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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
Book a stay at this beach vacation home in Kaanapali. Enjoy private pools, a beach locale, and a fitness center. Popular attractions Whalers Village and Kaanapali ...
#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
Stay at this vacation home in Hana. Enjoy free WiFi, a garden, and laundry facilities. Our guests praise the helpful staff in our reviews. Popular attractions ...
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
Stay at this 3-star vacation home in Paia. Enjoy free WiFi, laundry facilities, and concierge services. Our guests praise the property condition in our reviews. ...
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
Book a stay at this family-friendly vacation home in Hana. Enjoy free WiFi, a garden, and laundry facilities. Popular attractions Hana Bay Beach and Hana Cultural ...
Fisher's Hana Bay Hale, Across from Hana Bay
Beautiful 3-bedroom townhome in Kihei

Beautiful 3-bedroom townhome in Kihei

Kihei
Stay at this vacation home in Kihei. Enjoy laundry facilities and air conditioning. Popular attractions Maalaea Bay Beaches and Sugar Beach are located ...
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
Book a stay at this family-friendly vacation home in Napili. Enjoy private pools, a garden, and laundry facilities. Popular attractions Whalers Village and Kaanapali ...
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
Book a stay at this beach vacation home in Honokowai. Enjoy private pools, a beach locale, and a fitness center. Popular attractions Whalers Village and Kaanapali ...
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
Stay at this vacation home in Makawao. Enjoy free WiFi, private pools, and a garden. Popular attractions Enlighten Up Massage and Makawao Park are located ...
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
Book a stay at this beach vacation home in Kaanapali. Enjoy a beach locale, laundry facilities, and patios. Popular attractions Whalers Village and Kaanapali ...
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
124 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
Stay at this 3.5-star hotel in Kihei. Enjoy free WiFi, free parking, and 2 outdoor pools. Our guests praise the breakfast and the pool in our reviews. Popular ...
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
Stay at this 4.5-star luxury hotel in Kaanapali. Enjoy 3 outdoor pools, a full-service spa, and 2 restaurants. Our guests praise the helpful staff and the property ...
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
Stay at this 5-star luxury resort in Kihei. Enjoy free WiFi, 3 outdoor pools, and a full-service spa. Our guests praise the helpful staff and the property condition ...
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
Stay at this 5-star luxury resort in Kihei. Enjoy free WiFi, 9 outdoor pools, and a full-service spa. Our guests praise the pool and the helpful staff in our ...
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.