A1Vacations is part of HomeAway.com, the world’s leading vacation rentals marketplace.
Search over 150,000 vacation rentals properties now!   Click here to see more Vacation Homes


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.

  1. Wailea Grand Beach Villa
    $750/night Wailea Beach Villa for 8-View Rated Perfect By Guests — Property 230622

    Vacation Villa rental in Maui area
    • Villa
    • 4 bedrooms , sleeps 10
    • 3 bathrooms
    • beach, resort
    • pool
    Fall Special & Thanksgiving Treat
    S P E C I A L    O F F E R
    Rates (shown in USD)
    $7665 - $10500 per property per week
  2. Wailea Grand Beach Villa-Piano
    Most Popular Wailea Beach Villa Trip Advisor Rates Perfect-$750/nite for 8 — Property 164181

    Vacation Villa rental in Maui area
    • Villa
    • 4 bedrooms , sleeps 10
    • 3 bathrooms
    • beach, waterfront
    • pool
    Rates (shown in USD)
    $6965 - $10500 per property per week
  3. Beachfront! 20 ft. From the Water's Edge! — Property 134452

    Vacation Condo rental in Kaanapali area
    • Condo
    • 1 bedroom , sleeps 5
    • 1 bathroom
    • beach, near the ocean
    • balcony
    Rates (shown in USD)
  4. The Pikake
    Beachfront! - 20 Short Steps to the Water! — Property 134703

    Vacation Condo rental in Kaanapali area
    • Condo
    • 1 bedroom , sleeps 4
    • 1 bathroom
    • beach, waterfront
    • internet access
    Rates (shown in USD)
  5. The Palms At Wailea
    The Palms- $150/nt for Remaining Dates in 2009!! — Property 163145

    Vacation Condo rental in Wailea area
    • Condo
    • 2 bedrooms , sleeps 6
    • 2 bathrooms
    • beach, near the ocean
    • pool
    Rates (shown in USD)
    $1365 - $2450 per property per week
  6. April-Oct. 2009 $129/Night Special - Kamaole Sands Resort Condo, Kihei, Wailea — Property 160452

    Vacation Condo rental in Kihei area
    • Condo
    • 2 bedrooms , sleeps 6
    • 2 bathrooms
    • beach, near the ocean
    • pool
    Rates (shown in USD)
  7. Westin Kaanapali Ocean Resort
    Great Oceanview 2 Bedroom Suite, Great Sunsets, Waves & Whales — Property 244735

    Vacation Villa rental in Kaanapali area
    • Villa
    • 2 bedrooms , sleeps 8
    • 2 bathrooms
    • beach, resort
    • pool
    Rates (shown in USD)
    $2500 - $6500 per property per week
  8. Deluxe Wailea Ekahi Village, 2 Bedroom Condo — Property 110359

    Vacation Condo rental in Wailea area
    • Condo
    • 2 bedrooms , sleeps 6
    • 2 bathrooms
    • beach, village
    • air-conditioning
    Rates (shown in USD)
  9. Deluxe Wailia, Ekahi Village 1 Bedroom Condo — Property 107053

    Vacation Condo rental in Wailea area
    • Condo
    • 1 bedroom , sleeps 4
    • 2 bathrooms
    • beach, village
    • air-conditioning
    Rates (shown in USD)

Refine Your Search

You refined by:
Maui remove
Golf Index remove
(remove all)
Find by availability dates: