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The Daily Dish Shopping

You Need to See & Book These Over-the-Top Family Vacation Rentals


By Patricia Cunningham

Wasn’t it just yesterday we were ringing in the start of summer with some Yacht Rock and a flamingo-themed party and letting the kids run around outside barefoot and unsupervised (let’s be honest)? And now it seems like Labor Day is just around the corner. Yikes! Where does the time go?

Yet even though autumn and back-to-school season are nearly within sights, that doesn’t mean you can’t get the most out of those golden rays of summer with one last family adventure!

We’ve culled together a list of some of the most amazing vacation rental properties out there that still have availability this month and next. From expansive homes with enchanting themed rooms near Disney to breathtaking canyonland escapes, to your own damn private island, these are places where you and your kids can create memories to last a lifetime. Better start packing. Bon voyage!

THE PROPERTY: Disneyland House

LOCATION: Anaheim, California

THE LOWDOWN: I’ve always been of the persuasion that if you’re going to do Disney, you’ve gotta be all in. That’s right, I’m talking mouse ears and dorky T-shirts, or why bother? It’s not just ANY amusement park, after all. Likewise, your accommodations should be tricked out for a memory-making time or forget it. This home is the perfect place for that. The kids are going to freak out over the fantasy bedrooms, the giant heated pool and game room with billiards, foosball and ping pong; and mommy is going to love the 400-square-foot outdoor space and all the tasteful, luxurious furnishings. Sleeps 15, so bring the cousins. 

RENT FROM: Home Away, from $575/night, sleeps 15


LOCATION: Moab, Utah

THE LOWDOWN: Didn’t we all have a set of Lincoln Logs at one point or another? The classic building toy that lets you to erect forts and cabins straight out of the wild American frontier. Well, here’s the real thing—a completely deluxe log cabin right in the middle of one of the most staggeringly beautiful places on earth. The house offers views in every direction—snow-capped mountains, red rock and pastureland, and unforgettable sunsets and starscapes. Arches and Canyonlands National Parks are a short drive away. The area is great for active families as rafting, hiking and biking trails, horse riding and other activities are all nearby (and the house comes equipped with bikes, a kayak and hiking gear). Super plush, you won’t even need to pack a robe.

RENT FROM: Home Away, from $495/night, sleeps 8

THE PROPERTY: Private Island

LOCATION: Florida Keys

THE LOWDOWN: A private island has become the ultimate status symbol for the rich and famous— billionaires hide away from the sweaty masses on them, celebrities escape to them when it’s time to consciously uncouple and even ex-presidents are in on the game. Few of us can afford ever to own one, but you can rent one! Say hello to Seabird Key, a private 10-acre tropical island hideaway in the heart of the Florida Keys. Yup, you get it all to yourself. An ideal family getaway, the island comes with a tiki-tastic beach house, 19-foot Boston Whaler for your personal use and everything you need for beachside fun—kayaks, paddle boards and tubes, fishing and snorkeling gear, and a hammock perfectly situated for sea breezes. 

RENT FROM: Home Away, from $899/night, sleeps 8

THE PROPERTY: 727 Airplane Home

LOCATION: Costa Rica

THE LOWDOWN: Okay, there’s memorable and then there’s your-kids-will-never-stop-talking-about-this-one-and-it’s-getting-kind-of-embarrassing memorable, which is what happens when you stay in a vintage Boeing 727 airplane, remade into a two-bedroom home perched high in the rainforest jungle in Costa Rica! Located between Manual Antonio National Park and the Pacific Ocean, this truly one-of-a-kind home offers panoramic ocean and jungle views and is steps away from a white sand beach. Wake up to the sound of howler monkeys and befriend sloths, toucans and countless species of birds. An adjacent hotel provides three cliff-side pools to enjoy. Waterfalls, hiking, zip-lining, surfing and jungle adventures are all part of the fun. You only live once. 

RENT FROM: Home Away, from $283/night, sleeps 6

THE PROPERTY: Beachfront Treehouse

LOCATION: Vashon Island, Washington

THE LOWDOWN: Sometimes you just want to check out to cooler climes and calmer waters, be enveloped by the flow of nature and get back to basics with your crew. This secluded treehouse is for you. Situated on lush Vashon Island (and a short ferry ride to Seattle and the Olympic Peninsula), it comes equipped with all you will need for taking in the great outdoors—a beachfront cabana is stocked with canoe, paddle board, life vests and firewood. Take in the scenery from the private dock or sit around the campfire at night and tell stories—that away-from-it-all feeling will commence immediately. Ahh, I can almost smell the fir trees from here.

RENT FROM: VRBO, from $174/night, sleeps 6

THE PROPERTY: Disney World House

LOCATION: Kissimmee, Florida

THE LOWDOWN: Do you have a little girl who wears an Elsa dress 24/7, even to bed? One who still can’t stop requesting “Let It Go” even though you have outlawed it in the car? This house might be her nirvana. Sure, it’s luxuriously appointed and has a private pool and game room and is situated on an amazing resort that includes a 50-foot waterslide and kids splash zone, dining options, shuttle to Disneyworld and access to all Orlando has to offer. But most importantly it has a bedroom devoted entirely to Frozen—she may never want to leave. (Oh, and there’s a Harry Potter room for her brother, too.)

RENT FROM: Home Away, from $329/night, sleeps 15

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