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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-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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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 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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Castello di Galbino
Galbino

Castello di Galbino

A fairy tale castle in the country of Saint Francis - CLASS LISTED / LANDMARKED BUILDING

Tucked away into the hills of Arezzo lies the magic Castello di Galbino, a large and welcoming family castle surrounded by seemingly endless fields and hills covere...

Key activities:

Cultural sightseeing, discovery of an unknown Tuscany, excellent resturants, tennis (village)

As from €

19 10 8 Pool Internet Access Florence: 120 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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Villa Melissa & Casa Vittoria
Fighine

Villa Melissa & Casa Vittoria

Luxury villa set in an enchanting garden within a Tuscan hilltop hamlet

Villa Melissa and Casa Vittoria are two separate buildings within the same garden. They can be rented together for groups up to 14 guests. Both houses have their ow...

Key activities:

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

As from 9530.00 €

14 7 7 Pool Internet Access Perugia 60km, Florence 120km, Rome 170km
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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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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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Duna Grande
Fontanili

Duna Grande

Beachfront Villa with Pool on the Coast in Tuscany

Duna Grande is a unique venue in Italy. In Tuscany you will rarely find a nearly isolated house with direct access to the beach, sur...

Key activities:

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

As from 3525.00 €

10 5 4 Pool Internet Access Roma Fiumicino: 100 km
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