Compare Chianti Region Villas

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Featured Villas in Chianti Region

Beautiful rustic villa in Tuscany in Monteriggioni, between Siena and Florence.

Beautiful rustic villa in Tuscany in Monteriggioni, between Siena and Florence.

Guests of this villa enjoy features like an outdoor pool, a hot tub, and laundry facilities. Transportation is made easy with limo/town car service. Other amenities at this family-friendly villa include a garden and barbecue grills.
Pool
Hot Tub
Your panoramic house in Tuscany between vineyards and olive groves.

Your panoramic house in Tuscany between vineyards and olive groves.

At this villa, guests have access to a terrace, laundry facilities, and barbecue grills. This villa also has a garden.
Pool
Kitchen
Luxury converted barn with hilltop views in chianti wine region, Tuscany

Luxury converted barn with hilltop views in chianti wine region, Tuscany

Guests staying at this villa enjoy an outdoor pool, a terrace, and laundry facilities. Other amenities at this family-friendly villa include barbecue grills and a garden.
Pool
Kitchen
VILLA in FLORENTINE HILLS. 300+ EXCELLENT REVIEWS. 100% travelers recommend.

VILLA in FLORENTINE HILLS. 300+ EXCELLENT REVIEWS. 100% travelers recommend.

Guests staying at this villa enjoy an outdoor pool, a terrace, and laundry facilities. Additional amenities include barbecue grills and a garden.
Pool
Kitchen
ISOLA SERENA Newly Expanded Private Luxury Villa, Tuscany, Infinity Pool & Views

ISOLA SERENA Newly Expanded Private Luxury Villa, Tuscany, Infinity Pool & Views

Guests of this villa enjoy features like an outdoor pool, a gym, and a library. 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 family-friendly villa include a terrace, laundry facilities, and a garden.
Pool
Kitchen
Charming Villa Torre in Chianti, 8 ensuite bedrooms, pool, Florence, Wi-Fi, A/C.

Charming Villa Torre in Chianti, 8 ensuite bedrooms, pool, Florence, Wi-Fi, A/C.

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, barbecue grills, and a garden.
Pool
Kitchen
Charming Villa w/ pool nestled in Chianti vineyards, with AC, close to Florence

Charming Villa w/ pool nestled in Chianti vineyards, with AC, close to Florence

Guests staying at this villa have access to laundry facilities, barbecue grills, and a garden.
Pool
Kitchen
Exclusive 7BR-8BA Villa with pool, a few mins from town, yet in the countryside

Exclusive 7BR-8BA Villa with pool, a few mins from town, yet in the countryside

Guests of this villa enjoy features like an outdoor pool, a gym, and laundry facilities. Other amenities at this golf villa include local meal delivery service, a garden, and barbecue grills.
Pool
Kitchen
Villa Salivolpe - on top of a Chianti hill - Private swimming pool

Villa Salivolpe - on top of a Chianti hill - Private swimming pool

Guests of this villa enjoy features like an outdoor pool, a hot tub, and a terrace. Transportation is made easy with limo/town car service. Other amenities at this family-friendly villa include laundry facilities, local meal delivery service, and a garden.
Pool
Hot Tub
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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 Borgo di Cortefreda Relais

    Hotel Borgo di Cortefreda Relais

    Via Roma 191, Barberino Tavarnelle, FI
    The price is $138 per night from May 12 to May 13
    $138
    includes taxes & fees
    $119 per night
    May 12 - May 13
    9.2/10 Wonderful! (409 reviews)
    Castello di Spaltenna- Small Luxury Hotels of the World

    Castello di Spaltenna- Small Luxury Hotels of the World

    Via Spaltenna 13, Gaiole in Chianti, SI
    The price is $497 per night from May 12 to May 13
    $497
    includes taxes & fees
    $442 per night
    May 12 - May 13
    9.4/10 Exceptional! (222 reviews)
    Hotel Ristorante Alcide

    Hotel Ristorante Alcide

    Viale Marconi, 67/A, Poggibonsi, SI
    The price is $75 per night from May 11 to May 12
    $75
    includes taxes & fees
    $62 per night
    May 11 - May 12
    8/10 Very Good! (443 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
578 Villas
Lowest Price
$75
Highest Price
$497
Popular accommodation
Beautiful rustic villa in Tuscany in Monteriggioni, between Siena and Florence. , Your panoramic house in Tuscany between vineyards and olive groves., Luxury converted barn with hilltop views in chianti wine region, Tuscany, VILLA in FLORENTINE HILLS. 300+ EXCELLENT REVIEWS. 100% travelers recommend., ISOLA SERENA Newly Expanded Private Luxury Villa, Tuscany, Infinity Pool & Views, Charming Villa Torre in Chianti, 8 ensuite bedrooms, pool, Florence, Wi-Fi, A/C., Charming Villa w/ pool nestled in Chianti vineyards, with AC, close to Florence, Exclusive 7BR-8BA Villa with pool, a few mins from town, yet in the countryside, Villa Salivolpe - on top of a Chianti hill - Private swimming pool

Villas in Chianti Region

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