The best Airbnbs in Tuscany, Italy range from luxury rentals in Florence to exotic villas, vineyards, and farmhouse accommodations in the countryside. If you’re looking for a unique stay in Tuscany, this article has got you covered with lots of beautiful vacation rentals on VRBO and Airbnb with pools, wineries, and Tuscan scenery.
Located in the center of Italy, Tuscany is an enchanting region filled with gently rolling hills, historic vineyards, luxury villas, and tasty food. If it’s not already on your bucket list, these Tuscany Airbnbs will surely change your mind. Stay in a centuries-old castle or villa with a pool overlooking a lush valley or an authentic Tuscan farmhouse with farm animals and agriculture. Whether you’re planning a romantic getaway like a honeymoon or a family/group trip, these types of Tuscany vacation rentals will make your trip to Italy much more authentic and memorable than a traditional hotel.
Here, we’ve ranked some of the coolest Airbnbs in Tuscany, which include places like Florence, Lucca, Montepulciano, Pienza, Pisa, San Gimignano, Siena, and more. Now, let’s find you a beautiful vacation rental in Toscana, Italia!
The Coolest Airbnbs in Tuscany: Top Vacation Rentals in 2021
Here are the best Airbnbs in Tuscany by category, taking into account different amenities, trip types, and budgets. The subsequent sections will cover each listing in more detail.
Top Airbnb in Tuscany: Tuscan Villa with Outdoor Pool
Best Luxury Rental Tuscany: Florence Airbnb with Duomo Views
Top Romantic Airbnb in Tuscany: Luxury Villa with Infinity Pool
Best Tuscany Airbnb for Large Groups: Siena Retreat on a Vineyard
Best Cheap Airbnb in Tuscany, Italy: Historic Honeymoon Rental in Tuscany
Coolest Tuscany Villa Airbnb: Unique Tuscany Villa with Private Pool
Best Airbnb Vineyard in Tuscany: Farmhouse Rental with a winery
Best Tuscany Airbnb on the Coast: Boat and Breakfast
Most Unique Airbnb in Tuscany: Unique Italy Treehouse Rental
12 Best Airbnbs in Tuscany, Italy
If Tuscan countryside homes, castle-turned-Airbnbs, romantic villas with pools, and luxury rentals in Florence all sound good to you, get excited! Below are some of the most unique stays in Tuscany:
1. Romantic Treehouse Airbnb in Tuscany
Location: Florence, Tuscany, Italy
Rates from: $303 per night
Accommodates: 2 guests
Experience the magic and allure of Tuscany from this Airbnb treehouse rental in Florence. This luxury treehouse is in a tranquil wooded area and is decked out with a wraparound deck and outdoor furniture for you to get some fresh air while you enjoy some fresh air and fine wines.
The inside of the treehouse is incredibly unique. There are floor-to-ceiling windows everywhere, which adds lots of natural lighting so you can enjoy the view. Also, take advantage of the fireplace, outdoor kitchen and patio, rain shower, air conditioning, private pool, and chalk walls so that you can leave your mark for the next guest. If you’re seeking an Airbnb Tuscany near Florence, it doesn’t get any better than this unique treehouse rental.
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2. Villa Fonteintanata – A Tuscany Airbnb with a Saltwater Pool
Location: Casino di Terra, Toscana, Italy
Rates from: $461 per night
Accommodates: 6 guests
For luxury travelers, it doesn’t get any better than this Airbnb villa in the heart of Tuscany. Located in Casino di Terra, Villa Fonteintanata is a private luxury retreat hidden away in a forest for up to six guests. The interior is truly one of a kind, with eclectic decor and furniture that, when put together, just happens to work! This accommodation exudes character at every turn.
This Tuscan villa rental has a living room, full kitchen, three bedrooms, three bathrooms, a dining room, a family room, and an outdoor area with a private pool overlooking the Tuscany mountains. There are also three outdoor areas, including a patio with furniture if you’d rather dine outside! With so much luxury and personality, this private villa is easily among the best Airbnbs in Tuscany.
Read next: Top Airbnb Rentals with a Private Pool
3. Luxury Tuscany Vacation Rental with Infinity Pool
Location: Radicondoli, Toscana, Italy
Rates from: $299 per night
Accommodates: 6 guests
Infinity pools are all the rage because they are incredibly unique and picturesque, and this one in Tuscany is no different. This romantic villa can host six guests and features a private infinity pool overlooking the mountains. Imagine waking up to a sunrise from here!
This Tuscan accommodation is truly enchanting and is fully equipped with luxurious amenities. Take advantage of the two bedrooms, three bathrooms, an outdoor patio with furniture, a full kitchen, a living room, and a dining room. This Tuscany Airbnb is also pet-friendly!
For a romantic stay in Italy, look no further than this exotic Tuscan villa on Airbnb.
4. Charming Farmhouse Airbnb in Tuscany with Vineyard Views
Location: Greve in Chianti, Toscana, Italy
Rates from: $182 per night
Accommodates: 5 guests
This charming farmhouse rental in Greve in Chianti is situated inside of a barn, making it one of the coolest places to stay in Tuscany. It can host five guests and looks like something out of a fairy tale and has an incredibly romantic feel.
The home has excellent views of Chianti’s Hills and features a large garden and outdoor area with a grill. The house was recently restored, and while it does have historic remnants throughout, it’s mostly modern now. Guests are encouraged to utilize the garden when they cook, which is filled with cucumbers, tomatoes, and other fresh produce. Is this one of the most beautiful Airbnb villas in Tuscany, Italy? 100%!
Read next: Coolest Wine Regions Worldwide
5. Contemporary Toscana Airbnb Apartment in Florence
Location: Florence, Tuscany, Italy
Rates from: $296 per night
Accommodates: 6 guests
This contemporary Airbnb apartment for rent in Florence can host six guests at a time and is incredibly central. It’s next to both Ponte Vecchio and a train station so guests can easily get around the city.
This Tuscany vacation rental has lots of amenities, including heating, air conditioning, an outdoor patio with great views, and even a treadmill. The décor throughout the home also feels elegant, as there’s a vibrant chandelier in almost every room! If you’re planning the ultimate Tuscany getaway, there’s no better home base to spend at least a couple days than this Toscana Airbnb.
6. Siena Airbnb Retreat in the Heart of Tuscany
Location: Siena, Tuscany, Italy
Rates from: $545 per night
Accommodates: 10 guests
Located in Siena, this stunning Tuscan accommodation is one that you won’t want to overlook. This villa can host ten guests at a time, making it an ideal place to stay at if you are traveling around Italy with a larger group.
The home was built in the 18th century and is nestled in an area where a family has been growing grapes and olive trees for ten generations and counting. Guests will have access to a private pool, private wine tasting at the winery, private parking, and can even request private chefs or butlers if needed during their stay. The excellent location coupled with the stunning villa views makes this among the coolest Tuscany Airbnbs in Siena.
7. Historic Apartment Vacation Rental in Bagnoregio – One of the Best Honeymoon Airbnbs in Tuscany
Location: Bagnoregio, Lazio, Italy
Rates from: $182 per night
Accommodates: 2 guests
Looking for a romantic Airbnb rental for a honeymoon in Tuscany? This vacation rental in Bagnoregio, a popular day trip from Tuscany, is incredibly unique and will make you feel like your staying in your very own Airbnb Tuscany castle.
The interior is one of a kind and features exposed stone walls everywhere, exuding the accommodation’s vast history. You’ll truly feel like you are living inside of a castle!
This house for rent is in a historic village and is filled with unique amenities. Guests will have access to a private outdoor terrace, a luxury bathroom, and more. If you are looking for a unique place to stay in and around Tuscany, this historic apartment rental has got you covered.
8. Boat & Breakfast Accommodation – Top Airbnb on the Tuscany Coast
Location: La Spezia, Italy
Rates from: $351 per night
Accommodates: 8 guests
During your next visit to Italy, consider staying on a boat. This one in La Spezia, right on the border between Liguria and Tuscany, is incredibly unique that the host even calls it a ‘boat and breakfast’! Eight guests can stay here at a time, so it’s much bigger than it looks!
Guests will have epic views of the water and access to a full kitchen and a Bose speaker system so they can jam to music while taking in the windswept coastlines. There’s no better way to wake up every morning than to the sound of the waves outside your window. In many ways, Italy’s maritime heritage can be just as impressive as its viticulture, so you’ll want to experience them both during a visit to Tuscany and Liguria.
Coolest Luxury Yacht Airbnb Rentals
9. San Lorenzo Villa Airbnb in Tuscany with Jacuzzi
Location: Monticchiello, Toscana, Italy
Rates from: $424 per night
Accommodates: 6 guests
Looking for a cool Airbnb in Tuscany with a Jacuzzi and pool? This epic villa in Monticchiello can host six guests and has been recently renovated and refurbished with lavish amenities.
This UNESCO Heritage accommodation boasts unique architecture, looking like something out of a fairytale. It has three bedrooms, three bathrooms, an outdoor pool, jacuzzi, full kitchen, living room, and dining room.
The outdoor space at this villa is what makes it well worth the price. It’s overgrown yet well taken care of, so there’s beautiful greenery and flowers everywhere you look. Plus, there are spectacular views out of every window. What more could you want in a top Tuscany Airbnb rental?
10. Romantic Medici Apartment for Rent in Florence
Location: Florence, Toscana, Italy
Rates from: $242 per night
Accommodates: 2 guests
If you’re traveling with a significant other, this romantic apartment Airbnb in Florence is the perfect launchpad. The ceiling is a classic Italian fresco painting from the 17th century, which is an incredible view to wake up to every morning.
This Firenze Airbnb feels incredibly historical and even has a spiral staircase from the 13th century. Guests will have access to a Smart TV, jacuzzi, king-size bed, air conditioning, and more. The kitchen comes fully equipped, so guests don’t have to worry, and breakfast is also included! Is this among the best Airbnbs in Tuscany, Italy? It sure is!
11. Charming Airbnb Tuscany Villa with Pool
Location: Castiglion Fiorentino, Tuscany, Italy
Rates from: $279 per night
Accommodates: 8 guests
This Airbnb Tuscany villa with pool in Castiglion Fiorentino is incredibly spacious, accommodating eight guests. There are four bedrooms, three bathrooms, a unique dining room, fully equipped kitchen, and a living room. Plus, there’s a private outdoor pool that overlooks the rolling Tuscan countryside, olive trees, and vineyards.
Amenities are abundant and include a fireplace, outdoor dining table, coffee machine, hot tub, free parking, and more. For a classic Tuscan getaway, this villa is truly the perfect place to experience the best of this rustic countryside. In just a short drive, guests can get to some nearby villages that sell authentic Italian food. However, after stepping foot inside this Tuscany Airbnb on a vineyard, it will be hard to leave!
12. Florence Airbnb Penthouse with Duomo Views
Location: Florence, Toscana, Italy
Rates from: $515 per night
Accommodates: 4 guests
Last but not least on this round-up of the best Tuscany Airbnbs is this penthouse in Florence, which happens to be right next to the Duomo. From the luxury rooftop patio, watch the sunrise or the sunset directly over the Duomo, a view that not many tourists will ever get to experience!
This apartment Airbnb rental in Florence boasts a living room, full kitchen, two bedrooms, one and a half bathrooms, and a dining room in addition to the panoramic views. There is also air conditioning, a sound system, smart TV, and an espresso machine. With so much charm and stunning views, you won’t find a Tuscany vacation rental quite like this one in Florence!
Read next: Coolest Penthouse Rentals around the World
Coolest Airbnbs in Tuscany, Italy: Florence, Siena, San Gimignano + More
Have you ever stayed in a unique vacation rental in Tuscany? Let me know in the comments or on Insta, as I’m always looking to add to this round-up of the best Tuscany Italy Airbnb rentals!
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