Amelia Island, FL
Spacious waterfront loft in Amelia Island
Sun seekers of all ages will love this breezy waterfront space steps from a 13-mile stretch of prime Florida beach. Ocean views and clean, modern lines accent this fully equipped two-story townhouse’s spaciousness. It sleeps eight people and has two living rooms and three outdoor areas. Children, young adults, and grandparents may seamlessly commingle in the second level’s main area and around the big dining table at mealtimes. With easy access to historic Fernandina Beach’s downtown area, and four notable golf courses—not to mention Amelia Island’s boating, fishing, biking, and horseback riding diversions—there are activities for the entire family.
U.S. Virgin Islands
Private villa in St. John
Treat yourself! Is a weeklong stay at a private villa on a cliff in the Virgin Islands something you may be interested in? Live like royalty with your entourage in this palatial waterfront property boasting four Master Bedroom suites with private entrances and balconies, private beach, secluded hot tub, poolside bar, and heated Infinity Edge pool overlooking St. John’s Fish Bay. With amenities like a gourmet kitchen complete with wine cooler, a wet bar, and an indoor/outdoor music system, you may never leave, but Kaleidoscope Villa is also minutes from the attractions of Cruz Bay Village and the excellent snorkeling in Ditleff Bay.
Hilton Head, SC
South Carolina family beach house
Desperately in need of a timeout? Pack up your crew and head for laid-back Hilton Head. Up to 22 vacationers will fit inside this fully updated house in North Forest Beach. With an expansive dining area, a cutting-edge media room, and a stocked game room, entertainment options abound. Sprawling outdoor spaces include a huge pool and hot tub, sun decks, a covered kitchen and fireplace, and another guesthouse. Just steps from the beach, a short drive from the area’s legendary golf courses, and a mile from buzzing Coligny Plaza, this spot is perfect for exploring one of South Carolina’s most beloved isles.
Lavish beachfront escape in Oahu
Say goodbye to gray winter skies and aloha to blue Hawaiian waters! The lavish nine-bedroom, seven-bathroom Waimanalo Beach Estate grandly sits on one of the world’s most coveted beaches. Think stunning ocean and mountain views of Oahu from each floor, luxurious accommodations for up to 20, and endless amenities—ranging from guest wings that convert into mini-resorts with separate living areas and exercise rooms to a lava rock waterfall and a waterslide. The property also offers extra sanctuary in the middle of this hopping island paradise with a private gated yard, covered patio, outdoor bar, pool, and hot tub.
Bound for the region that’s home to Florida’s most famously magical destination? Make it exciting for every member of the family by retreating to this fully equipped, five-bedroom home with room for 10. Located in one of the Orlando area’s most relaxing gated communities, Watersong Resort is 20 minutes from Disney World, aka Mecca for the wee members of your clan, in addition to the other popular theme parks, spas, restaurants, and nightlife this region is known for. There is also a clubhouse area with a pool, an exercise room, and a hot tub—perfect for winding down after a day chock-full of adventure.
Southwestern desert getaway
Soak up gorgeous mountain and desert views from the comfort of a swanky refuge in North Scottsdale. Primed for easy entertaining, this luxurious abode sleeps 14 and features dining room seating for 16, a theater room, a custom-built bar, a fully equipped gourmet kitchen, an enclosed sunroom, and an in-house gym. The pool area’s amenities include a gas fire pit, a TV, a grill, and a fireplace if you decide to take the party outside. Minutes from world-class golf courses, excellent hiking trails, and this Arizona city’s countless shopping, restaurant, and nightlife enclaves, there are endless entertainment options should you venture outside your Southwestern retreat.
Orange County, CA
Relaxing Orange County townhouse
Chasing the sun and wishing upon a star this vacation? Relax at a comfortable Anaheim condo after a full day of making your crew’s Disneyland dreams come true. Literally across the street from the legendary theme park, this three-bedroom rental is a five-minute walk from its trams and monorail. It has room for 10 members of your group, ample shared living areas, a fully equipped kitchen, and a private patio for grilling. This newly renovated townhouse also boasts proximity to a gated community pool area from which to view Disneyland’s nightly fireworks.