Renting a Villa in Tuscany - a Guide

by Mike Bringhurst, Designer Travel

Dreaming of the perfect Tuscan getaway? Renting a villa in Tuscany is the way to go! With rolling hills, world-class wine, and charming medieval hill-top towns, it’s the ultimate way to soak in the Italian countryside. Here’s everything you need to know to plan your perfect villa vacation.

Below is a guide for all the things to consider before renting a villa in Tuscany.

When to go to Tuscany

Timing is key! Tuscany shines brightest between May and October, with spring flowers or golden autumn vines stealing the limelight. July and August are hot, bustling with tourists, and coincide with Italy’s national holidays like Ferragosto (mid-August), when many Italians take vacations. Also keep in mind that 2025 is the jubilee and Italy is likely to be extra crowded. If you like fewer crowds and milder weather, consider May, early June, or September.

Where to Stay in Tuscany? Pick the region first.

Tuscany is filled with picture-perfect spots, each with its own charm and character. Here’s a roundup of some of the best regions and towns to help you decide where to stay.

Known as the “Town of Fine Towers,” San Gimignano is famous for its medieval skyline. Staying here feels like stepping into a fairy tale. Pros? The views are incredible, and it’s conveniently located for exploring nearby Siena or Volterra. Cons? It tends to be busy with day-trippers, so early mornings and evenings are your best bet for quieter moments.

This dreamy hilltop town is a haven for wine enthusiasts. Surrounded by vineyards that produce the renowned Vino Nobile, it’s a perfect blend of relaxation and indulgence. Take wine tours, stroll cobblestone streets, and soak in nearby hot springs like Bagno Vignoni. The only drawback? It’s further off the beaten path if you’re planning to visit major cities.

Chianti is Tuscany’s legendary wine region, offering rolling vineyards, charming villages, and some of the best food and wine you’ll taste anywhere. Towns like Greve and Castellina are ideal home bases. Pros? You’ll wake up to stunning countryside views and have endless wine-tasting opportunities. Cons? It’s quieter compared to bigger towns, so nightlife isn’t a strong suit here.

If you’ve read or seen Under the Tuscan Sun, you’ve likely dreamed of staying in Cortona. This small hilltop town is filled with charm, sweeping views, and that quintessential Tuscan vibe. Besides exploring its delightful streets, it’s a great spot to visit Lake Trasimeno or the nearby province of Umbria. It can be small for those seeking more bustling towns, but that’s part of its appeal!<

Lucca is a gem for history buffs and those who love a quieter, less touristy vibe. Its well-preserved Renaissance walls are perfect for cycling or strolling with a gelato in hand. A pro tip? Lucca’s central location makes it a great launching point for trips to Pisa or the beaches of Viareggio. Cons? It doesn’t have the dramatic hilltop views of other Tuscan towns.

The Val d’Orcia is postcard Tuscany. Rolling hills, cypress-lined roads, and quaint villages like Pienza and Montalcino await. Don’t miss the opportunity to explore the local Pecorino cheese and Brunello di Montalcino wine. It’s idyllic, but you’ll definitely need a car to get around.

Moving toward the coast, Maremma is Tuscany’s untamed side, with wild beaches, thermal baths, and a more rustic feel. Argentario, a stunning peninsula, offers luxury with seaside resorts and rugged cliffs. Kick back at Porto Ercole or explore hidden coves by boat. The pro? Fewer crowds compared to inland regions. The con? It’s less central for day trips inland.

No matter where you choose to stay, each region in Tuscany offers its own version of paradise. Pick what fits your vibe—or better yet, rent a car and venture out to visit a few to truly experience it all!

Know Where to Book

Avoid the “too good to be true” deals you might find on questionable websites or even Airbnb. You never know what you’ll get or who you’ll be dealing with when booking online. Instead, work with a reputable travel agency and property manager who specializes in Tuscany. They’ll ensure the property matches your expectations, from location to amenities and that you’re protected with a solid contract. At Designer Travel, we have trusted connections for Tuscan Villas and can help with all the planning so your trip goes smoothly. Most villas require a minimum 7 night stay but there are some with a shorter minimum.

What to Look For in a Tuscan Villa

Beyond the obvious; number of bedrooms, bathrooms and square footage, check for recent renovations. Authentic charm is great, but you’ll want modern comforts too. Air conditioning is a must in the hotter months, and if there’s a pool, confirm if it’s heated. Read contracts carefully for cleaning fees, damage policies, minimum night stays and cancellation rules. Using a trusted travel advisor like Designer Travel in Salt Lake City, Utah is a must to negotiate pricing, contracts and a person to call if something goes wrong.

Transportation in Tuscany

Here’s the deal—public transportation is sparse in Tuscany’s countryside. Renting a car is essential for day trips to outlying vineyards, charming villages, coastal towns or nearby cities. Driving through Tuscany is part of the adventure, with stunning views at every turn!

How to Start Planning

Feeling overwhelmed? That’s where Designer Travel comes in. With trusted connections and experience backed by over 35 years in the industry, we’ll help you find the perfect villa, plan your itinerary, and make your Tuscan dream a reality. Get ready for a vacation where every sip, sunset, and hilltop view feels straight out of a movie. Tuscany awaits!

If you’re dying to go to Tuscany and are considering renting a villa, we can help. We can also plan out your perfect custom itinerary so give us a call! Call 801-935-8652, email us at in**@de******************.com or book a discovery call to start planning.