Tuscan Villa - Casa del Sole in Cortona Southern Tuscany

Tuscan Vacation Rentals – Things To Know

Nothing captures the allure of old-world Italy like staying in a Tuscan vacation rental. Click here to view the Casa del Sole property above, located in Cortona, Southern Tuscany. Hotels are lovely, but Tuscan vacation rentals allow you to experience Tuscany, Italy from a different point of view. For example, if you choose to rent a Tuscan villa, farmhouse, or large estate, you have the opportunity to see and experience Tuscany like a local Italian, even if it’s only for a week or so. Whether it’s a 17th-century farmhouse, a world-famous villa, or an apartment in the heart of the city, you can expect a view, all the amenities of modern living, and a rich dose of authenticity. Tuscan vacation rentals come in all shapes and sizes; it’s all about finding what works for you, your group and your itinerary. 

Casa di Loggia Tuscan Farmhouse Monticiano Southern Tuscany
Casa di Loggia, a Tuscan farmhouse in Monticiano, Southern Tuscany. Click for more details.

Planning your vacation to Italy can be simple but there are many factors to consider. Which museums will you visit? Which medieval towns will you day-trip to? What fabulous art will you see? What delicious Tuscan wines will you try and what vineyards will you visit? 

However, there are factors way beyond your itinerary planning that need to be considered to avoid a bad travel experience. Below, we have gathered a list of some important things to know and consider before planning your vacation to Tuscany. Or, to make it easy, contact us at Tuscan Travel Group, we have the expertise to help you design your own experience in Tuscany, without the stress.

Planning Your Trip to Tuscany

Brandy Stroh and Laura Kavanaugh of Tuscan Travel Group

At Tuscan Travel, we’ve visited Tuscany more times than we can count. We make sure to try various forms of travel, we stay at all types of villas, we dine and shop at both well-known and hidden spots, and are still discovering new and unique things to do in Tuscany. We always make sure to carve out time though, for our favorite places and people that we’ve come to know well and love. We know what works and what doesn’t. We created our business out of the excitement we get from sharing the magic of Tuscany with others. We only send our clients to places where we would send our own friends and family.

Tuscan Vacation Rentals – Things To Know & Consider

Casa di Viti Rossi is a Private Tuscan Villa in Chianciano Terme Southern Tuscany
Casa di Viti Rossi is a private Tuscan villa in Chianciano Terme, Southern Tuscany. Click for more details.


  • Tuscan Villas Cost Less – Aside from the authentic Italian experience, choosing a Tuscan vacation rental in the form of a charming villa is typically much less expensive than staying in a hotel, especially for a family or larger group.
  • Beware of Cheaper Rates – Rates that seem too good to be true…usually are. If it’s a travel agency, read reviews. If it’s a villa owner, ask about amenities and possible extra costs. Always verify that the website you’re using is authentic and safe. If you’re using a travel agent, make sure to use an agency that has personally experienced the villa and the travel accommodations that they are recommending to you. Your agent should be able to give you the tips and tricks to make your vacation a great one and prepare you for what to expect. A first-hand experience goes a long way in this regard.
  • Additional Costs for Activities – Depending on the location of your vacation rental, you may need to adjust your budget to cover transportation. Whether that be a bike rental, car rental, buses, or the cost of a tour. Many times gorgeous villas are located in hilltop-towns right outside of the city.

Space and Freedom

A Tuscan Farmhouse Estate Casa di Lusso in Barberino Val d’Elsa Close to Siena
The Tuscan farmhouse estate, Casa di Lusso located in Barberino Val d’Elsa, close to Siena. Click for more details.
Casa di Pietra is a Private Tuscan Villa in Chianciano Terme Southern Tuscany
Casa di Pietra is a Private Tuscan Villa in Chianciano Terme, Southern Tuscany. Click for more details.
  • A Relaxed & Flexible Vacation Environment – Tuscan vacation rentals typically offer a more relaxed environment with the freedom to do your own thing. There is usually more room for your group to spread out and relax. Villas tucked in the countryside are famously known for allowing you (or your private chef!) to cook your own meals with local fresh ingredients and lounge around the on-site garden and swimming pool.
  • A Travel Base – Renting a vacation villa is also helpful if you’d like a home base to come back to each night. Some days you can choose to day-trip and some days you can lounge by the pool and take in the local wine and fresh food, etc. The point is that it’s flexible, comfortable, and all up to you. However, you must plan out travel times in advance in order to make sure your day-trip destinations are within driving distance of where you’re staying.

Tuscan Vacation Rental Details

  • Is my Tuscan vacation rental a villa? Farmhouse, villa, apartment, home, hotel. These are common vacation rental types and sometimes they are mistakenly used interchangeably, so it’s good to clarify (especially if traveling as a group). Some places can sleep 10-30 people, some are divided into apartments. Tuscan farmhouses are one of Tuscany’s true treasures but it’s good to know that their rooms are typically smaller with non-vaulted ceilings as a traditional villa would have. Some properties that you’ll be staying in are outside of the main house, or inside, or divided into apartments. A good website will provide you with clear pictures so that you know what you’ll be renting. 
  • Duration of stay – Many times in Tuscany, vacation rentals have specific check-in and check-out times and must be rented for a pre-determined amount of days. For example and most typically, Saturday-Saturday. This is something to keep in mind as you view properties.
  • What amenities will my Tuscan villa have? – Make sure to ask a lot of questions. Is there daily housekeeping and is it included in the price? Will there be air conditioning and are there restricted times in using it or an additional cost? Will there be a kitchen and how equipped will it be? How does laundry service work? Is WiFi included?
Casa Storica is a Historic Tuscan Vacation Rental This 17-Century Estate is located in Monteriggioni Close to Siena Click for more details
Casa Storica is a historic Tuscan vacation rental. This 17th-Century estate is located in Monteriggioni, close to Siena. Click for more details.
  • Location – Staying in the countryside is magical and really provides an Italianissimo experience. However, it may be a 20-minute drive from a walkable town, vineyard or sights to see. If this is an issue, an apartment or villa closer to the city may be best. Or, maybe a rental car will solve all your worries. Make sure to ask about the area…is there a local store or cafe nearby, am I walking distance to a number of sights, can I utilize public transportation, etc? Ask Tuscan Travel Group about all these details when booking.
Appartamento dell’Arno is a 2 bedroom apartment in City Center Florence
The view from Appartamento dell’Arno, a 2-bedroom apartment in City Center, Florence with quite the view! Click for more details.
  • Topography – What’s the topography going to be like where you’re staying? You’re likely expecting the picturesque sun-drenched fields and cypress-lined roads if you’re staying in the countryside but your villas may be in an area that is more mountainous with forested terrain. Talking to Tuscan Travel Group or an Italian local really helps clear up any wrong assumptions that you may have. Italy is such a beautiful place no matter where you stay, but if you have planned your dream vacation around a wrong assumption, you may feel disappointed when you get there, dampening your experience.
The incredible view from our Tuscan vacation rental, La Bandita, a Farmhouse B & B located in Pienza, Southern Tuscany. Click for more details.
The equally incredible view from our Tuscan vacation rental, Casa Carina, a private villa located in Chianciano Terme, Southern Tuscany. Click for more details.
  • Neighbors? – Does your villa have neighbors or any structures blocking your view of those gorgeous Tuscan rolling hills? Any known noise that may be bothersome? Or, do you have an amazing view that beats all the rest?
Casa dei Giardini is a luxury Tuscan villa in Chianciano Terme, Southern Tuscany. Click for more details.
  • Property Host or Contact – Any Tuscan vacation rental needs to provide you with contact information for someone who speaks English and can be contacted in the case of something breaking down or an emergency. This comes standard for all of our Tuscan vacation rentals.

We hope that this article helps you as you start planning your 2020 trip to a Tuscan vacation rental. With just a little bit of planning and some advice from Tuscan Travel Group, you will successfully find yourself in a relaxing and fulfilling Tuscany vacation that you’ll remember for a lifetime.

Tuscan Travel Agency Signatures

Have questions, need advice, or want to book your group for a vacation in Tuscany? Call us at 650.644.7175 or Contact Us Here!

Here are a few more options that may help you find a Tuscan vacation rental that’s right for your group:

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