Perhaps it’s the hills, impossibly green and endlessly rolling. 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 in any sort of undiscovered quality it more than makes up for in, well, everything else. Among 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 of a matter of how, but rather, 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 $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

If you’re planning a rendezvous with the Tuscan countryside, a historic rental provides a quintessential home base. What to expect at such charming accommodations? All of it: al fresco pizza ovens, infinity pools overlooking the vineyards, wood-burning fireplaces, and architectural appurtenances like exposed wood beams, clay tiles, and arched doorways.

Below, discover 16 of the most atmospheric stays in Tuscany, many of which are well-suited for groups making a memorable journey to Italy together.

Luxury Apartment

Siena’s historic city center is unlike anywhere else in Italy. Seize the opportunity to sleep within a medieval fortress by booking this apartment, which is arranged over the top two floors of a traditional Sienese building. There are three large bedrooms (one even has French doors that lead to a garden terrace), and features like ceiling beams and terracotta floor tiles dial up the architectural charm.

Rooms: 3 bedrooms, 2 bathrooms

Amenities: Washer, AC, heating.

Location: Siena

Cipressini

These two 17th-century stone houses are ideal for couples traveling together who want to stay on the same property, but maintain a bit of privacy. (They can also be rented separately as one-bedrooms.) While the interiors offer classic Tuscan charm, the outdoor areas steal the show 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

Beautiful Country House

Experience a side of Tuscany missed by many at this four-bedroom countryside house offering views to the sea (on clear days, you can even spot Elba and Corsica in the distance). The beach is just 20 minutes away, but even closer is a charming local village where cozy cafes and shops await. While on property, enjoy an afternoon by the infinity pool, and shared meals at the long dining table beside a large window. The property is new as of this year, so you’ll be among the first to experience its beautifully designed interiors.

Rooms: 4 bedrooms, 3 bathrooms

Amenities: Bathtub, outdoor shower, washer, fireplace, fire pit, BBQ, pool, free parking.

Location: Riparbella

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

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