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 Rossa
Fighine

Casa Rossa

Elegant Villa set in privately owned medieval village in Tuscany

Casa Rossa has a large elegant sitting room with working fireplace, beamed ceilings and stone flagged floors.

There is a beautifully equipped modern kitchen whic...

Key activities:

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

As from 2797.00 €

4 2 2 Internet Access Perugia 60km, Florence 120km, Rome 170km
Place an option / Make a Booking Find out more
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
Place an option / Make a Booking Find out more
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
Place an option / Make a Booking Find out more
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
Place an option / Make a Booking Find out more
Rocchetto
Le Rocchette

Rocchetto

Delightful 3 BR villa with great pool between Siena and Arezzo

Small villas (this one sleeps 4 to 6 guests) with private pools are a rarity. Rocchetto is perfectly located, has great charm, and a lovely pool.

Over the last t...

Key activities:

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

As from 2300.00 €

6 3 3 Pool Internet Access Florence: 110 km
Place an option / Make a Booking Find out more
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)
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 – Ronda
Chiarentana

Chiarentana – Ronda

Apartment for 6 built around a magical courtyard and dominating the Orcia valley

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 2121.00 €

6 3 3 Pool Internet Access Florence 150km
Place an option / Make a Booking Find out more
Chiarentana – Beco
Chiarentana

Chiarentana – Beco

6 generous holiday 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 1645.00 €

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

Livietta

A romantic cottage in Tuscany in walking distance of a village

Situated on the fringes of the splendid hilltop village of Cetona, this carefully restored one-bedroom cottage is the ideal base for a romantic getaway in Tuscany...

Key activities:

touring towns, cultural sightseeing, visiting wine producers, spa treatments, hiking, biking, golf, watersports

As from 1284.00 €

2 1 1 Pool Internet Access Perugia 68km, Florence 140km, Rome 190km
Place an option / Make a Booking Find out more