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Featured Holiday Homes in Maui

#1 Luxury BEACHFRONT! Pickleball, Sand Volleyball, 2 Gyms, Pool

#1 Luxury BEACHFRONT! Pickleball, Sand Volleyball, 2 Gyms, Pool

2 out of 5
Lahaina
When you stay at this vacation home in Kaanapali, you'll be on the beach, a 4-minute drive from Whalers Village and 7 minutes from Kaanapali Beach.
#1 Luxury BEACHFRONT! Pickleball, Sand Volleyball, 2 Gyms, Pool
Fisher’s Hana Bay Hale - In Hana Town across from the Bay STHA-2017 0002

Fisher’s Hana Bay Hale - In Hana Town across from the Bay STHA-2017 0002

Hana
Located in Hana, this vacation home is in a rural location, within a 15-minute walk of Hana Bay Beach and Hana Cultural Center.
Fisher’s Hana Bay Hale - In Hana Town across from the Bay STHA-2017 0002
Kaiholo Hale

Kaiholo Hale

3 out of 5
25 Kaiholo Place, Paia, HI
With a stay at Kaiholo Hale in Paia, you'll be in the historical district, just a 4-minute walk from Kuau Bay Beach and 14 minutes by foot from Paia Bay.
Kaiholo Hale
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Fisher's Hana Bay Hale, Across from Hana Bay

Fisher's Hana Bay Hale, Across from Hana Bay

Kahului
With a stay at this vacation home in Hana, you'll be by the sea, just a 4-minute walk from Hana Bay Beach and 6 minutes by foot from Hana Cultural Center.
Fisher's Hana Bay Hale, Across from Hana Bay
Beautiful 3-bedroom townhome in Kihei

Beautiful 3-bedroom townhome in Kihei

Kihei
With a stay at this vacation home in Kihei, you'll be within a 15-minute walk of Maalaea Bay Beaches and Sugar Beach.
Beautiful 3-bedroom townhome in Kihei
The #1 Vacation Rental on Maui!!  Steps to Maui's Best Beach! Pickle Ball Ct!

The #1 Vacation Rental on Maui!! Steps to Maui's Best Beach! Pickle Ball Ct!

Lahaina
With a stay at this vacation home in Napili, you'll be by the sea, a 4-minute walk from Napili Bay and 13 minutes by foot from Kapalua Beach.
The #1 Vacation Rental on Maui!! Steps to Maui's Best Beach! Pickle Ball Ct!
The #1 Luxury OCEAN FRONT Mansion!  Sleeps 32

The #1 Luxury OCEAN FRONT Mansion! Sleeps 32

lahina
When you stay at this vacation home in Honokowai, you'll be on the beach, within a 10-minute drive of Whalers Village and Kaanapali Beach.
The #1 Luxury OCEAN FRONT Mansion! Sleeps 32
Historic Upcountry Maui Property With Pool, 7Bedrooms, Sleeps 16

Historic Upcountry Maui Property With Pool, 7Bedrooms, Sleeps 16

Makawao
With a stay at this vacation home in Makawao, you'll be within a 5-minute drive of Hui Noʻeau Visual Arts Center and Maui Gold Pineapple Farm.
Historic Upcountry Maui Property With Pool, 7Bedrooms, Sleeps 16
Remodeled, Ground floor studio; Inquire about specials from 4/21 - 6/25

Remodeled, Ground floor studio; Inquire about specials from 4/21 - 6/25

Lahaina
When you stay at this vacation home in Kaanapali, you'll be on the beach, within a 10-minute drive of Whalers Village and Kaanapali Beach.
Remodeled, Ground floor studio; Inquire about specials from 4/21 - 6/25
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Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Maui Holiday Houses

Do you love last minute road trips and late-night food runs and sunrises on the beach? Do words like “schedule” and “calendar” make you shout, “Don’t box me in!”? You might be a little bit of a rebel. But you’re a rebel with a cause: having a smashing holiday. Itinerary? What’s that? Our Maui vacation homes are the perfect way for you to wing it.

Holiday houses in Maui let you live life on your own terms. You’ll have so much space, you’ll wish you had more friends and family—but you can always invite over the neighbours. You can often have luxury amenities, but with all the attractions of Maui in your backyard, budget holiday homes will do just fine, too. That will just leave you more dough to spend on the important things: cocktails, brunch, and local Maui adventures, obvs.

If your adventure buddy happens to have fur and four legs, you just might find a pet-friendly holiday house in Maui with your name on it.

No need to spend big bickies for a holiday beach house the size of Buckingham Palace—unless you’re really in trouble with bae. We’ve got a great selection of Maui vacation homes with everything you need for a seriously amazing getaway. Throw out that daily planner and hit “reject” on all those meeting invites. You’re off to a place where there are no rules.

Maui Holiday Homes essential information

Accommodation
128 Holiday Homes
Lowest Price
Highest Price
Popular accommodation
#1 Luxury BEACHFRONT! Pickleball, Sand Volleyball, 2 Gyms, Pool, Fisher’s Hana Bay Hale - In Hana Town across from the Bay STHA-2017 0002 , Kaiholo Hale, Fisher's Hana Bay Hale, Across from Hana Bay, Beautiful 3-bedroom townhome in Kihei, The #1 Vacation Rental on Maui!! Steps to Maui's Best Beach! Pickle Ball Ct!, The #1 Luxury OCEAN FRONT Mansion! Sleeps 32, Historic Upcountry Maui Property With Pool, 7Bedrooms, Sleeps 16, Remodeled, Ground floor studio; Inquire about specials from 4/21 - 6/25

Top trending hotels in Maui

Maui Coast Hotel

Maui Coast Hotel

3.5 out of 5
2259 S Kihei Rd, Kihei, HI
Fully refundableReserve now, pay when you stay
Located in Kihei, Maui Coast Hotel is in a shopping district, a 3-minute walk from Kamaole Beach Park and 6 minutes by foot from Cove Park.
Maui Coast Hotel
The Westin Maui Resort & Spa, Ka'anapali

The Westin Maui Resort & Spa, Ka'anapali

4.5 out of 5
2365 Kaanapali Pkwy, Lahaina, HI
Fully refundableReserve now, pay when you stay
When you stay at The Westin Maui Resort & Spa, Ka'anapali in Kaanapali, you'll be on the beach, just steps from Kaanapali Beach and 5 minutes by foot from Whalers ...
The Westin Maui Resort & Spa, Ka'anapali
Four Seasons Resort Maui at Wailea

Four Seasons Resort Maui at Wailea

5 out of 5
3900 Wailea Alanui Drive, Kihei, HI
With a stay at Four Seasons Resort Maui at Wailea in Kihei (Wailea), you'll be within a 15-minute walk of Wailea Beach and Polo Beach.
Four Seasons Resort Maui at Wailea
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Grand Wailea Maui, A Waldorf Astoria Resort

Grand Wailea Maui, A Waldorf Astoria Resort

5 out of 5
3850 Wailea Alanui Drive, Kihei, HI
With a stay at Grand Wailea Maui, A Waldorf Astoria Resort in Kihei (Wailea), you'll be within a 10-minute walk of Wailea Beach and Shops at Wailea.
Grand Wailea Maui, A Waldorf Astoria Resort
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Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

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^Subject to availability and chosen travel dates.