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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. Wailea Sunset Bungalow — Property 95991

    Vacation Cottage rental in Maui area
    • Cottage
    • 2 bedrooms , sleeps 4
    • 1 bathroom
    • accept credit card
    • activities guide
    Rates (shown in USD)
    $3150 - $4550 per cottage per week

  2. 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

  3. Affordable Luxury 2 Bedroom - Specials Available — Property 215093

    Vacation Cottage rental in Lahaina area
    • Cottage
    • 2 bedrooms , sleeps 6
    • 2 bathrooms
    • beach, near the ocean
    • internet access
    Rates (shown in USD)
    $1250 per property per week

  4. 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

  5. West Maui Cottages -2 secluded and convenient Cottages — Property 213296

    Vacation Cottage rental in Lahaina area
    • Cottage
    • 3 bedrooms , sleeps 10
    • 1 bathroom
    • beach, mountain
    • air-conditioning
    Rates (shown in USD)
    $910 per property per week

  6. My Waii Beach Cottage
    My Waii Beach Cottage — Property 259220

    Vacation Cottage rental in Kihei area
    • Cottage
    • 1 bedroom , sleeps 4
    • 2 bathrooms
    • beach
    • air-conditioning
    Rates (shown in USD)
    $1750 - $2415 per property per week

  7. Private 2BR Tropical Cottage with Waterfall Pool Near Wailea — Property 166795

    Vacation Cottage rental in Kihei area
    • Cottage
    • 2 bedrooms , sleeps 5
    • near the ocean, resort
    • pool
    Rates (shown in USD)
    $1225 per property per week

  8. Beautiful, Private, Romantic Cottage w/ Spectacular Ocean/Sunset View King Bed, — Property 204592

    Vacation Cottage rental in Haiku area
    • Cottage
    • 1 bedroom , sleeps 2
    • 1 bathroom
    • near the ocean, rural
    • garden
    Rates (shown in USD)
    $1218 per property per week

  9. Beach Cottage, white sand, private, windsurf and kite surf from our beach — Property 238842

    Vacation Cottage rental in Spreckelsville area
    • Cottage
    • 2 bedrooms , sleeps 4
    • 1 bathroom
    • 1 half bathroom
    • beach, waterfront
    • pets considered
    Rates (shown in USD)
    $4200 per property per week

  10. Fabulous Oceanview Kaanapali Cottage — Property 130213

    Vacation Cottage rental in Kaanapali area
    • Cottage
    • 2 bedrooms , sleeps 6
    • near the ocean, resort
    • pool
    Rates (shown in USD)
    $1603 - $1953 per property per week

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