Last Updated October 28, 2021 10/28/2021

14 Dreamy Airbnbs in Tuscany

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One of the most popular regions of Italy, Tuscany is a vast region with medieval hilltop villages, vineyard-covered landscapes, and countless historic treasures. The food and the wine produced here is often ranked among the world’s best. For the ideal base, choose from any one of these fabulous Airbnbs, whether you’re looking for a magnificent stay in the city or the countryside.

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Borgia Castle in Tuscany - Passignano Sul Trasimeno
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Borgia Castle in Tuscany, Italy

Borgia Castle in Tuscany - Passignano Sul Trasimeno

If you’ve ever wanted to live like royalty, if only temporarily, this magnificent castle residence is a fairytale property that lies alongside a lake on the border of Tuscany and Umbria. There are nine hectares of parkland with gorgeous gardens that surround the castle, along with an outdoor pool and tennis court. The interior is stunning with frescoes and antique furnishings, multiple large fireplaces, and a large living room that overlooks the lake. There’s also a terrace overlooking the lake and picturesque surrounds, along with many other high-end features. It’s perfect for a wedding or any event, with seven bedrooms and large halls for entertaining and formal dinners.

B&B in a Charming Castle near Siena - Monteroni d'Arbia
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B&B in a Charming Castle Near Siena

B&B in a Charming Castle near Siena - Monteroni d'Arbia

While you won’t get the entire castle to yourself, you can rent a room (B&B-style) at this beautiful castle with a seasonal saltwater pool. Cooking classes, bicycle rentals, wine and food tastings, and dinners (two times each week) can all be arranged too. The double room includes your own private bathroom down the hall and a generous breakfast buffet featuring local items like fresh ricotta and pecorino cheese, ham, and homemade goods, including tarts, breads, and croissants that can be enjoyed with marmalades made from fresh fruit that comes from the property’s garden.

Boutique Penthouse Near the Duomo - Florence
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Boutique Penthouse with Duomo View

Boutique Penthouse Near the Duomo - Florence

This boutique penthouse is right next to the Duomo and from its incredible rooftop patio you can watch sunrises and sunsets right over Florence’s most iconic symbol. It’s filled with luxuries and breathtaking views, complete with a full kitchen that has an espresso machine, a Smart TV and sound system. There are two bedrooms, sleeping up to four, but this one might just be the ultimate place for honeymooners.

Typical Tuscan Country House - Greve in Chianti
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Typical Country House

Typical Tuscan Country House - Greve in Chianti

Enjoy a farm stay in a restored typical Tuscan country house located on one of the hills in Chianti that dominates the Arno river valley. It offers lush views of the green landscape and the heart of Florence in the distance, with stays in independent three-bedroom apartments that have full kitchens, a washing machine, and a private furnished outdoor space for dining. You’ll have access to a BBQ grill as well as a shared pool with panoramic views. Enjoy walks through the property’s woods and a grass field for outdoor games and sports too.

Podere Piazza - Siena
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Podere Piazza Siena, Tuscany, Italy

Podere Piazza - Siena

Enjoy a stay in a three-bedroom home that was part of a larger estate established in the 15th century. Podere Piazza was constructed in the early 17th century, the former residence of a nobleman who was appointed Archbishop of Siena in 1747, and it still bears his coat of arms today. While it’s within walking distance of the city of Siena, it boasts an uninterrupted view of Tuscan’s rolling hills, set on a ridge that overlooks an incredible panorama that includes Monte Amiata, Crete Senesi, and the hamlets of Montalcino and Montepulciano. It accommodates up to six and includes all the modern amenities like Wi-Fi and a TV with Disney+ and Netflix, along with a full kitchen and BBQ grill.

Sull'Albero a Pochi Minuti da Firenze - Florence
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Splendida Casa sull'Albero a Pochi Minuti da Firenze

Sull'Albero a Pochi Minuti da Firenze - Florence

Enjoy the best of both worlds at this luxury treehouse, immersing yourself in nature while being close to the city of Florence. Accommodating up to two guests, it makes an idyllic couples’ stay, located in a peaceful wooded area while boasting floor-to-ceiling windows and a wrap-around furnished deck for enjoying the views indoors or out. You’ll have a rain shower, air-conditioning, and an indoor fireplace too. Outside, the common area includes an outdoor kitchen, private pool, and tennis court.

Privacy and Relax at Villa Fonteintanata - Casino di Terra
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Privacy and Relax at Villa Fonteintanata

Privacy and Relax at Villa Fonteintanata - Casino di Terra

Located in the heart of Tuscany, this spectacular villa offers a private luxury retreat hidden in the forest. It accommodates up to six in three bedrooms with a unique interior that oozes character throughout. The outdoor spaces are especially enticing, including a private pool that overlooks the mountains and a furnished patio for outdoor dining. The host is an excellent cook who can even prepare dinners and tastings.

Infinity View - Casale
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Infinity View - Casale, Tuscany

Infinity View - Casale

This romantic villa looks like something out of a dream with its own private infinity pool that overlooks the Tuscan mountains and glorious sunrises. It’s also perfectly situated within easy reach of popular destinations like Florence, just 35 minutes away. There are multiple places to relax and enjoy the outdoors while you’re here, including a garden and an outdoor dining area with a grill. Sleeping up to six in two bedrooms, both with en-suite bathrooms, you’ll have a modern kitchen, living room with a fireplace, TV, and Wi-Fi too.

Idyllic Retreat with Splendid View - Siena
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Idyllic Siena Retreat

Idyllic Retreat with Splendid View - Siena

A stunning wine estate villa, this six-bedroom home for up to 10 guests provides a luxurious secluded retreat on a property where a 10th generation family is still growing organic grapes and olive trees. It’s the place to experience the “old Chianti lifestyle” as it was 300 years ago as the hosts note, with the main circa 1760 villa still inhabited by the original owners. There are also activities on-site like wine tasting at the organic winery, art and cooking classes, and a professional tennis coach for lessons. A private chef, butler, masseuse, driver, and just about any other service or excursion can also be arranged.

L'Incanto di Civita - Bagnoregio
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L'Incanto di Civita

L'Incanto di Civita - Bagnoregio

This one might be the most romantic of all Tuscan Airbnbs, perfect for a honeymoon. It sits in the hilltop village of Civita di Bagnoregio, which can only be accessed via a pedestrian bridge. Once you’ve stepped through the ancient wooden door, you’ll feel as if you’re staying in a castle, with stone walls, exposed wooden beams, and brick floors throughout. You’ll know you’re not in ancient times, however, as it has modern amenities like Wi-Fi, TV, a washing machine, and an ultra-lavish bathroom. Plus the view from the terrace can’t be beat and your host even supplies an assortment of tasty breakfast foods, all included in the rate.

Rooftop Attic with 360 Degree View - Lucca
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Rooftop Attic with 360 Degree View

Rooftop Attic with 360 Degree View - Lucca

An elegant rooftop apartment set within a medieval building in Lucca’s historic center, from here you’ll enjoy a panoramic view over the city which includes one of its main attractions, the 125-foot-tall Guinigi Tower, which is just outside your window. Access it by elevator, rare to find in these historic buildings, and enjoy plenty of character with coffered ceilings and a gorgeous inlaid parquet floor. It sleeps up to two guests in a spacious bedroom with a queen-size bed and comes with all the modern essentials, including a full kitchen with a dishwasher and washing machine, a/c, free Wi-Fi, and a flat-screen TV.

The Artists' Tower 4 Pax - San Gimignano
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bedroom with a view at The Artists' Tower

The Artists' Tower 4 Pax - San Gimignano

The Artists’ Tower is located in San Gimignano, a stunningly well-preserved medieval walled hilltop village often referred to as the “City of Towers” with its skyline of 14 stone towers dramatically rising out of the Tuscan countryside. You’ll be staying in a medieval building in the center of town, completely surrounded by the enchanting towers on the famous Piazza della Cisterna. It sits on the third floor and includes two bedrooms, sleeping up to four, and two bathrooms, one of which has a Jacuzzi tub. You’ll have a full kitchen and a living room that showcases a fabulous view over the hills and towers, as well as a veranda for relaxing with a picturesque view over the piazza. Wi-Fi, TV, and a washing machine are included too.

Montepulciano Centro Storico - Montepulciano
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View from Montepulciano Apartment

Montepulciano Centro Storico - Montepulciano

An affordable one-bedroom for four on the top floor of a historic building, this apartment is located on the main street of Montepulciano, a dreamy hilltop town famous for its Vino Nobile red wine. Just next door there’s an outstanding restaurant while shops are right across the street. You’ll have breathtaking views over it all and an interior with all the modern comforts. It boasts gorgeous details, including woodworking that was done by the host himself who is happy to provide advice and even help you with dinner reservations.

Alice's Homes, Apartment Schiara - Fezzano
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Rooftop with a view

Alice's Homes, Apartment Schiara - Fezzano

This beautiful modern one-bedroom apartment overlooks the small fishing port in pretty Fezzano village. The highlight is the furnished terrace which includes a dining table, umbrella, and loungers, all of which can be enjoyed with a sea view. You’ll enjoy that same view from the bedroom along with everything you need to feel at home. There’s a kitchenette with a coffee maker, a washing machine, Wi-Fi, TV, and air-conditioning.

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