Grosseto, Tuscany

Discover Grosseto — Private Tours, Experiences & Custom Travel

Overview

Multi-Day Holidays Tours

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

PRICING

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Hotels

Villas

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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Apartment

Photo Gallery

Our Featured Properties

Wonders Room featured rental property in Grosseto Italy

Italy,Tuscany,Montepulciano

Apartment

Wonders Room

1 Beds 1 Baths 2

Air Conditioning +6 more

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Cottage Riccio featured rental property in Grosseto Italy

Italy,Tuscany,Chianti,Castellina in Chianti

Estate

Cottage Riccio

Air Conditioning +7 more

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Giardino Blu featured rental property in Grosseto Italy

Italy,Tuscany,Montepulciano

Apartment

Giardino Blu

2 Beds 1 Baths 5

Air Conditioning +8 more

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Italy,Tuscany,Val D'Orcia

Villa

Villa Gabriella

8 Beds 8 Baths 16

Bathroom with Shower +15 more

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Italy,Tuscany,Montepulciano

Villa

Villa Tanoak

Swimming Pool +1 more

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Italy,Tuscany,Florence

Apartment

Central Apartment in Florence with frescoed ceiling

3 Beds 7

Air Conditioning +10 more

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Apartment Virgo featured rental property in Grosseto Italy

Italy,Tuscany,San Gimignano

Estate

Apartment Virgo

1 Beds 1 Baths 3

Air Conditioning +7 more

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La Dimora del Gazebo featured rental property in Grosseto Italy

Italy,Tuscany,Siena

Apartment

La Dimora del Gazebo

3 Beds 2 Baths 6

Air Conditioning +16 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 8

BBQ +10 more

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Duetto Classico featured rental property in Grosseto Italy

Italy,Tuscany,Montepulciano

Apartment

Duetto Classico

2 Beds 1 Baths 4

Air Conditioning +8 more

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Italy,Tuscany,Castiglion Fiorentino

Villa

Villa San Martino Cortona

3 Beds 5 Baths 12

BBQ +10 more

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Italy,Tuscany,Bagno Vignoni

Villa

Villa in Val D'Orcia

8 Beds 21

BBQ +10 more

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Private Transfer Routes in Grosseto

Seamless connections between key destinations across the region

Rome Florence

Private Transfer

Rome Naples

Private Transfer

Rome Venice

Private Transfer

Florence Venice

Private Transfer

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Explore Towns and Cities in Grosseto

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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 team took a huge burden off of me! I would like to start of by saying "THANK YO”

[Read More] Ann Brownell, KHM Travel Group

“I am a travel agent with All About Honeymoons and I would highly recommend Italy Vacation Specialists. Jessica was wonderful in helping us plan in a last minute anniversary vacation during high season without any issues. She even checked on our clients while on vacation to make sure things were going well. I plan on using them again soon ”

[Read More] Tammy Joyce, All About Honeymoons

“The trip was great; we appreciate all the hard work you and your team invested to make our experience a once in a lifetime trip. We appreciate all the attention to the details, in particular Giuseppe spending the time and the focus with us on the road and as we were exploring your great country.”

[Read More] Leon and Michele

“As a travel agent, but also a traveler to Italy, thee is no other company I would recommend than the Italy Vacation Specialists. Not only do they really care about what they are doing, they also really know Italy and try to educate many people about ways they can best see the country and not fall into tourist traps. I have been on 4 trips”

[Read More] Laura Chomiak, Travel Agent

“In August 2018, my family of four and myself travelled from Vancouver, BC to Rome Italy and spent 3 weeks touring Italy with IVS. This company had come highly recommended by many friends and associates of ours who had used them before and indeed to say they do an outstanding job is an understatement. You can tell while being in Italy that”

[Read More] Vijaya Sunil CPA, CGA

“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 high praise for the quality and efficiency of your work. BTW, Guiseppe was an absol”

[Read More] Jo Ann West

“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 work ethic which I feel is second-to-none in the travel industry. All of the sta”

[Read More] Nicole Haddad, Lebanese Travel Agent

“I traveled with JoAnn West through your services, guided by Giuseppe, in July of this year. What a wonderful experience; your service is really top notch! If I return to Italy for a tour, I will absolutely use your services again and recommend you to my friends!”

[Read More] Lucretia Brower

“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 wonderful. The staff were very friendly and helpful and made the first portion of ou”

[Read More] Ron and Deb Crosby

“This company really knows their stuff and recommended our family to stay longer in each location. We didn't listen to them, but wished we had in every single place we went. They recommended Sestri Levante over the Cinque Terre which was our favourite destination on our entire trip. We visited Rome where we stayed in the outstanding Hotel ”

[Read More] Sean & Veet Chapman, CGA