Luxury Villas in Tuscany, Italy, with Private Pools Among Rolling Vineyards

Why Rent a Private Villa in Tuscany, Italy?

Renowned for its charming villages and rolling hills, Tuscany offers an exceptional setting for a relaxing getaway. Our collection of villas in Tuscany includes historic homes with private pools, elegant estates with breathtaking views, and exceptional villas that blend rustic charm with modern luxury. From private Tuscany villas surrounded by lush vineyards in the Chianti region to opulent properties in the Val d’Orcia, each one provides a serene retreat. These luxury villas in Tuscany offer expansive living spaces, impeccable service, and an authentic Italian atmosphere. Ideal for family vacations, romantic escapes, or group getaways, our villa rentals in Tuscany offer a perfect way to enjoy the region’s natural beauty and rich culture.

These are the 102 most popular villa rentals in Tuscany, Italy. Narrow your search above.

  • From $3,181 to $5,655 per night
  • Pool
  • AC

Feronia

20 Bedrooms
19 Bathrooms
  • From $12,699 to $19,049 per night
  • Pool
  • AC

Daniela

16 Bedrooms
15 Bathrooms
  • From $4,052 to $4,711 per night
  • Pool
  • AC
  • From $3,629 to $8,081 per night
  • Pool
  • AC

Veltuna

7 Bedrooms
6 Bathrooms
  • From $4,486 to $5,277 per night
  • Pool
  • AC

Orfea

12 Bedrooms
10 Bathrooms
  • From $3,595 to $5,179 per night
  • Pool
  • AC

Chiara

10 Bedrooms
9 Bathrooms
  • From $1,650 to $2,656 per night
  • Pool
  • AC
  • From $11,545 to $13,854 per night
  • Pool
  • AC

Villa Boheme

19 Bedrooms
18 Bathrooms
  • From $15,668 to $17,317 per night
  • Pool
  • AC
  • From $6,315 to $8,707 per night
  • Pool

Leila

8 Bedrooms
8 Bathrooms
  • From $3,534 to $6,597 per night
  • Pool
  • AC

Morea

6 Bedrooms
5 Bathrooms
  • From $1,557 to $2,474 per night
  • Pool
  • AC
  • From $25,399 to $25,399 per night
  • Pool
  • AC

Fleda

7 Bedrooms
7 Bathrooms
  • From $1,814 to $3,298 per night
  • Pool
  • From $2,144 to $2,803 per night
  • Near Beach
  • Pool
  • From $1,362 to $2,251 per night
  • Pool
  • AC

Donato

12 Bedrooms
11+ Bathrooms
  • From $7,389 to $10,229 per night
  • Pool
  • AC
  • From $3,629 to $4,618 per night
  • Pool

Anna

7 Bedrooms
7 Bathrooms
  • From $2,944 to $4,826 per night
  • Pool
  • AC

Danica

5 Bedrooms
5 Bathrooms
  • From $1,803 to $3,615 per night
  • Pool

Astra

8 Bedrooms
8 Bathrooms
  • From $3,059 to $4,387 per night
  • AC

Amarika

7 Bedrooms
7 Bathrooms
  • From $5,189 to $5,849 per night
  • Pool
  • AC

Augusta

6 Bedrooms
6 Bathrooms
  • From $3,941 to $4,107 per night
  • Pool
  • AC
  • From $2,309 to $3,925 per night
  • Pool
  • AC

Vinia

10 Bedrooms
10 Bathrooms
  • From $9,236 to $9,236 per night
  • Pool
  • AC
  • From $5,277 to $11,611 per night
  • Pool
  • AC
  • From $2,199 to $3,298 per night
  • Pool
  • AC
  • From $11,875 to $34,965 per night
  • Pool
  • AC

Colli

7 Bedrooms
7 Bathrooms
  • From $3,131 to $4,793 per night
  • Pool
  • AC

Jobaldo

7 Bedrooms
7 Bathrooms
  • From $1,814 to $3,298 per night
  • Pool
  • AC

About Tuscany, Italy

From rolling vine-laced hills cloaked in early morning mist, to the art-rich cities that birthed the Renaissance, Tuscany’s tranquil landscapes offer an unforgettable taste of quintessential Italy. Whether you come for a city-break or countryside escape, you’re sure to be seduced by the romantic romanesque heritage this enchanting region is famed for. Marvel at masterpieces in Florence, from Michelangelo to Botticelli and the gold-tipped peak of Brunelleschi’s Dome. Wander nearby Pisa’s pretty piazzas, or stop off in stunning Siena for a glass of Brunello di Montalcino made with the local Sangiovese grapes. To the southwest, you’ll find Tuscany’s little-known coast, Elba among seven island gems shining in the azure waters.

Stroll the charming streets of medieval Tuscan villages, red roofs and fortified walls clinging to the hilltops, from charismatic Cortona to the towering spires of San Gimignano. Survey your surrounds from your 14th-century hilltop estate, vine-striped hills and olive groves below, dotted with clusters of cypress trees. As the evening draws in, have your chef prepare a menu of regional specialities, handmade truffle pasta and locally sourced beef. Savour a glass of the ubiquitous Chianti from the vineyards below, bathed in the golden Tuscan light as the setting sun disappears behind the distant Apennine mountains.

What's Special About a Villa Holiday in Tuscany, Italy?

Rolling vineyards, sun-warmed stone villages, and endless cypress-lined roads create the unmistakable backdrop of Tuscany. Choosing a Tuscany vacation rental places you within this iconic landscape, offering not just space and privacy but the freedom to savour life at your own pace. More intimate than a hotel stay, a Tuscany holiday home invites you to slow down with leisurely breakfasts on the terrace, unhurried afternoons exploring historic towns, and home-cooked dinners shared together. For families and groups, a private villa in Tuscany offers a cost-effective, comfortable way to experience this timeless part of Italy with authenticity and ease.

Set across the region’s most scenic corners, our collection of Tuscany villas with private pools includes traditional farmhouses in the Val d’Orcia, hillside estates in Chianti, and stylish retreats near Florence and Siena. Many of these Tuscany holiday villas feature shaded pergolas, panoramic terraces, and gardens filled with olive trees and lavender. Family-friendly villas in Tuscany are thoughtfully designed with spacious interiors, multiple living areas, and outdoor spaces perfect for shared moments. From rustic-luxe Tuscany private villas to sophisticated properties with sweeping countryside views, each of our villas and vacation rentals captures the essence of Italian country life with understated elegance and true comfort.

Tuscany, Italy Villa Rental FAQ

Q: Why is Tuscany such a popular choice for villa holidays?
A: Tuscany blends rolling vineyards, Renaissance towns, and golden countryside into one postcard-perfect region, ideal for relaxing in a villa with views and vineyard breezes.
Q: Why do villa rentals in Tuscany offer a more immersive experience?
A: Unlike hotels, Tuscan villas often sit among olive groves or medieval hamlets, giving you privacy, space, and a real taste of Italian life, with time to enjoy long, alfresco meals.
Q: What’s the best time of year to book a villa in Tuscany?
A: Late spring to early autumn is ideal for weather and scenery, but the quieter months (April, October) offer better rates and fewer tourists while still being beautiful.
Q: How close are your villas to local attractions and towns?
A: Many of our villas are just a short drive from historic towns like Siena, Lucca, and San Gimignano, so you can explore the region’s art, food, and culture at your leisure.
Q: Is Tuscany a good destination for food and wine lovers?
A: Tuscany is a paradise for culinary travellers, with farm-to-table dining, truffle hunting, local markets, and world-renowned wines like Brunello and Chianti Classico.
Q: What part of Tuscany should I stay in for the best villa experience?
A: Depending on whether you prefer the cultural buzz of Florence, the hilltop charm of Chianti, or coastal vibes in Maremma, Tuscany offers villa options to match every pace and preference.
Q: Are your villas in Tuscany suitable for multi-generational families or groups?
A: Yes, many of our properties are spacious with multiple bedrooms, large gardens, and private pools, perfect for family reunions, milestone celebrations, or relaxed group getaways.
Q: Do your Tuscan villas come with special extras?
A: Yes - think wine cellars, pizza ovens, infinity pools, or even vineyard access. Some of our properties also include concierge services for wine tours, private chefs, and bike rentals.