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

Villas with Private Pools (24 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 Valentina’s Vineyard Farmhouse (#441)-OWNER DIRECT-
Sleeps 2 - 14: 4 bedrooms, 4 bathrooms,
€ 450 – 2,600 / week
Lucca , Tuscany

Ideally situated close to the famous Tuscan town of Lucca and within easy reach of Florence and Pisa, the farmhouse offers a peaceful base from which to explore the region.

TuscanyHolidayVilla.com Rosario’s Country Villa (#351)-OWNER DIRECT-
Sleeps 2 - 14: 4 bedrooms, 5 bathrooms,
Euro 490 - 2700/wk
Sansepolcro, Tuscany

Historical Farmhouse comprising 5 charming apartments, finished and furnished with great attention to detail.

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 Mel & Gill's Mill house (#333)-OWNER DIRECT-
Sleeps 6 - 7: 3 bedrooms, 3 bathrooms,
€ 875 - 1,595 / week
Lucca, Tuscany

Perfect location within 15 minutes of the famous walled Tuscan city of Lucca plus close proximity to Florence (1 hr), Pisa (45 mins) and the Versillian coast (35 mins).
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 Annalisa’s Girasole Farmhouse (#324)
Sleeps 2 - 4: 2 bedrooms, 2 bathrooms,
€ 1,400 – 1,850 / week
Gioella, Umbria

Beautifully restored, characteristic brick farmhouse set in the glorious Umbrian countryside with panoramic views across fields of wheat and sunflowers from which the house derives its name.
TuscanyHolidayVilla.com Caterina's Country Villa (#334)
Sleeps 6 - 8: 3 bedrooms, 3 bathrooms,
EUR 1,750 - 2,200 / week
Marsciano, Umbria

Spacious, tastefully restored and characteristic stone farmhouse in a picturesque Umbrian valley. The property is fully fenced with views of the surrounding gentle hills and the odd Medieval Village or Castle!
TuscanyHolidayVilla.com Mirren's Villetta (#221)
Sleeps 2 - 4: 2 bedrooms, 2 bathrooms,
€ 1,450 – 1,950 /week
Caprese Michelangelo, Tuscany

Superbly rustic yet deluxe Tuscan villa with panoramic views of classic chestnut woods plus private heated pool, charming gardens & pergolas.
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 Violetta's Villa (#11)
Sleeps 6 - 8: 3 bedrooms, 3 bathrooms,
€ 1,850 – 2,850 / week
Sansepolcro, Tuscany

Spacious and characteristic Tuscan Farmhouse featuring large and charming garden with pool, fully fenced with electric gates. Wireless internet connection.
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 Alessia's Villa (#541)-OWNER DIRECT-
Sleeps 8 - 10: 5 bedrooms, 4 bathrooms,
€ 2,025 - 3,975 /wk
Caprese Michelangelo, Tuscany

Characteristic & enchanting Tuscan villa with breathtaking views ... it's like living a dream.
TuscanyHolidayVilla.com Caterina's Villa (#323)
Sleeps 6 - 6: 3 bedrooms, 2 bathrooms,
€ 2,150 – 2,550 / week
San Giovanni D'Asso, Tuscany

A delightful Villa located right in the village of San Giovanni d’Asso but enjoying panoramic Tuscan countryside views.
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
Città 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.