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. Super specials! Rent owner-direct and save $$$ — Property 168646

    Vacation Condo rental in Maui area
    • Condo
    • 1 bedroom , sleeps 4
    • 1 bathroom
    • beach
    • accept credit card
    Owner-direct for $75/nt thru Dec 14th!!
    S P E C I A L    O F F E R
    Rates (shown in USD)
    $503 - $1110 per property per week

  2. Wailea Vacation Rental - Ekahi 53D Fabulous Ocean View Newly Renovated 1BR/1BA — Property 194155

    Vacation Condo rental in Wailea area
    • Condo
    • 1 bedroom , sleeps 4
    • 1 bathroom
    • beach, resort
    • accept credit card
    7th night free! July 20 to September 30
    S P E C I A L    O F F E R
    Rates (shown in USD)
    $1785 - $2450 per property per week

  3. Maui Mandalay — Property 220479

    Vacation House rental in Lahaina area
    • House
    • 3 bedrooms , sleeps 10
    • 3 bathrooms
    • beach
    • accept credit card
    Summer in Mandalay Sale
    S P E C I A L    O F F E R
    Rates (shown in USD)
    $2443 - $3465 per property per week

  4. Direct Oceanfront, Licensed, Paypal — Property 312005

    Vacation Condo rental in Maalaea Bay area
    • Condo
    • 2 bedrooms , sleeps 5
    • 2 bathrooms
    • village, waterfront
    • swimming pool
    Stay for 7 Nights, Pay for 5 Thru Nov 30
    S P E C I A L    O F F E R
    Rates (shown in USD)
    $1120 per property per week

  5. Oceanfront Paradise — Property 193053

    Vacation Condo rental in Maalaea Bay area
    • Condo
    • 2 bedrooms , sleeps 5
    • 2 bathrooms
    • waterfront
    • swimming pool
    Summer Sale - 15% off regular rates!
    S P E C I A L    O F F E R
    Rates (shown in USD)
    $1225 - $1575 per property per week

  6. Luxury Condo in the Heart of Historic Lahaina, Maui — Property 147263

    Vacation Condo rental in Lahaina area
    • Condo
    • 2 bedrooms , sleeps 6
    • 2 bathrooms
    • downtown, near the ocean
    • swimming pool
    July August Special
    S P E C I A L    O F F E R
    Rates (shown in USD)

  7. 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

  8. Luxury Designer Condo with Spectacular Ocean Views. — Property 146417

    Vacation Condo rental in Kihei area
    • Condo
    • 2 bedrooms , sleeps 6
    • 2 bathrooms
    • beach, village
    • accept credit card
    Save in Style!! This is The One!!
    S P E C I A L    O F F E R
    Rates (shown in USD)
    $1155 - $1365 per property per week

  9. Super Special Rates!! Rent owner-direct and save $$$ — Property 182248

    Vacation Condo rental in Kihei area
    • Condo
    • 1 bedroom , sleeps 4
    • 2 bathrooms
    • beach
    • accept credit card
    SPECIAL - $99/nt from July - Dec. 14th!!
    S P E C I A L    O F F E R
    Rates (shown in USD)
    $675 - $1245 per property per week

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

    Vacation Condo rental in Kihei area
    • Condo
    • 1 bedroom , sleeps 4
    • 1 bathroom
    • beach, near the ocean
    • accept credit card
    SUMMER/FALL SPECIAL-Only $79 per night!
    S P E C I A L    O F F E R
    Rates (shown in USD)
    $553 - $819 per property per week

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