Home Destinations My Six Picks: Great Maui Vacation Rentals for Multi-Gen Family Vacations

My Six Picks: Great Maui Vacation Rentals for Multi-Gen Family Vacations

by Shelly Rivoli
Rainbow Hale

MAUI, Multi-Generational Family Vacation Rentals – I’ve just returned from an epic 80th birthday family reunion celebration with thirteen Rivolis sleeping under the same roof—with plenty of beds and bathrooms for all—I am feeling especially attuned to the comforts and conveniences a vacation rental can provide for a multi-gen family vacation.

This week, I’m taking a look at family-friendly Maui vacation rentals in particular. Here are six of my hand-picked recommendations that are ideal for family vacations with grandparents, aunties and uncles, and various combinations of friends and families. These rentals sleep from six people up to sixteen, as noted. This sponsored post contains affiliate links.

maui vacation rentals for multi-gen family vacation

1. Kapalua – Ocean Breeze (value pick)

Ocean Breeze is ideally situated for golfing enthusiasts.
Ocean Breeze is ideally situated for golfing enthusiasts.

Sleeps 6 / 3 Bedrooms / 3 Bathrooms

If the family that golfs together stays together, they’d likely like to stay here. Ocean Breeze is within the Kapalua Golf Residences, located just off of one of the two courses here. It’s a great option for the family of four plus grandparents, with two king bedrooms and one bedroom with two twins.

Each bedroom has its own en suite bathroom. Guests have four swimming pools to choose from at the resort, and Kapalua Beach is just a 5- to 10-minute free shuttle ride away. Tennis enthusiasts can also be on the Kapalua courts with just a 5-minute walk.

2. Puunoa Beach Estates – Condominium 104

This Puunoa Beach condo is just a 5-minute walk to Maui's Baby Beach.
This Puunoa Beach condo is just a 5-minute walk to Maui’s Baby Beach.

Sleeps 6 / 3 Bedrooms / 3 Bathrooms

Aside from each of its three bedrooms featuring its own bathroom (hooray!), this ground-level condo may be ideal for many families because it is just that: ground level. There’s no worry of stairs or wait for elevators here, and grandparents can step out onto the terrace for fresh air, ocean views, and lounge chairs with ease.

Two bedrooms feature king-size beds, and a third offers up two queen-size beds. Better still? It’s only a 5-minute walk to Baby Beach (Puunoa Beach), so pack your stroller and soft-side cooler and leave the car where it is.


3. Wailea Beach Villas Resort – Sandcastles Suite

Open (your doors) wide and say, "Ahhhhh...." at Wailea Beach Villas
Open (your doors) wide and say, “Ahhhhh….” at Wailea Beach Villas

Sleeps 8 / 4 Bedrooms / 3 Bathrooms

Sure, this penthouse villa offers sweeping views from a prestigious Maui address. But it also comes loaded with en suite entertainment “goodies” like Xbox, DVD/Blue ray/CD player, Netflix, Pandora downloads, and then some. And yes, you can feel like a rock star with your own private elevator entrance to this Maui vacation rental.

The spacious kitchen and dining area were designed with a group in mind and include a breakfast bar plus a dining table that can seat all eight of you. The resort offers two swimming pools–one for those with children (including a shallower area for smaller swimmers) and one for those without and is just a 5-minute walk to Wailea Beach and also to the Shops at Wailea.


Extra perks are available for extra fees, including butler service, private chef, or access to the neighboring Grand Wailea pool & water slides. (You can read about our stay in a similar villa at Wailea Beach Villas in “Postcards from the Penthouse” at our sister site.)

4. Ka’anapali – Rainbow Hale Estate

spacious family vacation rental in Maui with views
With 2,400 square feet of lanai and views like this, you may forget to go inside.

Sleeps 8 / 4 Bedrooms / 3.5 Bathrooms / Private Pool

Want plenty of space to yourselves? Sit pretty in this 3,600 square-foot private estate with its own infinity swimming pool and hot tub perched within a working coffee plantation. There’s also plenty of room for extended family to enjoy the breeze outdoors and ocean views from 2,400 square feet of lanais and lounging areas.

Though you’ll be driving to get to the beach (1.1 miles to Kahekili Beach Park, 2.1 miles to Ka’anapali Beach), it is still within easy reach of great snorkeling, shopping, and dining.


5. Kihei – Shambala Estate (bucket list pick)

luxury pick vacation rental in Maui
Your own private paradise–in paradise.

Sleeps 12 / 6 Bedrooms / 9 Bathrooms / Private Pools

For the ultimate family reunion, consider this 2-acre gated estate with three grotto-esque swimming pools, water falls, water slide, and hot tub. There’s also an open-air pool bar with billiards, volley ball, and private putting green complete with sand traps. Inside, enjoy a snorkel-free view of the underwater world with the sizable salt water reef aquarium.

And if your family holds fast to the adage that “many hands make light work,” meal prep will be a breeze in the commodious gourmet kitchen with two islands–and for variety, there’s an outdoor kitchen with its own dining area as well. Two of the six bedrooms offer two twin-size beds for family-style flexibility. And yes, it really has nine bathrooms.

6. Lanai – Maui Oasis Estate and Lahaina Oasis (big family pick)

great vacation rental for big groups in Maui
Great views for big groups at this private estate vacation rental in Maui.

Sleeps 18 / 8 Bedrooms / 8 Bathrooms / Private Pool

Extended family can extend throughout three separate buildings on this private property: the five-bedroom Maui Oasis and the three-bedroom Lahaina Oasis with its detached third bedroom. The architecture maximizes views of the Pacific and island of Lanai on one side, and verdant West Maui Mountain views on the other.

A swimming pool and hot tub invite all to step out beyond a covered lanai that’s more like an outdoor living room. There are also plenty of ways for your group to get its game on here with foosbol and ping-pong tables, badminton, and croquet sets at this Maui vacation rental.


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