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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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San Polino
San Polo in Rosso

San Polino

A spacious villa in the heart of Chianti, perfect for family gatherings or retreats

This group of restored farmhouses lies in the heart of Chianti and is part of a medieval estate perched on a hill overlooking vineyards, olive groves and ancient oa...

Key activities:

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

As from 12600.00 €

18 9 9 Pool Internet Access Rome Fiumicino airport 275km – 3h, Florence airport 70km – 1h10, Pisa airport 115km – 1h50
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Villa Fontanili-Leccio
Fontanili

Villa Fontanili-Leccio

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, 3 km. from th...

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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Chiarentana – Bersagliere
Chiarentana

Chiarentana – Bersagliere

6 generous apartments overlooking the Val d'Orcia, with salt water pool

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 1022.00 €

2 1 1 Pool Internet Access Florence 150km
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Villa La Loggia
Tombolino Bolgheri

Villa La Loggia

New stylish villa steps from the beach in Tuscany

Encircled by a lush garden of roses, bougainvillea, cyprus trees and pines, this attractive recently built villa provides the perfect setting for a heavenly Italian...

Key activities:

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

As from €

8 6 4 Internet Access Pisa airport 67 km (under one hour)
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Castelrotto
Castelnuovo Tancredi

Castelrotto

An authentic, beautifully restored farmhouse on an organic wine estate near Montalcino south of Siena

Nestled within gently rolling vineyards, olive groves and grain fields, this lovingly renovated farmhouse is part of a vast 600-hectare estate which has been owned ...

Key activities:

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

As from 8400.00 €

20 10 8 Pool Internet Access 115 km Florence, 200 km Rome
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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 1787.00 €

6 3 3 Pool Internet Access Perugia 68km, Florence 140km, Rome 190km
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Il Mulino
La Badia

Il Mulino

Stunning villa with pool on organic estate in central Tuscany

Mulino in Italian means Mill and this house used to be the mill of the La Badia estate. It still...

Key activities:

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

As from 3725.00 €

10 6 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 1505.00 €

4 2 1 Pool Internet Access Florence 150km
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Casa di Pietro
Vivo d'Orcia

Casa di Pietro

Charming 2 bedroom cottage with pool near village Montalcino area - UNESCO World Heritage

Casa di Pietro is a two storied house with walled in garden on the Vivo d'Orcia estate. It is one of a row of cottages built for the people working on the estate, b...

Key activities:

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

As from €

4 2 2 Pool Internet Access Florence: 150 km
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Orangerie
Tombolino Bolgheri

Orangerie

A converted orangerie

The orangerie lies in the south looking basement of the Villa Tombolino, next to the orchard of the estate, which has become the Limonaia's private garden.

The m...

Key activities:

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

As from 1617.00 €

4 2 2 Internet Access Pisa airport 67 km (under one hour)
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