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Best Maui vacation rentals for large groups and families
Have you decided on Maui as the destination for your next group vacation or family reunion? Then this selection of Maui vacation rentals for large groups is for you.
Whether you’re planning a social gathering or a multigenerational trip, Maui offers something for everyone. You can spend your days lazing at the beach, exploring the underwater world, or experiencing the island’s verdant heart.
After a day of fun, everyone gathers in one of the amazing Maui vacation rentals for families and friends. The majority of holiday homes to rent for large groups can be found in Kaanapali and Napili (West Maui), Kihei (South Maui), and Paia (North Shore Maui).
I hand-picked what I believe are the top Maui vacation rentals for large families on VRBO and Airbnb. The result is a list of modern Maui resort villas and luxury homes for all budgets. All are located on manicured grounds and most come with a private pool or access to a resort swimming pool.
So, are you ready to discover the best vacation rentals in Maui for large groups? Then let’s dive in!
In a nutshell
This article features a curated selection of modern Maui vacation rentals for large groups and families, from beachfront estates to multi-bedroom resort condos and penthouses. The article concludes with a FAQ section about vacation rentals in Maui.
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Short on time? Here’s a quick list of the top vacation rentals for large groups in Maui:
A quick note on VRBO and Airbnb rentals in Maui for large groups
This selection only includes vacation rentals that can accommodate a minimum of 10 persons. Unfortunately, this excludes some of the most coveted villa resorts in Maui, the Wailea Beach Villas resort for one, which is limited to 8 guests. But rest assured that I found some amazing alternatives that are sure to delight you. The largest vacation rental in Maui can even accommodate up to 32 people!
Note that permitted short-term rental homes may not have more than 6 bedrooms. But there’s an exception to the rule: Maui vacation rentals for large groups that are located in e.g. districts zoned for hotel use do not need this kind of permit, and therefore, do not have this restriction.
If you read my informative article on Maui rentals vs. hotels, then you know that I may use Airbnb as a catch-all for vacation rentals. However, I do prefer VRBO as a booking platform over Airbnb. Plus, VRBO lists a higher number of big vacation homes than Airbnb. That’s why this article on Maui vacation rentals for large groups links exclusively to VRBO listings and not Airbnb listings.
My selection of Maui vacation rentals for large groups
For every short-term rental in this list, I include the number of rooms, the number of persons it sleeps, the location, the license number, and the average cost per night. That way you can see at a glance if the rental home is spacious enough and if it fits within your budget.
Every spacious Maui house in this list links out to the corresponding listing on VRBO or Airbnb. 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 online booking.
Now, without further ado, here’s my personal selection of the best vacation rentals in Maui for large groups.
Psst… At the end of this article, you’ll find a map showing the location of all listings.
1. Huge luxury home with pool slide
Specifications: 7 bedrooms, sleeps 26 people.
Location: Napili (West Maui). Steps away from Napili Bay Beach.
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.
First on this list of the best Maui vacation rentals for large groups and family gatherings is this spectacular gated home. 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, in-water lounge chairs that sit on a shallow shelf, and the pièce de résistance: a twisting water slide. This is the only Maui vacation rental for large families with a pool slide. 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. This rental is located in a hotel zone so expect lively surroundings.
2. Hawaiian-style beachfront villa
Specifications: 8 bedrooms, sleeps 18 people.
Location: Kihei (South Maui). Tucked away in a quiet residential neighborhood.
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 Maui vacation rental is equipped to accommodate groups of up to 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 this beachfront house.
3. Hawaiian-style gated home with resort-style private pool
Specifications: 6 bedrooms, sleeps 14 people.
Location: Napili (West Maui). Within walking distance from Keonenui Bay.
Registration: TAT #TA-075-875-5328-01 | TMK #430030190000 | License #STWM 2017/0002.
Average rate per night: $2,252 plus taxes and fees.
If a generously sized resort-style private pool is high on your wish list, then this beautiful Napili home is for you. The pool and hot tub are the eye-catchers in the tranquil garden of this gated residence. It connects to a game area with a foosball and ping pong table, as well as a large bar. So, entertainment-wise, you’re all set.
Two bedrooms, including the master bedroom with its ensuite bathroom and ocean-view lanai, are located on the main floor. A spacious living and dining room with spectacular ocean views can be found here as well. The other bedrooms can be found on the lower floor. All rooms feature a luxurious Hawaiian-style interior.
Restaurants and a grocery store can be found within walking distance. The gorgeous beaches of Napili Bay and Kapalua Bay are just a short drive away. Tiny Keonenui Bay Beach can be reached on foot but note that there’s no sidewalk along the road that leads there.
4. Palatial coastal mansion with salt-water lap pool
Specifications: 6 bedrooms, sleeps 16 people.
Location: Kihei (South Maui). Within walking distance from Kalepolepo Beach Park.
Registration: TAT #TA-206-597-1200-01 | TMK #390390440000 | License #BBKM 2020/0003.
Average rate per night: $1,796 plus taxes and fees.
Next on our list of Maui vacation rentals for large groups is this opulent mansion set in a mature tropical garden. The grand entrance, with its majestic fountain, circular driveway, and monumental double staircase is guaranteed to make an impression.
No effort was spared to make this vacation rental stand out. From the chef’s kitchen with its butler’s pantry to the elegant bedrooms and lavish bathrooms. The high-end finishes, clever light plan, and custom designs make this spectacular house one of the most luxurious places to rent on Maui.
The outdoor area is just as impressive as the indoor area. A 50ft saltwater pool with in-water lounge chairs, water fountains, and a generously sized hot tub are the heart of the garden. Whip up a delicious meal in the fully-equipped outdoor kitchen with top-of-the-line amenities. When the sun sets, you and your fellow travelers can enjoy a magical light show on the pool and the water walls in the color(s) of your choice.
This gorgeous property enjoys a highly central location, allowing for easy trips to Wailea, Kaanapali, Iao Valley, Paia, Upcountry Maui, and the Road to Hana. It makes for a wonderful place to retreat to after a day of exploration. If you’re looking for the amenities of a luxury resort without the lack of privacy, then this is it.
5. Affordable vacation home with ocean views
Specifications: 6 bedrooms, sleeps 12 people.
Location: Paia (North Shore Maui). Within walking distance from Kuau Cove.
Registration: TAT #TA-075-934-5151-01 | TMK #260120080000 | License #STPH 2013/0017.
Average rate per night: $1,160 plus taxes and fees.
The layout of this beautiful vacation rental is very well thought out. It’s a bit triplex-like, combining private sleeping arrangements and convivial gathering areas such as the kitchen and the living and dining room. There are plenty of lanais, some overlooking the garden and others featuring partial ocean views.
It’s located in a nice North Shore residential area that’s also home to the iconic Mama’s Fish House restaurant. The sheltered Kuau Cove, with its cozy beach, is just steps away. It’s a popular hangout for honu (Hawaiian green sea turtles) and features a beautiful tidepool.
The North Shore is a fabulous location for a second visit to Maui and for those who plan on exploring the island. It’s an excellent jumping-off point for day trips to the Road to Hana, Upcountry, and Central Maui.
6. Spectacular Kaanapali beachfront estate
Specifications: 8 bedrooms, sleeps 20 people.
Location: Kaanapali (West Maui). Steps away from Kahekili Beach (a.k.a. Airport Beach), 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.
This is one of the most opulent Kaanapali Beach rentals.
The jaw-dropping estate with its indoor-outdoor living concept is nothing short of spectacular. It houses 8 bedrooms and 9.5 bathrooms, all lavishly decorated with high-quality materials. The same high-end finishes and craftsmanship can be found in the chef’s kitchen and living room. The suites on the second floor come with their panoramic lanai while those on the main floor are equipped with a kitchenette.
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.
7. Trio of luxury villa residences at a family resort
Specifications: 9 bedrooms, sleeps 24 people.
Location: Napili (West Maui). Within walking distance from Keonenui Bay.
Registration: TAT #TA-175-718-1952-01 | TMK #440140060642 + #440140060643 + #440140060644 | License n/a due to zoning.
Average rate per night: $3,315 plus taxes and fees.
This concerns an arrangement of 3 separate residences that are part of the same villa. Each residence comprises 3 bedrooms, 3 full bathrooms, and a spacious open-plan living area with a sleeper sofa and a gourmet kitchen with high-end appliances.
The garden-view lanais are equipped with a grill, kitchenette, and comfy seating arrangements. Each residence also comes with a garage parking space and an additional parking space in the driveway.
This unit is one of the Luana Garden Villas, the luxury villas on the site of the Outrigger Honua Kai Resort with its many amazing amenities. Guests of the villa have access to additional Luana amenities as well. Plenty of beach gear is provided.
Residences 2A, 2B, and 2C are 3 out of 4 residences that make up Villa 2. Units 2A and 2B are ground-floor residences directly adjacent to each other. There is, however, no adjoining door. Unit 2C is located directly above Villa 2A. This is the perfect compromise for a family who loves to spend time together but also values their privacy.
Location-wise, the Luana Garden Villa 2 residences are among the ones closest to the pool complex and to the beach. The Honua Kai Resort is one of the best family resorts in Maui so kids of all ages are sure to have a great time.
8. Beachfront penthouse at a small-scale resort
Specifications: 5 bedrooms, sleeps 10 people.
Location: Kihei (South Maui). Located right on Kam II beach.
Registration: TAT #TA-167-911-4240-01 | TMK #390050060049 | License n/a due to zoning.
Average rate per night: $3,375 plus taxes and fees.
Next on our list of best Maui vacation rentals for large groups is this 5-bedroom penthouse at a privileged and convenient location in Kihei. It features 3 king bedrooms with ensuite bathrooms and 2 queen bedrooms that share a full bath.
The lanai looks out over the golden sands of Kam II Beach, one of the rare lifeguarded beaches on the island. It’s a wonderful place to watch the sunrise and sunset or to enjoy a family meal. Boogie boards, kayaks, and a stand-up paddle board are available to guests.
The penthouse is located in a tranquil corner on the grounds of the small-scale resort The Hale Pau Hana resort. Shops, bakeries, and restaurants can be found just around the corner.
9. Family-friendly home at a luxury resort
Specifications: 3 bedrooms and a queen sleeper sofa, sleeps 14 people.
Location: Kapalua (West Maui). Steps away from Kapalua Bay Beach and Oneloa Beach.
Registration: TAT #TA-103-503-4624-01 | TMK #420040280031 | License n/a due to zoning.
Average rate per night: $3,634 plus taxes and fees.
Next on our list of vacation rentals in Maui for a family reunion is this luxury residence in Kapalua. It’s perfect for two families with kids thanks to the layout of the third bedroom. This room has been fitted with 3 bunk beds, each consisting of a queen and a twin bed. A queen sleeper sofa in the living room completes the sleeping arrangements.
The Pama Residence is located on the grounds of the upscale Montage Kapalua Bay. This particular ground-floor unit gives out to the garden so that your little ones have plenty of space to run around while the parents relax on the spacious lanai.
Two beautiful beaches, Kapalua Bay Beach and Oneloa Beach, can be found just around the corner. Of course, guests are also invited to enjoy the Beach Club Infinity Pool and the other Montage facilities.
The coastal-chic interior design and gourmet kitchen will make you feel at home from the moment you arrive. Montage-Pama comes with plenty of storage space as well as a children’s package, an entertainment package, and plenty of beach gear.
10. Ocean-view residence at a luxury villa resort
Specifications: 4 bedrooms, sleeps 10 people.
Location: Wailea (South Maui). Within walking distance of Wailea Beach.
Registration: TAT #TA-057-211-1360-01 | TMK #210081190034 | License n/a due to zoning.
Average rate per night: $1,599 plus taxes and fees.
Next on our list is one of the few Wailea luxury rentals that are large enough to accommodate a group of up to 10 people. This beautiful vacation home is located in the Hoolei Resort, a gated luxury villa complex across the street and uphill from the Grand Wailea Resort.
The villa complex comes with its own pool, jacuzzi, waterfalls, swim-in-grotto, and restaurant as well as daily housekeeping and on-site concierge services.
This gorgeous luxury villa features 3 well-appointed bedrooms with ensuites and king beds as well as an additional room with 2 queen beds. 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. Enjoy unobstructed views of the resort area and Wailea Beach from the lanai.
Note that this Hoolei Maui villa doesn’t offer Grand Wailea Resort privileges. Only some Hoolei Villas do, and that extra privilege is reflected in the price.
11. Gated modern home steps from the beach
Specifications: 4 bedrooms, sleeps 12 people.
Location: Napili (West Maui). Within walking distance from Kalepolepo Beach Park.
Registration: TAT #TA-111-969-6896-01 | TMK #430020450000 | License n/a due to zoning.
Average rate per night: $1,581 plus taxes and fees.
This recently built house is the perfect hideaway for a carefree Maui vacation. It features an open and airy living area, 4 well-appointed bedrooms, and 3 modern bathrooms. One of the bedrooms has a bunk bed in addition to the king bed. There’s also an additional queen sleeper sofa in the living room.
Sliding glass doors connect the indoor area to the cozy lanai. The house is fully gated, making it an excellent place to stay with little ones.
There’s a grocery store just up the road. Whip up a delicious meal in the well-stocked chef’s kitchen or on the grill. And if you don’t feel like cooking, you’ll find plenty of restaurants within walking distance.
This beautiful home is located in a family-friendly area, steps from the golden sands of Napili Bay Beach. Beach gear and snorkeling equipment are supplied by your hosts. The house also comes with a nice pool that has a shallow section with in-water loungers.
12. Modern 10-bedroom house close to the beach
Specifications: 10 bedrooms, sleeps 32 people.
Location: Napili (West Maui). Within walking distance from Kalepolepo Beach Park.
Registration: TAT #TA-151-061-9648-01 | TMK #430060060000 | License n/a due to zoning.
Average rate per night: $3,995 plus taxes and fees.
This huge modern home is a great option for a group of friends or family members who value their sense of privacy while still enjoying each other’s company.
The sleeping arrangements comprise 10 elegant master bedrooms. Each comes with an ensuite bathroom and some are equipped with a sleeper sofa. There’s also a bunk bed room that can sleep an additional 8 persons. The two dining areas and kitchen are perfect gathering spaces, as is the cozy outdoor space which is equipped with a full outdoor kitchen and a BBQ area.
Note that there’s no elevator to connect the 4 floors of living spaces.
Entertainment-wise, you’ll find a fitness center, a media room, an outdoor ping pong table, a corn hole, and a swimming pool that can be heated on request.
This vacation rental is located behind a small-scale condo building but there’s a private entrance path that leads directly to the beach. Honokowai Beach Park is located well within walking distance.
General booking policies of Maui vacation rentals for large groups
There are loads of cancellation and booking policy settings that VBRO and Airbnb renters can implement. So, to help protect you when booking your stay, it’s ideal to look for properties that have the following policies:
Large group vacation rental booking policies to look for
Multiple installment plans: This is best for group stays that can cost a fair amount. The maximum number of installments offered is three. Try and find a Maui vacation rental for large groups that offers installment plans, as this can help you budget.
Long-stay payment plans: Airbnb doesn’t offer installment plans for long-term stays. On the other hand, VRBO does. This is another reason why I prefer VRBO listings.
Large group vacation rental cancellation plans to look for
Moderate cancellation policy: This entitles you to a full refund if you cancel up to 30 days in advance and a 50% refund for cancelations up to 14 days in advance.
Relaxed cancellation policy: If you cancel up to 14 days in advance, you will receive a full refund and a 50% refund for cancellation up to 7 days in advance.
Cancellations with multiple installment plans: Some accommodations won’t offer refunds for installment bookings. For example, if you have paid 50% of your booking and cancel your stay, some renters won’t charge you for the remaining 50%. However, you won’t receive a refund for the paid fee. Keep an eye out for these policies when booking.
Which of these large group vacation rentals in Maui caught your eye?
Chances are that you’ve found the dream vacation rental for your family reunion or social gathering. If not, then have a look at my other wish lists to discover even more amazing Maui vacation rentals.
Also, rest assured that all featured Maui vacation rentals for families are operating legally with the required county permits and that all suggestions are hand-picked and thoroughly researched.
Vacation rentals in Maui for large groups FAQ
South Maui and West Maui are the best places to stay on the island for large groups and families. These areas offer easy access to some of the best Maui beaches, shops, restaurants, and entertainment. It’s also where snorkeling tours and whale-watching cruises leave from.
North Shore has some excellent beaches too but these are more suitable for surfing than they are for swimming due to the strong currents. It’s a very scenic part of the island that offers easy access to the Road to Hana and Upcountry Maui. It’s the perfect place to stay in Maui for a second visit or for a more authentic experience away from the crowds.
If you’re not familiar with the lay of the island, then have a look at the interactive map of Maui that I created.
While it’s hard to define the exact characteristics of a large group rental in Maui, the following qualities are what I look for when choosing a large Maui rental:
I always look for properties that have been recently updated or redecorated.
It should offer enough comfortable sleeping arrangements with ensuite bathrooms so that every travel member has his or her own privacy.
Space is a necessity for a large group vacation rental in Maui. You and your travel company should be able to comfortably gather in a pleasant living area both inside and outside.
It should come with parking for several cars.
The kitchen should be well-equipped and there should be outdoor BBQ facilities.
An in-unit washer and dryer are essential if you’re traveling with a group.
Air conditioning is a huge bonus and almost a necessity in my book.
Make sure it matches your personal taste.
The unit should preferably be located within walking distance of one of the Maui beaches.
Yes, Airbnb in Maui is legal but it’s strictly regulated. Maui County defines transient vacation rental as accommodation rented for less than 180 days and requirements and permits vary according to the type of rental.
So always check if your rental has all its permits.
Here’s a list of the different certifications they should have depending on the permit type:
Transient Accommodation Tax (TAT or W) number.
Tax Map Keys (TMK).
Permit numbers starting with either “ST”, “CP”, or “BB”. Exceptions exist for special zoning districts.
PS: I’ve done the work for you. All the listings I include have the correct permits.
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Hand-picked by author and Maui accommodation expert Sarah
Sarah is a seasoned traveler with a professional background in luxury hotel management, experience as a hotel inspector for Forbes Travel Guide, and comprehensive knowledge of the Maui accommodation landscape. To present you with the fine fleur of places to stay in Maui, she carefully scans hotel booking sites and vacation rental platforms such as Airbnb and VRBO, meticulously checks reviews, and verifies rental permits.