Top 10 Holiday Villas In Tuscany, Italy - Updated 2021

holiday villas in tuscany

Blessed with captivating verdant landscapes of low hills, olive groves, pristine beaches, picturesque hill towns, vineyards, and beautiful fields of bright sunflowers, Tuscany is the most famous region in Italy. It is home to several best-loved Italian cities, namely Siena, Pisa, Florence, Lucca, and many more. Art lovers will love exploring the capital Florence, as it is world-famous for its impressive Renaissance art and splendid architecture. Marvel at the magnificent Renaissance paintings at Uffizi Gallery in Florence. You can’t miss capturing your photo with the Leaning Tower of Pisa when touring through Tuscany. And, staying in a cozy holiday villa in Tuscany along with your family or group of friends will make your excursion more pleasant than usual. Check out some of the top holiday villas in Tuscany, Italy, to settle back.

1. Pleasant villa amid Tuscan hills in Pisa (from USD 242)

Tucked away in the heart of Tuscan Hills, this white-washed sprawling villa serves as an outstanding retreat that greets you to unwind during your excursion in Tuscany. Serene nature in the surroundings and vicinity to the spellbinding cities of Tuscany make this holiday villa ideal for your stay. The indoor fireplace here helps you stay warm when indoors. Have a dip in the pleasant waters of the infinity pool and feel rejuvenated. Family-friendly features, such as baby bath, baby monitor, children’s tableware, toys and books for children, and many more, help you enjoy great family time. Explore various pathways that encircle the villa. Add fun to your excursion by adding a cooking class. Also, do not miss exploring the organic kitchen garden.

Tenuta Chiudendone in Tuscany
Pisa, Tuscany, Italy
135 reviews
Entire villa 4 Beds 2 Bedrooms 2 Bathrooms
Top guest reviews
Amenities & Room:
the pool is gorgeous and the view stunning
peaceful with lovely views over the pool towards the hills
it’s a real wow moment when you arrive and see the stunning views beautiful home pool and grounds
what a beautiful stay from the pool to the views and the stylish space we couldn't have been happier
pictures do not do the view from the pool justice and the whole place is beautiful
very clean and comfortable
so clean and open
the place was clean and gorgeous
we found everything to be spotlessly clean
the house is beautiful and clean
wonderful hosts and very responsive to any requests
the hosts were responsive and lovely
they are wonderful hosts and their accommodation is without peer
isabella and francesco were amazing hosts
wonderful suggestions of where to explore by our hosts
the location is just breathtaking
located between pisa and florence it was a great location for day trips
this was a perfect location for exploring tuscany
the location is absolutely stunning and so was the house
it is a great location if you want to visit pisa and florence
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2. Charming cottage in the heart of Tuscany (from USD 89)

Set in an ancient stone quarry in Carmignano, this lovely cottage serves as a cozy accommodation to rest during your holidays to Tuscany. Tuscan-styled furniture adorn the interiors of the house, and modern installations and amenities ensure your best comfort. Cook warm, delicious meals using the grill and wood-burning oven available here. Spend a relaxing time in the garden which surrounds the cottage. Enjoy playing a game of basketball in the basketball court, which you have access to during your time here. Make sure that you visit the beautiful village of Artimino, which is just 2 kilometers (1.24 miles) away.

Charming Cottage in the Heart of Tuscany
Carmignano, Toscana, Italy
231 reviews
Entire villa 3 Beds 2 Bedrooms 1 Bathroom
Top guest reviews
Amenities & Room:
beautiful stylish space underfloor air conditioning made it so cool and comfortable
the cottage is very comfortable (we especially loved the heated floors) and the grounds are lush
best shower ever felt like we were under a waterfall and the hotwater was consistent and plentiful
property is very nice and house itself had a/c and was extremely comfortable
the cottage and property are beautiful cozy fully equipped and in a peaceful environment
extra clean house with extra clean bed sheets pillows and towels
everything was very clean
the space is very clean and well decorated
the house was beautiful the bed was very comfortable and everything was clean and tidy
facilities are clean tidy and the beds are comfy
cristina was a wonderful host
cristina was a great host
she was super accommodating and kind
she was very kind and nice
very friendly and helpful host
a lovely apartment in a lovely location
we absolutely love this space and location
florence is a 20 minute train ride away and there is free parking near the train station
vinci is a beautiful drive from this location
a beautiful setting and excellent location in the heart of tuscany
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3. Sprawling abode in Chianti hills (from USD 292)

If you are a big group of 14 vacationing in Tuscany, stay in this beautiful, big villa to enjoy authentic Tuscan countryside experience. Typical terraced olive groves present in its surrounding grace the house. Unwind in the hot tub and have a pleasant time reading in the enchanting garden here. Capture spellbinding views of the Chianti hills and Arno Valley from the scenic terrace of the villa as you feast on barbecue. Have fun playing in the waters of the pool. Enjoy playing a game of golf in the golf course, which is just a 30-minute drive away.

Villa Oliveta - Tuscan villa in the Chianti hills
Loro Ciuffenna, Toscana, Italy
138 reviews
Entire villa 7 Beds 5 Bedrooms 3 Bathrooms
Top guest reviews
Amenities & Room:
it has enough room to sleep 12 comfortably and with 2 people sharing the sofa beds even 14
wonderful large kitchen/dining room with a fireplace (wood) which we used
the villa was well appointed with everything that we needed for a comfortable stay
everything is clean and it has a true tuscan charm
very clean house and very great garden
the house was clean and the setting beautiful
the villa was very clean and is well equipped
the villa was described accurately and was very clean and tidy
the owners were kind and helpful
if you have any questions he's more than happy to help and is extremely responsive
matteo was a fantastic host
in addition to this matteo was extremely helpful throughout pre & post booking
matteo was a fantastic host at this beautiful villa
perfect location close to firenze siena arezzo and cortona
we had a wonderful time in this delightful location and loved the nearby loro ciufenna with its weekly market
wonderful villa in an amazing location with exceptional hosts
we would absolutely come back and recommend this place to friends
we stayed a week and it was easy access to almost any place we chose to visit
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4. Idyllic retreat with recreational facilities in Siena (from USD 597)

If you are looking forward to experience serenity during your upcoming holidays to Tuscany, opt for this luxurious villa amid lush green landscape. Have a dip in the calm waters of the pool here that overlooks the rolling hills of Tuscany. Enjoy the opportunity to experience the old Chianti lifestyle. The abode not only offers you modern amenities for a comfortable stay but also offers you various recreational opportunities to make your time here memorable for the lifetime. Enjoy family photo sessions here and learn to play tennis from the professional coach. Also, hone your art and cooking skills by attending art and cooking classes, and sample wine at the organic winery present here.

Idyllic Siena Retreat-Splendid View
Siena, Tuscany, Italy
199 reviews
Entire villa 6 Beds 6 Bedrooms 5 Bathrooms
Top guest reviews
Amenities & Room:
evenings on the deck and days by the pool were amazing
the pool was wonderful and the views absolutely stunning
the views were spectacular and the rooms were all comfortable and included their own bathrooms which was nice
the house is really cozy with beautiful views
the rooms were big for everyone to have their own space the views are absolutely breathtaking
the house itself is clean rustic and airy
the house is spacious clean and well furnished
the property was excellent; warm clean spacious and perfect for a group of cyclists
the property was perfect - comfortable clean and peaceful and eugenia and family were warm and welcoming
the host is extremely accommodating and kind
the hosts were very communicative and provided many helpful tips
our hosts were welcoming and couldn't have done more to help us
alessandro and his mother are the sweetest most gracious hosts
alessandro and his parents are the best hosts and made us feel very welcome
good location to travel around the region
the location was perfect for our visit
perfect location to explore siena and surrounding towns
an amazing property in an amazing location
i highly recommend this location
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5. Tuscan-styled paradise amid vineyards and olive groves in San Gimignano (from USD 450)

Amid scenic vineyards and beautiful olive groves, this spacious villa is a perfect retreat for a family or group of 12 individuals. Experience pleasant Tuscan setting with peculiar rustic Tuscan-styled architecture adorning the interiors of the home. Ancient trees, exquisite gardens with eye-catching meadows, terraces, and cozy outdoor areas make the villa a serene place to settle back. Enjoy swimming with your kids in the pool and savor delicious barbecue delicacies on the terrace. Take in the views of towers of San Gimignano as you relax. Visit San Gimignano Communal Palace, which is 0.3 miles (0.48 kilometers) from here.

San Gimignano villa with pool, 5 rooms en suite, A/C, wi-fi, panoramic view
34 reviews
villa 5 Bedrooms 6 Bathrooms
Top guest reviews
Amenities & Room:
plenty of room with all the basics necessary to enjoy your stay
stunning views and exceptional old world villa attention to detail in every room and garden
the infinity pool with views over vineyards which also enjoys great sunsets was a real bonus
we loved the table tennis and football as well as the infinity pool with its amazing views
the kitchen is well equipped which allows one to take advantage of the local markets
the villa was very clean throughout and the kitchen well equipped for preparing meals when dining in
we would certainly return to this wonderful home and host
the hosts are amazing and super hospitable
we enjoyed a wonderful meal cooked for us arranged by alessandro who was very helpful
alessandro was very helpful and an excellent host
alessandro is a gracious host and was available if we had any questions while respecting our privacy
the location can't be beat: in the countryside but close to lovely san gimignano (and a handy supermarket)
the location of the property makes for easy sightseeing for florence pisa and sienna
one could find fancier and more expensive places but this suited our family perfectly
lovely property in beautiful location alessandro very friendly and helpfulwe enjoyed a very relaxing holiday
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6. Elegant home above the walled village of Lucca (from USD 607)

Experience the charm of staying in a 12th-century abode by booking this beautiful villa that sits on the hills of Tuscany and above Lucca. Please your eye with captivating nature views as you sip on a cup of hot coffee on the terrace. The villa is spacious for a group or family of 10 visitors. The sprawling pool here invites you to enjoy splashing in the water with your family. Learn the techniques to make savory Tuscan cuisines by attending the cooking class here. Explore Pinocchio Park, which is 3.2 miles (5.14 kilometers) away, with your kids.

XII century villa on the hills above Lucca with chef,cooking lesson,wine tastin
63 reviews
villa 6 Bedrooms 3 Bathrooms
Top guest reviews
Amenities & Room:
the old stone building kept us cool and comfortable although there was no ac and the weather was hot
the pool was a wonderful retreat after a day of sightseeing
monica and giovanni were wonderful and attentive hosts
' i just wanted to thank you for your kindness and friendly hospitality
monica and giovani are fantastic hosts and they treat you like family
giovanni and monica were so helpful with any need that we had
they are hard-working kind and generous of spirit
there is a reason this place has so many positive reviews
the farmhouse is also close to the mountain villages lucca and lots of other interesting and beautiful places
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7. Stone-built sanctuary with pergola and pool in Montalcino (from USD 483)

Are you longing to experience the Tuscan countryside? If yes, choose to stay in this elegant 17th-century Tuscan villa. Built with stones, it imparts a countryside feel. Utilize all modern amenities, such as web access, washing machine, iron, ironing board, and more, for your convenience. Sit back in the shade of the pergola relaxing after having a dip in the pleasant waters of the pool. Also, you can prepare barbecue delicacies and devour them leisurely.

Villa at Montalcino,stunning wiews!!! Wi-fi,
Montalcino, IT
5 Bedrooms 5 Bathrooms

8. Seafront haven with infinity pool in Elba Island (from USD 498)

Fulfill your dream to stay in a beachside abode during your sabbatical in Tuscany by booking this luxurious villa. The presence of oleanders, Mediterranean bush, pines, and rosemary in the surroundings and its vicinity to the gorgeous beaches of Fetovaia, Seccheto, and Cavoli enhance its beauty. 19th-century antiques, beautiful paintings, prints, and other elegant décor grace the interiors of the villa. Reconnect with nature by spending some time in the sunny and tree-shaded areas of the garden here. Enjoy cooking your meals in the well-equipped kitchen, whose doors take you to the garden. Go for a beach excursion to spellbinding Cavoli beach, which is just 0.4 miles (0.64 kilometers) away, and visit pleasant Seccheto village, which is at a walking distance of five minutes.

Seafront property with infinity pool near the beach in the best location of Elba
Campo nell'Elba, EB, IT
64 reviews
villa 8 Bedrooms 4 Bathrooms
Top guest reviews
the owner is super kind and the house keeper as well
we were welcomed very warmly uncomplicated and friendly by the owner and her daugther
we were welcomed very warmly uncomplicated and friendly by the owner and her daugther
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9. Lavish dwelling with stone terrace, pergola, and pool in Pescia (from USD 245)

Create lasting memories of your holidays to Tuscany by choosing to stay in this traditional farmhouse. The elegant abode not only comprises a living room, kitchen, two bathrooms, dining rooms, three bedrooms, and various modern facilities, but also features an exquisite sprawling terrace, swimming pool, and pergola to make your time here enjoyable. Have al fresco dinner on the stone terrace and pergola with your beloved family, and please your eyes with sweeping views of the Tuscan countryside and hill village. Visit Lucca, which is just a 35-minute drive away, and explore various walking trails.

Beautiful Tuscan farmhouse with stunning view and pool
44 reviews
villa 3 Bedrooms 2 Bathrooms
Top guest reviews
Amenities & Room:
la spinosa is peaceful and tranquil with stunning views and an inviting pool
the property itself is fantastic but the views the gardens and the pool area are something else
truly lovely tuscan farmhouse with the most amazing view beautiful gardens lovely pool and interesting wildlife
the house itself is authentic tuscan updated with a nice sitting area with a tv
the house was very nice and clean with all what we needed
nice walks good restaurants the host was amazing
paul was super helpful and easy to contact
paul was extremely friendly and helpful when we arrived
paul was a charming man - very helpful but unobtrusive
everyone we met was very friendly and welcoming
shopping for food is also easy with lots of options ca 20 minutes away
g florence lucca pisa for day trips but equally it is a perfectly peaceful location to just be
the best one was a 10 minute walk into a small town of castelvecchio
we loved the isolated location with fantastic views
a great place
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10. Beautiful getaway with pool near Siena

Experience the leisure of staying in an authentic Tuscan rustic-styled home by choosing to stay in this old yet elegant farmhouse. Artistic décor adorns the interiors of the villa. Sunspots in the main garden and hammock beneath the chestnut tree greet you to unwind here. Have a great exploring the herb garden outside the kitchen. Enjoy swimming in the sprawling pool and watch captivating views of the landscape and scenic nature. Visit the City of Siena, which is just 20 kilometers (12.42 miles) away, to watch Palio.

Beautiful Villa + Pool near Siena
La Cetina, Toscana, Italy
62 reviews
Entire villa 3 Beds 3 Bedrooms 2 Bathrooms
Top guest reviews
Amenities & Room:
relaxing by the pool eating dinner in the loggia and exploring the tuscan hills
the villa surroundings were exactly what we expected and the pool and patio was always kept clean
the pool would would be great place to relax when the weather is warm
the pool was a huge hit and we cooked most nights in the small but well equipped kitchen
the house was clean and there were plenty of towels and comfortable beds
the house was clean spacious and with a lovely garden
the house has anything that you need and it was all clean and tidy
the house itself was clean and the hosts had prepared it well for us
the house is very spacious and well equipped and the pool was beautifully nestled into the landscaped garden
gemini and gabor were wonderful hosts
the hosts gave us great tips which we followed and proved to be enjoyable as promised
this home is amazing a beautiful setting gorgeous home and wonderful hosts made our stay very memorable
the hosts were very friendly and accommodating having dinner with them is warmly recommended
most importantly gesine and gabor are charming hosts
quiet and peaceful retreat just 25 minutes from central siena
the location was perfect as we visited wineries in toscana almost everyday
the house was very quiet and a beautiful relatively short drive away from siena (~30 minutes)
gesine & gabors place is a very cute classic tuscan farm house
if you like to stay in a quiet countryside italian house this is the place
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Escapade in Tuscany

Tuscany is a beautiful region in Italy with abundant natural and cultural attractions. And, staying in a holiday villa will make your sabbatical here full of fun and comfort. So, be quick, book one of these top holiday villas in Tuscany, Italy, and head out for an exciting excursion in Europe.

Disclosure: Trip101 selects the listings in our articles independently. Some of the listings in this article contain affiliate links.

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Manjiri Kochrekar is a travel blogger from India. She loves exploring and learning various destinations, their history, culture, and peculiarities. Writing is her passion, which means she enjoys...Read more

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