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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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Montecucco
Vivo d'Orcia

Montecucco

Restored farmhouse south of Siena with pool and views onto the vineyards of Montalcino

Villa Montecucco is located at an altitude of 400 metres above sea level, twenty minutes’ drive from the castle estate of Vivo D’Orcia. It benefits from absolut...

Key activities:

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

As from 2954.00 €

8 4 4 Pool Internet Access Florence: 150 km
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Villa Fontanili-Lentisco
Fontanili

Villa Fontanili-Lentisco

Paradise in Maremma, the southern Tuscan coast

Surrounded by trees, the Villa Fontanili stands in extensive landscaped grounds which blend into the olive groves and fields of the estate. The beach, 3km from the ...

Key activities:

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

As from 1082.00 €

6 3 2 Pool Internet Access Roma Fiumicino: 100 km
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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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Villa Fontanili-Ginepro
Fontanili

Villa Fontanili-Ginepro

Paradise in Maremma, the southern Tuscan coast

Surrounded by trees, the villa Il Fontanili stands in extensive landscaped grounds which blend into the olive groves and fields of the estate. The beach, 3 km. from...

Key activities:

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

As from 1085.00 €

6 3 2 Pool Internet Access Roma Fiumicino: 100 km
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Gallinaio
Vivo d'Orcia

Gallinaio

Charming 1 bedroom cottage in the Orcia valley south of Siena - CLASS LISTED / LANDMARKED BUILDING

Il Gallinaio, the former chicken coop of the castle, has been converted into a charming cottage for 2. The small house stands a little apart from the castle, surrou...

Key activities:

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

As from €

2 1 1 Internet Access Florence: 150 km
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Casaccia
Chiarentana

Casaccia

Artist’s abode flooded with light and colours

La Casaccia belongs to the son of one of the owners. He has transformed the former stables of his house into a comfortable house with 3 bedrooms and 3 bathrooms. He...

Key activities:

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

As from 2996.00 €

6 3 3 Pool Internet Access Florence 150km
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Parretti Due
Fighine

Parretti Due

Luxury bed and breakfast with views, set in a privately owned 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 Faraona
San Polo in Rosso

Casa Faraona

Secluded Chianti villa with pool and wheelchair accessibility.

Enjoy an authentic and idyllic rural holiday at this secluded villa with a pool found deep in Chianti. Sitting on the edge of a hamlet, the beautifull...

Key activities:

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

As from 3775.00 €

6 3 3 Pool Internet Access Rome Fiumicino airport 275km – 3h, Florence airport 70km – 1h10, Pisa airport 115km – 1h50
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Gonzola
Chiarentana

Gonzola

Fragrant herbs and roses surround this authentic and beautifully restored farm building

A Gonzola lies in the middle of open farmland, surrounded by fields of wheat and sunflowers on one side and a small wood and the strange shapes of the distinctive c...

Key activities:

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

As from 5243.00 €

10 5 4 Pool Internet Access Florence 150km
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