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Perhaps it’s the rolling hills, impossibly green and endlessly undulating. Maybe it’s the clusters of stone villas and terracotta roofs. Or even how the sky and its painterly clouds seem to carry on and on in perpetuity. Can any destination evoke such a portrait of perfection as Tuscany? The Italian region needs little introduction and zero PR—it’s among the most visited areas in the country. What it lacks any sort of undiscovered quality it more than makes up for in, well, everything else. Among the most authentic ways to experience the landscape’s splendor is by staying at one of the best Airbnbs in Tuscany, where checking into a centuries-old villa is all too possible.
Vogue’s Favorite Airbnbs in Tuscany:
- For Couples Traveling Together: The Holly in Chianti, from $303 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 $1567 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
As the great Diane Lane purported in the 2003 cult classic Under the Tuscan Sun, “who wouldn’t want to buy a villa in Tuscany?” But if a real estate investment isn’t in the cards at the moment, settle for the next best thing by renting one of the many villas currently listed on Airbnb. What to expect at such extravagant accommodations? All of it: al fresco pizza ovens, infinity pools overlooking the countryside, wood-burning fireplaces, and architectural appurtenances like exposed wood beams, terracotta tiles, and arched doorways.
Below, discover 15 of the most atmospheric stays in Tuscany, many of which are well-suited for groups making a memorable journey to Italy together.
The Chianti Sun
Halfway between Florence and Siena, this 100-year-old farmhouse is a Tuscan idyll. Olive and cypress trees surround the property, and the home (though renovated) retains 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 and a mosaic-clad whirlpool overlooking verdant 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
Villa Sublimis
This 19th-century villa just west of Siena is as impressive as they come. Accommodating up to 12 guests, the vacation rental sits in the hilltop town of Casole d’Elsa. Spend your days relaxing by the pool or sharpening your culinary chops with an in-villa cooking class. When you’re ready to stretch your legs, take an afternoon day trip to get lost in the surrounding medieval village (which is 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
La Balza
Those with a proclivity for old, beautiful homes will fall for this 1700s-era farmhouse crafted from historic Tuscan stone. The two-story villa features a wraparound terrace for panoramic views complete with a barbecue, private pool, and garden (a tip-top spot for savoring fresh cheeses and 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
Villa La Fonticina
With a guest capacity of eight, this 19th-century stone villa makes an elegant destination for a group exploring Tuscany together. The home is chock-full of charm: A wood-burning oven, adjoining stable and barn, and hand-reclaimed terracotta floors are just a few of its highlights. On sunny days, head out to the garden for a spritz and 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
The Casina
This design-centric villa sits within a historic tower and has been renovated to include a glass pavilion that looks out over the Tuscan countryside. Though The Casina can accommodate up to four people, it would make a top-notch honeymoon spot thanks to the eye-popping 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
Villa Sarah Tenuta Melograni
Gaze upon the towers of San Gimignano from this magnificent villa hosting up to 10 guests. It’s tough to pick which detail of the home is its pièce de résistance—the four-sided infinity pool, outdoor kitchen, and dramatic dining table overlooking rolling vineyards in the distance all come to mind. And since you can book extra on-site activities, like a private chef or massage, you ll never really have 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
The Barn of Montesoli
High ceilings, arched doorways, wooden floors—this handsome villa in the countryside near Siena is everything you imagine when you dream up the ideal Tuscan getaway. The home comes with plenty of spaces for unwinding, from sun loungers by the pool’s terrace to the vegetable garden. Why not enjoy a game of bocce ball before grilling up dinner to enjoy at the patio dining table?
Rooms: 4 bedrooms, 4 bathrooms
Amenities: Pool, washer, air conditioning, heating, BBQ, bocce ball court, sun loungers.
Location: Siena
Hilltop Views
Eschew the norm and head farther west for the hidden village of Metato. More specifically: to this hilltop farmhouse. This magical home comes with a plunge pool and covered balcony that have views of the Mediterranean Sea, while design details like terracotta floors and original wood fixtures cement the historic ambience. If you’re keen to explore the beaches of the Versilia coast, make this your tranquil home base.
Rooms: 3 bedrooms, 2 bathrooms
Amenities: Washer/dryer, indoor wood-burning fireplace, BBQ, outdoor dining area, pool.
Location: Metato
Stone Farmhouse
Enveloped by olive groves and a lush park, this countryside farmhouse is just the ticket for those looking to unplug. The property dates back to the 19th century and features photogenic details like exposed stones and vibrant tiling throughout its various spaces. Read your book by the fireplace or enjoy a picnic out on the sprawling lawn; at this home, there’s no pursuit too leisurely.
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
Villa in Montepulciano
This villa is part of an agriturismo (one of the first in the area), which sits on the old church of Santa Maria del Serraglio and was founded in 1536. The antique fireplace is among the home’s most beautiful details, with the wooden ceiling beams coming in a close second. Pour a glass of wine and head out to enjoy the property’s pool that feels suspended on a rolling hillside, hugged by vineyards and groves.
Rooms: 2 bedrooms, 2 bathrooms
Amenities: Washer, air conditioning, heating, indoor fireplace, backyard, shared pool and hot tub.
Location: Montepulciano
Tuscany Farmhouse
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 speak to the nostalgia of the space, and an expansive lawn offers a scenic focal point for games and gatherings. And while you’re outside, keep your eyes peeled for frequently-spotted neighbors including 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
Traditional Stone House
Shaded by centuries-old trees and oozing with a homey atmosphere, this traditional stone house can accommodate up to 11 guests (it s also pet-friendly!). From its massive fireplace to the exposed wooden beams and stone archways, every detail feels plucked from the past. The exterior is equally compelling, with a large private pool and plenty of nooks for quiet moments and aperitivo hours alike.
Rooms: 5 bedrooms, 4 bathrooms
Amenities: Bathtub, washer, mosquito net, record player, indoor wood-burning fireplace, central heating, fire pit, BBQ, pool, fire pit, outdoor furniture and dining area.
Location: Cortona
The Holly
Journey back to 18th-century Chianti in this traditional stone villa that’s ideal for a family or two couples traveling together. While you’ll be positioned practically a stone’s throw from the region’s best wineries, you might find it hard to pry yourself away from the home s opulent details (infinity pool, anyone?). There’s also an atmospheric loggia equipped with a dining table, providing a dreamy hub for outdoor pasta parties.
Rooms: 2 bedrooms, 2 bathrooms
Amenities: Washer, mosquito net, AC, indoor fireplace, dishwasher, BBQ, pool.
Location: Chianti
Panoramic Villa
Sitting near the border of Tuscany and Umbria, this striking stone villa is befitting of a magical Italian getaway. There’s a pizza oven for interactive dinners, a ping pong table for competitive types in the group, and a long pool presiding over the splendor of the countryside. What s not to love?
Rooms: 4 bedrooms, 4 bathrooms
Amenities: Outdoor shower, washer/dryer, ping pong table, AC, indoor fireplace, heating, fire pit, hammock, BBQ, outdoor dining area, pool.
Location: Todi
Church of the Vaioni
More of an ancient church than a traditional villa, this historic rental immersed in the Tuscan countryside is among the most unique in the region. The home is designed with a loft structure on two separate mezzanines, while outside, there’s an equipped kitchen with a wood-burning barbecue and fragrant gardens. Perhaps the most distinct detail is the internal staircase, which was built by the Antica Fonderia Michelucci (a prominent foundry of the epoch).
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
