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

Il Nascondiglio Verde featured rental property in Grosseto Italy

Italy,Tuscany,Arrezzo

Villa

Il Nascondiglio Verde

2 Beds 2 Baths 4

Air Conditioning +11 more

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La Dimora Regale 2 featured rental property in Grosseto Italy

Italy,Tuscany,Arrezzo

Villa

La Dimora Regale 2

2 Beds 2 Baths 4+2

Air Conditioning +11 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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Italy,Tuscany,Florence

Villa

Villa Fiori d'Arte

8 Beds 8 Baths 16-18

Air Conditioning +13 more

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Eleganza Spaziosa featured rental property in Grosseto Italy

Italy,Tuscany,Montepulciano

Apartment

Eleganza Spaziosa

2 Beds 2 Baths 6

Air Conditioning +8 more

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Italy,Tuscany,Lucca

Villa

Villa Amore: Great Villa for Groups in Tuscany Walking Distance from Town with full Yoga Studio

15 Beds 15 Baths 30

Air Conditioning +15 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 San Martino Cortona

3 Beds 5 Baths 12

BBQ +10 more

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Italy,Tuscany,Arrezzo,Arezzo

Villa

Luxury Villa in Arezzo

10 Beds 20

Air Conditioning +12 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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Cottage Talluri featured rental property in Grosseto Italy

Italy,Tuscany,Chianti,Castellina in Chianti

Estate

Cottage Talluri

2.5 Beds 5

Air Conditioning +9 more

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La Casa Fiorita featured rental property in Grosseto Italy

Italy,Tuscany,Florence

Apartment

La Casa Fiorita

4 Beds 4 Baths 4/8

Air Conditioning +11 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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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

“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

“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

“We're home now from the most amazing trip to Italy! I can't thank you enough for your efforts and coordination of what was without question the finest vacations I've been on to date.”

[Read More] Carol Carson

“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

“I went to high school with the owner of the company who organized my honeymoon for myself and my now wife from Tokyo. We spent three short weeks seeing Piedmont and experiencing wine paradise there, then heading to Nice in France with our private driver and flying to Rome where honestly 4 days is NOT enough. They keep saying to spend more”

[Read More] Robin and Kumi Bruun, Tokyo Japan

“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.”

[Read More] Bob & Sandy

“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 to drive ourselves. Having traveled with them many times and done business on se”

[Read More] JoAnne Beaudoin, Retired Nurse

“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

“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