Compare Siena Villas

Earn Orbucks instantly: $1 Orbuck = $1 USD, good toward hotels

Save 10% or more on select hotels with Insider Prices

Book on the app to instantly earn 5% on 350,000+ hotels

Featured Villas in Siena

15th century barn fully renovated in a stylish style with gorgeous swimming pool

15th century barn fully renovated in a stylish style with gorgeous swimming pool

Toscana Provincia di Siena
At this villa, guests have access to an outdoor pool, laundry facilities, and barbecue grills. Other amenities at this family-friendly villa include a garden and a living plant wall.
Pool
Kitchen
Fienile: luxury countryside villa, shared pool, ideal base to discover Tuscany

Fienile: luxury countryside villa, shared pool, ideal base to discover Tuscany

Siena Toscana
At this villa, guests have access to an outdoor pool, laundry facilities, and barbecue grills. This family-friendly villa also has a garden.
Pool
Kitchen
Gorgeous view on vineyards, Stone Tuscan private Villa

Gorgeous view on vineyards, Stone Tuscan private Villa

Toscana Provincia di Siena
Guests staying at this villa enjoy a hot tub, laundry facilities, and a garden. This smoke-free villa also has barbecue grills.
Pool
Hot Tub
Siena Exclusive Luxury Villa. Private Pool, Garden, Relax, Holiday, Tuscany!

Siena Exclusive Luxury Villa. Private Pool, Garden, Relax, Holiday, Tuscany!

Siena Toscana
Guests of this villa have access to an outdoor pool, a gym, and a sauna. Other amenities at this family-friendly villa include a hot tub, express check-in, and express check-out.
Pool
Hot Tub
4-bedroom stonehouse with stunning pool in the Chianti countryside with WiFi, AC

4-bedroom stonehouse with stunning pool in the Chianti countryside with WiFi, AC

Radda in Chianti Italy
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
Legnaia countryside luxury property, shared pool, ideal base to discover Tuscany

Legnaia countryside luxury property, shared pool, ideal base to discover Tuscany

Siena Toscana
At this villa, guests have access to an outdoor pool, laundry facilities, and barbecue grills. This family-friendly villa also has a garden.
Pool
Kitchen
Le Redi: sustainable geothermal country villa, amazing views over Chianti hills

Le Redi: sustainable geothermal country villa, amazing views over Chianti hills

Quercegrossa Tuscany
Guests staying at this villa have access to laundry facilities, barbecue grills, and a garden.
Kitchen
Washer
Luxury converted barn with hilltop views in chianti wine region, Tuscany

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

Castellina in Chianti 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
Private villa in the heart of chianti with view of siena

Private villa in the heart of chianti with view of siena

Fonterutoli Provincia di Siena
At this villa, guests have access to features like laundry facilities.
Washer
Dryer
Don't see what you're looking for?
See all available properties in Siena
View all properties
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 Siena

    Hotel Athena

    Hotel Athena

    P Mascagni 55 Siena SI
    $175 nightly
    The price is $198 total per night from Apr 13 to Apr 14
    $198 total
    Apr 13 - Apr 14
    Total with taxes and fees
    9.2/10 Wonderful! (1,004 reviews)
    Hotel Chiusarelli

    Hotel Chiusarelli

    Viale Curtatone 15 Siena SI
    $139 nightly
    The price is $159 total per night from Apr 16 to Apr 17
    $159 total
    Apr 16 - Apr 17
    Total with taxes and fees
    8.8/10 Excellent! (1,002 reviews)
    Palazzo Ravizza

    Palazzo Ravizza

    Pian dei Mantellini 34 Siena SI
    $180 nightly
    The price is $204 total per night from Apr 12 to Apr 13
    $204 total
    Apr 12 - Apr 13
    Total with taxes and fees
    9.4/10 Exceptional! (774 reviews)

Luxury Villas

Book luxury villas in Siena
There are plenty of ways to up your vacation game, but one of the best is by staying in a luxury villa in Siena. 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 Siena, so book one now. You’ll feel like a million bucks before you even check in.

Spacious luxury villas in Siena
You won’t have a problem finding your own space in Siena. 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 Siena on your own and use a one-bedroom villa as your home base.

A top-end villa experience in Siena 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!

Siena Villas essential information

Accommodation
80 Villas
Lowest Price
$159
Highest Price
$204
Popular accommodation
15th century barn fully renovated in a stylish style with gorgeous swimming pool, Fienile: luxury countryside villa, shared pool, ideal base to discover Tuscany, Gorgeous view on vineyards, Stone Tuscan private Villa, Siena Exclusive Luxury Villa. Private Pool, Garden, Relax, Holiday, Tuscany!, 4-bedroom stonehouse with stunning pool in the Chianti countryside with WiFi, AC, Legnaia countryside luxury property, shared pool, ideal base to discover Tuscany, Le Redi: sustainable geothermal country villa, amazing views over Chianti hills, Luxury converted barn with hilltop views in chianti wine region, Tuscany, Private villa in the heart of chianti with view of siena