Tuscany
A luxury villa rental or renovated farmhouse in Tuscany, Italy brings to fruition dreams of Italian country living - its food, its wine, and its glorious vistas. Spend a week in a vacation rental in the Chianti, the hills around San Gimignano, Siena, hill towns of Castellina, Radda or Arezzo and immerse yourself in la dolce vita.
| Property | Area | Sleeps | Price | |
|---|---|---|---|---|
 |
Cassia Estate - Sangiovese Looking for the perfect Tuscany vacation rental that won’t require a second mortgage? This may be it. Between Florence and Siena you’ll find this family-run working estate, spanning Chianti hillsides covering 70 acres, and providing the kind of authentic, typically rustic and rural travel experience appreciated by the true adventure seeker. |
Staggia | 2 | $1,050 |
 |
Terra Cotta 4 Terra Cotta is an ancient complex in Tuscany once belonging to a noble Italian family. A manor house and 15 apartments have been restored into beautiful Tuscany vacation rentals and furnished with modern conveniences including air conditioning. |
San Gimignano | 2 | $1,975 |
 |
Cassia Estate - Ciliegiolo Looking for the perfect Tuscany vacation rental that won’t require a second mortgage? This may be it. Between Florence and Siena you’ll find this family-run working estate, spanning Chianti hillsides covering 70 acres, and providing the kind of authentic, typically rustic and rural travel experience appreciated by the true adventure seeker. |
Staggia | 2 | $1,050 |
 |
Terra Cotta 1 Terra Cotta is an ancient complex in Tuscany once belonging to a noble Italian family. A manor house and 15 apartments have been restored into beautiful Tuscany vacation rentals and furnished with modern conveniences including air conditioning. |
San Gimignano | 2 | $1,766 |
 |
Terra Cotta 9 Terra Cotta is an ancient complex in Tuscany once belonging to a noble Italian family. A manor house and 15 apartments have been restored into beautiful Tuscany vacation rentals and furnished with modern conveniences including air conditioning. |
San Gimignano | 4 | $2,827 |
 |
Medieval Tuscany F3 Enjoy stunning views of the Tuscan countryside and Monteriggioni from this historic estate in the region’s most sought after locations near Siena. |
Monteriggioni | 4 | $2,719 |
 |
Borgo Cavalli Typical Tuscany farmhouse apartment in the Chianti, great for families; pool, tennis, horseback riding. |
Cavriglia | 4 | $1,025 |
 |
Cassia Estate - Trebbiano Looking for the perfect Tuscany vacation rental that won’t require a second mortgage? This may be it. Between Florence and Siena you’ll find this family-run working estate, spanning Chianti hillsides covering 70 acres, and providing the kind of authentic, typically rustic and rural travel experience appreciated by the true adventure seeker. |
Staggia | 4 | $1,181 |
 |
Cypress In the heart of the Chianti not far from Florence, on a hillside covered with vineyards and olive groves, are two farmhouses which make up this classic Tuscan estate. |
Tavarnelle Val di Pesa | 4 | $1,755 |
 |
Terrazzo This modern apartment rental just outside the walls of Lucca, Tuscany was recently restored to a high standard. The owner refurbished and refurnished the place to create a comfortable and efficient space for guests. |
Lucca | 4 | $1,603 |
 |
Terra Cotta 6 Terra Cotta is an ancient complex in Tuscany once belonging to a noble Italian family. A manor house and 15 apartments have been restored into beautiful Tuscany vacation rentals and furnished with modern conveniences including air conditioning. |
San Gimignano | 4 | $2,409 |
 |
Certosa Delightful cottage adjoining an historic villa just south of Florence, boasting splendid views of the countryside and the medieval city. |
Galluzzo | 4 | $2,008 |
 |
Cassia Estate - Malvasia Looking for the perfect Tuscany vacation rental that won’t require a second mortgage? This may be it. Between Florence and Siena you’ll find this family-run working estate, spanning Chianti hillsides covering 70 acres, and providing the kind of authentic, typically rustic and rural travel experience appreciated by the true adventure seeker. |
Staggia | 4 | $1,181 |
 |
Giglio Cozy restored barn with lovely garden and pool, great for a couple or small family near Colle Val d’Elsa, Tuscany. |
Pievescola | 4 | $3,265 |
 |
Cassia Estate - Merlot Looking for the perfect Tuscany vacation rental that won’t require a second mortgage? This may be it. Between Florence and Siena you’ll find this family-run working estate, spanning Chianti hillsides covering 70 acres, and providing the kind of authentic, typically rustic and rural travel experience appreciated by the true adventure seeker. |
Staggia | 5 | $1,838 |
 |
Casa Tra Vigne Typical stone-built hayloft for rent in Tuscany, which has been recently renovated and is pleasantly furnished, located inside a pretty property situated amidst the hills in a panoramic position overlooking the hills of the Chianti Classico, near Cerbaia and San Casciano. |
Cerbaia | 5 | $1,832 |
 |
Casa della Campanella A place to call home – Rent this charming stone Farmhouse in Tuscany outside Lucca, enjoy stunning views and a carefree holiday; space for kids to run and within walking distance of a small village. |
Lucca | 6 | $3,845 |
 |
Palio Centrally located on the second floor of an historic building close to the Piazza del Campo where the famous horse race is held, the Palio. |
Siena | 6 | $2,900 |
 |
Casa Trecento Ancient stone house in the center of Cortona dating back to the year 1300 AD. |
Cortona | 6 | $1,669 |
 |
Terra Cotta 15 Terra Cotta is an ancient complex in Tuscany once belonging to a noble Italian family. A manor house and 15 apartments have been restored into beautiful Tuscany vacation rentals and furnished with modern conveniences including air conditioning. |
San Gimignano | 6 | $4,444 |
 |
Granaino This is an authentic apartment rental in a farmhouse in Tuscany fifteen minutes from Florence. |
San Casciano | 6 | $2,492 |
 |
Terra Cotta 12 Terra Cotta is an ancient complex in Tuscany once belonging to a noble Italian family. A manor house and 15 apartments have been restored into beautiful Tuscany vacation rentals and furnished with modern conveniences including air conditioning. |
San Gimignano | 6 | $3,949 |
 |
Anfiteatro This is a high quality, nicely furnished apartment rental in Lucca facing the Amphitheater in the historic center of this charming walled town in Tuscany. |
Lucca | 6 | $3,206 |
 |
Cassia Estate - Cabernet Looking for the perfect Tuscany vacation rental that won’t require a second mortgage? This may be it. Between Florence and Siena you’ll find this family-run working estate, spanning Chianti hillsides covering 70 acres, and providing the kind of authentic, typically rustic and rural travel experience appreciated by the true adventure seeker. |
Staggia | 7 | $2,625 |
 |
Brunello Beautifully restored villa rental in southern Tuscany situated about 500 meters from the historical center of Montalcino. |
Montalcino | 7 | $4,510 |
 |
Casa Belfiore Unique apartment rental in Cortona; history comes to life in a Medieval stone house in the town center. |
Cortona | 8 | $4,015 |
 |
Gallina Looking for peace and quiet? A room with a view over the Tuscan hills? Look no farther. This classic stone farmhouse is set amidst the tranquil landscape of the Chianti Classico – olive groves and vineyards as far as the eye can see. |
Panzano-in-Chianti | 8 | $4,638 |
 |
Villa Lucia Enjoy stunning views of the Tuscan countryside and Monteriggioni from this historic estate in the region’s most sought after locations near Siena. |
Monteriggioni | 8 | $9,744 |
 |
Casa di Pietra Casa di Pietra is a large, welcoming and restored farmhouse, now a luxury villa rental, set on a hillside between Florence and Siena. |
Poggibonsi | 8 | $8,282 |
 |
Fiamma Originally an olive press and surrounded on one side by beautiful terraced olive groves, this recently restored luxury villa rental in Tuscany has been converted into a comfortable vacation home. |
Vorno | 8 | $12,375 |
 |
Casina Collina This is a charming and typical stone farmhouse rental in Tuscany, well-furnished and equipped with lovely views of the Italian countryside. The house lies in the Chianti hills about 2 miles from the town of San Casciano, where you will find all kinds of shops and restaurants. |
San Casciano | 9 | $5,368 |
 |
Nido Nearby the medieval fortified town of San Casciano lies this charming and characteristic Italian farmhouse in the Chianti for rent once part of the Medici family estates during the 15th century. |
San Casciano | 10 | $8,676 |
 |
Villa Le Rose This is a classic villa from the end of the 1800s, situated just a short distance (about 100 meters) from the main piazza of Impruneta, an important center for the production of the famous 'Tuscan terracotta'. |
Impruneta | 10 | $4,595 |
 |
Val d'Orcia - Gypsy This is an imaginatively designed luxury villa rental in Tuscany set in one of the most magnificent landscapes in Italy, the Val d’Orcia. |
Near Pienza | 10 | $10,560 |
 |
Villa Tiramisu Beautiful Tuscany villa rental dating back to the 18th century which has been recently restored situated only 4 miles from the center of Florence. |
La Lastra | 10 | $5,950 |
 |
Villa Villaggio In the heart of the Chianti not far from Florence, on a hillside covered with vineyards and olive groves, are two farmhouses which make up this classic Tuscan estate. |
Tavarnelle Val di Pesa | 11 | $4,033 |
 |
Villa Cigno Nestled in a small, lush hamlet near the village of Vorno, Italy, this luxury villa rental's idyllic surroundings make for an elegant Tuscany vacation. Dine al fresco, sun bathe by the pool, or simply watch the resident swan in your own little lake when you make this Tuscany villa rental your vacation home. |
Vorno | 12 | $20,250 |
 |
Villa Caprifoglio Villa Caprifoglio is a recently renovated Tuscan villa rental, originally a noble mansion with the charm and uniqueness of an historic palace. This gracious villa is built on a hillside near the town of Staggia, a short drive from Siena and within easy reach of the Chianti hill towns, Florence and Pisa. |
Staggia | 12 | $10,500 |
 |
Girasole Girasole is an elegant six-bedroom luxury rental property on the Villa Floreale estate. Dine "al fresco" in the garden surrounded by the scent of lemon trees; enjoy peaceful views of charming farmhouses and Tuscan olive groves. |
Vorno | 12 | $21,446 |
 |
Villa Anima Bella Delight in a superbly renovated villa steeped in history, on a Tuscan hill with magical views. Come, sit down and relax, the staff is waiting to please. |
Terranuova Bracciolini | 12 | $7,980 |
 |
Villa Chiaro di Luna Savor the best Tuscany has to offer in a luxury villa rental near Lucca with a private Roman-style pool and 6 en-suite bedrooms. |
Vorno | 12 | $21,500 |
 |
Rosa Rosa is a pretty terra-cotta washed luxury rental property in Lucca, Tuscany on the Villa Floreale estate with its own pool and private garden. |
Vorno | 12 | $11,832 |
 |
Villa La Pergola Experience an elegant holiday rental in Tuscany made-to-measure, to be combined with the culture, gastronomy and the recreational activities that the splendid Lucca area offers. |
Lucca | 12 | $16,180 |
 |
Villa di Castello Elegant aristocratic villa rental in the Chianti not far from Florence; ideal for 5-6 couples. |
Castelfiorentino | 12 | $17,905 |
 |
Villa Tesoro Villa Tesoro is a luxury Tuscany villa rental in the heart of the Chianti countryside. This villa is a splendid mix of ancient architecture and modern comfort. The estate owes its quality to a 14th century tower dominating the construction, with parts of the home dating back to the 11th century, carefully restored to welcome up to 14 guests. |
Impruneta | 14 | $11,310 |
 |
Villa Antica Luxury villa rental in Tuscany in an evocative setting with Montepulciano in the distance, this ancient property will delight the senses. |
Montepulciano | 15 | $11,400 |
 |
Villa Floreale The expansive gardens of this luxury villa rental in Tuscany will delight you with its extensive grapevine pergola, ancient grottos, fountains and swimming pool. |
Vorno | 18 | $40,673 |
 |
Villa Arezzo Villa Arezzo is a spacious, traditionally furnished Tuscany villa rental well suited to groups of couples; the location makes for easy day trips to the hill towns of both southern Tuscany and Umbria. It is possible to rent the villa for a maximum of 12 persons, please inquire for reduced price. |
Arezzo | 18 | $8,475 |
 |
Villa Nocino Villa Nocino is an ancient manor house available for weekly rent set inside a 1,000-year old medieval hamlet just outside Tavernelle, in the heart of the Chianti region in Tuscany. |
Tavarnelle Val di Pesa | 18 | $11,250 |
 |
Bellaria Villa rental in the Chianti with superb location for visiting the hill towns yet keeping Florence at arm’s length. Tour the less-traveled Casentino, source of the Arno river where you’ll find enchanting villages and monasteries scattered over forested mountains and plains. |
Bucine | 18 | $12,667 |
 |
Val d'Orcia - Pleasures This is a stunningly decorated luxury villa rental set in one of the most magnificent landscapes in Italy, the Val d’Orcia. |
Near Pienza | 19 | $20,400 |
 |
Villa San Donato Ancient large Tuscany villa rental whose origins date back to 14th century, completely restored with care and taste, set inside an enclosed park with age-old trees. It is possible to rent the villa for a maximum of 14 people (please inquire for lower price). |
San Donato in Collina | 20 | $8,011 |
 |
Casa Quindici Casa Quindici, part of an outstanding 16th century estate near Lucca, is a gorgeous example of Tuscan country-style architecture and furnishing. |
Vorno | 22 | $33,750 |
 |
Villa Cacciatore For those whose refined tastes crave the best Tuscany has to offer in luxury villa rentals, Villa Cacciatore has it all. Once the hunting lodge of a Lucchese Count, the villa features the elegance of Italy's aristocratic golden age -and every modern convenience and indulgence. This Tuscany luxury villa is perfect for gatherings, celebrations, or a tranquil family retreat, promising to delight its guests with the best Tuscany has to offer. |
Vorno | 24 | $45,000 |