Who didn’t dream about staying in a villa in Italy? And what better area to look for than the magical hills of Tuscany? With this article, we’ve collected some of the Tuscany villa rentals that are available for anyone who’s planning to spend their vacation in a holiday villa in Tuscany. As you can imagine, there are many more places where to stay in Tuscany, and if you’re looking town by town, you’ll actually be overwhelmed by the option. However, on this list, we wanted to make sure we’re bringing only the best of the best!
15 Best Tuscany villa rentals – Where to stay in Tuscany?
I know, I know… You want to know where to stay in Tuscany. Based on ratings, facilities, location, and design, we’ve picked for you some stunning places. If you’re looking for a private villa in Tuscany, to enjoy your holiday without anyone around, you’ll find an option for that too. You’ll also find the type of Tuscany villa rental where more people can stay, but also plenty of villa in Tuscany with private pool.
Those who love these charming villas on top of the hill, surrounded by olive groves and vineyards, might want to consider visiting an agriturismo Tuscany has. There are plenty of agriturismos in the region, and we’ve also listed a few that hit a certain rating for holiday stays. To make it easier, agriturismos mean farmhouses, so you’ll be looking at some farmhouse rentals Tuscany offers below too!
1. Villa Cora – Florence
If you’re looking for a Tuscany holiday villa, and you want one that’s in Florence, we have Villa Cora for you. One of the most charming, best rated, beautiful 5* villas where to stay in Tuscany if you’re looking for a less country-side style, more elegant villa. Villa Cora is a 19th-century building that’s surrounded by a beautiful park area and an outdoor swimming pool.
Now, if it’s important for you that the accommodation is close to the city center, but it’s only 2 km from it. You can be in the central area in 20 minutes by walk, or about 10 minutes by bus. At Villa Cora, you’ve got beautiful rooms decorated in classic style, with antique furniture, and they are equipped with everything from air-conditioning to Tv, wifi, and a minibar.
At Villa Cora, you also have wellness options which include a Turkish bath, fitness center, and sauna. Also, massage and beauty treatments are available for you. The hotel has a private restaurant serving Italian cuisine and Tuscan wines. On top of that, you can get at the bar drinks and snacks around the day.
Villa Cora address: Viale Machiavelli 18, 50125 Florence, Italy
2. Castello Di Vicarello
If you’re looking for the most amazing villas in Tuscany to stay at, and you want something that’s elegant yet absolutely countryside style, and offers an amazing experience, Castello Di Vicarello is for you! Castello Di Vicarello has a 9.4 rating on booking.com, and it truly offers an amazing Tuscan experience! The formal castle was transformed into a luxurious Mediterranean retreat that is also pet friendly.
Castello Di Vicarello offers a spa, and infinity pool surrounded by lush gardens, elegant suites, and rooms with the highest quality furniture and indoor decorations. You can find here a restaurant with an outdoor seating area, which gives you a beautiful view of the Tuscan hills too. The gourmet menus are based on local Tuscan recipes using the castles’ own wines from the local vineyards.
The flora of this place is amazing well, with beautiful flowers, lemon and olive trees, and all melting into the Tuscan countryside views. There’s an amazing breakfast served every day, and they organize cooking classes as well as other activities. Castello Di Vicarello is 11 km from Paganico and 36 km from Grosseto. It’s an amazing and high-end place to run away from the world in a wonderland.
3. Borgo San Felice – Castelnuovo Berardenga
Borgo San Felice is a beautiful pick for Tuscany villa rentals, and if you’re looking for a charming holiday villa in Tuscany, you will most like fall in love with this one. Now, Borgo San Felice is in the heart of the beautiful wine region, Chianti, so if you’re looking for farmhouse rentals Tuscany offers in a wine region, to join some wine tastings, and eat some great Tuscan food, you want to book this one!
The hotel boasts 2 restaurants, of which il Poggio Rosso offers gourmet cuisine and they’ve got a selection of over 500 types of fine wines. They also have a somewhat more informal restaurant, Osteria del Grigio, which offers modern Tuscan cuisine and they are open at lunch and dinner time. Oh, and there’s also a bar on-site.
This accommodation has 5 stars, so there’s more than the charm that you’ll find here! At Borgo San Felice you can find a health center too, which offers numerous beauty treatments and they specialize in wine therapy as well as massage. The rooms are fully equipped and beautiful. As for the location, the hotel is set on a hill surrounded by olive groves and vineyards. A dream! Also, if you’re looking at which bigger city is close by, Siena will be only 30 minutes away!
Borgo San Felice address: Loc San Felice, 53019 Castelnuovo Berardenga, Italy
4. Podere Lucignano Secondo Agriturismo – Gaiole in Chianti
We had to include a bonus accommodation, which is one of the cutest Tuscany villa rental and the best agriturismo in Tuscany. Podere Lucignano Secondo Agriturismo houses are so cozy and the surroundings are beautiful. The building itself is located on the hills of Gaiole in Chianti and the building is from 1898. There are a total of two rustic apartments.
If you have read any love stories of Tuscany then this is the type of villa you would imagine in the books. It is equipped with everything you need, from the kitchen to the bathrooms and all of the accessories. The outside terrace also includes a BBQ. The owners even offer to deliver groceries in case you don’t wish to go to the city to buy them.
What can you do here? Well, besides enjoying the beauty of the building and rooms, you can also enjoy the view of the vineyards and Tuscan hills. This place is specifically for a private retreat, something you could rent with your friends as it fits over 10 people. Podere Lucignano Secondo Agriturismo has a rating of 9.8 stars. If you were wondering where to stay in Tuscany, closer to Siena, Podere Lucignano is one of the best farmhouse rentals Tuscany offers.
Podere Lucignano Secondo Agriturismo location: Strada Comunale 24, 53013 Gaiole in Chianti, Italy
5. Villa Medicea di Lilliano – Grassina
Villa Medicea di Lilliano is another beauty on our Tuscany villa rentals list. If you’re looking to rent a villa in Tuscany for holiday, one that’s not completely private, you’ll love Villa Medicea di Lilliano. The accommodation is located in Grassina, which is right outside Florence, only 13 km away from the city. Since it’s not private accommodation, you will have a continental and American breakfast served in the morning.
At Villa Medicea di Lilliano you’ll have fully equipped accommodation with Wifi and private parking as well as a seating area, TV, and private bathroom. Some of these rooms have a private patio or/and balcony that have pool and garden views. With that said, you will have an outdoor swimming pool at your disposal, as well as you can just relax and enjoy the garden, or go cycling, maybe hiking. A high-rated Tuscany holiday villa to consider.
Villa Medicea di Lilliano address: Via Lilliano e Meoli 82, 50012 Grassina, Italy
6. Rosewood – Castiglione del Bosco
If you’re still asking where to stay in Tuscany, our other recommendation is Rosewood. This place will be especially attractive for those who are looking for a villa in Tuscany with a private pool because the luxury hotel in the Tuscan countryside is offering that too! Rosewood is about 12 km from Montalcino, in Castiglion del Bosco, which is just north of Siena.
For those searching for a villa in Tuscany for a perfect, relaxing holiday, this place is a top pick. Beautiful views, an infinity pool, comfortable rooms, and everything you need for a relaxing vacation. Rooms have private bathrooms, and seating areas and all of them offer views over the Tuscan hills. Rosewood is a 5-star hotel, and they offer generous breakfast, while also the restaurant offers traditional Tuscan food and wine.
There’s a fitness center, sauna, and Turkish bath as well. Rosewood offers wine-tasting tours in its own cellars and winery. Oh, and before you leave, you better know that the accommodation is situated on the UNESCO site, the beautiful Val d’Orcia, so you can drive around to see the most beautiful side of Tuscany, go cycling, hiking, or even fishing.
Rosewood address: Località Castiglion del Bosco, 53024 Castiglione del Bosco, Italy
7. Relais Borgo Santo Pietro – Chiusdino
Relais Borgo Santo Pietro is another gem when it comes to Tuscany villa rentals. This is also a luxurious place to stay since we preferred to pick a handful of Tuscany Italian villa holiday rentals that can actually leave you speechless. Relais Borgo Santo Pietro is just outside Chiusdino, in the Tuscan countryside. The property lies on 5 hectares it’s actually dating back to the 13th century.
Relais Borgo Santo Pietro features a swimming pool along a bar and outdoor terrace. The rooms and suites are really elegant and beautiful, all decorated with Baroque style and stunning, hand-painted wall art, as well as silk tapestries. Of course, all rooms are well-equipped and they feature modern bathrooms too.
In the mornings at this holiday villa in Tuscany, you can enjoy a great breakfast, as well as you can try the organic Tuscan cuisine at dinner in Santo Pietro’s restaurant. Moreover, you’ll have spa facilities with a hot tub, an outdoor tennis court, and a bbq area. Also, the rooms have a common lounge area with a patio too. A relaxing, elegant, and historic place to stay in Tuscany. Also, Relais Borgo Santo Pietro is about 40 minutes away from Siena.
Relais Borgo Santo Pietro address: San Galgano Loc. Palazzetto, 53012 Chiusdino, Italy
8. Relais & Châteaux Il Falconiere – Cortona
I’m sure most of you heard/seen/read the famous book Under the Tuscan Sun by Frances Mayes which takes place in the charming village of Cortona. Well, if you’re a fan of this piece, I’m sure you’ll be happy to hear about Relais & Châteaux Il Falconiere which is situated in the beautiful Cortona. When we’re looking for farmhouse rentals Tuscany offers, in other words, the best agriturismo in Tuscany, we want to find places where we can actually experience the Tuscan countryside life.
At Relais & Châteaux Il Falconiere is a place like that. A 17th-century manor that lies just outside the town and boasts a Michelin-starred restaurant, along with a luxury wellness center, and outdoor and indoor pools. The Etruscan Spa offers a sensory shower, Turkish bath, and sauna, as well as massage and beauty treatments. Yes, it’s not literally the Tuscan country life, because as we’ve revealed, it’s a luxury place, but with that, you’ll have the possibility to experience Tuscan life at a more comfortable, more beautiful, high-end level.
The Relais & Châteaux Il Falconiere has also vineyards and olive groves, and the rooms are located in different places around the estate. The restaurant is set in a covered orangery and they serve delicious traditional Tuscan dishes. On top of that, you can sample the estate’s own Baracchi wines, and roll into a cooking class as well. Relais & Châteaux Il Falconiere is about 2.5 km from the historic center of Cortona, and 15 minutes away from Lake Trasimeno.
Relais & Châteaux Il Falconiere address: Loc. S. Martino 370, 52044 Cortona, Italy
9. Villa La Massa – Bagno a Ripoli
Villa La Massa is another villa rental in Tuscany you can consider. This one isn’t a private villa that you could have for yourself, but it is indeed a beautiful place to stay if you’re looking for a villa in Italy to spend your holiday. The luxury villa, Villa La Massa is set in a green area, featuring a garden, a swimming pool, a spa, and a restaurant that has a terrace overlooking the Arno river.
Villa La Massa is located about 8 km from the historic center of Florence, so it’s easy to get there if you’re flying into Florence. The villa features colorful indoor decoration, classic-style fabrics, and carpeted floors, and some come with wood-beamed ceilings. At the restaurant, you’ll have a buffet breakfast where they serve traditional dishes and homegrown products.
There are also cooking classes organized by the chef, and you can also roll into a wine tasting in the wine cellars of the estate. Moreover, at Villa La Massa you can enjoy the spa which includes a Turkish bath, sauna, and hot tub. You can roll into beauty treatments and massage as well, or you can use the tennis court and the fitness center too. On top of that, you get bikes for free at the property to do some exploring in the area.
Villa La Massa address: Via della Massa 24, 50012 Bagno a Ripoli, Italy
10. Agri Resort & SPA Le Colline del Paradiso – Vaglia
Agri Resort & SPA Le Colline del Paradiso is another of the Tuscany villa rentals that you should definitely consider. The accommodation is 18 km away from Florence, set between the Tuscan hills. If you’re looking for the best agriturismo in Tuscany, you should definitely consider this too. It’s another of those that isn’t a traditional agriturismo, but it’s the type of Tuscany holiday villa where you can relax while enjoying the beautiful region.
Agri Resort & SPA Le Colline del Paradiso features a seasonal outdoor swimming pool, restaurant, bar, and shared lounge in Vaglia. This is a 5-star resort that offers room service and luggage storage as well. There’s free parking, the rooms are well equipped and they come with private bathrooms, and some have terraces too. There’s a continental breakfast available in the morning, and a hot tube indoors.
Agri Resort & SPA Le Colline del Paradiso address: Via del Viliani 756, 50036 Vaglia, Italy
11. Castello di Bossi – Castelnuovo Berardenga
Castello di Bossi is a gem when you’re asking where to stay in Tuscany, especially if you’re looking for a villa in Tuscany with a private pool, olive groves, peace, and quiet. The accommodation is located in Castelnuovo Berardegna, which is close to Siena, Arrezzo, and some other beautiful locations like the Valle d’Orcia.
Castello di Bossi is a villa in Tuscany where you can enjoy privacy and the Tuscan countryside. They offer wifi, air conditioning, and access to the garden, where you can find the outdoor swimming pool. The units have a fully equipped kitchen and dining area, fridge, kettle, stovetop, and seating area. The farm stay of Castello di Bossi offers a la carte Italian breakfast, BBQ, tennis court, and the possibility to go cycling.
Castello di Bossi address: Località San Felice, 53019 Castelnuovo Berardenga, Italy
12. Villa Fonteintanata – Miemo
Villa Fonteintanata is located close to the Tuscan coast, Volterra, San Gimignano, and Livorno. Pisa is 60 km away, while Livorno is 69 km away. Volterra is the closest beauty you should see and that’s only 40 minutes away from the property. Villa Fonteintanata is a Tuscany holiday villa that is a so-called sassi house, so a typical stone house.
If you’re looking for a villa in Tuscany with a private pool, closer to the area of Florence, and close to the seaside, then this one would be a lovely option. Villa Fonteintanata offers private parking, wifi, kitchen equipped with a dishwasher, oven, and kettle as well. There’s a flat-screen TV, hammam, and an outdoor swimming pool where you have space to relax and enjoy the Tuscan sun.
Villa Fonteintanata address: Via Provinciale di Miemo, 28, 56040 Miemo, Italy
13. Villa Vignacce – Bettolle
Villa Vignacce is one of those Tuscany villa rentals we couldn’t leave off this list! The accommodation is located in Bettolle, which is also really close to Siena. If you’re looking for a more budget-friendly Tuscany Italian villa to spend your holiday at, Villa Vignacce is one to consider if you want to stay in the area of Siena.
Villa Vignacce features private parking and wifi, and some of the units are fitted with air conditioning. There’s a TV, washing and coffee machine, as well as a well-equipped kitchen. At the country house, you can enjoy a great Italian breakfast, and use the sun terrace. You can use the swimming pool, relax, tan, go hiking, go cycling, or even use the BBQ facilities. A place to pick if you want more privacy, and fewer guests sharing the accommodation!
Villa Vignacce address: loc vignacce 6, 53040 Bettolle, Italy
14. Agriturismo San Lorenzo – Serre di Rapolano
We still didn’t run out of choices for the best holiday villa in Tuscany, and the best agriturismo in Tuscany. Here’s one that you’ll love if you’re looking for rustic feelings, and traditional food that you can find only in agriturismos in Italy. At Agriturismo San Lorenzo you’ll find that! A characteristic stone village basically with multiple buildings on-site, which is located close to Terme di Rapolano spa town.
Agriturismo San Lorenzo is close to Siena, and it’s a place you should absolutely check out. The accommodation features an outdoor swimming pool, rooms with a private bathroom, a rustic vibe with wood beams, and stone walls. The views around the agriturismo are amazing, and they also produce their own olive oil, which is another great reason to visit! You could also find delicious local Tuscan dishes, homemade pastries, and other delicious food to try.
Agriturismo San Lorenzo address: Località San Lorenzo, 53040 Serre di Rapolano, Italy
15. Al Giardino Degli Etruschi – Chiusi
Al Giardino Degli Etruschi is a beautiful Tuscany villa rental set in a historic farmhouse which is dating back to the early 19th century. The accommodation is set on a 1-hectare park on a hilltop which is overlooking the Chiana valley. Al Giardino Degli Etruschi is a villa in Tuscany with a private pool, so if you’ve been looking for this type of farmhouse holiday, you’ll love this one!
Now, the accommodation is about 3 km away from Chiusi, and 20km away from the famous wine town, Montepulciano. The interesting in this farmhouse is that each room is named after one of the Etruscan gods, and they come with wood-beamed ceilings and a geothermal system for heating and cooling. The rooms are also well equipped, and they have views over the garden and the Tuscan countryside.
Al Giardino Degli Etruschi address: Località Dolcianello 32, 53043 Chiusi, Italy
Bonus: Villa Ancora Tenuta Lonciano – Gualdo
Wrapping up our Tuscany villa rentals with the last villa in Tuscany that made our list, Villa Ancora Tenuta Lonciano. This villa is located in Gualdo, and it’s a boasting accommodation with a private pool, terrace, and gardens. If you want to get away from the world, this place could work perfectly, and it’s only about 45 km from San Gimignano, which in our experience is one of the most beautiful areas to stay in the Tuscan countryside.
If you’re looking for private accommodation for your holiday, Villa Ancora Tenuta Lonciano has 2 bedrooms, 3 bathrooms, and it’s fully equipped with everything you might need. It was a dining area and a fully equipped kitchen, and they’d also provide linen and sheets. If you are looking to visit a bigger group that can fill the villa, you can easily rent the whole accommodation for yourselves.
Villa Ancora Tenuta Lonciano address: Via di Vara e Lonciano, 50019 Gualdo, Italy
Wrapping up the 15 best Tuscany villa rentals
So, we hope you’ve found the perfect inspiration and we’ve found the answer to your question about where to stay in Tuscany! If you’re looking to rent a villa in Tuscany, step by at an agriturismo (farmhouse rentals Tuscany offers) or you’re looking for a relaxing holiday villa in Tuscany with a private pool, we’ve listed the 15 best Tuscany villa rentals you can book safely through the booking platform we’ve linked under each place. If you’re visiting Tuscany, make sure to check out our articles for the best towns to visit in Tuscany, as well as spas, and some city guides, such as for Siena or Florence!