Compare Chianti Region Villas

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Featured Villas in Chianti Region

Villa with concierge service & heated pool at 20 minute from Florence center

$1,146 nightly

$1,150 total

Jan 7 - Jan 8, 2026

Total with taxes and fees

Guests of this villa enjoy features like an outdoor pool, free WiFi in public areas, and a terrace. Transportation is made easy with limo/town car service. Staff members can answer questions about accommodations, and also provide concierge services. Other amenities at this golf villa include laundry facilities, local meal delivery service, and barbecue grills.

Pool

Kitchen

Villa between Florence Siena and Pisa. 1 km to village. A/C in all rooms-Wi Fi

Guests staying at this villa have access to laundry facilities, a garden, and barbecue grills.

Pool

Kitchen

Guests of this villa enjoy features like an outdoor pool, a hot tub, and laundry facilities. Other amenities at this family-friendly villa include barbecue grills and a garden.

Pool

Hot Tub

Guests of this villa have access to a seasonal outdoor pool and a garden.

Pool

Kitchen

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 a garden.

Pool

Kitchen

Private villa in the heart of chianti with view of siena

At this villa, guests have access to features like laundry facilities.

Washer

Dryer

At this villa, guests have access to a library, laundry facilities, and a garden. This smoke-free villa also has barbecue grills.

Pool

Kitchen

At this villa, guests have access to an outdoor pool, laundry facilities, and a garden. This family-friendly villa also has barbecue grills.

Pool

Kitchen

Villa Buonagrazia: A charming three-story villa in the characteristic style of the Tuscan countryside.

At this villa, guests have access to features like laundry facilities. This villa also has a garden.

Pool

Kitchen

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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

Hotel Ristorante Alcide

Viale Marconi, 67/A Poggibonsi SI

$47 nightly

$52 total

Dec 21 - Dec 22

Total with taxes and fees

8/10 Very Good! (460 reviews)

Hotel Borgo di Cortefreda Relais

Via Roma 191 Barberino Tavarnelle FI

$84 nightly

$100 total

Jan 6 - Jan 7, 2026

Total with taxes and fees

9.4/10 Exceptional! (472 reviews)

Hotel Toscana Ambassador

Via Salceto, 11 Poggibonsi SI

$69 nightly

$76 total

Dec 23 - Dec 24

Total with taxes and fees

8/10 Very Good! (310 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	600 Villas
Lowest Price	$52
Highest Price	$1,150
Popular accommodation	Villa with concierge service & heated pool at 20 minute from Florence center, Villa between Florence Siena and Pisa. 1 km to village. A/C in all rooms-Wi Fi, Spectacular Villa sleeping 12, Large private Pool, 9 km South of Florence City, Luxury Villa Basilio Chianti, Charming Villa Torre in Chianti, 8 ensuite bedrooms, pool, Florence, Wi-Fi, A/C., Private villa in the heart of chianti with view of siena, Villa Orchidea - Historical villa with pool, 4-bedroom stonehouse with stunning pool in the Chianti countryside with WiFi, AC, Villa Buonagrazia: A charming three-story villa in the characteristic style of the Tuscan countryside.