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Chianti Region Vacation Rentals

Chianti Region Vacation Rentals

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Vacation Rentals in Chianti Region

See all Vacation Rentals in Chianti Region
Villa Il Palagio

Villa Il Palagio

Via Il Palagio 59, Rignano sull'Arno
1 others viewing this property now

Situated in Rignano sull'Arno, this apartment is 1.1 mi (1.8 km) from Fashion Valley and within 3 mi (5 km) of The Mall Luxury Outlet and Castello di Volognano. ...

$145

$145
Camping Village Norcenni Girasole Club

Camping Village Norcenni Girasole Club

Via Norcenni 7, Figline Valdarno
Last booking: 12 hours ago
4.2 out of 5 (42 reviews)

This family-friendly Figline Valdarno apartment is located in a rural location, 2.3 mi (3.6 km) from Franciscan Monastery of St. Francis, and within 9 mi (15 ...

$79

$79
Casa Landi

Casa Landi

Località San Martino 25, Castellina in Chianti
Last booking: 3 days ago
3.0 out of 5 (1 reviews)

Situated in Castellina in Chianti, this townhouse accommodation is within a 15-minute walk of Casa Vinicola Luigi Cecchi, Montecalvario, and Archaeological Museum ...

$75

$75
Il Paluffo

Il Paluffo

Via Citerna 144 Fiano, Certaldo
4.5 out of 5 (6 reviews)

Situated in a rural location, this apartment is within 6 mi (10 km) of Tenuta Maiano, Vine and Wine Museum, and Santa Lucia al Borghetto Church. Pasta Fresca ...

$144

$144
Residenze San Giovanni

Residenze San Giovanni

Via Mannozzi 26, San Giovanni Valdarno
2.0 out of 5.0
Last booking: 9 hours ago
4.0 out of 5 (2 reviews)

Located in the heart of San Giovanni Valdarno, this residence is 0.2 mi (0.4 km) from Museum of Terranuova Tuscany and within 6 mi (10 km) of Museum of San Lorenzo ...

$64

$64
Villa Barberino

Villa Barberino

Viale Barberino 19, Cavriglia
1 others viewing this property now
4.5 out of 5 (2 reviews)

Located in Meleto, this apartment is within 9 mi (15 km) of Museum of Terranuova Tuscany, Franciscan Monastery of St. Francis, and Gianfranco Carla Fineschi ...

$105

$105
La Ferriera Residence

La Ferriera Residence

Via Ferriera 4, Loro Ciuffenna

Situated in Loro Ciuffenna, this residence is 1.4 mi (2.2 km) from La Pieve di San Pietro a Gropina and within 9 mi (15 km) of Soffena Abbey and Mulino Ad Acqua. ...

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Locanda La Capannuccia

Locanda La Capannuccia

Localita La Capannuccia 53, Castellina in Chianti
4.5 out of 5 (2 reviews)

This family-friendly Castellina in Chianti townhouse accommodation is located in a rural location, within 3 mi (5 km) of Montecalvario and Casa Vinicola Luigi ...

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Residenza San Leo

Residenza San Leo

Via Badia Montescalari 11, Figline Valdarno
5.0 out of 5 (2 reviews)

Situated in a rural location, this apartment is within 9 mi (15 km) of Franciscan Monastery of St. Francis, Wine Museum, and Piazza Matteotti. Museum of Terranuova ...

$117

$117
Villa San Filippo

Villa San Filippo

Strada delle Ginestre, 6, Barberino Val d'Elsa
4.0 out of 5.0
3.5 out of 5 (2 reviews)

Located in San Filippo, this residence is 2.6 mi (4.3 km) from Santa Lucia al Borghetto Church and 2.7 mi (4.4 km) from Pasta Fresca. Sant'Appiano Parish Church ...

$289

$289
Antica Pieve B&B

Antica Pieve B&B

Strada della Pieve,1, Tavarnelle Val di Pesa
5.0 out of 5 (2 reviews)

Situated in Tavarnelle Val di Pesa, this townhouse accommodation is within a 15-minute walk of Pasta Fresca and Poggio al Bosco. Santa Lucia al Borghetto Church ...

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Residence Casprini da Omero

Residence Casprini da Omero

Via Giovanni Falcone 68/70, Greve in Chianti
3.0 out of 5.0

Located in Passo dei Pecorai, this residence is within 6 mi (10 km) of Piazza Matteotti, Wine Museum, and Piazza Garibaldi. Sezzate Castle and Poggio al Sole ...

$56

$56
Villa Cristina

Villa Cristina

Via Fiorentina 34, Castellina In Chianti
1 others viewing this property now
3.8 out of 5 (6 reviews)

Situated in a rural location, this townhouse accommodation is within a 5-minute walk of Casa Vinicola Luigi Cecchi and Montecalvario. Archaeological Museum of ...

$96

$96
Castello di Montegufoni

Castello di Montegufoni

Via Montegufoni, 18, Montespertoli
2.5 out of 5 (2 reviews)

Situated in a rural location, this residence is within 3 mi (5 km) of Azienda Agricola Ammirabile, Castello Sonnino, and Piazza Machiavelli. Castle of Poppiano ...

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Villa Albertina

Villa Albertina

Via Trecento 104, Montespertoli
5.0 out of 5 (1 reviews)

Situated in Montespertoli, this apartment is 1.8 mi (2.9 km) from Tenuta Maiano and within 6 mi (10 km) of Castello Sonnino and Piazza Machiavelli. Vine and ...

$105

$105
Fontebussi Tuscan Resort

Fontebussi Tuscan Resort

Loc Fontebussi, Cavriglia
1 others viewing this property now
4.6 out of 5 (24 reviews)

Located in Montegonzi, this apartment is 0.8 mi (1.3 km) from Le Miccine and within 6 mi (10 km) of Museum of San Lorenzo and Accademia Valdarnese del Poggio ...

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La Locanda di Pietracupa

La Locanda di Pietracupa

Via Madonna di Pietracupa, 31, Tavarnelle Val di Pesa
5.0 out of 5 (1 reviews)

Situated in Tavarnelle Val di Pesa, this townhouse accommodation is within 1 mi (2 km) of Fattoria di Montecchio, Casa Sola - Chianti Winery, and Chianti Observatory. ...

$96

$96
Rocca di Castagnoli

Rocca di Castagnoli

Localita di Castagnoli, Gaiole in Chianti
4.5 out of 5 (4 reviews)

Situated in Gaiole in Chianti, this townhouse accommodation is 0.3 mi (0.5 km) from Cantalici Winery and 3.1 mi (5 km) from PoggioBrandani. Church of San Sigismondo ...

$128

$128
Map

Any good vacation involves wine, and a trip to Chianti, Italy, is no exception. In fact, this central region in Tuscany is known for its superb vineyards, inviting enoteche (wine bars), and of course, the variety of wine named after the territory itself. While wine flows like water in this area, there is more to do than just grape-influenced activities. See for yourself when you book one of our vacation rentals in Chianti, which offer the perfect opportunity to experience the area like a local. Instead of staying in a hotel with hundreds of tourists, you can get to know the town like an Italian citizen.

With the keys to your private rental in Chianti, you’re unlocking your Italian adventure. Drop off your luggage and settle in—open the curtains, kick off your shoes, and start planning your itinerary. If getting a taste of the famous vino is at the top of your list, then a wine tour is a must. Visit the wineries, learn about the local history, and sample the local varieties. Once you’ve sipped your way through the region, make room in your belly for olives and olive oil that come straight from the grove. There’s more to this region then just pleasing your palate, though—explore the Saturday market in the plaza at Greve, check out the Archeological Museum of Chianti Senese, and make your way to the Chianti Sculpture Park. After your adventures in the wine country, head back to the best of Chianti vacation rentals and rest up for the next day’s activities.

When it comes to finding short-term apartment rentals in Chianti, Expedia makes it easier than ever. Take a peek at our vast selection, pick your dates, and make your reservation. You can also contact the property manager to make additional arrangements after booking. Pack your bags and prep your palate: Chianti is waiting.