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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 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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Fontalgozzo
La Foce

Fontalgozzo

Converted farmhouse with the best known view in Tuscany

The house stands on its own, surrounded by olive groves, wheat fields and cypresses, and looks onto the famous cypress road that winds up the 'crete' on the opposit...

Key activities:

cultural sightseeing, winemaking area, tennis, spas, hiking

As from 5.00 €

8 4 5 Pool Internet Access Florence: 150 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 Lilli
Vivo d'Orcia

Casa di Lilli

Charming 1BR cottage south of Siena - Village in walking distance - UNESCO WORLD HERITAGE

Casa di Lilli is a small 2 storeyed house located next to the romanesque church of Vivo d’Orcia. It was fully restored and turned into a charming retreat for two....

Key activities:

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

As from 714.00 €

2 1 1 Pool Internet Access Florence: 150 km
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Casa di Giulio
Vivo d'Orcia

Casa di Giulio

Cottage with private garden and pool in walking distance of village - UNESCO World Heritage

Casa di Giulio stands at the far end of the private hamlet, at the foot of the castle of Vivo d...

Key activities:

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

As from 1351.00 €

5 3 2 Internet Access Florence: 150 km
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B&B Palazzolo
La Foce

B&B Palazzolo

B&B in a traditional Tuscan farmhouse overlooking Orcia valley

B&B Palazzolo is only 500m from the central La Foce Villa, on the road that leads to Chiarentana. The house is one of the farmhouses rebuilt by Antonio Origo in...

Key activities:

cultural sightseeing, winemaking area, tennis, spas, hiking

As from €

2 2 1 Pool Internet Access Florence: 150 km
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Ringoni
Via del Pellegrino

Ringoni

Tuscan farmhouse holiday rental with heated pool in the Val d'Orcia

A charming 300 years old stone farmhouse, lying high up in the Orcia valley, facing south-west with a stunning view over hills of what is considered one of the most...

Key activities:

cultural sightseeing, winemaking area, spas, hiking, mountain biking

As from 5000.00 €

10 5 4 Pool Internet Access Perugia 1 hour, Florence 1.5 hours, Rome and Pisa 2 hours
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Cerrettaia
Tenuta Thun

Cerrettaia

Comfortable 2 bedroom cottage, near Capalbio and the coast

The gorgeous pool 12x5 m is open to guests of Cerrettaia 27 July to 30 August (exclusive use).

Key activities:

beachlife, spas, wineries, bicicling, hiking, golf, hot springs

As from 1500.00 €

4 2 2 Internet Access Roma Fiumicino: 130 km
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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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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 1620.00 €

4 2 1 Internet Access Roma Fiumicino: 100 km
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