Grosseto, Tuscany

Overview

Discover Grosseto: Private Tours, Experiences & Custom Travel

Plan Your Experience

Explore Grosseto

Multi-Day Holidays Tours

Whole journeys, planned end to end

Christmas in Rome & Maremma: A Spa and Shopping Escape

Experience the best of Rome and Tuscany on this 10-day holiday tour. Shop the festive streets of Rome, explore iconic sights, and visit Christmas markets. Then relax in Maremma’s luxury spa resorts, enjoy wine tastings, and discover charming Tuscan v...

Private

10 Days / 9 Nights

Villas

Private homes with stories of their own

Italy,Tuscany,Grosseto,Montemerano

Villa

Bella Villa di Campagna

11 Beds 12 Baths 26

Air Conditioning +17 more

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Italy,Tuscany,Grosseto

Villa

Villa Serenissima

9 Beds 9 Baths 18

Air Conditioning +12 more

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Pitigliano

Sorano

Pitigliano

Sorano

Our Featured Properties

Stays we picked one by one

Italy,Tuscany,Volterra

Villa

Luxury villa near Volterra

4 Beds 11

Air Conditioning +13 more

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Casa della Acacia featured rental property in Grosseto

Italy,Tuscany,Florence

Apartment

Casa della Acacia

2 Beds 2 Baths 4

Air Conditioning +11 more

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Duetto Classico featured rental property in Grosseto

Italy,Tuscany,Montepulciano

Apartment

Duetto Classico

2 Beds 1 Baths 4

Air Conditioning +8 more

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Casa della Quiete featured rental property in Grosseto

Italy,Tuscany,Florence

Apartment

Casa della Quiete

2 Beds 2 Baths 4

Air Conditioning +12 more

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Cottage Talluri featured rental property in Grosseto

Italy,Tuscany,Chianti,Castellina in Chianti

Estate

Cottage Talluri

2.5 Beds 5

Air Conditioning +9 more

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Casa Divina featured rental property in Grosseto

Italy,Tuscany,Montepulciano

Apartment

Casa Divina

2 Beds 2 Baths 4

Air Conditioning +9 more

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Villa Amore Toscana: Ideal Villa for Groups and Large Families with Gorgeous Private Pool featured rental property in Grosseto

Italy,Tuscany,Castiglion Fiorentino

Estate

Villa Amore Toscana: Ideal Villa for Groups and Large Families with Gorgeous Private Pool

16 Beds 16 Baths 26

BBQ +11 more

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Italy,Tuscany,Lucca

Villa

Gorgeous villa near Lucca

3 Beds 6

Balcony +11 more

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Italy,Tuscany,Arrezzo

Villa

Villa Vinaia

5 suite rooms and 3 apartments Beds 5 Baths 18 + 6

Air Conditioning +9 more

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Italy,Tuscany,Castiglion Fiorentino

Villa

Villa Buccelletti: Great Option for Small Families, Couples of Group of Friends

4 Beds 4 Baths 10

BBQ +10 more

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Italy,Tuscany,Chianti

Villa

Villa Castrum

5-7 Beds 10-14

Air Conditioning +4 more

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Cottage near Cortona featured rental property in Grosseto

Italy,Tuscany,Cortona

Villa

Cottage near Cortona

2 Beds 6

Air Conditioning +10 more

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Popular Transfer Routes in Grosseto

The rides our guests ask for most, with a driver who knows the way.

Italy Vacation Specialists provides licensed private transfer services throughout Italy, including Grosseto and surrounding areas. With over 20 years of experience, our professional English-speaking drivers offer both Business Class and Luxury Class vehicles for airport transfers, city-to-city rides, and full-day chauffeur services. All vehicles are fully insured, well-maintained, and operated by vetted local drivers who know the roads, traffic patterns, and best routes across the region.

Rome Florence

Private Transfer

Rome Naples

Private Transfer

Rome Venice

Private Transfer

Florence Venice

Private Transfer

Milan Venice

Private Transfer

Naples Amalfi

Private Transfer

Rome Amalfi

Private Transfer

Milan Lake Como

Private Transfer

Florence Siena

Private Transfer

Naples Sorrento

Private Transfer

Every journey is different. Tell us where you need to go.

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In their words

Stories That Stay With You

Here's what our guests share about their unforgettable journeys

“In September of 2018 I brought a group of 12 from Venice to Sicily and organized all of my services with the Italy Vacation Specialists. Being a travel agent and in the business, I know how complicated organizing travel arrangements can be in Italy and the IVS…”
Ann Brownell, KHM Travel Group Read their story

“I am a travel agent from Lebanon and have organized several group tours as well as individual tours of Italy with Italy Vacation Specialists. I highly recommend them as one of the very best tour operators in Italy to work with, given their professionalism and…”
Nicole Haddad, Lebanese Travel Agent Read their story

“Jesse & Giuseppe, Sandy and I have been looking through my slides of our trip to Southern Italy. We had such a good time with you and Giuseppe that we wanted to let you know again. You were the best guides ever”
Bob & Sandy Read their story

“Dear Guiseppe and Jesse, We just returned from our most wonderful vacation to Italy and wanted to first thank you for putting together such a wonderful trip, and second to provide some feedback for the future. Hotels 1. Hotel Sovestro in San Gimignano was wond…”
Ron and Deb Crosby Read their story

“Jesse, There are no words to describe the fabulous time we had in Italy. Everything went as you promised. Absolutely no problems! The venues were fabulous. The guides were punctual and helpful. It couldn't have worked out better. You and your staff deserve hig…”
Jo Ann West Read their story

“I have traveled to Italy 2x with the IVS for my own pleasure trips and 2x for business with IVS. These guys really pay attention and make your trip go like clockwork. Italy is nuts, just saying! There are so many rules and restrictions now, so we did not want…”
JoAnne Beaudoin, Retired Nurse Read their story