
Chianti Region Vacation Rentals
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Our top choices for Chianti Region vacation rentals


hu Firenze Certosa camping in town
hu Firenze Certosa camping in town

Villa Curina Resort
Villa Curina Resort
B&B La Fonte del Machiavelli
B&B La Fonte del MachiavelliFind vacation rentals that suit your style
Top Chianti Region Hotel Reviews

Villa I Barronci Resort & Spa
Find out more about Chianti Region
You always said you would go on a dream vacation someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannon ball into the deep end. Go ahead, unplug and unwind in style. When you book one of our vacation rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment or room. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your vacation just got upgraded.
As much as you love your short-term rental, it’s always good to get out and explore to soak up . Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in . Seeing all the best attractions is bound to make you fall in love with Chianti Region. Who knows, you may even be tempted to extend your vacation rental stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true.
It’s your escape so why share it? You deserve your own slice of paradise. Booking your vacation rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in short-term rentals, that won’t be hard to do.
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- Enchanting Tuscany Vacation Rental in Medieval Fortress Town Panoramic Views
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- Agriturismo San Sano
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- B&B in Chianti Region
- Agriturismo Casavecchia
- Villa SARA Gracious vineyard home
- Hotels with Tennis Courts in Greve in Chianti
- 5 Star Hotels in Chianti Region
- La Capanna
- Borgo Livernano
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- Hotel Wedding Venues Hotels in Castellina in Chianti
- Villa Cristina
- Stunning private villa for 3 people with A/C
- Villas in Greve in Chianti
- Figline e Incisa Valdarno Hotels
- Winery Hotels in Greve in Chianti
- Gaiole in Chianti Hotels
- Farmstay in Chianti Region
- Radda in Chianti Hotels
- Castello di Fonterutoli Wine Resort
- Winery Hotels in Radda in Chianti
- Adults Only Resorts & in Chianti Region
- Panzano in Chianti Hotels
- Meleto Hotels
- Castles in Greve in Chianti
- Podere Palazzolo
- Villas in Chianti Region
- Montefioralle Hotels
- Volpaia Hotels
- Lgbt Friendly Hotels in Chiocchio
- Chianti Craft House Badia a Passignano
- Monsanto Hotels
- Borgo Castelvecchi
- Brolio Agriroom
- Beach Hotel Hotels in Chianti Region
- Tavarnelle Val di Pesa Hotels
- Nice apartment for 5 people with WIFI
- Isola SERENA Newly Expanded Private Luxury Villa
- Villa Bella Lisa in Chianti with Pool+Jacuzzi!
- Hotels with Tennis Courts in Chianti Region
- Farmhouse with beautiful pool and jacuzzi
- Hotels with Balconies in Chianti Region
- Hotels with Hot Tubs in Chianti Region
- Greve in Chianti Hotels
- Casa PILAR villa with pool and jacuzzi for exclusive use in chianti.
- Holiday home features with Italian garden and free Wifi
- Visit Ponte Agli Stolli
- Visit Sicelle
- Le Miccine
- Visit Le Bolle
- Visit Castellina in Chianti
- Visit Castelnuovo dei Sabbioni
- Visit Cortine
- Visit Panzano in Chianti
- Church of San Sigismondo
- Visit Poggio Alla Croce
- Visit Greve in Chianti
- Visit Chianti Region
- Visit Radda in Chianti
- Visit Vertine
- Visit Lilliano
- Visit Chiocchio
- Buondonno Winery
- Visit Gaiole in Chianti



















































































