Holiday Rental Listings

At TuscanyHolidayVilla.com we have 2 types of listings:
1. Owner Direct: your inquiries are directed to the property owner and you arrange your booking directly.
2. THV Managed: the property owner has employed THV to manage inquiries and bookings for them.


Want help planning?

Please complete our simple inquiry form, identifying the size of your group, your holiday dates and any other requirements. I will email you a list of available properties that meet your requirements.

Holiday Rental Accommodations

For large groups (17 properties)

TuscanyHolidayVilla.com Elisabetta's Farmhouse (#74)
Sleeps 2 - 16: 7 bedrooms, 4 bathrooms,
€ 450 - 2,950 / week
Caprese Michelangelo, Tuscany

Charming country farmhouse in picturesque and tranquil surroundings.
TuscanyHolidayVilla.com Teresa's Villa (#531)
Sleeps 4 - 14: 5 bedrooms, 3 bathrooms,
€ 750 – 2,600 / week
Todi, Umbria

Charming Umbrian Villa newly restored and tastefully redecorated in warm earthy tones. Breathtaking 360 degree panorama!
TuscanyHolidayVilla.com The Count's Hamlet (#1816)-OWNER DIRECT-
Sleeps 4 - 36: 18 bedrooms, 16 bathrooms,
€ 950 € 14,400 / week
Cortona, Tuscany

An entire stone Village fully restored retaining original features in charming grounds with thousands of roses, lavender, rosemary bushes and outdoor areas just minutes from the famous Tuscan town of Cortona.
TuscanyHolidayVilla.com Cosetta's Country Farmhouse (#631)-OWNER DIRECT-
Sleeps 10 - 15: 6 bedrooms, 3 bathrooms,
€ 1,625 – 2,500 / week
Monterchi, Tuscany

Ideally located on the border between the famous regions of Tuscany and Umbria, the Farmhouse sits on a hilltop 800 m above sea level and offers a complete escape for those in need of peace and tranquillity.
TuscanyHolidayVilla.com Lizzie's Country Farmhouse (#751)
Sleeps 8 - 24: 7 bedrooms, 5 bathrooms,
€ 1,750 – 4,150 / week
Sansepolcro, Tuscany

If you are seeking a beautiful, gloriously spacious Tuscan farmhouse set high in the mountains with stunning views over the Tiber Valley, look no further.
TuscanyHolidayVilla.com Sue's Villa (#75)-OWNER DIRECT-
Sleeps 10 - 10: 5 bedrooms, 3 bathrooms,
EUR 1,990 - 3,990 / week
Anghiari, Tuscany

Luxurious Villa with sweeping views of lake & mountains and heated swimming pool.
TuscanyHolidayVilla.com Andrea's Farmhouse (#143)-OWNER DIRECT-
Sleeps 10 - 15: 5 bedrooms, 3 bathrooms,
EUR 2,200 – 3,650
Cortona, Tuscany

Delightful country farmhouse with swimming pool in picturesque and tranquil surroundings overlooking 10th century castle.
TuscanyHolidayVilla.com Janne's Castle (#533)
Sleeps 8 - 10: 5 bedrooms, 3 bathrooms,
€ 2,400/day – 5,900 / 6 nights
Sansepolcro, Tuscany

Beautifully restored Castle with breathtaking views. An exclusive & romantic Wedding venue.
TuscanyHolidayVilla.com Federica's Country Villa (#971)-OWNER DIRECT-
Sleeps 12 - 18: 9 bedrooms, 7 bathrooms,
€ 2,480 – 2,950 / week
Cittΰ di Castello, Umbria

Furnished and decorated with extreme care, a perfect harmony of luxury and simplicity situated amongst the green hills of Umbria and Tuscany.
TuscanyHolidayVilla.com Kathleen's Villa in the Village (#543)-OWNER DIRECT-
Sleeps 10 - 10: 5 bedrooms, 4 bathrooms,
EUR 2,650 – 3,950 / week
Pienza, Tuscany

Picture perfect Tuscan vista from ancient olive grove garden complete with private pool, along with bonus that the villa is within easy walking distance of restaurants and shops.
TuscanyHolidayVilla.com Federica & Lilli's Castle (#249)
Sleeps 4 - 26: 13 bedrooms, 9 bathrooms,
€ 80 /pp night - 13,450 / week
Monterchi, Tuscany

An impressive 12th century castle where you can relive first-hand the rich history of the area.
TuscanyHolidayVilla.com Orietta's Umbrian Farmhouse (#651)
Sleeps 10 - 16: 6 bedrooms, 6 bathrooms,
€ 2,800 – 3,500 /wk
Todi, Umbria

Beautifully restored with romantic vista over the Umbrian countryside and the medieval hilltop town of Todi.
TuscanyHolidayVilla.com Fede & Lilli's Farmhouse (#105)
Sleeps 18 - 20: 10 bedrooms, 5 bathrooms,
€ 3,300 - 4,700 /week
Monterchi, Tuscany

Tastefully restored 16th century stone farmhouse within the grounds of magnificent castle on the Tuscan Umbrian border.
TuscanyHolidayVilla.com Martina's Panoramic Fortress (#851)
Sleeps 16 - 28: 8 bedrooms, 5 bathrooms,
EUR 3,370 - 6,850 / week
Pistoia, Tuscany

An historical "Rocca" completely restored offering all the modern comforts, commanding views over the Montalbano Valley and close proximity to Florence, Lucca, Pisa and more.
TuscanyHolidayVilla.com Federica's Tuscan Residence (#852)
Sleeps 8 - 21: 8 bedrooms, 6 bathrooms,
€3950 - 8700/wk
San Giovanni D'Asso, Tuscany

An elegant, luxurious and historical Villa with private pool and garden, panoramic countryside views within a small village in the Province of Siena.

TuscanyHolidayVilla.com Giovanna's Farmhouses (#84)
Sleeps 16 - 18: 8 bedrooms, 4 bathrooms,
€ 2,200 - 3,200 / week
Sansepolcro, Tuscany

True Tuscan countryside charm and hospitality just 5 minutes from the historical centre.
TuscanyHolidayVilla.com Piero's Deluxe B&B (#1212)-OWNER DIRECT-
Sleeps 1 - 26: 15 bedrooms, 15 bathrooms,
€ 85/nt - 1,090/wk
Sansepolcro, Tuscany

An historical residence dating back to the fourteenth century, located in the heart of the historical centre of Sansepolcro. every room has been furnished in harmony with the restored frescoes and in a traditional style while providing all modern comforts