Abercrombie & Kent
While the 45-year-old tour operator is best known for its upscale guided safaris through the African savanna, Abercrombie & Kent also rents a variety of luxe houses in Europe. Guests choose between "concierge" villas, which come with on-location hosts (and rooms prestocked with toiletries), and more affordable, staff-free "sanctuary" properties.
Caveats: Location options are limited to France, Italy, and Spain, and they don't come cheap.
Details: From $10,000 to $67,200 a week.
Family favorite: The Villa Rosa: two newly restored Tuscan farmhouses with eight bedrooms between them, as well as a pool, a barbecue, and nearby plum and fig orchards.
Baby-Friendly Boltholes
Each of these properties in the U.K., France, Italy, and Spain is chosen by the company's owner, a London-based mother. Ideal for new parents who don't want to haul the whole nursery on vacation, the houses come with far more than the standard baby amenities—monitors, cribs, and high chairs, as well as toys and kids' DVDs and books.
Caveats: These are mostly country retreats geared toward young kids; children ages 10 and up may need more diversions.
Details: From $400 a weekend to $16,000 a week.
Family favorite: Gitcombe House Country Cottages, six units of varying sizes (from two to four bedrooms) set in the English countryside. Amenities cater to guests of all ages—there's a wooden jungle gym and a playroom for kids, and a sauna, a tennis court, and a steam room for parents.
Ciao Bambino!
Run by Bay Area mom Amie O'Shaughnessy, who has personally tested many of the properties with her 4-year-old son, Ciao Bambino! directs travelers to stylish, family-oriented accommodations in the U.K., France, Italy, and Spain. Its website offers advice that demystifies travel to Europe with a child and classifies rental options by age appropriateness.
Caveats: While all the properties are vetted, the site only connects you with the villa owners; you do all the follow-up.
Details: From $200 a night to $20,000 a week.
Family favorite: Limonaia, a converted lemon conservatory outside Siena that fulfills every Tuscan fantasy, with six bedrooms, big open patios overlooking the valley, and acres of lawns for games of tag.
HomesAway
Toronto-based HomesAway is choosy about the places it represents, with 70 villas throughout Europe. At each, guests are connected with a local expert who can arrange spectacular group activities (from a hot-air-balloon ride to a chocolate-making lesson at a centuries-old Provençal shop) or simply direct them to the best playground.
Caveats: There are extensive options in France, but the selection in the rest of Europe is more limited.
Details: From $5,000 to $36,000 a week.
Family favorite: The Mas des Ruches, a six-bedroom villa near St. Rémy tucked into 20 acres of olive groves. It has two kitchens—great for multiple families—and is near a goat farm (for fresh cheese and petting time).
Luxury Retreats International
This Canadian company has more than 1,300 beautiful villas all over the world, even in areas where quality and style can be hard to come by. It has Europe and the States covered (with homes everywhere from Greece to Paradise Valley, Arizona) and provides access to a fleet of 250 yachts for sea trips.
Caveats: The vast selection can be overwhelming.
Details: From $200 to $45,000 a night.
Family favorite: Windmill Heights, a six-bedroom house off Nantucket's Main Street that evokes the Kennedy compound—kids riding their bikes back and forth to the beach, and everyone sipping lemonade on the sweeping porch.
One Key
Clients can buy packages of either 15 or 25 nights per year to stay at villas worldwide. Unlike residence clubs and time-shares, the company doesn't tie guests to a specific portfolio of places. Instead, it works with local real-estate agencies to find exactly what you're looking for—whether it's an antebellum house in North Carolina or a jungle bungalow in Costa Rica—and arranges for an on-the-ground coordinator.
Caveats: This flexibility is pricey, so it makes the most sense for large families that can split the cost.
Details: From $34,900 for 15 nights to $49,900 for 25 nights.
Family favorite: St. Jean's Beach Home in St. Barths, which has an open-deck pool, an eat-in kitchen, and five bedrooms (one with a bunk bed) off the main living space.
The Right Vacation Rental
Each of these European properties is hand-selected by Untours, a company that puts together travel packages that don't feel touristy; profits go to the Untours Foundation, which provides low-interest loans to small businesses. Villas as well as harder-to-find large city apartments are available.
Caveats: The site only connects you to the rental host—you're on your own from there.
Details: From $900 to $7,000 a week.
Family favorite: The flat in Barcelona, which is housed in an 1847 mansion. It has a big bedroom, plus four sleeper sofas for the kids, and is a few minutes' walk from Las Ramblas.
Villazzo
These rentals offer a full staff (chef, concierge, etc.) in a private home. Most are in Europe, with a few in Miami and Aspen; all come with swanky amenities (flat-screen TVs, ample wine collections) and whatever snacks, diapers, and gear you request.
Caveats: While they are private, the houses are mostly located near bustling tourist hot spots.
Details: From $2,000 to $5,000 a day.
Family favorite: La Niche, a modern five-bedroom house 10 minutes from Aspen's slopes with a barbecue and a patio (views sweep out to the peaks), as well as a Jacuzzi to ease muscles sore from skiing or snowman-building.
WIMCO
This firm focuses on select rentals in the Caribbean and Europe. Its site lets you search by dates and location, as well as pool availability and child-friendliness (there's also a list of family reunion-appropriate spots).
Caveats: The website doesn't offer many pictures, so it's best to call for specifics.
Details: From $800 to $100,000 a week.
Family favorite: The Cool Runnings villa on the quiet island of Virgin Gorda, where you'll find three cathedral-ceilinged bedrooms, lots of deck space, a pool, and paths leading down to the sea turtles of Mahoe Bay.
