 bathrooms, sleeps 10 people.
• Location: Steps away from Kahekili Beach a.k.a. Airport Beach (West Maui), Whaler’s Village is less than a mile away.
• Registration: TAT #TA-024-679-8336-01 | TMK #440140130001 | License n/a due to zoning.
• Average price per night: $6,099 plus taxes and fees.

This amazing beachfront home is what Maui dreams are made of. Hawaiiana Hale is a Plantation style home with premium finishes and a true Hawaiian feel. Five well-appointed rooms sleep up to 10 people.

Two of the bedrooms are oceanview master suites that come with a private lanai offering front-row seats to breaching whales and porpoising dolphins.

The backyard is a wonderful place to relax thanks to the heated pool, hot tub, and hammock. The lanai offers plenty of seating arrangements as well as a gazebo with a grill, sink, and fridge. A beautiful tropical garden separates the property from the beach, guaranteeing your privacy.

This luxurious Maui villa comes with concierge services and daily housekeeping. It’s located in a hotel zone so don’t expect the most tranquil residential area.

VRBO

6. Oceanfront villa in Paia Bay

• Specifications: 4 bedrooms, sleeps 8 people.
• Location: Oceanfront, steps away from lively Paia town and Paia Bay (North Shore Maui).
• Registration: TAT #TA-070-457-9584-01 | TMK #260040250000 | License #STPH 2013/0013.
• Average rate per night: $1,500 plus taxes and fees.

This amazing oceanfront villa is located in the heart of Paia. It’s a fenced property with a private garden lined with swaying coconut palms.

There are 3 bedrooms in the main house, all with balcony and ocean views. In addition, this home offers an attached cottage with a studio.

The modern and fresh decor with wooden accents gives the interior an elegant vibe. The well-equipped kitchen connects to a covered lanai equipped with a BBQ grill, seating area, and lawn chairs.

This property doesn’t have a pool. Then again, Baldwin Beach Park – a.k.a. Baby Beach, one of the few lifeguarded beach parks in Maui – is located within walking distance. So is Paia with its boho vibe, quaint restaurants, and interesting boutiques.

Plus, North Shore offers direct access to the Hana Highway, no better way to get a head start of other day trippers on the Road to Hana. Also, Upcountry and Haleakala National Park are within easy reach from Paia.

VRBO

7. Luxury resort penthouse at a prestigious hotel

• Specifications: 3 bedrooms, 4 bathrooms, sleeps 8 people.
• Location: On the grounds of the luxurious Andaz Maui resort in Wailea (South Maui).
• Registration: TAT #149-382-8608-02 | TMK #210080670010 | License n/a due to zoning.
• Average rate per night: $3,750 plus taxes. There’s also a $50 daily resort fee to be paid upon check-in.

If you like to enjoy the facilities of a luxury resort on vacation without being cramped up in a hotel room, then a luxury resort rental is the perfect compromise.

Hoomaha Kahakai is one of the most luxurious residences on the ground of the equally luxurious Andaz Maui Resort.

This exclusive penthouse has 3 spacious bedrooms. Each comes with its ensuite bathroom with a rain shower and a large tub. luxury resort amenities. There’s a bright and spacious open-concept living area with floor-to-ceiling doors and a chef’s kitchen.

The comfortable lanai is a wonderful place to relax. It offers views over the sprawling resort grounds and the ocean. It’s equipped with a private hot tub, a Hestand BBQ grill, and an outdoor fridge. Mokapu Beach is just steps away from this Maui luxury retreat.

Guests have access to all swimming pools and resort amenities, as these are included in the resort fee. Valet parking is available for an extra fee.

VRBO

8. Spectacular beachfront mansion in Kaanapali

• Specifications: 8 bedrooms, 9+ bathrooms, sleeps 20 people.
• Location: Steps away from Kahekili Beach a.k.a. Airport Beach (West Maui), Whaler’s Village is less than a mile away.
• Registration: TAT #TA-026-477-5168-01 | TMK #440140110000 | License n/a due to zoning.
• Average rate per night: $9,896 plus taxes and fees.

One of the most opulent beach houses for rent in Maui can be found in Kaanapali.

This jaw-dropping mansion with its indoor-outdoor living concept is nothing short of spectacular. It houses 8 bedrooms and 9.5 bathrooms, all opulently decorated with high-quality materials. The suites on the second floor come with their panoramic lanai while those on the main floor are equipped with a kitchenette. The same high-end finishes and craftsmanship can be found in the chef’s kitchen and living room.

The lavish outdoor space comprises four gorgeous heated pools, a hot tub, and a shaded pavilion. Fabulous panoramic ocean views are part of the experience. A beautiful lawn separates the property from Kahekili Beach so that guests enjoy complete privacy.

A game room, a library, and a media room conclude the list of amenities.

Guests of this jaw-dropping vacation home can enjoy complimentary transportation to various West Maui attractions in a private shuttle.

VRBO

9. Classy beachfront villa steps from Kihei

• Specifications: 8 bedrooms, 6+ bathrooms, sleeps 18.
• Location: Tucked away in a quiet residential neighborhood of Kihei (South Maui).
• Registration: TAT #TA-164-463-0016-01 | TMK #390070250000 | License #STKM 2013/0017.
• Average rate per night: $3,575 plus taxes and fees.

This Hawaiian-style home with its hardwood floors and premium finishes is a sight to behold. With luxury mattresses, quality sheets, a pillow menu, a chef’s kitchen, ultra-silent air conditioning, and more, it offers everything you need for a carefree stay.

This luxury Maui home rental comfortably sleeps 16 adults and offers additional bedding for 2 kids. Most of the bedrooms offer panoramic ocean views. Outside, you’ll find a spacious lanai. Follow the private path that meanders through the garden and you’ll arrive at the beach.

Villa Moana is tucked away in a quiet residential street just over a block away from the Kihei action. Restaurants, cafés, shops, and sports facilities can be found within walking distance. There’s parking in front of the house.

VRBO

10. Luxury oceanfront Resort residence in Kapalua

• Specifications: 3 bedrooms, 3 bathrooms, sleeps 10 people.
• Location: Oceanfront residence on the resort grounds of the luxurious Montage Kapalua Bay (West Maui).
• Registration: TAT #TA-103-503-4624-01 | TMK #420040280008 | License n/a due to zoning.
• Average rate per night: $3,012 plus taxes and fees. This includes a rental car!

The gorgeous Montage Anuenue home is one of the most luxurious Maui villa rentals in the Kapalua area. The ocean views alone are worth staying here.

This ground-floor residence has 3 bedrooms, one of which is equipped with 2 queen beds, and there’s a pull-out sofa bed available for groups of up to 8 people including kids. The house is beautifully designed with high-quality finishes throughout.

The beautiful lanai and private lawn area are fabulous places to relax. But it doesn’t end there. Guests of this resort residence enjoy full access to all Montage amenities including the pools, beach, and spa.

And to top it off, this luxury vacation rental in Maui comes with a four-door rental car that can be picked up and dropped off at the airport. No better way to start exploring the island.

VRBO

Map of all listed luxury vacation rentals

For your convenience, I created this map showing the location of all listings by listing number.

Which of these Maui luxury vacation rentals caught your eye?

Chances are that you’ve found your dream home for that long-awaited Maui vacation. If not, then have a look at my other wish lists to discover even more amazing vacation rentals in Maui.

As a result of my previous career as a luxury hotel professional and bespoke event planner, I have a keen eye for quality. So, you can rest assured that only the fine-fleur of Maui luxury home rentals made this list.

Also, rest assured that all featured luxury homes in Maui are operating legally with the required county permits and that all suggestions are hand-picked and thoroughly researched.

Luxury home rentals in Maui FAQ