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Classic Villa Vacations

Villas & Apartments
Puglia, Alberobello Trulli homes, UNESCO site, Come enjoy the amazing region or Pugliawith us. Experiences & Adventures
Experience Food & Wine

Classic Villa Vacations & Experiences

Italy is our Passion, we know it well.

We have driven the highways and byways to find hidden gems, we have cooked, tasted, biked, hiked and experienced what Italy has to offer. Let us help you do the same.

  • Villas, Apartments, Agriturismo, Charming hotels. Experience food & wine with the locals, walk the vineyards, the historic streets, and so much more.

Featured collection

We present a collection of carefully curated villas & apartments throughout Italy: Our Villas in Tuscany have been personally chosen by our expert team. Rather than spending hours on many sites we offer a special collection which we have personally vetted, add one of our unique experiences to truly live like a local.

We also offer unique experiences throughout Italy, so please scroll around and find one that entices you, whether you add it to a villa stay or only enjoy this one experience.

Rent a villa in Tuscany, set amidst the vineyards, winding roads and cypress trees. Renting a villa in Tuscany: Everyone’s dream is different…come experience yours.

Each area of Tuscany has different things to recommend it: the main areas of Lucca ( a lovely walled town west of Florence, not far from Pisa) - the Chianti area, which is the heart of the Italian wines we all know so well, with little villages and winding roads and the area around Cortona, made famous by the book “Under the Tuscan Sun”  which has some lovely well priced properties. The val d’Orcia – the calendar photos of Tuscany….















Collection list

Villa in Tuscany this villa is near Cortona
Villas in Tuscany 42 items
Florence Apartments & More 4 items
Rome skyline apartment rental rome
Rome Apartments & More 2 items
Rome - Experiences & beyond
Rome - Experiences & beyond 5 items

Northern Italy - Stay,Savour & Experience 3 items
Food & Wine Experiences All 4 items
Southern Italy - Amalfi Coast, Puglia, Sicily
Southern Italy - Amalfi Coast, Puglia, Sicily 5 items
Cinque Terre and the Italian Riviera
Cinque Terre and the Italian Riviera 1 item

Testimonials June 2023 Villa CentoTrentaUno

  • “You can find a villa or apartment on any generic website when planning your trip to Italy. What you won’t find are the back-door, off-the-beaten-path people and places that make your trip truly memorable. From private wine and food tastings or private Vatican tours, to bicycling through a beautiful property in the Parma region near the Po River, classicvacationrental.com will work with you to plan your trip of a lifetime. Avoid crowds, see hidden gems and truly experience the hospitality of the Italian people. Our family has planned 3 trips to Italy (each one so different) with CVV and we’ve never been disappointed with accommodations or experiences that she’s arranged for us!”

    Davidson Family – Seattle, Washington, USA

  •   Every experience during our trip has exceeded our expectations. We added an additional tour into Florence. Our guides have been exceptional - - sophisticated and knowledgeable.   All the Italians with whom we have come in contact are friendly, gracious, and helpful.   We added 2 dinners, totaling 8, with Claudio and his wife, Elisabetta. Their food has been extraordinary and our evenings gorgeous - - such a happy time for our whole family. Thank you for all you have done to make our Italian dream come true.  

    A. Fitzhugh
    www.example.com

  •  My family and I so enjoyed our tour of Lucca today!  Daniel, our driver, and Gabriel, our guide, took good care of us.  Daniel was gracious and professional, his driving was excellent. Gabriel gave a fascinating, informative, delightful tour of the lovely city of Lucca and we enjoyed every moment! 

    Anne
    www.example.com

  • Wedding in Ravello - Anna Sorrentino is a lovely woman - very helpful, knowledgeable and generous with her time and information. I would definitely recommend using her services - she came recommended by Carina of ClassicVacationRental.com after we stayed in her lovely villa in Ravello.

    Sarah

  • I wanted to say how much we enjoyed our trip to Italy and the Villa. We couldn’t have scripted an better week and had the perfect mix of activities and down time.

              The Villa was certainly the highlight and a perfect fit for the 21 of us. As you mentioned many times,  the outside was spectacular and we utilized every part of the grounds. While some people were poolside, others we reading in one of the many lounge areas!  

              We cannot thank you enough for arranging “Lucca” day!!  We loved riding our bikes in our own little “Peleton” and the lunch in the vineyard was one the most unique, amazing experiences I’ve ever had.

              Thank you Carina, you really enhanced how holiday

    We will be in touch for our next adventure.

    Craig
    www.example.com

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    John Doe
    www.example.com

  • Good Morning Carina: We are back from Italy now and slowly adjusting to the Pacific time zone. I just wanted to thank you for all your advice, bookings and Italian details and tips that helped make our family trip full of wonderful moments together. We had such fun in Chianti. The villa suited our family needs perfectly and Allesandra was the best property manager as well as an extremely kind and helpful person. We even managed to find Gabrialo in Gaiole that rented us eight e-bikes to ride through the small hamlets to see the countryside. Another by chance encounter was finding the San Felice Hotel nearby where we booked a birthday lunch and spent a wonderful afternoon together. Rosanna was a marval and such a lovely person. We enjoyed our dinners with her and we are all on her instagram now and making her potato salad and green beans and asparagus recipes all with Rocca di Montegrossi olive oil. The tours all worked out well, no easy task when herding eight of us around crowded cities, but they were all informative and accommodating to our needs. We particularly enjoyed the Coliseum day, St. Peter's Basilica, and discovering the gardens at the Palace Pitti in Florence as well as learning about the art of Florentine mosaics. 
    Our favourite time though was being in the villa with everyone just enjoying our surroundings. A great option when travelling with family and one we will try to do again in the near future! 
    Thank you again for all your help and guidance explaining the process of travel in Italy. I can see why you fell in love with the country and culture. 
    All the best,
    Meryl  June 2023
    ps.  Also a quick mention of Simone who drove the "kids" up to Florence. They all enjoyed him immensely and mentioned that he was so informative during the drive. He took the time to tell them about olives which they were all very interested in and now have a new appreciation for olive oil and all the different varieties of olives.   

    Meryl from Vancouver

  • Carina
    of ClassicVacationRental put together an incredible trip to Italy for my wife and me.  Carina had previously helped us in 2008 with a 2 week trip to Italy with our family of 12 people, ages from 5 - 70.  It was a wonderful experience!  So of course, we contacted Carina when we decided to take a month-long trip as a couple, with the last week including our kids and their spouses.  We gave Carina a vision of what we wanted the trip to be, with some broad parameters.....a week in Florence, experience the Palio in Siena, two weeks in the country but walking distance to a town, and then a week in the Amalfi Coast for 7 people to wrap up the trip.  Carina, as we expected, found wonderful places to stay in great locations. She also made suggestions, as we expected, of things to do and see to fill in the experience.  We believe where Catrina goes above and beyond is her intimate knowledge of Italy, and the contacts she has made there.  She has visited so many areas of Italy that she can share from her personal experience, her wins and the things she had to navigate which adds up to a great trip for her clients!!  She can truly hear a vision and map out the perfect experience!  She
    was the perfect person....again...to put together not just an excellent
    trip where you see all the things, but a memorable trip with
    yes...great locations to stay at and great experiences, but also small
    insights on where to go, things to see and do.  Her experience in Italy
    is invaluable when it comes to planning travel to Italy.  Thank you,
    Carina!  You took a bunch of thoughts and ideas in our heads and made an incredible trip out of it that our family will talk about for years to
    come!  We are very grateful.  Mary and Doug Leddon

    Mary and Doug Leddon

  • Testimonial – 2018 extensive trip through Italy -

    I just wanted to thank you again for your help planning our
    incredible Italy trip!  We all had such an amazing time and truly loved
    the food, the accommodations, the wine and the tours!  I am sure Chris and Cathy will give you feedback for the trip as well but thought i would for the parts I booked thru you and including Rome.

    Our guide, Gabrielle, for the Lucca tour was incredible.  He made the history come alive and all 8 of us thought he was great!  Lucca was charming and we only wished we had more time to explore
    and do a little shopping as well. We would have loved to spend the rest of the day roaming around, renting bikes, and do a little shopping. Definitely will have to return and visit it again.

    The BBQ lunch we had on the farm again was spectacular - literally sat on a picnic bench with our own private cook BBQing  behind
    us.  Lots of wine and food was great!

     Rome: the hotel was in a perfect location and  both of
    us couples were upgraded to suites which was a nice treat at the end of our vacay! Would definitely stay here again.

    Our first night we did the progressive dinner and we all had
    no idea what to expect.  This was one of the highlights for me and any
    foody would enjoy this tour.  Our host, Marino,took us around to places we
    would have never ventured which were all amazing and he was definitely knowledgeable and charming.  I would highly recommend this dinner tour to
    anyone!  In fact the four of us ventured out the next day and returned to one of the spots he took us to. Supplizio was a big hit!

    Kev and I had Barbara for our private tour of the Vatican and she utilized every second to give us facts and history on this amazing
    place.  She was fun and entertaining as well and we really enjoyed
    spending the morning with her and walked away with a deeper appreciation for the Vatican and the deep history.

     The four of this went on to the Colosseum and met up with
    Nina who was a little light of energy who's passion and love for what she does is very evident.  Again, the tour was full of info and history and she was great.  Unfortunately Kev and I were pretty tired and the weather was very hot so for us it was a bit too long of a day but this is by no means a complaint against her...just too much to try and fit in for one day.  

    Once again thank you for all your help planning this amazing
    bucket trip for us!  I included a couple pics for you!

    Tanja 

     

    Tanja

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