Key

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.

Find out more »
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
Place an option / Make a Booking Find out more
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
Place an option / Make a Booking Find out more
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 4600.00 €

8 4 5 Pool Internet Access Florence: 150 km
Place an option / Make a Booking Find out more
Villa Melissa
Fighine

Villa Melissa

19th century luxury villa with pool in Tuscan hamlet between Florence and Rome

Villa Melissa is a large villa set within its own private garden. The beautiful swimming pool with pool house and full changing and shower facilities lies 2 minute ...

Key activities:

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

As from 6099.00 €

8 4 4 Pool Internet Access Perugia 60km, Florence 120km, Rome 170km
Place an option / Make a Booking Find out more
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
Place an option / Make a Booking Find out more
Maramai
Tenuta di Gracciano

Maramai

Comfortable villa with great pool on wine estate near Montepulciano and Pienza

Maramai, now a charming country house, used to be a small farm with 3 separate buildings. It is named after the Tuscan farmer’s family who lived there until the e...

Key activities:

visiting the wine estate, cultural sightseeing, excellent food, hiking, tennis (village)

As from 3350.00 €

9 5 5 Pool Internet Access Florence: 120 km
Place an option / Make a Booking Find out more
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
Place an option / Make a Booking Find out more
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
Place an option / Make a Booking Find out more
Chiarentana – Vespa
Chiarentana

Chiarentana – Vespa

6 generous Tuscan 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 holiday ...

Key activities:

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

As from 1505.00 €

4 2 2 Pool Internet Access Florence 150km
Place an option / Make a Booking Find out more
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
Place an option / Make a Booking Find out more