Maybe it’s the impossibly green, rolling hills. Or the clusters of stone villas with terracotta roofs. Maybe it’s how the sky, with its painterly clouds, seems to stretch on forever. Can any place feel as perfect as Tuscany? This Italian region hardly needs an introduction—it’s one of the most visited spots in the country. It may not be undiscovered, but it makes up for that in just about every other way. One of the most authentic ways to experience this landscape is by staying at one of the best Airbnbs in Tuscany, where checking into a centuries-old villa isn’t a question of how, but which one.
Vogue’s Favorite Airbnbs in Tuscany:
For Couples Traveling Together: Cipressini in Chianti, from $673 a night
For a City Option: Luxury Apartment in Siena, from $300 a night
For an Al Fresco Pizza Oven: Villa La Fonticina in Rignano sull’Arno, from $495 a night
For a Picturesque Honeymoon: The Casina in Sovicille, from $984 a night
For an Infinity Pool: Villa Sarah Tenuta Melograni in San Gimignano, from $1,567 a night
For Lush Outdoor Spaces: Hilltop Views in Metato, from $533 a night
For Quintessential Countryside Design: Tuscany Farmhouse in Cetona, from $348 a night
If you’re planning a trip to the Tuscan countryside, a historic rental makes a perfect home base. What can you expect from these charming places? Everything: outdoor pizza ovens, infinity pools overlooking vineyards, wood-burning fireplaces, and architectural details like exposed wood beams, clay tiles, and arched doorways.
Below, discover 16 of the most atmospheric stays in Tuscany, many of which are great for groups making a memorable trip to Italy together.
Luxury Apartment
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Siena’s historic city center is unlike anywhere else in Italy. Take the chance to sleep inside a medieval fortress by booking this apartment, which spans the top two floors of a traditional Sienese building. It has three large bedrooms (one even has French doors leading to a garden terrace), and features like ceiling beams and terracotta floor tiles add to the architectural charm.
Rooms: 3 bedrooms, 2 bathrooms
Amenities: Washer, AC, heating
Location: Siena
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Cipressini
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These two 17th-century stone houses are perfect for couples traveling together who want to stay on the same property but still have some privacy. (They can also be rented separately as one-bedrooms.) The interiors have classic Tuscan charm, but the outdoor areas really stand out with stunning views of Chianti’s rolling vineyards—best enjoyed from the pool, of course.
Rooms: 2 bedrooms, 2 bathrooms
Amenities: Washer, central AC, fireplace, outdoor dining area, BBQ, sun loungers, pool, free parking
Location: Chianti
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Beautiful Country House
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Experience a side of Tuscany that many miss at this four-bedroom countryside house with views of the sea (on clear days, you can even spot Elba and Corsica in the distance). The beach is just 20 minutes away, and even closer is a charming local village with cozy cafes and shops. On the property, enjoy an afternoon by the infinity pool and shared meals at the long dining table next to a large window. The property is new this year, so you’ll be among the first to enjoy its beautifully designed interiors.
Rooms: 4 bedrooms, 3 bathrooms
Amenities: Bathtub, outdoor shower, washer, fireplace, fire pit, BBQ, pool, free parking
Location: Riparbella
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The Chianti Sun
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Halfway between Florence and Siena, this 100-year-old farmhouse is a Tuscan dream. Olive and cypress trees surround the property, and the home (though renovated) keeps original details like open-beam ceilings, brick arches, and terracotta floors. Sole del Chianti can host groups of 16 to 20 people and features impressive amenities like an automatic Shiatsu massage bed.A mosaic-lined whirlpool overlooks green, rolling hills.
Rooms: 12 bedrooms, 9 bathrooms
Amenities: Pool and hot tub, washer/dryer, central air conditioning and heating, property manager, breakfast, outdoor shower, sauna, foosball and ping pong table, BBQ, pizza oven, ice machine, EV charger, pool house, gym, massage table.
Location: Tavarnelle Val di Pesa
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Villa Sublimis
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This 19th-century villa just west of Siena is as impressive as they come. It sleeps up to 12 guests and sits in the hilltop town of Casole d’Elsa. Spend your days relaxing by the pool or sharpening your cooking skills with an in-villa cooking class. When you’re ready to stretch your legs, take an afternoon trip to explore the nearby medieval village—considered one of the most beautiful in all of Tuscany.
Rooms: 6 bedrooms, 5.5 bathrooms
Amenities: Heated pool, washer/dryer, central air conditioning and heating, outdoor shower, BBQ, outdoor dining area, sun loungers.
Location: Casole d’Elsa
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La Balza
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If you love old, beautiful homes, you’ll fall for this 1700s farmhouse built from historic Tuscan stone. The two-story villa has a wraparound terrace with panoramic views, a barbecue, a private pool, and a garden—perfect for enjoying fresh cheeses or hosting your own wine tasting.
Rooms: 3 bedrooms, 2.5 bathrooms
Amenities: Outdoor shower, washer, mosquito net, indoor fireplace, dishwasher, fire pit, BBQ, outdoor kitchen, pool, sun loungers.
Location: Chianti
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Villa La Fonticina
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Sleeping up to eight guests, this 19th-century stone villa is an elegant choice for a group exploring Tuscany together. The home is full of charm: a wood-burning oven, an adjoining stable and barn, and hand-reclaimed terracotta floors are just a few highlights. On sunny days, head to the garden for a spritz and a nap in the hammock, or take a few leisurely laps in the swimming pool.
Rooms: 4 bedrooms, 3 bathrooms
Amenities: Bathtub, washer, mosquito net, ping pong table, indoor fireplace, central heating, portable fans, fire pit, hammock, BBQ, outdoor kitchen, pool.
Location: Rignano sull’Arno
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The Casina
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This design-focused villa is set inside a historic tower and has been renovated to include a glass pavilion overlooking the Tuscan countryside. Though The Casina can sleep up to four people, it would make a fantastic honeymoon spot thanks to the stunning views, infinity pool, and atmospheric pergola. Plus, Siena is just 15 minutes away by car.
Rooms: 1 bedroom, 2 bathrooms
Amenities: Infinity pool, steam room, hot tub, washer/dryer, air conditioning, heating, breakfast, indoor fireplace, bikes, BBQ.
Location: Sovicille
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Villa Sarah Tenuta Melograni
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Gaze at the towers of San Gimignano from this magnificent villa that sleeps up to 10 guests. It’s hard to pick the home’s best feature—the four-sided infinity pool, outdoor kitchen, and dramatic dining table overlooking rolling vineyards all come to mind. And since you can book extra on-site activities like a private chef or massage, you may never want to leave.
Rooms: 5 bedrooms, 5 bathrooms
Amenities: Pool and whirlpool, washer/dryer, air conditioning, outdoor shower, indoor wet bar, foosball table, BBQ, ice machine.
Location: San Gimignano
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The Barn of Montesoli
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High ceilings, arched doorways, wooden floors—this handsome villa in the countryside near Siena is everything you imagine when you dream of the perfect Tuscan getaway. The home offers plenty of spaces to unwind, from sun loungers by the pool terrace to the vegetable garden. Why not enjoy a game of bocce ball before grilling dinner and eating at the patio dining table?
Rooms: 4 bedrooms, 4 bathroomsAmenities: Pool, washer, air conditioning, heating, BBQ, bocce ball court, sun loungers.
Location: Siena
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Hilltop Views
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Skip the usual and head further west to the hidden village of Metato. More specifically, to this hilltop farmhouse. This magical home comes with a plunge pool and a covered balcony overlooking the Mediterranean Sea. Design touches like terracotta floors and original wood fixtures add to the historic feel. If you want to explore the beaches of the Versilia coast, make this your peaceful home base.
Rooms: 3 bedrooms, 2 bathrooms
Amenities: Washer/dryer, indoor wood-burning fireplace, BBQ, outdoor dining area, pool.
Location: Metato
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Stone Farmhouse
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Surrounded by olive groves and a lush park, this countryside farmhouse is perfect for anyone looking to disconnect. The property dates back to the 19th century and features charming details like exposed stone and colorful tiles throughout. Read by the fireplace or enjoy a picnic on the large lawn—at this home, there’s no activity too relaxing.
Rooms: 5 bedrooms, 6 bathrooms
Amenities: Washer, ping pong table, air conditioning, central heating, indoor wood-burning fireplace, BBQ, sun loungers, outdoor dining area, fire pit.
Location: Sarteano
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Villa in Montepulciano
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This villa is part of an agriturismo (one of the first in the area), built on the site of the old church of Santa Maria del Serraglio, founded in 1536. The antique fireplace is one of the home’s most beautiful features, with the wooden ceiling beams coming in a close second. Pour a glass of wine and head outside to enjoy the pool, which feels suspended on a rolling hillside, surrounded by vineyards and groves.
Rooms: 2 bedrooms, 2 bathrooms
Amenities: Washer, air conditioning, heating, indoor fireplace, backyard, shared pool and hot tub.
Location: Montepulciano
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Tuscany Farmhouse
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This country house dates back to the second half of the 19th century and is just three kilometers from the village of Cetona. From the living room to the bedrooms, the cozy interiors capture the nostalgia of the space, and a large lawn provides a scenic spot for games and gatherings. While you’re outside, keep an eye out for frequent visitors like pheasants, hares, and fawns.
Rooms: 5 bedrooms, 3 bathrooms
Amenities: Outdoor shower, washer, ping pong table, hammock, BBQ, outdoor dining area, pool, sun loungers.
Location: Cetona
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Traditional Stone House
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Shaded by centuries-old trees and full of a cozy, homey feel, this traditional stone house can sleep up to 11 guests (and it’s pet-friendly!). From the massive fireplace to the exposed wooden beams and stone archways, every detail feels like it’s from the past. The outside is just as inviting, with a large private pool and plenty of spots for quiet moments or aperitivo hour.
Rooms: 5 bedrooms, 4 bathrooms
Amenities: Bathtub, washer, mosquito net, record player, indoor wood-burning fireplace, central heating, fire pit, BBQ, pool, outdoor furniture and dining area.
Location: Cortona
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Church of the Vaioni
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More like an ancient church than a traditional villa, this historic rental set in the Tuscan countryside is one of the most unique in the region. The home is designed with a loft structure on two separate mezzanines. Outside, there’s an equipped kitchen with a wood-burning barbecue and fragrant gardens. Perhaps the most distinctive feature is the internal staircase, built by the Antica Fonderia Michelucci, a famous foundry from the time.
Rooms: 2 bedrooms, 2.5 bathrooms
Amenities: Washer, record player, central AC and heating, indoor wood-burning fireplace, BBQ, outdoor kitchen and dining area, sun loungers.
Location: Pistoia
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Frequently Asked Questions
Here is a list of FAQs about the 16 Airbnbs in Tuscany that let you live out your villa dreams written in a natural conversational tone
1 What kind of villas are we talking about Are they all super fancy
Most are classic Tuscan farmhouses or historic villas with modern amenities They range from cozy romantic cottages to large estates with private pools and vineyards Fancy is relativethink rustic elegance rather than palacestyle luxury
2 Do these villas have WiFi and air conditioning
Almost all do but its worth doublechecking the listing Many rural villas have spotty cell service so they often invest in reliable WiFi Air conditioning is common in bedrooms but not always in living areas
3 How many people can these places sleep
They vary widely Youll find options for couples up to large groups Many are ideal for family reunions or friend trips
4 Are the pools heated
Usually not Most pools are seasonal and unheated If you need a heated pool filter your search or message the hostsome offer it for an extra fee
5 Is it safe to book an Airbnb in Tuscany
Yes but stick with Superhosts or highly reviewed listings Check cancellation policies and read recent reviews about cleanliness and host communication
6 Whats the best time of year to rent one of these villas
MayJune and SeptemberOctober are perfect warm fewer crowds and the countryside is green or harvestready JulyAugust is hot and busy but pools are a lifesaver
7 Do I need a car
Absolutely These villas are in the countryside not in town centers A car lets you explore hilltop villages wineries and supermarkets Just be ready for narrow winding roads
8 Are there any hidden costs I should know about
Yes Watch for cleaning fees security deposits and tourist taxes Some hosts charge extra for heating firewood or pool heating Always read the full price breakdown
9 Can I cook in these villas
Most have fully equipped kitchens with stoves ovens and basics like pots and pans But don