Whether atop a craggy Capriote cliff or amid the vineyards of the Val d’Orcia, an Italian villa vacation is on the bucket list of just about every traveler. To find the best of these storied retreats, Robb Report asked the leading villa-rental agencies for the keys to their most exclusive estates. Here’s what we discovered.


Huw and Rossella Beaugié’s love affair with Sicily began in November 2000, when the newlywed couple—he a French engineer and she an Italian biologist—came to the Mediterranean island in search of an escape from the cold of their Parisian home. “We climbed to the top of Mount Etna and looked out over the sparkling water, with the brilliant sun shining down on our heads,” Huw recalls. “And in that moment, we decided we wanted to stay.

Thus was born Think Sicily, the couple’s London-based villa-rental agency. Today the company, which launched in 2002, operates under a different name: The Thinking Traveller manages 190 properties throughout Sicily, Puglia, and the Sporades and Ionian Islands of Greece. Sicily remains the Beaugiés’ biggest destination, with 100 residences scattered from Marsala in the west to Syracuse in the east. “We have many favorites,” Huw says. “But when it comes to a true home away from home—one with authentic Sicilian service and style—nothing beats Don Arcangelo all’Olmo.

Set on the island’s east coast, the 18th-century farmhouse has been reimagined as a magnificent 12-bedroom villa adorned with lava-stone floors, vaulted ceilings, and ceramic tiles from Caltagirone. On the estate grounds, guests can wander among olive tree–lined gardens and swim in a private pool; farther afield, experiences may include helicopter rides over the Aeolian Islands and picnics atop Mount Etna. (from about $17,760 per week)

Also in Sicily . . . 

Masseria Costanza ➤ LOCATION Within the Vendicari Nature Reserve, on Sicily’s southeast coast. SIZE Sleeps 14 in seven bedrooms, each with an en suite bathroom. AMENITIES A cinema room, a swimming pool, a full staff, and a courtyard. HIGHLIGHT An alfresco dinner on the terrace overlooking the reserve’s salt pans. (from about $9,485 per week)

Rocca delle Tre Contrade ➤ LOCATION Atop a verdant hill on Sicily’s east coast, near Santa Venerina. SIZE Sleeps 24 in 12 bedrooms, each with an en suite bathroom. AMENITIES Five living rooms, a wine cellar, an 82-foot infinity-edge swimming pool, a full staff, and expansive gardens filled with lemon trees. HIGHLIGHT Homemade olive oil from the estate’s traditional lava-stone oil press. (from about $12,740 per week)

Lave Combo

The whole point of villa travel is to have your own experience—not the same experience every other tourist is having,” says Mara Solomon, founder of the Italian villa-rental agency Homebase Abroad. To that end, Solomon devotes much of her business to creating exclusive itineraries. “Our aim is to provide something really exciting that will make our clients’ hearts sing,” she says. Indeed, since launching her agency in 1995, she has arranged such unforgettable experiences as a visit with a legendary Palio di Siena rider for an equestrian enthusiast and a private performance in a local church for a young organist.  

Solomon’s quest for the extraordinary extends to her portfolio of 52 villas throughout Italy, including a handful of truly over-the-top estates on Lake Como. “Lake Como is the most elegant destination in Italy, with arguably the nicest villas in Italy,” she says. Perhaps the region’s most spectacular is Villa Sola Cabiati, a 10-acre, six-bedroom baroque estate that Solomon calls Lake Como’s “most historically important villa.” Constructed in the 16th century for the dukes of Serbelloni, the restored property remains a living artifact adorned with Italian silks, marbles, frescoes, and antiques. As for the unforgettable experiences available to Sola Cabiati guests, Solomon’s team can arrange seaplane flights over the lake, kayaking adventures to “the last quiet place in Bellagio,” and more. ($54,100 per week)

Also on Lake Combo...

Villa La Cassinella ➤ LOCATION On the edge of Lake Como, near the historic town of Lenno. SIZE Sleeps as many as 17 guests in a six-bedroom villa plus a two-bedroom terrace house. AMENITIES Heated swimming pool, private boat landing, full staff, tennis court, home theater, and fitness center. HIGHLIGHT Breakfast on the dining loggia overlooking the lake. (from $125,100 per week)

Villa Maria Taglioni ➤ LOCATION On Lake Como, just opposite the famed Villa d’Este resort. SIZE Sleeps 14 guests in seven bedrooms, each with an en suite bathroom. AMENITIES Heated swimming pool, private garden, elevator, game room, full staff, and underground garage. HIGHLIGHT Cruising Lake Como in the villa’s private watercraft. ($63,200 per week)


Launched in 2011 by a former director at Abercrombie & Kent, Red Savannah represents properties throughout Europe, Africa, and the Caribbean, and in select locations in Asia. Still, the agency prides itself on its intimate size and personal touch. “We don’t have thousands of villas,” says Charlie Stephenson, the U.K.-based tour outfitter’s managing director of villas. “We have a small portfolio that is entirely handpicked.”

Of the company’s 18 villas in Umbria, Stephenson places the five-bedroom Palazzo—located within the 2,700-acre Castello di Reschio estate—at the top. Set on a secluded hill overlooking the Niccone Valley, the property features reclaimed terra-cotta tiles, hand-painted wallpapers, and a grand, cantilevered travertine staircase. Sleek furnishings bring a contemporary touch to the villa, which includes a wine cellar, a billiard room, an infinity-edge pool, and a fitness center.  

Like many of Red Savannah’s properties, Palazzo comes with the services of a full staff. The villa’s dedicated concierge can arrange everything from VIP access to Umbria’s famed jazz festival to a motorcycling journey through the surrounding hills. (from $27,800 per week)

Also in Umbria . . . 

Castello di Bagnara ➤ LOCATION Within the Tenuta di Bagnara estate and reserve, near the Tuscan border. SIZE Sleeps as many as 15 in seven bedrooms, each with an en suite bathroom. AMENITIES Billiard room, swimming pool, private gardens, chapel, full staff, and manicured gardens. HIGHLIGHT Mountain biking in the midst of medieval castles, ancient olive trees, lakes, and a farm on the 1,500-acre Bagnara estate. (from $9,465 per week)

Mandola Piccola ➤ LOCATION Set along a gently sloping hill, a 20-minute drive from the town of Todi. SIZE Sleeps eight in four bedrooms, each with an en suite bathroom and terrace. AMENITIES Swimming pool, private gardens, housekeeping service, and chef (upon request). HIGHLIGHT Bistecca Fiorentina, grilled by your personal chef in the villa’s outdoor fire pit. (from $7,015 per week) 


Joe Poulin created Luxury Retreats more than 15 years ago, when, he says, villa-rental companies were plagued by capricious standards and unfulfilled promises. “Renting a villa was a gamble because these companies couldn’t promise the kind of reliability and predictability that hotels could,” he explains. “It was my goal to bring that standard to villa rentals.”

Poulin launched his Montreal-based agency with just a handful of villas in Barbados in 1999. Since then, Luxury Retreats has built a portfolio of over 3,000 properties in more than 30 countries. Each villa has passed Poulin’s 150-point checklist and is serviced by a personal concierge. 

In Italy, Poulin’s concierges have indeed mastered the art of the extravagant. “We’ve arranged private dinners under the David in Florence. We’ve sent guests truffle hunting in Tuscany,” he says. “Whether it includes cooking lessons or an after-hours tour of the Vatican, every itinerary is built from scratch.”

For the ultimate home base in Puglia, Poulin suggests the four-bedroom Villa Baraquiel Relais, set among olive groves near the town of San Michele Salentino. Crafted in the Itria Valley’s centuries-old architectural style, the villa includes 11 trullo conical roofs, three of which are more than 150 years old. Inside, the design juxtaposes colorful and contemporary furnishings with ornate brick archways and barrel-vaulted ceilings. Outside, the smell of jasmine flows from the verdant gardens to the two terraces and swimming pool. (from $1,000 per night)

Also in Puglia . . .

Villa Magnifica ➤ LOCATION Within the Borgo Egnazia resort, roughly one mile from the port of Savelletri. SIZE Sleeps six in three bedrooms, each with an en suite bathroom. AMENITIES Swimming pool, home theater, courtyard, private gardens, and full staff (upon request). HIGHLIGHT Access to the restaurants and amenities of Puglia’s most exclusive resort. (from $1,180 per night)

Villa Pizzorusso ➤ LOCATION A restored 16th-century masseria in the countryside near the village of Mesagne. SIZE Sleeps 12 in six bedrooms, four with en suite bathrooms. AMENITIES Home theater, swimming pool, full staff and chef (upon request), and outdoor dining area. HIGHLIGHT History abounds, from the 18th-century frescoes in the main wing to the 17th-century stables turned kitchen. (from $800 per night)


According to Simon Ball, the eternal appeal of Tuscany is rooted in reality. “When you come to Tuscany, you are stepping into history alive,” says Ball, who founded the villa-rental agency Tuscany Now & More with his wife, Barbara, in 1990. “You are living in something that is not a copy. It is something real that has been there for centuries. It’s not a magic you can create; it either exists or it doesn’t.”

Ball, a British entrepreneur who grew up in a 300-year-old farmhouse in the Tuscan village of Reggello, represents 130 properties in the region. “We’re run on a very personal basis,” he says. “We know the culture, we speak the language—it is a real love affair.”

The 12-bedroom Villa Lungomonte captures Ball’s deep-seated appreciation for the region’s art, architecture, and culture. Set at the foot of the Pisano mountain range, the 15th-century country estate is adorned with vaulted ceilings and furnished with centuries-old antiques. Outside, the panoramas extend all the way to Pisa—including a postcard-perfect view of the city’s famous leaning tower. 

While in residence, guests can lounge by Lungomonte’s swimming pool and dine under the shade of an ancient ginkgo tree. Off-site, Ball’s team can arrange such experiences as private visits with local artists and tours in a vintage Fiat 500. (from about $10,625 per week)

Also in Tuscany...

Estate di Petroio ➤ LOCATION Set within a private wine-and-olive-oil estate in the hills above Rufina. SIZE Sleeps 30 in 16 bedrooms, with 15 bathrooms. AMENITIES Tennis court, two swimming pools, expansive gardens, billiard room, soccer field, outdoor pizza oven, and full staff (upon request). HIGHLIGHT Wandering among the estate’s 900 acres of woodlands, orchards, and farmland. (from about $10,620 per week)

Villa Caprolo ➤ LOCATION On a hillside near the Chianti town of Greve, just outside Florence. SIZE Sleeps 16 in eight bedrooms, each with an en suite bathroom. AMENITIES Infinity-edge saltwater swimming pool, chapel, alfresco dining for as many as 20, and on-site caretaker/cook (additional staff upon request). HIGHLIGHT A leisurely game of boccie on the villa’s cypress tree–lined lawn. 


‘When you are in Venice, you want to feel like a Venetian,” says Cédric Reversade of Unique Properties & Events. “You want to experience the city like a local, and to do that means to adopt a refined way of life.” 

Refinement is a given when traveling with Reversade, who founded his London-based firm with partner Paul-Maxime Koskas in 2003. The company’s collection of more than 120 staffed villas around the world—from Portofino and Capri in Italy to Punta Mita and Careyes in Mexico—is enhanced by the partners’ solid foundation of friends. “We have a very strong network,” Reversade says. “We can call Alain Ducasse if we need a chef. Our butlers come from the Élysée Palace.” 

For an authentic Venetian experience, Reversade recommends Palazzo L.A., a five-bedroom villa on the Grand Canal. “This is one of the most impressive Grand Canal palazzi in the entire city,” he says. “It once belonged to a noble family and still today includes the family’s valuable antiques and paintings. And yet, when you are looking at the canal, you really feel at home.”  

Beyond the palazzo, Reversade can arrange such experiences as an after-hours tour of St. Mark’s Basilica and a private visit to the Empress Sisi’s apartment in the royal palace. “And when you return home,” he says, “dinner on your terrace is fresh gnocchi with white truffles.” (from about $15,230 per week) 

Also in Venice . . .

Palazzo A ➤ LOCATION On the Grand Canal, just opposite the Santa Maria della Salute and a short walk from St. Mark’s Square. SIZE Sleeps six in three bedrooms, each with an en suite bathroom. AMENITIES Media room, full staff (butler and chef upon request), and study with Grand Canal–view balcony. HIGHLIGHT An extensive art and antiques collection with pieces from the 17th through 19th centuries. (from about $32,670 per week)

Palazzetto Guardi ➤ LOCATION Next door to the San Pietro di Castello, a 16th-century basilica designed by the Italian architect Andrea Palladio. SIZE Sleeps 16 in six bedrooms, each with an en suite bathroom, plus a loft. AMENITIES Three living areas, five dining areas, fitness room, swimming pool, full staff (upon request), and private deck. HIGHLIGHT Striking contemporary design within a historic site. (from about $15,240 per week)

Amalfi Coast


The Amalfi Coast is the epitome of Italian-ness,” says Steve Lassman, vice president of Villas of Distinction. “It has the winding roads, the romantic scenery, the crystal coast.” 

Until recently, however, the region’s villas were perhaps too Italian for international travelers. “Nobody spoke English,” Lassman explains. “There was no air-conditioning. Only in the last 10 years have the homes caught up with the times in terms of modern amenities and services.”  

Villas of Distinction’s portfolio—which comprises some 1,600 properties in 50 destinations around the world—includes several historic (and recently updated) estates along Italy’s fabled Amalfi Coast. In Positano, the 12-bedroom Villa Vicerè underwent a multimillion-dollar renovation that transformed a heap of cliffside ruins into a Mediterranean masterpiece decorated with sparkling chandeliers, original frescoes and antique sculptures, and baroque furnishings. Completed in 2013, the property also features an infinity-edge swimming pool, a traditional pizza oven, and an expansive terrace with 180-degree views of the coast.  

For guests staying at Villa Vicerè, Villas of Distinction’s local partner Bravo Holidays can arrange special experiences both on- and off-site, from cave snorkeling in Capri to an after-dinner fireworks display at home. (from about $3,275 per night)  

Also on the Amalfi Coast . . . 

Villa Dorata ➤ LOCATION Atop a cliff in Positano, a short walk from the sea. SIZE Sleeps nine in five bedrooms, each with an en suite bathroom. AMENITIES Wine cellar; two pizza ovens; spa with hammam, steam room, hot tub, and indoor swimming pool; private gardens; outdoor terraces; and full staff. HIGHLIGHT Baroque style—ornate chandeliers, frescoed ceilings, antique-tiled fountains—from top to bottom. (from about $2,180 per night)

Il Rubino ➤ LOCATION On a Capriote cliff top, a short drive from the Piazzetta. SIZE Sleeps 14 in six bedrooms, five with en suite bathrooms, plus a sitting room that may be used as a guest room. AMENITIES Heated swimming pool, hot tub, fitness center, hammam, and full staff. HIGHLIGHT Sunset on the sprawling rooftop terrace overlooking all of Capri and Monte Solaro. (from about $8,185 per night)

- Source: Robb Report            Photo: Robbreport.com