1Paso Robles, CA
AirbnbLocated on one of the area's premier wine trails, HammerSky is a beautifully restored farmhouse dating back to 1904. Try some of the area's wonderful wines, and then take a day trip to the Hearst Castle, Cambria and San Luis Obispo — all no more than 30 minutes away.
Farmhouse, sleeps 6, $575 a night on Airbnb.com.
2Charleston, NC
AirbnbFeatured on Tiny House Hunters, this houseboat is a fun place to rest your head as you explore the hopping Southern town. The gentle rock of the marina waves will lull you to sleep — and, if you're lucky, you'll catch sight of a dolphin or two.
Houseboat, sleeps 3, $289 a night on Airbnb.com.
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3Big Island, HI
AirbnbHigh up in the canopy near Volcano National Park, this secluded bamboo treehouse lets you live off the grid. Adventurous families only, please! The main living area is only accessible from a climbing ladder, and a few buggy friends may join you on your stay.
Treehouse, sleeps 1 family, $200 a night on Airbnb.com.
4San Diego, CA
VRBOThis gorgeous vacation home oozes SoCal vibes and is close to everything you'll want to check out: Coronado, La Jolla, SeaWorld, the San Diego Zoo, the Wild Animal Park and LEGOLAND. On the property, self-closing gates around the huge heated pool make it safe for young families.
Luxury Villa, sleeps 18, $932 a night on VRBO.com.
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5Ogunquit, ME
AirbnbHistoric towns, rocky shorelines, lobstah rolls — yes, you'll be able to check everything classically "Maine" off your list in this popular beach town.
The Loft, sleeps 6, $325 per night on Airbnb.com.
6Yosemite National Park, CA
AirbnbNestled inside Yosemite National Park, this newly built craftsman-style home has a farmhouse kitchen and covered front porch with rocking chairs. It's a little pricey, but Yosemite Valley and Wamona are just 20 minutes away, so you can't beat the location.
Craftsmen cottage, sleeps 8, $715 a night on Airbnb.com.
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7Palm Springs, CA
HomeAwayThis mid-century home is directly on the golf course in Indian Canyon, and the views are simply awe-inspiring, especially at sundown. But the modern kitchen and ultra-chic art will lure you to spend some time indoors, too.
Canyon ranch, sleeps 8, $450 a night on HomeAway.com.
8Tahoe City, CA
AirbnbWalkable to coffee shops, restaurants and the grocery store and near plenty of bike paths, this home is the perfect Tahoe pad for kids and adults alike.
Chalet, sleeps 9, $295 on Airbnb.com.
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9Isle of Palms, SC
HomeAwayPerfect for family reunions and milestone birthdays, this six-bedroom home has a private pool, an outdoor cooking cabana and dual master suites (no more family feuds!)
Luxury Home, sleeps 14, $654 a night on HomeAway.com.
10Key West, FL
HomeAwaySteps from world-famous Duval Street, fans of Jimmy Buffett's Margaritaville vibe will be pleased with this colorful townhouse. It's a short walk to Key West attractions like The Southernmost Point, The Hemingway House Museum and Ft. Zachary Taylor Beach.
Kate's Krawl, sleeps 4, $388 a night on HomeAway.com.
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11St. George, UT
VRBOThis Tuscan-style home is set into a tranquil hillside. Cook up a feast in the huge chef's kitchen, then take it to the courtyard for an al fresco family gathering.
Tuscan home, sleeps 16, $500 a night on VRBO.com.
12Smuggler's Notch, VT
AirbnbOutdoor pools, a spa and breweries make this an ideal spot for Northeast families. Grab a condo for up to 10, with access to all of the amenities at the Smuggler's Notch resort, including childcare.
Condo, sleeps 10, $216 a night on Airbnb.com.
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13Gulf Shores, AL
VRBOYour very own salt water pool with plenty of toys for the kids (and your pets!) make this a perfect base for your visit to the historic Fort Morgan Peninsula. Restaurants, live music and fun children's activities await in nearby Galveston, but you may just want to hang out on the property's cool pool deck.
Modern cottage, sleeps 10, $325 a night on VRBO.com.
14Anaheim, CA
VRBOThis cartoon-cute house is not only just a 20-minute walk from Disney, but its décor is also inspired by the most magical place on earth — down to the outdoor Mickey-shaped pool. The Minnie red polka dot room has bunk beds and is full of games, books, toys and dress-up clothes to keep kids busy for hours.
Suite Escapes House, sleeps 6, $260 a night on VRBO.com.
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15Point Reyes Station, CA
VRBODescribed by some as a "tree-top fantasy," this six-bedroom home is the perfect perch to explore the area's beautiful natural resources, including the Point Reyes National Seashore's endless hiking trails and Tomales Bay State Park swimming beaches.
Treehouse, sleeps 12, $645 a night on VRBO.com.
16Asheville, NC
TrippingWhether you're touring the area's breweries, the nearby Biltmore estate, or simply reveling in your very own swim pond on 20 acres of private land, this restored 1950s cabin will help you make lasting memories.
Sunset Hollow, sleeps 8, $275 a night on Tripping.com.
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17Gatlinburg, TN
TrippingAfter exploring every inch of Dollywood, you can retreat to this luxury cabin complete with a private sauna, movie room, Jacuzzi and queen-size bunk beds. Cook up trout from the nearby streams on the stainless steel gas grill, then take in the Smoky Mountain views from one of the three decks.
Basswood Lodge, sleeps 8, $230 a night on Tripping.com.
18Napa, CA
For families looking for something ultra-special, why not try your own private vineyard? This modern farmhouse high in the hills between Napa and Sonoma has a great room with 360-degree views and a pool overlooking the vineyard and pond below. Cheers to that!
Vineyard estate, sleeps 14, $1,850 a night on VRBO.com.
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19Myrtle Beach, SC
AirbnbFamilies with babies in tow, this is your spot. The homeowners provide a Pack 'n Play and beach toys to make things simple.
Beachside cottage, sleeps 7, $85 a night on Airbnb.com.
20Ashton, ID
VRBOLocated just a little over an hour from Grand Teton National Park and Jackson Hole, this luxury home is perfectly situated for taking in the area's incredible parks. Enjoy fishing, swimming, canoeing and paddle boating on the property's private lake.
Lodge, sleeps 30, $595 a night on VRBO.com.

Meghann Foye is the senior web editor of redbookmag.com. Her passions include cold-brew iced coffee, romantic comedies and CrossFit. And also enjoys playing the game Two Truths and a Lie.
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