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Holiday Villas Rental in Tuscany

Below you will find our entire range of holiday villas in Tuscany, Italy. To narrow down the list, you can select the number of persons and additional amenities (private pool, near the beach, air conditioning, etc.). Then click the search button.

 

Tuscany

The historical estates listed below have been carefully selected by Trust&Travel over the past years. Each property stands out for its beauty, its location, the interior decoration and the level of service. You can choose a charming agriturismo cottage, a stunning villa with private pool, an exclusive fully staffed luxury villa or a historical castle with pool.
Browse each of the following estates in Tuscany to find out more about the available rentals, their location and surroundings and the suggested services.

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Villa Aiale
Castelnuovo Tancredi

Villa Aiale

Beautifully restored, spacious Tuscan farmhouse with private pool set atop a prestigious wine estate.

Villa Aiale, completely restored in 2024,  is the newest treasure of the historic Castelnuovo Tancredi Estate, an exclusive sanctuary where timeless Tuscan charm me...

Key activities:

touring towns, cultural sightseeing, visiting wineries, spa treatments, hiking, biking, golf.

As from 10500.00 €

14 7 8 Pool Internet Access 115 km Florence, 200 km Rome
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La Tartaruga
Le Gore

La Tartaruga

Architect-restored villa with a pool, walking distance to a Medieval village

Nestled within an olive grove and the rolling fields of Southern Tuscany, this airy villa with a pool offers exceptional country living coupled with the convenience...

Key activities:

touring towns, cultural sightseeing, visiting wine producers, spa treatments, hiking, biking, golf, watersports

As from 4700.00 €

8 4 5 Pool Internet Access Perugia 68km, Florence 140km, Rome 190km
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Casa della Pineta
Tombolino Bolgheri

Casa della Pineta

Beachfront cottage on the Tuscany seaside, 3 bedrooms

The apartment lies on the ground floor of a small cottage on the estate. It is a very friendly and sunny house, and nearly all the rooms have french windows opening...

Key activities:

direct access to the beach, wine tasting, excellent restaurants, visiting the surrounding hilltop towns

As from €

6 3 2 Internet Access Pisa airport 67 km (under one hour)
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Casa dell’Ambasciatore
Vivo d'Orcia

Casa dell’Ambasciatore

2 BR Cottage in Southern Tuscany, village in walking distance - UNESCO World Heritage

Casa dell’Ambasciatore is a charming country house standing on its own on the edge of the hamlet, surrounded by a garden and wide stretching views onto open fields ...

Key activities:

cultural sightseeing, winemaking area, spas, excellent food, beautiful hiking, wild nature

As from 1190.00 €

4 2 2 Pool Internet Access Florence: 150 km
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Rocchetto Basso
La Badia

Rocchetto Basso

4 bedroom villa between Siena and Arezzo with private pool

Rocchetto Basso is a lovingly restored 18th-century Tuscan farmhouse that perfectly balances historic charm with modern comfort. This elegant stone-built villa feat...

Key activities:

Excellent starting point to visit most of Tuscany, cultural sightseeing, excellent food, hiking within the estate, tennis in the village

As from 4000.00 €

8 4 5 Pool Internet Access Florence: 110 km
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Chiarentana – Tiglio
Chiarentana

Chiarentana – Tiglio

6 generous apartments built around a magical courtyard

Chiarentana was once a medieval fortress and has been 'de-gentrified' over the centuries, becoming one of the main farm buildings on the property.

The 6 apartmen...

Key activities:

Siena, Florence, Montalcino, Montepulciano, Pienza, Orvieto, Cortona

As from 1652.00 €

4 2 1 Pool Internet Access Florence 150km
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Casa Livia
Cetona

Casa Livia

Medieval tower with pool, views and in walking distance of a village

Savor the best of southern Tuscany at this wonderful three-bedroom 14th century tower, set within bucolic gardens at the edge of the picturesque town of Cetona. Its...

Key activities:

touring towns, cultural sightseeing, visiting wine producers, spa treatments, hiking, biking, golf, watersports

As from 1875.00 €

6 3 3 Pool Internet Access Perugia 68km, Florence 140km, Rome 190km
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Duna Piccola
Fontanili

Duna Piccola

Beachfront cottage on the Maremma coast in south Tuscany

Duna Piccola is a unique venue in Italy. Rarely will you find a fairly isolated house with direct access to the beach, surrounded by romantic farmland, varied wildl...

Key activities:

private access to the sea, excellent sea food, cultural sightseeing, bicycling, tennis (village)

As from 1705.00 €

4 2 1 Internet Access Roma Fiumicino: 100 km
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Parretti Due
Fighine

Parretti Due

Luxury suite with views, nestled in a privately owned medieval hamlet in Tuscany

Beautifully appointed upper floor 1 bedroom apartment, ideal for guests visiting the *Michelin star restaurant of Key activities:

cultural sightseeing, visiting wine producers, excellent restaurants, spa treatments, hiking, mountain biking

As from 295.00 €

2 1 1 Internet Access Perugia 60km, Florence 120km, Rome 170km
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Casa Rossa
Fighine

Casa Rossa

Elegant Villa set in privately owned medieval village in Tuscany

Casa Rossa is one of the five luxurious villas in the medieval hamlet of Fighine. Casa Rossa has ...

Key activities:

cultural sightseeing, visiting wine producers, excellent restaurants, spa treatments, hiking, mountain biking

As from 2797.00 €

4 2 2 Internet Access Perugia 60km, Florence 120km, Rome 170km
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