I’m aware that Florence is the biggest draw in Tuscany, but the countryside of this beautiful region has been capturing much attention in recent years for its relaxing greenery, mild climate, and soft rolling hills. This is why so many travellers have been inquiring about the best villas in Tuscany with pool and have preferred to book their accommodation outside the city.
Especially perfect for travellers who enjoy their cultural sightseeing but then want to go back to a tranquil haven for the night. All of these villas in Tuscany with pool are fantastic accommodations for your holiday in Italy, but since they are all located in the countryside (that’s one of the perks!), you will need to rent a car for your transfers. Check out Discover Cars for offers and promotions.
Villa d’Epoca Carniani
This exceptional property in the lovely Arezzo countryside comprises four villas, the smallest of which can house four guests, while the remaining three have a capacity of six people.
This wonderful villa in Tuscany is housed in a historical building and offers its guests amenities such as an infinity pool with beautiful views, surrounded by a beautiful garden to relax and a large outdoor space for a stroll, an elegant dining area, a well-equipped kitchen and a private bathroom.
Located some ten minutes’ drive from Arezzo, an hour from Florence and Siena, less than an hour from Lake Trasimeno, and an hour and a half from Assisi, this villa with pool is a perfect choice for exploring Tuscany and Umbria.
Palazzo Paolo
This large villa of some 600 sq mt offers a luxury stay for large families or a group of friends. With five bedrooms and six bathrooms, Palazzo Paolo is another one of the favourite villas in Tuscany with pool because of its prime location and fantastic amenities.
Here, you have free parking inside the property to park your rental car, an outdoor swimming pool, a garden, barbecue equipment, a games room, and basic facilities such as a washing machine, air-conditioning, and WiFi connection.

Villa Medicea di Lilliano
This wonderful century-old estate sits on the hilltops just outside Florence and belonged to the illustrious Medici family. Boasting some ten centuries of history, today Villa Medicea di Lilliano is a luxury hospitality hub, a fine winery, an olive orchard, as well as an exclusive wedding venue.
In the heart of the famous Chianti countryside, it comprises several villas, each of them equipped with modern comforts and facilities including WiFi, parking, a fully-equipped kitchen, a private bathroom, an outdoor pool, and a beautiful garden. The cosy decor will make you feel at home away from home.
Villa Le Panteraie
Villa Le Panteraie is nestled in the exclusive hills of the thermal baths of Montecatini, not far from favourite Tuscan locations such as Florence, Lucca, Pisa, Siena, San Gimignano, Vinci, Forte dei Marmi, and Volterra.
Its strategic position makes it perfect for enjoying stunning views and for exploring the whole Tuscany region, an ideal option for travellers who want to soak in the local art and history but without staying in the middle of the traffic of the big city.
This villa in Tuscany with pool has five ensuite bedrooms, six bathrooms, spa facilities, a garden, and basic equipment such as a fully-fitted kitchen, a washing machine, a TV, and WiFi connection.
Rinidia Bio
Rinidia Bio is an organic agriturismo near Siena and the beautiful Val d’Orcia. Guests are welcome to use the outdoor pool and the outdoor fitness facilities such as a treadmill and a home bike as well as relax in the private garden.
All the apartments feature facilities such as king-size beds, a heating system, air-conditioning, a fully-equipped kitchen, WiFi connection, and TV. The decor is basic and traditional for a cosy stay.
Poggio ai Gelsi
This wonderful estate is located just outside the lovely town of Pienza and is close to favourite Tuscan destinations such as Val d’Orcia, Montepulciano, Bagni San Filippo thermal baths, and the Amiata Mount, but not far from the Umbria region.
This villa is elegantly furnished and perfectly combines a traditional look with modern comforts such as all the necessary kitchen appliances, a private bathroom, a living room, air-conditioning, WiFi, and a TV with satellite channels.

Villa Maona
This spacious villa with an outdoor swimming pool in Tuscany’s Montecatini Terme area is a fantastic base for your exploration of central Italy. Housed in a historical building dating to the 19th century, it takes its name from the natural grotto located nearby, a favourite destination for hikers and guided tours.
This villa in Tuscany with pool offers a truly pampering experience because, among basic equipment such as air-conditioning, a fully-fitted kitchen, and WiFi connection, it features unique amenities like a fitness room, an outdoor fireplace, a children’s playground, and a sun terrace.
Alfresco Luxury Villa
Alfresco is a truly luxurious villa in Tuscany offering its guests a heated pool with a beautiful view and other amenities such as a lush garden, a lounge, a games room, a tennis court, a bar, and a relaxing outdoor seating area.
The estate has six bedrooms and seven bathrooms, each of them with air-conditioning, a kitchen and free WiFi.
Borgo del Faggio – Case Vacanza
This beautiful villa with pool in Tuscany is located in Montepulciano near Pienza and the Umbria region.
Thanks to its swimming pool with amazing views, a luscious garden, and a large terrace, and an interior embellished with an elegant, cosy living room and a well-equipped bathroom and kitchen, you will easily enjoy both the interior and exterior of this property.
Borgo dell’Uccellaia – Quarzo
Borgo dell’Uccellaia is an exclusive holiday home in the Tuscan countryside offering its guests a pool from where you can enjoy swimming and a fantastic view of the surrounding hilltops, a garden and a sun terrace.
With free parking on-site, barbecue facilities, a relaxing outdoor seating area and being close to the beach, it makes a great accommodation option in Tuscany to rest far from the hustle and bustle of the big city and near the sea for a walk or sunbathing in summer.
Coppa di Sopra
Featuring six bedrooms and six bathrooms, Coppa di Sopra in Santa Cristina in the Arezzo province pampers its guests with an infinity swimming pool, a relaxing terrace with a beautiful view, and a pleasantly luscious garden perfect for relaxing surrounded by nature.
The house has all the facilities to ensure a comfortable stay without having to look for anything outside, so that guests can relax and just think about sightseeing and exploring the beautiful Tuscany and Umbria regions.
