15 Best Airbnbs in Tuscany: Stunning Villas & Charming Countryside Cottages

Introduction

Tuscany is synonymous with rolling hills, cypress-lined drives, medieval villages, and unforgettable food and wine. Whether you’re dreaming of a luxury villa with panoramic vineyard views or a rustic cottage in a sleepy hill town, Tuscany’s Airbnbs offer some of the most picturesque stays in Italy.

With tourism in Italy rebounding post-pandemic, Airbnb reports show a 25% increase in bookings across rural Tuscany, especially among travelers seeking authentic, immersive experiences. And Tuscany delivers—with options ranging from historic farmhouses to restored villas with infinity pools.

This curated list highlights the 15 best Airbnbs in Tuscany, including luxury estates for group getaways and intimate homes ideal for couples. Whether you’re visiting Florence, Siena, Chianti, or the Val d’Orcia, you’ll find the perfect place to stay in style, comfort, and classic Tuscan charm.

Outline

1. Why Choose an Airbnb in Tuscany?

this …

• More authentic and private than hotels.
  
• Ideal for longer stays, remote work, or group travel.
  
• Access to kitchens, outdoor patios, private pools, and local hosts.
  

Table: Airbnb vs. Traditional Hotel in Tuscany

2. Best Luxury Villas for Group Stays

1. Villa Gamberaia (Near Florence)

• Historic 17th-century estate with formal gardens.
  
• Sleeps 12+, full staff available, private chapel.
  

2. Villa Le Rose (Chianti)

• Surrounded by vineyards, with infinity pool and wine cellar.
  
• Ideal for weddings or extended family vacations.
  

3. Romantic Cottages for Couples

3. La Casetta nel Bosco (Val d’Orcia)

• Stone cottage with fireplace, private garden, and mountain views.
  

4. Olive Grove Cottage (Lucca Countryside)

• Nestled in an olive grove, with private terrace and sunset views.
  

4. Family-Friendly Farmhouses

5. Agriturismo La Fonte (Arezzo)

• Organic farm with animals, cooking classes, and playground.
  

6. Casa di Nonna (Pienza)

• Cozy two-bedroom with nearby bike trails and panoramic views.
  

5. Unique & Historic Properties

7. Medieval Tower Home (San Gimignano)

• Stay in a restored 13th-century tower with town views.
  

8. The Old Millhouse (Cortona)

• Converted mill on a creek with exposed stone and wood beams.
  

Table: Unique Airbnb Stays in Tuscany

6. Budget-Friendly Airbnbs with Style

9. Studio in Montepulciano Old Town

• Steps from cafes and wine bars, under $100/night.
  

10. Chianti Vineyard Apartment

• Vineyard views, private entrance, ideal for wine lovers.
  

7. Airbnbs with Spectacular Views

11. Villa Belvedere (Volterra)

• Infinity pool overlooking rolling hills and cypress rows.
  

12. Rustic Viewhouse (Montalcino)

• Terrace facing vineyards with morning fog views.
  

8. Best Airbnbs Near Tuscany’s Top Attractions

13. Loft near Florence Duomo

• Modern, walkable, and perfect for first-time visitors.
  

14. Siena Historic Center Apartment

• Elegant decor, walk to Piazza del Campo and cathedral.
  

15. Coastal Retreat near Elba Ferry

• Great for day trips to beaches and the Tuscan Archipelago.
  

Detailed Content Expansion

2. Best Luxury Villas for Group Stays

Tuscany is known for elegant countryside estates, many of which are now available as full-property Airbnbs for travelers seeking luxury, privacy, and panoramic scenery.

Villa Gamberaia – Near Florence

This 17th-century villa just 20 minutes from Florence combines aristocratic grandeur with modern comfort. The meticulously landscaped gardens, once featured in Architectural Digest, are a highlight. With 7 bedrooms, a staff of caretakers, and optional private chefs, it’s ideal for destination weddings, reunions, or milestone celebrations.

Villa Le Rose – Chianti Region

Set in the heart of Tuscany’s famous wine country, this villa sleeps up to 14 and features a private infinity pool, wine cellar, and multiple lounge areas. The property offers guided wine tastings, cooking classes, and even truffle hunts in autumn. It’s a dream retreat for groups who want a luxurious, fully immersive Tuscan experience.

Table: Luxury Villa Comparison

Pro Tip: Book at least 6 months in advance for high season (May–September), as these villas are popular for weddings and group tours.

4. Family-Friendly Farmhouses

Traveling with kids or a multigenerational group? These family-friendly Tuscan farmhouses combine scenic settings with practical amenities.

Agriturismo La Fonte – Arezzo Area

A true working organic farm, La Fonte offers kid-friendly experiences like feeding animals, pizza-making classes, and horseback riding. The on-site hosts also produce olive oil and seasonal vegetables for guests. Accommodations include multiple apartment units, making it ideal for families traveling together.

Casa di Nonna – Near Pienza

This warm and welcoming two-bedroom cottage feels like staying with your Tuscan grandmother. Guests love the fireplace, homemade pastries on arrival, and proximity to bike trails and hill towns like Montepulciano and Pienza. There’s also a cozy patio with sweeping countryside views—perfect for evening wine and cheese.

Table: Family-Friendly Airbnb Features

Tip for Families: Check listings for cribs, high chairs, and washer/dryer access—especially helpful for longer stays.

Conclusion

From hilltop villas with infinity pools to quaint cottages nestled among olive groves, Tuscany’s Airbnbs offer some of the most memorable accommodations in Europe. With options for every traveler—from honeymooners and solo explorers to families and wedding parties—each stay comes with a side of Italian charm, cultural immersion, and timeless countryside views.

Whether you’re sipping Chianti from your private terrace or waking up to foggy vineyards, these handpicked Airbnbs put you at the heart of Tuscany’s magic.