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Road Trips in Tuscany

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Road Trips in Tuscany: Recommended holiday rentals

Road Trips in Tuscany: find your perfect rental from just £14 per night!

Apartment Colle di Val d'Elsa
20 Dec - 27 Dec
Apartment ∙ 4 guests ∙ 2 bedrooms

Flat with terrace, barbecue & garden | Garden view | Pet-friendly

Colle di Val d'Elsa, Province of Siena, Tuscany
£67
per night
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£67
per night
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Apartment Follonica
24 May - 31 May
Apartment ∙ 4 guests ∙ 1 bedroom

Nice holiday apartment | Beach nearby | Pet-friendly

Follonica, Province of Grosseto, Tuscany
£69
per night
Excellent(22 ratings)
Vrbo
£69
per night
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Cottage Caldana di Sopra
-33%
14 Feb - 21 Feb
Cottage ∙ 5 guests ∙ 2 bedrooms

Fully equipped cottage with garden, terrace & BBQ | Pet-friendly

Caldana di Sopra, Sovicille, Tuscany
£91£61
per night
Outstanding(96 ratings)
Vrbo
£91£61
per night
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Villa Marciana
-33%
10 May - 17 May
Villa ∙ 6 guests ∙ 2 bedrooms

Villa with garden, terrace & BBQ | Nature view

Marciana, Province of Livorno, Tuscany
£187£126
per night
Outstanding(63 ratings)
Vrbo
£187£126
per night
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Apartment Marina di Castagneto Carducci
24 May - 31 May
Apartment ∙ 6 guests ∙ 2 bedrooms

Holiday apartment with 2 rooms for 6 persons

Marina di Castagneto Carducci, Castagneto Carducci, Tuscany
£82
per night
Excellent(31 ratings)
Vrbo
£82
per night
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Villa Castellina in Chianti
-25%
29 Mar - 5 Apr
Villa ∙ 6 guests ∙ 3 bedrooms

Villa with garden, heated pool & terrace | Nature view

Castellina in Chianti, Province of Siena, Tuscany
£240£180
per night
Outstanding(101 ratings)
Vrbo
£240£180
per night
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Apartment Capezzano
-17%
27 Sept - 4 Oct
Apartment ∙ 6 guests ∙ 2 bedrooms

Flat with barbecue, terrace & garden | Water view

Capezzano, Pietrasanta, Tuscany
£74£61
per night
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£74£61
per night
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Villa San Casciano in Val di Pesa
-23%
29 Mar - 5 Apr
Villa ∙ 12 guests ∙ 4 bedrooms

Fully equipped villa with garden, pool & terrace | Panoramic view | Dogs allowed

San Casciano in Val di Pesa, Metropolitan City of Florence, Tuscany
£225£174
per night
Outstanding(6 ratings)
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£225£174
per night
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House Peccioli
-51%
14 Feb - 21 Feb
House ∙ 4 guests ∙ 2 bedrooms

Child-friendly holiday home with garden, pool & barbecue | Nature view

Peccioli, Province of Pisa, Tuscany
£337£167
per night
Outstanding(54 ratings)
Vrbo
£337£167
per night
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Villa Quarrata
6 Sept - 13 Sept
Villa ∙ 6 guests ∙ 4 bedrooms

Villa with terrace, BBQ & garden

Quarrata, Province of Pistoia, Tuscany
£161
per night
Outstanding(48 ratings)
Vrbo
£161
per night
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Farmhouse Loro Ciuffenna
-28%
3 May - 10 May
Farmhouse ∙ 6 guests ∙ 3 bedrooms

Child-friendly farm with barbecue, garden & pool

Loro Ciuffenna, Province of Arezzo, Tuscany
£167£120
per night
Outstanding(23 ratings)
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£167£120
per night
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Villa Castiglion Fiorentino
-36%
3 May - 10 May
Villa ∙ 4 guests ∙ 1 bedroom

Lovely villa with private pool, garden & BBQ | Pet-friendly

Castiglion Fiorentino, Province of Arezzo, Tuscany
£189£122
per night
Outstanding(17 ratings)
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£189£122
per night
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Villa Asciano
-31%
4 Oct - 11 Oct
Free cancellation
Villa ∙ 6 guests ∙ 3 bedrooms

Villa with BBQ & garden

Asciano, Province of Siena, Tuscany
£160£111
per night
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£160£111
per night
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Apartment Lamporecchio
-40%
19 Apr - 26 Apr
Free cancellation
Apartment ∙ 5 guests ∙ 1 bedroom

Flat with hot tub, pool & barbeque | Pets are welcome

Lamporecchio, Province of Pistoia, Tuscany
£175£105
per night
Outstanding(8 ratings)
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£175£105
per night
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Villa Barberino Tavarnelle
-44%
13 Sept - 20 Sept
Free cancellation
Villa ∙ 4 guests ∙ 2 bedrooms

Villa with fast internet, barbecue & terrace | Mountain view

Barberino Tavarnelle, Metropolitan City of Florence, Tuscany
£161£91
per night
Outstanding(2 ratings)
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£161£91
per night
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Planning a Road Trip Through Tuscany

The central region of Italy is full of masterpieces that charm just about anyone. You can get lost in the middle of artistic wonders, especially in the main towns. Deciding on the perfect road trip itinerary for Tuscany is not an easy feat. If you dream of romantic sunsets, Italian dishes, and Tuscan wines, this schedule has you covered.
An Itinerary for the Perfect Road Trip in Tuscany

An Itinerary for the Perfect Road Trip in Tuscany

You can savour hilltop villages, renaissance art, and rolling valleys peppered with grapevines through road trips in Tuscany. The countryside is dominated by medieval hamlets and suburbs that add to the irresistible side of the city. Each region is unique in terms of physical features and products. You can start with the following 3-day itinerary.

  1. Florence

    Florence provides some of the best Renaissance art you could ever see. Be it fairy tale castles, churches, or paintings, you will find something delightful. Visit Galleria dell'Accademia to check out the statue of David. The colourful roads in Certaldo via Boccaccio are a sight not to be missed. They are such a marvellous lookout between Pisa and Florence. Find them 60km to the south of Florence. Certaldo traces its roots back to the Roman-Etruscan era. It is part of Elsa Valley and is famed for crystal glassware production. Drive through the narrow streets, small squares, and medieval structures.

  2. Chianti

    While in Tuscany, you would be remiss not to check out some wineries in Chianti estates such as Castellare di Castellina. The estate welcomes travellers for wine tastings and appointments. And for the love of art, drive o Castello di Ama. Set in a peaceful corner of the Chianti Classico, Castello di Ama grabs people's attention not only for the quality reds but also its artistic masterpieces in an open-air museum, including standout pieces like the telescope are set up to monitor the countryside. Drop-in at Il Ristoro di Ama kitchen where only locally-grown veggies are served for some pappa al Pomodoro.

  3. Siena

    The province of Siena stuns with medieval architecture. Wander through the narrow cobblestone streets set against ancient buildings, and be sure not to miss the prime location of San Gimignano. This hilltop town, equidistant from Florence and Siena, has a long history of Roman trade, so you will be learning a bit of history during your self-drive tour.

  4. Maremma

    This southern region in Tuscany is unique due to a variety of holiday features including long blue beaches, woods superimposed upon hills, thermal waters, black rocks, and marshes. It is a timeless location with antique heritage. Stumble upon a Michelin-starred restaurant in the Maremma region that serves Italian foods in the most inviting 9-table dining rooms. Enjoy refined dishes such as tomato sorbet, fresh Argentario anchovies, and wild boar.

Best Places to Stay for Road Trips in Tuscany

Cottage San Martino In Freddana-monsagr
8 Apr - 15 Apr
-9%
£120
£109 per night
Cottage ∙ 4 guests ∙ 1 bedroom

Cottage with private pool, garden & barbeque | Nature view

4.8
Outstanding(44 ratings)
San Martino In Freddana-monsagr, Pescaglia, Tuscany
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Apartment Casciana Terme Lari
26 Apr - 3 May
-15%
£92
£78 per night
Apartment ∙ 4 guests ∙ 1 bedroom

Children-friendly wonderful apartment with pool & BBQ | Pet-friendly

5.0
Outstanding(3 ratings)
Casciana Terme Lari, Province of Pisa, Tuscany
Free cancellation
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House Bugiana
11 Oct - 18 Oct
-18%
£90
£74 per night
House ∙ 4 guests ∙ 2 bedrooms

Children-friendly house with barbecue, terrace & pool | Nature view

4.7
Excellent(8 ratings)
Bugiana, Monte San Savino, Tuscany
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Information about Road Trips in Tuscany

💳 Highest rates in August
🥳 Busiest month January
🛏️ Popular accommodation types Apartment rental and House rentals
🌡️ Warmest weather July and August
🥶 Coldest weather 2 °C in January and February
🌧️ Rainiest months 13 rainy days in May and November

Road Trips in Tuscany: frequently asked questions

Road Trips in Tuscany: what's the average price for a holiday apartment?

Holiday homes are currently available within the price range of £107 - £186, with discounts up to 26%!

Can I find holiday homes for Road Trips in Tuscany that can host a family or large group?

When plannin a trip for a big family it's great to know that average Apartment rental in Tuscany can fit in 5 guests and costs around £173 per night.

What types of holiday rentals are available for Road Trips in Tuscany?

Apartment rental and House rentals are the most popular types of holiday rental for Road Trips in Tuscany.

Average Nightly Rental Prices in Tuscany

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Holiday Letting Price Information in Tuscany

Holiday Rental Availability in Tuscany

Rental availability information in Tuscany

Holiday rentals near Tuscany with popular amenities

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Check out other holiday accommodation options in Tuscany

Check out holiday rentals with popular amenities in Tuscany

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