Search for vacation rental homes on Maui

Family Time in Maui

It’s easy to believe that Hawaii is a place for lovers. It also serves as the ideal backdrop for a ladies-only getaway filled with carefree exploring and plenty of bonding, but what about family vacations? If you’re undertaking the task of bringing the kids to the Aloha State, Maui is your best bet.


This island is more developed than Molokai or Kauai (save those for your honeymoon or anniversary) yet not as packed with people as Oahu (definitely worth seeing but possibly overwhelming at times). It is undeniably beautiful and offers up an assortment of activities that range from serenely soothing to challenging and cathartic, but most importantly, that middle ground known for being fun-but-family-friendly is well covered. Without compromising your own happiness or asking too much of the younger ones, a good time can be had by all.


After settling into your vacation condo in one of Maui’s enticing towns (Kihei, Wailea, and Kaanapali are fine places to consider), your job of crafting a fabulous itinerary will take little effort. With choices like whale-watching cruises, glass-bottom boat tours, surfing lessons and visits to the lush inland areas adorned with exotic flora and fauna, everyone will be kept constantly entertained. Sometimes splitting up is in order (big kids here, little kids there…) – by now you’ve learned that can be a very good thing.


Everyone will end up back at “home” at the end of the day of course, swapping stories over snacks on the lanai, squeezing in a board game or a nap before going out to dinner, or running down to the beach for one more dip before the sun sets.


With ideal conditions that include plenty of accommodating beach houses and condos the stage is set for success. Gather your family and travel with confidence because Maui has what it takes to please.

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  1. Affordable South Maui Condo, Close to Beach & Activities — Property 157781

    Vacation Condo rental in Maui area
    • Condo
    • 1 bedroom , sleeps 4
    • 1 bathroom
    • beach, near the ocean
    • accept credit card
    SUMMER SPECIAL---Only $79.00 per night!
    S P E C I A L    O F F E R
    Rates (shown in USD)
    $679 - $819 per property per week

  2. Beautiful - Luxury Condo without Luxury Price - 2 Blocks to Beach — Property 156100

    Vacation Condo rental in Maui area
    • Condo
    • 1 bedroom , sleeps 4
    • 1 bathroom
    • beach
    • accept credit card
    $10 discount per night! Book Now!
    S P E C I A L    O F F E R
    Rates (shown in USD)

  3. Beachfront-Honeymooner Delight!! - Kihei Sands on Sugar Beach — Property 141757

    Vacation Condo rental in Maui area
    • Condo
    • 1 bedroom , sleeps 2
    • 1 bathroom
    • beach, waterfront
    • accept credit card
    $135/nt- Beachfront & Remodeled
    S P E C I A L    O F F E R
    Rates (shown in USD)
    $1330 - $1575 per property per week

  4. Beachfront Luxury West Maui Rental Condo with View of the ocean & 2 Islands — Property 138697

    Vacation Condo rental in Kahana area
    • Condo
    • 1 bedroom , sleeps 4
    • 1 bathroom
    • beach, resort
    • swimming pool
    Last Minute Special Offer
    S P E C I A L    O F F E R
    Rates (shown in USD)
    $1085 - $1365 per property per week

  5. Beautiful Dream Home with Private Pool and Jacuzzi — Property 158910

    Vacation House rental in Kihei area
    • House
    • 3 bedrooms , sleeps 8
    • 3 bathrooms
    • near the ocean, rural
    • accept credit card
    Book For 14 Nights, Get the 15th Free!
    S P E C I A L    O F F E R
    Rates (shown in USD)
    $1820 per property per week

  6. Wailea Beach Villa Baby Grand - Ocean View - Special — Property 164181

    Vacation Villa rental in Wailea area
    • Villa
    • 4 bedrooms , sleeps 9
    • 3 bathrooms
    • beach, waterfront
    • accept credit card
    $1100 May Special - Wailea Beach Villa
    S P E C I A L    O F F E R
    Rates (shown in USD)
    $9975 - $22050 per property per week

  7. Maui Mandalay — Property 220479

    Vacation Villa rental in Lahaina area
    • Villa
    • 3 bedrooms , sleeps 10
    • 3 bathrooms
    • beach
    • accept credit card
    Sun-sational Getaway Sale!
    S P E C I A L    O F F E R
    Rates (shown in USD)
    $2625 - $3500 per property per week

  8. Beachfront condo with mountain view - newly remodeled studio — Property 171364

    Vacation Condo rental in Lahaina area
    • Condo
    • studio , sleeps 2
    • 1 bathroom
    • beach, near the ocean
    • accept credit card
    One Free Night
    S P E C I A L    O F F E R
    Rates (shown in USD)
    $870 - $990 per property per week

  9. Exclusive Newly Built House - 180 degree Ocean Views - West Maui — Property 155201

    Vacation House rental in Lahaina area
    • House
    • 2 bedrooms , sleeps 6
    • 2 bathrooms
    • beach, near the ocean
    • air-conditioning
    CANCELLATION Special - $289 per night
    S P E C I A L    O F F E R
    Rates (shown in USD)
    $1950 - $3850 per property per week

  10. Stunning Luxury Oceanview Condo in Spectacular Luana Kai, Convenient — Property 139616

    Vacation Condo rental in Kihei area
    • Condo
    • 1 bedroom , sleeps 4
    • 1 bathroom
    • beach, waterfront
    • accept credit card
    Summer Special
    S P E C I A L    O F F E R
    Rates (shown in USD)
    $973 - $1150 per property per week

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