Compare Chianti Region Villas
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Featured Villas in Chianti Region
Relais Badia a Passignano
Via Martiri di Pratale 12 Barberino Tavarnelle FI
Guests of this villa have access to a seasonal outdoor pool and a garden.
Pool
Kitchen
Authentic Private Tuscan Villa for 12 people in Greve: the Heart of Chianti
Greve in Chianti (Firenze) Toscana
Guests of this villa enjoy features like a gym, a hot tub, and laundry facilities. Transportation is made easy with limo/town car service. Staff members can help with accommodation requests, and provide concierge services. Other amenities at this family-friendly villa include local meal delivery service, a garden, and barbecue grills.
Pool
Hot Tub
CASA PILAR villa with pool and jacuzzi for exclusive use in chianti.-20% 12_21/5
Strada In Chianti Città Metropolitana di Firenze
Guests of this villa have access to an outdoor pool, a gym, and a hot tub. Transportation is made easy with limo/town car service. Additional amenities include laundry facilities, a garden, and barbecue grills.
Pool
Hot Tub
Villa Bartolini Baldelli - Authentic XV century villa with garden and pool
Toscana Città Metropolitana di Firenze
At this villa, guests have access to features like laundry facilities. This smoke-free villa also has a garden.
Pool
Kitchen
La Ruota - Village house rental in Duddova, Chianti
Duddova Tuscany
Guests staying at this villa have access to laundry facilities, a garden, and barbecue grills.
Pool
Kitchen
Marvelous home just steps from the Chianti and beyond
cavriglia Tuscany
Guests staying at this villa have access to laundry facilities, barbecue grills, and a garden.
Kitchen
Washer
"Villa Torre in Chianti" Vrbo Vacation Rental of the Year 2026- 8 bedrooms A/C
San Casciano in Val di Pesa Tuscany
Guests of this villa enjoy features like an outdoor pool, a gym, and a terrace. Staff members can help with accommodation requests, and provide concierge services. Other amenities at this family-friendly villa include laundry facilities, local meal delivery service, and barbecue grills.
Pool
Kitchen
Exclusive Tuscan Winery Escape: Charming Villa with Pool & Breathtaking Views.
Radda in Chianti Provincia di Siena
At this villa, guests have access to an outdoor pool, laundry facilities, and a water dispenser. Other amenities at this family-friendly villa include a garden and barbecue grills.
Pool
Kitchen
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
Hotel Options in Chianti Region
Fattoria di Vegi
Località Vegi, 16 Castellina in Chianti SI
$345 nightly
The price is $386 total per night from Oct 12 to Oct 13
$386 total
Oct 12 - Oct 13
Total with taxes and fees
10/10 Exceptional! (21 reviews)
Villa I Barronci Resort & Spa
Via Sorripa 10 San Casciano in Val di Pesa FI
$148 nightly
The price is $169 total per night from Sep 14 to Sep 15
$169 total
Sep 14 - Sep 15
Total with taxes and fees
Castello di Spaltenna- Small Luxury Hotels of the World
Via Spaltenna 13 Gaiole in Chianti SI
$418 nightly
The price is $471 total per night from Oct 5 to Oct 6
$471 total
Oct 5 - Oct 6
Total with taxes and fees
9.6/10 Exceptional! (282 reviews)
Luxury Villas
Book luxury villas in Chianti Region
There are plenty of ways to up your vacation game, but one of the best is by staying in a luxury villa in Chianti Region. Villas, with their thoughtful layout and elegant décor, let you travel in style. They come in a variety of sizes and offer a great experience, whether you’re traveling on your own or with a group of friends. Orbitz has fantastic deals on villas in Chianti Region, so book one now. You’ll feel like a million bucks before you even check in.
Spacious luxury villas in Chianti Region
You won’t have a problem finding your own space in Chianti Region. If you’re traveling in a group, go for a three-bedroom or larger villa; separate bedrooms can make it that much easier to keep the peace, especially when you’re all staying in one house. You can also explore Chianti Region on your own and use a one-bedroom villa as your home base.
A top-end villa experience in Chianti Region rivals that of a luxury resort. Float in a swimming pool with an elaborate mosaic bottom, work out in your own gym, and let the daily housekeeping staff clean up after you while a private chef whips up one delicious meal after another. This is the life!
Chianti Region Villas essential information
Accommodation | 555 Villas |
|---|---|
Lowest Price | $169 |
Highest Price | $471 |
Popular accommodation | Relais Badia a Passignano, Authentic Private Tuscan Villa for 12 people in Greve: the Heart of Chianti, CASA PILAR villa with pool and jacuzzi for exclusive use in chianti.-20% 12_21/5, Villa Bartolini Baldelli - Authentic XV century villa with garden and pool, La Ruota - Village house rental in Duddova, Chianti, Marvelous home just steps from the Chianti and beyond, "Villa Torre in Chianti" Vrbo Vacation Rental of the Year 2026- 8 bedrooms A/C, Exclusive Tuscan Winery Escape: Charming Villa with Pool & Breathtaking Views., Villa Poggio - An oasis in the florentine countryside |
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