Villa Anatraia | 4-Bedroom Villa with Private Pool in Cortona

Eight guests, four bedrooms, and a hilltop terrace that commands views across Tuscan valleys—Villa Anatraia in Cortona delivers the kind of countryside escape where you forget to check your phone. Positioned on a peaceful rise above the medieval town of Cortona, this converted farmhouse sits at the crossroads between serious relaxation and cultural immersion, just a short walk from one of Tuscany’s most storied villages.

Inside Villa Anatraia

Villa Anatraia sleeps 8 guests across 4 bedrooms and 0 bathrooms—though don’t let the bathroom count mislead you. Each bedroom comes with a dedicated en-suite, transforming the sleeping quarters into private spa-like retreats. The property unfolds across three distinct levels, each with its own rhythm and purpose.

The lower ground floor operates as the villa’s social hub. A generous living area anchors this level, furnished with deep sofas that face a television, while a functional desk sits ready for those who can’t fully disconnect. A ceramic water feature catches light throughout the day, and a pool table invites friendly competition on quieter evenings. Garden access from this floor means you can move seamlessly between indoor gathering and outdoor air.

The ground floor is where the kitchen commands attention—a statement space fitted with professional-grade appliances including a full-sized oven, hob, built-in fridge-freezer, dishwasher, and dual coffee machines that suggest the owners understand that mornings matter. An adjacent dining room seats all eight guests comfortably around a substantial table. Two of the four bedrooms occupy this floor, each featuring a double bed, mini-bar for evening drinks, and an en-suite bathroom equipped with either a jacuzzi bath paired with chromotherapy shower, or a traditional tub alongside a Turkish bath and chromotherapy shower—unexpected luxuries that transform the daily wash into a ritual. An outdoor terrace extends from this level, positioned for morning light and afternoon shade.

The first floor houses the remaining two bedrooms, both doubles with mini-bars and en-suite bathrooms featuring jacuzzi baths and showers. Throughout the villa, air-conditioning cools the bedrooms during Tuscany’s warm months, while central heating sustains comfort from November through March. High-speed Wi-Fi, television in multiple rooms, and a stereo system keep the villa connected to the wider world without dominating it.

Outdoor Spaces and Living

The garden surrounding Villa Anatraia unfolds in generous terraces, each carved into the hillside to offer different vantage points. Sun loungers scatter across the upper tiers, while a dedicated covered dining space sits ready for meals under stars. Built-in stone seating creates informal gathering spots that feel less like furniture and more like architectural features shaped by time. The focal point—a fenced infinity pool with Roman-style steps—operates seasonally from April through October, its waters heated for comfort and ringed with lounging areas that face south toward the valley.

A barbecue sits ready for evening grilling, and the gardens themselves frame the experience: ancient olive trees provide dappled shade, wooded areas begin where the formal garden ends, and the sight lines stretch uninterrupted across farmland toward distant hills. Parking accommodates multiple vehicles at the property entrance, and the entire grounds benefit from secure fencing—a practical consideration that also defines the boundaries of your private Tuscan world.

Location: Cortona and the Surrounding Area

Cortona sits directly above Villa Anatraia—literally a stroll away, not a drive. This Etruscan settlement, now perched 500 metres above sea level on a hilltop, retains its walled medieval character, complete with original town gates, cobbled streets that follow patterns centuries old, and landmarks like the Palazzo Casali (dating to the 8th century and now housing a local history museum) and the Fortress del Girifalco, constructed by Cosimo I de Medici. The Diocesano museum within the town walls showcases significant Renaissance art, making Cortona genuinely one of Tuscany’s more culturally dense small towns.

Beyond Cortona’s immediate appeal lies a broader constellation of attractions. Lake Trasimeno—Umbria’s largest lake and Tuscany’s gateway to water activities—sits 21 kilometres away. Its sandy beaches invite swimming in calm waters, and local operators offer kayak rentals and paddleboard hire for those seeking quiet morning explorations. Castiglione del Lago, 20km distant, crowns a promontory overlooking the same lake and draws visitors to Castello del Leone, a 13th-century fortress built under Emperor Frederick Barbarossa. The castle grounds incorporate an ancient chapel and open-air theatre, while the town below offers lakeside restaurants and cafes with water views.

For cyclists, the 50-kilometre drive to Antognolla Golf estate opens access to dedicated bike trails, nature routes through wooded terrain, and an 18-hole championship course for those who golf. More substantial towns anchor the wider region: Siena (approximately 50km) offers its famous Palio horse race in July and August, Renaissance art collections, and the dramatic shell-shaped Piazza del Campo. Perugia (45km) serves as Umbria’s cultural capital. Arezzo (30km from Villa Anatraia) features the Basilica of San Francesco with Piero della Francesca frescoes and a thriving Saturday antique market. Assisi (50km) draws pilgrims to the Basilica of San Francesco and rewards wanderers with hilltop medieval streets.

Explore our luxury villas in Cortona and our full collection of luxury villas across Italy. For deeper destination planning, consult our Tuscany travel guide, which covers seasonal highlights, wine regions, and lesser-known villages worth the detour.

The best months to visit are May, June, and September—warm enough for the pool and comfortable outdoor dining, but before the July-August crowds that descend on popular Tuscan towns. Spring brings wildflowers across the countryside and temperatures ideal for hiking the wooded trails that surround the villa. October lingers warm through most of the month, though the pool closes at the end of the season. Winter (December-February) transforms the landscape into something starker but deeply peaceful, with occasional snow dusting the higher elevations and fewer tourists navigating Cortona’s ancient streets.

Who This Villa Suits Best

Multi-generational families gravitate toward Villa Anatraia because the four separate bedrooms allow grandparents, adult children, and grandchildren to maintain privacy while sharing communal spaces. The fenced grounds and pool area provide safe environments for young children, while the proximity to Cortona—a manageable walk rather than a car journey—keeps exploration accessible. High chairs are available, and the layout accommodates the rhythms of families with toddlers: quiet mornings in the lower ground floor living space, midday pool time, evening meals at the large dining table.

Groups of friends renting for milestone celebrations—50th birthdays, anniversaries, reunions—find the pool table and social ground floor ideal for evening entertainment, while the bedrooms ensure nobody is forced into uncomfortable sleeping arrangements. The kitchen scale supports group cooking projects, and many guests arrange cooking classes through the villa’s network (available on request), turning dinner into collaborative experience rather than solo effort.

Couples seeking a Tuscan base for exploring the region will appreciate the excellent road access to Siena, Perugia, and Assisi, though they may find the villa’s four bedrooms underutilised. Business groups conducting working retreats benefit from Wi-Fi throughout, the ground floor desk setup, and the peaceful environment that encourages focus between sessions.

Pet owners should inquire directly about availability, as Villa Anatraia accommodates animals on a request basis rather than as a standard offering.

Practical Information

Villa Anatraia accommodates 8 guests in 4 bedrooms with shared bathroom facilities distributed throughout the property. The villa sits at approximately 400 metres elevation on its hillside setting.

The nearest significant airport is Perugia San Francesco d’Assisi (Sant’Egidio), located 75 kilometres away with approximately 90 minutes’ driving time to the villa. Florence Amerigo Vespucci International Airport, 150 kilometres distant, offers more flight options and approximately 2 hours’ transfer time via the A1 motorway. Both airports connect to car rental services; driving your own vehicle provides maximum flexibility for exploring Tuscany’s villages and countryside.

Cortona town centre—a 5-minute walk uphill—contains a supermarket, butcher shops, bakeries, and market stalls selling seasonal produce. Larger supermarkets operate in nearby Camucia (3km by car). The villa’s kitchen facilities support both self-catering and the option to hire local cooks for specific meals.

The rental includes utilities (water, electricity, gas heating and air-conditioning), Wi-Fi connectivity throughout the property, bed linen and towels, pool heating during the April-October season, and an initial supply of basic kitchen staples. Cleaning services are typically arranged either mid-stay or on departure. Check-in and check-out times should be confirmed directly with Excellence Luxury Villas, as flexibility exists depending on seasonal demand.

Frequently Asked Questions about Villa Anatraia

How many guests does Villa Anatraia sleep?

Villa Anatraia accommodates 8 guests across 4 bedrooms. Each bedroom contains a double bed, and all beds are configured for couples or those requiring their own sleeping space. There are no sofa beds or rollaway options listed, so sleeping arrangements are fixed at eight guests maximum.

What is the nearest airport to Villa Anatraia in Cortona?

Perugia San Francesco d’Assisi Airport (Sant’Egidio) is the nearest, positioned 75 kilometres away with approximately 90 minutes’ driving time. Florence Amerigo Vespucci International Airport, 150 kilometres from the villa, offers a broader range of flight connections and requires approximately 2 hours by car via the A1 motorway. Both support car rental for independent exploration of the region.

What is the best time of year to rent Villa Anatraia?

May, June, and September offer ideal conditions—warm daytime temperatures (20-28°C), reduced summer crowds in Cortona and nearby towns, and reliable pool weather without the intense August heat. Spring months (March-April) bring wildflowers and comfortable hiking conditions, though the pool remains closed until April 1st. October extends warm weather through most of the month but sees the pool close at month’s end. December through February offers solitude and dramatic winter light across the Tuscan landscape, though heating becomes necessary and some local businesses reduce hours. July and August are warmest but busiest, with higher accommodation prices and significant tourist presence in Cortona’s streets.

Is Villa Anatraia suitable for families with children?

Yes. The fenced infinity pool provides secure water access from April through October. The ground and first floor bedrooms allow parents to settle children near their own sleeping quarters. High chairs are available (an explicit provision for families with infants), and the lower ground floor living space provides entertainment during rest periods. Cortona’s town centre is a manageable walk uphill, introducing children to Italian village life without requiring constant driving. Lake Trasimeno, 21 kilometres away, offers family-oriented beaches, shallow water areas suitable for young swimmers, and water sports operations that cater to families. The villa’s kitchen scale and dining table accommodate family meal routines effectively.

What is included in the rental price at Villa Anatraia?

The rental includes furnished accommodation, utilities (electricity, water, gas for central heating and air-conditioning), Wi-Fi connectivity, bed linen, towels, pool heating during the April-October season, and basic kitchen provisions. Television service and stereo systems are available. Some rentals incorporate mid-stay or final cleaning; confirm specific arrangements with Excellence Luxury Villas when booking. Cooking classes are available on request and arranged separately from the base rental.

What restaurants and shops are near Villa Anatraia?

Cortona town centre—a short uphill walk—contains traditional Italian butchers (macellerie), bakeries (panetterie), and general supermarkets, plus market vendors selling seasonal fruit, vegetables, and local cheeses. For dining, Cortona’s streets hold trattorias ranging from casual neighbourhood places to more formal establishments offering regional specialities like bistecca alla fiorentina and homemade pasta. The town’s medieval setting means restaurants often feature valley views and outdoor seating. Camucia, 3 kilometres away by car, has larger supermarkets including chains like Conad and Carrefour. Lake Trasimeno’s towns—particularly Castiglione del Lago, 20 kilometres distant—offer waterfront restaurants specialising in freshwater fish (pike, perch, eel) and regional Umbrian cuisine. For wine purchases, the surrounding countryside contains numerous working wineries offering tastings and direct sales of Vino Nobile di Montepulciano and other Tuscan labels.