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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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Palazzetto
Barberino

Palazzetto

A small jewel of Renaissance architecture in Chianti - CLASS LISTED / LANDMARKED BUILDING

The villa looks onto the main street of the historical village Barberino Val d’Elsa (which is...

Key activities:

cultural sightseeing, visiting wine producers, excellent restaurants, tennis (village)

As from €

16 8 7 Pool Internet Access Florence: 45 km
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Casa di Donata
La Foce

Casa di Donata

Elegant villa with pool and tennis overlooking the Orcia valley near Pienza

Donata’s house offers all the special charm, character and seclusion of a private home and garden, with the additional advantage of having the restaurant, tennis,...

Key activities:

cultural sightseeing, winemaking area, tennis, spas, hiking

As from €

10 5 5 Pool Internet Access Florence: 150 km
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Guardia 1
Borgo di Pietrafitta

Guardia 1

The gamekeepers abode

What used to be the gamekeepers dwelling lies on the edge of the Pietrafitta hamlet ...

Key activities:

cultural sightseeing, Chianti wine making, excellent restaurants, golf, hiking & biking

As from 1085.00 €

3 2 1 Pool Internet Access Florence 47km
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Villa Le Palme
Tombolino Bolgheri

Villa Le Palme

Stylish contemporary beach house on the Tuscan coast

The sea and sun are reflected throughout this bright and airy beach house a short walk from a stunning beach of the Maremma coast. When you’re not on the beach, y...

Key activities:

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

As from €

8 4 4 Internet Access Pisa airport 67 km (under one hour)
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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 1470.00 €

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

La Pergola

Finely restored spacious ground floor apartment of a farmhouse

The spacious Pergola apartment lies on the ground floor of the villa I Cavallini. A large living room leads onto a vine covered pergola with a stunning view onto th...

Key activities:

beachlife, spas, bicicling, hiking

As from 545.00 €

5 3 2 Pool Internet Access Roma Fiumicino: 130 km
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Dario 4
Borgo di Pietrafitta

Dario 4

The main farmbuilding of the estate

This farm used to house the sharecroppers who lived on the Borgo di Pietrafitta esta...

Key activities:

cultural sightseeing, Chianti wine making, excellent restaurants, golf, hiking & biking

As from 1357.00 €

4 2 2 Pool Internet Access Florence 47km
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Villa Strozzi
Collegalli

Villa Strozzi

Entire wing of an Tuscan villa with out of this world views and pool

Situated on the grounds of the Collegalli Estate in Montaione, the origins of Villa Strozzi date back to the 12th century. With its 19th century interior...

Key activities:

pool dipping, sun bathing, wine sipping, culture, local markets, glorious countryside and day trekking

As from €

14 7 5 Pool Internet Access Pisa 60 km (1h)
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