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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. Koali Ranch Cottage
    Miles of Open Coastline in Full View Across a 70 Acre Preserve — Property 253815

    Vacation Cottage rental in Maui area
    • Cottage
    • 1 bedroom , sleeps 2
    • 1 bathroom
    • near the ocean, rural
    • balcony
    Rates (shown in USD)
    $945 per property per week

  2. Private cottage 1 block from the beach. Clean, quiet and comfortable. — Property 238126

    Vacation Cottage rental in Kihei area
    • Cottage
    • 1 bedroom , sleeps 4
    • 1 bathroom
    • beach, near the ocean
    • air-conditioning
    Rates (shown in USD)
    $630 per property per week

  3. Thanksgiving Spcl! Secluded&Very Private Cottage! Walk to Beach* — Property 139311

    Vacation Cottage rental in Kaanapali area
    • Cottage
    • 2 bedrooms , sleeps 6
    • 2 bathrooms
    • beach, near the ocean
    • satellite or cable
    Rates (shown in USD)
    $1255 - $1590 per property per week

  4. Private Garden Cottage Within Walking Distance of the Beach! — Property 315874

    Vacation Cottage rental in Kihei area
    • Cottage
    • 1 bedroom , sleeps 2
    • 1 bathroom
    • beach, near the ocean
    • garden
    Rates (shown in USD)
    $630 per property per week

  5. Wailea Sunset Bungalow — Property 95991

    Vacation Cottage rental in Wailea area
    • Cottage
    • 2 bedrooms , sleeps 4
    • 1 bathroom
    • adventure
    • air-conditioning
    Rates (shown in USD)
    $3150 - $4550 per cottage per week

  6. Makena Beach Rental
    Hale Lamalamaka'ili — Property 149705

    Vacation Cottage rental in Makena area
    • Cottage
    • 2 bedrooms , sleeps 4
    • 1 bathroom
    • 1 half bathroom
    • beach, near the ocean
    • air-conditioning
    Rates (shown in USD)
    $2800 per property per week

  7. Lahaina Beachside Cottage
    Steps to the Beach and the Front Street! Great location for everybody. — Property 320332

    Vacation Cottage rental in Lahaina area
    • Cottage
    • 2 bedrooms , sleeps 6
    • 1 bathroom
    • beach, downtown
    • garden
    Rates (shown in USD)
    $1575 - $1960 per property per week

  8. Old Hawaii Plantation Bungalow 2 BR/1 BA — Property 259521

    Vacation Cottage rental in Kihei area
    • Cottage
    • 2 bedrooms , sleeps 5
    • 1 bathroom
    • air-conditioning
    • internet access
    Rates (shown in USD)
    $770 - $980 per property per week

  9. Beautiful private cottage — Property 184587

    Vacation Cottage rental in Kihei area
    • Cottage
    • 1 bedroom , sleeps 2
    • beach, near the ocean
    • garden
    Rates (shown in USD)
    $630 per property per week

  10. Great Ocean Views in Quiet Seclusion! — Property 158710

    Vacation Cottage rental in Kihei area
    • Cottage
    • 1 bedroom , sleeps 4
    • 1 bathroom
    • 1 half bathroom
    • pool
    • balcony
    Rates (shown in USD)
    $1000 - $1225 per property per week

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