Tuscan Retreats: A Guide to the Most Luxurious Villas for Rent
Introduction
Tuscany remains the quintessential Italian dream destination, where rolling hills blanketed in vineyards and olive groves give way to medieval villages and Renaissance masterpieces. For the discerning traveler, the region offers an extraordinary collection of luxury properties—restored castles, converted monasteries, and historic estates that blend centuries of heritage with contemporary comfort. From the Chianti wine country to the UNESCO-protected Val d’Orcia, these ten exceptional hotels represent the finest accommodations Tuscany has to offer, each promising an authentic yet thoroughly luxurious Italian experience.
Top 10 Luxury Hotels in Tuscany
1. Castello di Casole, A Belmond Hotel
Price: €1,200-2,500/night
This magnificent 10th-century castle crowns a 4,200-acre estate in the province of Siena, offering 39 suites plus private villas and farmhouses scattered across the property. The meticulous restoration honors traditional Tuscan methods, incorporating reclaimed wood beams, ceramic tiles, and terracotta throughout. Guests enjoy an infinity pool with panoramic valley views, the Essere Spa, a private winery producing estate wines, and access to a championship golf course. The property’s two restaurants showcase authentic Tuscan cuisine paired with wines from the estate’s 25 acres of organic vineyards.
Best season: Mid-March through October (property closes for winter)
Insider tip: Request one of the newly designed Etruria Suites, featuring 1950s Italian contemporary design with De Chirico paintings and Gio Ponti-inspired carpets.
Book Now: Official Website | Hotels.com | Booking.com | Expedia
2. Rosewood Castiglion del Bosco
Price: €1,500-4,000/night
Owned by the Massimo Ferragamo family, this 900-year-old estate spans 5,000 acres in the heart of the Val d’Orcia UNESCO World Heritage Site. The property features 42 elegant suites and 11 exclusive private villas, many housed in restored 17th and 18th-century farmhouses with private heated pools. The Michelin-starred Ristorante Campo del Drago offers sophisticated Italian cuisine, while the estate’s winery ranks as the fifth-largest producer of Brunello di Montalcino. Guests enjoy Italy’s only private golf club, La Canonica cooking school, and a world-class spa.
Best season: April through October (closed January 6 to March 21)
Insider tip: Book a wine experience in September to participate in the annual harvest, learning to pick Sangiovese grapes alongside the winemakers.
Book Now: Official Website | Hotels.com | Booking.com | Expedia
Price: €600-1,400/night
A meticulously restored medieval hamlet in the heart of Chianti Classico, this Relais & Châteaux property was the first of its kind in the region. The 60 accommodations—30 rooms and 30 suites—are scattered throughout the village, preserving the authentic atmosphere while offering contemporary luxury. The Michelin-starred Il Poggio Rosso restaurant showcases Chef Stelios Sakalis’s Italian cuisine with Greek influences, while the more casual Osteria Il Grigio serves traditional Tuscan fare. The property operates as a certified Zero Waste Hotel using 100% renewable energy.
Best season: April through October (closed November to early April)
Insider tip: Reserve Villa Casanova, a 9-bedroom villa with private pool, perfect for multi-generational family gatherings with full access to all resort amenities.
Book Now: Official Website | Hotels.com | Booking.com | Expedia
Price: €800-2,000/night
Set within a 740-acre estate in the Chianti wine region, this 12th-century castle represents COMO Hotels’ first property in continental Europe. The 50 rooms and suites feature light, modern interiors by Milanese designer Paola Navone, juxtaposed against original 18th-century frescoes and terracotta floors. The Michelin-starred La Torre restaurant occupies the former stables, while the COMO Shambhala Retreat offers holistic wellness programs including complimentary yoga sessions. The property sits just 30 minutes from Florence and 40 minutes from Siena.
Best season: Year-round, with spring and autumn offering ideal weather for exploration
Insider tip: Book the olive grove dinner experience—a magical al fresco dining event among ancient olive trees with a specially curated menu.
Book Now: Official Website | Hotels.com | Booking.com | Expedia
Price: €1,800-4,500/night
This 13th-century estate near Chiusdino has been transformed into one of Tuscany’s most acclaimed boutique hotels, earning Three MICHELIN Keys for 2025. The 22 individually designed rooms and suites showcase baroque elegance with hand-painted wall art, silk tapestries, and antique furnishings. The 300-acre organic estate produces everything from vegetables and cheeses to the acclaimed Seed to Skin skincare line. The Michelin-starred Saporium restaurant and the charming Trattoria sull’Albero—literally built around a centuries-old oak tree—exemplify the farm-to-table philosophy.
Best season: Late April through October (closed November to late April)
Insider tip: Book the Pool House suite for ultimate privacy, complete with private pool and lavender-scented everything from towels to bedding.
Book Now: Official Website | Hotels.com | Booking.com | Expedia
Price: €900-2,200/night
Named after the Italian composer Claudio Monteverdi, this restored medieval village in Castiglioncello del Trinoro overlooks the pristine Val d’Orcia. American owner Michael L. Cioffi purchased the property in 2003 and hired designer Ilaria Miani to create 20 rooms and suites plus three private villas, all featuring intelligent design that honors local materials and traditions. The property includes a contemporary art gallery, performing arts venue, and spa with wellness programs. Located 90 minutes from Florence and 2 hours from Rome, it offers the perfect blend of seclusion and accessibility.
Best season: April through November for optimal weather and full services
Insider tip: Book during one of the seasonal music programs to experience world-class performances in the property’s 14th-century church.
Book Now: Official Website | Hotels.com | Booking.com | Expedia
Price: €500-1,200/night
This beautifully restored 11th-century monastery and medieval village sits in the Ombrone Valley, just 23 kilometers from Siena. A proud member of The Leading Hotels of the World, the property offers 74 rooms and suites plus the three-bedroom Villa Lavanda with private pool. The two restaurants operate under a partnership with Gordon Ramsay, including the Michelin-starred Contrada and the more casual La Cantina in the vaulted wine cellars. The expansive 1,000-square-meter spa specializes in wellness programs developed by Dr. Mosaraf Ali, including weight loss and detox retreats.
Best season: Year-round, with autumn offering truffle season experiences
Insider tip: Book a cooking course created by Gordon Ramsay and the resident chef for hands-on Tuscan culinary instruction.
Book Now: Official Website | Hotels.com | Booking.com | Expedia
8. Il Borro
Price: €700-3,500/night
Purchased by Ferruccio Ferragamo in 1993, this 2,700-acre estate between Florence and Arezzo encompasses an entire restored medieval village, now a Relais & Châteaux property. The 58 suites within the village plus three private villas and farmhouses offer authentic Tuscan style with contemporary comforts. The organic estate produces 14 different wines from 85 hectares of vineyards, extra virgin olive oil from 40 hectares of groves, and seasonal vegetables from dedicated gardens. Executive Chef Andrea Campani oversees dining at Osteria del Borro and the more casual Tuscan Bistro, both celebrating farm-to-table excellence.
Best season: May through September for full pool and outdoor activities
Insider tip: Visit the artisan workshops in the village where craftspeople still practice traditional techniques in jewelry, shoes, textiles, and ceramics.
Book Now: Official Website | Booking.com | Expedia
Price: €1,000-5,000/night
Ranked among the World’s 50 Best Hotels, this urban sanctuary comprises two Renaissance palazzos—the 15th-century Palazzo della Gherardesca built in 1473 and the 16th-century Palazzo del Nero—connected by Florence’s largest private garden spanning 11 acres. The 116 rooms and suites feature original frescoes, antique furnishings, and modern Four Seasons comforts. The Michelin-starred Il Palagio restaurant, the contemporary coastal Onde restaurant, and the atmospheric Atrium Bar offer exceptional dining, while an exclusive partnership provides private dinner access on Ponte Vecchio’s only open-air terrace—reserved solely for hotel guests.
Best season: Year-round city destination, with spring and fall offering pleasant weather
Insider tip: Request a suite in Palazzo della Gherardesca with original Baroque frescoes for the most historically immersive experience.
Book Now: Official Website | Hotels.com | Booking.com | Expedia
Price: €1,400-3,500/night
Perched in the Fiesole hills overlooking Florence, this 15th-century former monastery features a facade attributed to Michelangelo. The 46 rooms and suites, including the stunning three-bedroom Limonaia Villa, offer panoramic views of the Tuscan capital below. The Italian gardens, La Loggia restaurant, and infinity pool with city views create an atmosphere of refined tranquility just minutes from Florence’s historic center. A complimentary shuttle service connects guests to the city.
Best season: Reopening April 28, 2026 after comprehensive renovation
Insider tip: Book well in advance for the reopening season to secure the newly renovated accommodations at this legendary property.
Book Now: Official Website
Expert Travel Tips
For the optimal Tuscan experience, consider renting a car to explore the winding roads through wine country at your own pace. Most luxury properties offer complimentary parking and can arrange vintage car or Vespa rentals for memorable day trips through the countryside.
Book dining reservations well in advance, particularly for Michelin-starred restaurants during peak season. Many properties offer cooking classes and wine experiences that should be reserved prior to arrival to ensure availability.
The shoulder seasons of April-May and September-October offer the best combination of pleasant weather, fewer crowds, and full hotel services. Summer months bring intense heat and tourist crowds, while winter sees many countryside properties close entirely.
Consider combining a countryside estate stay with a night or two in Florence for the complete Tuscan experience. Properties like Four Seasons Firenze provide the perfect urban counterpoint to rural retreats.
Ask about AmEx Fine Hotels + Resorts or Virtuoso benefits when booking, as many of these properties offer complimentary upgrades, breakfast, and property credits through luxury travel advisor programs.
FAQs
Q: What is the best time of year to visit Tuscany’s luxury hotels?
A: The ideal months are April through June and September through October. Spring offers wildflowers and pleasant temperatures, while autumn brings harvest season, truffle hunting, and spectacular fall colors. Many countryside properties close from November through March, making advance planning essential.
Q: Do I need a car when staying at these properties?
A: For countryside estates like Rosewood Castiglion del Bosco, Borgo Santo Pietro, or Monteverdi, a rental car is highly recommended for exploring the region independently. Properties typically offer complimentary parking and can arrange transfers from airports and train stations. Four Seasons Firenze in Florence city center does not require a car.
Q: What should I budget for a luxury Tuscan holiday?
A: Expect to spend €600-2,500 per night for accommodations, with ultra-luxury suites and villas reaching €4,000-5,000+. Add €200-400 daily for dining, €100-300 for spa treatments, and budget for wine tours, cooking classes, and other experiences. A week-long luxury Tuscan experience typically ranges from €8,000-25,000 per couple depending on property choice and activities.
Conclusion
Tuscany’s finest hotels offer far more than mere accommodation—they provide immersive experiences in Italian heritage, gastronomy, and art of living. Whether you choose a restored medieval village like Il Borro, a wellness sanctuary like Borgo Santo Pietro, or the urban elegance of Four Seasons Firenze, each property represents the pinnacle of Italian hospitality. These are destinations where centuries of history meet contemporary luxury, where farm-to-table dining showcases the region’s legendary produce, and where every sunset over the rolling hills reminds you why Tuscany remains the eternal dream of luxury travelers worldwide.
