Compare Pienza 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 Pienza

Casa La Fonte - Luxury Villa Rental with swimming pool in Cortona, Tuscany

Casa La Fonte - Luxury Villa Rental with swimming pool in Cortona, Tuscany

Cortona Tuscany
At this villa, guests have access to features like laundry facilities. This smoke-free villa also has a garden.
Pool
Kitchen
Villa with private pool, air conditioning near wineries at 3km from village

Villa with private pool, air conditioning near wineries at 3km from village

CHIANCIANO terme Tuscany
This villa offers an outdoor pool, a sauna, and a hot tub. Transportation is made easy with limo/town car service. Additional amenities include laundry facilities, local meal delivery service, and barbecue grills.
Pool
Hot Tub
Il Poggio dell'Eremita

Il Poggio dell'Eremita

Sinalunga Tuscany
$178 nightly
The price is $181 total per night
$181 total
Apr 14 - Apr 15
Total with taxes and fees
Guests staying at this villa have access to a garden and barbecue grills.
Kitchen
Free WiFi
Charming Tuscany Villa with magical Garden, shared pool, Chianti Area

Charming Tuscany Villa with magical Garden, shared pool, Chianti Area

Castelnuovo Berardenga Siena
At this villa, guests have access to features like laundry facilities. This villa also has a garden.
Pool
Kitchen
Montalcino: Private villa in the heart of Tuscany, private pool, A/C

Montalcino: Private villa in the heart of Tuscany, private pool, A/C

Montisi Tuscany
At this villa, guests have access to an outdoor pool, laundry facilities, and a garden. This smoke-free villa also has barbecue grills.
Pool
Kitchen
Relax in a private Tuscan Villa with pool and open hill views

Relax in a private Tuscan Villa with pool and open hill views

Montefollonico Torrita di Siena SI Tuscany
Guests staying at this villa have access to laundry facilities, a garden, and barbecue grills.
Pool
Kitchen
Private Pool Villa near Cortona. Secluded, Perfect for Families.

Private Pool Villa near Cortona. Secluded, Perfect for Families.

Toscana Provincia di Arezzo
Guests staying at this villa enjoy an outdoor pool, laundry facilities, and local meal delivery service. Other amenities at this family-friendly villa include a garden and barbecue grills.
Pool
Kitchen
Stunning private villa for 4 guests with A/C, pool, WIFI, TV and terrace

Stunning private villa for 4 guests with A/C, pool, WIFI, TV and terrace

Asciano Tuscany
Guests staying at this villa have access to laundry facilities, a garden, and barbecue grills.
Private and cozy retreat in Montalcino with private pool surrounded by vineyards

Private and cozy retreat in Montalcino with private pool surrounded by vineyards

Siena Tuscany
At this villa, guests have access to a terrace, laundry facilities, and barbecue grills. Transportation is made easy with limo/town car service. This family-friendly villa also has a garden.
Don't see what you're looking for?
See all available properties in Pienza
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 Pienza

    Hotel Relais II Chiostro di Pienza

    Hotel Relais II Chiostro di Pienza

    Corso Rossellino 26 Pienza SI
    $76 nightly
    The price is $91 total per night from Apr 9 to Apr 10
    $91 total
    Apr 9 - Apr 10
    Total with taxes and fees
    8.8/10 Excellent! (637 reviews)
    Hotel San Gregorio

    Hotel San Gregorio

    Via Della Madonnina 4 Pienza SI
    $171 nightly
    The price is $195 total per night from Apr 9 to Apr 10
    $195 total
    Apr 9 - Apr 10
    Total with taxes and fees
    9.4/10 Exceptional! (140 reviews)
    Hotel Corsignano

    Hotel Corsignano

    Via Della Madonnina 11 Pienza SI
    $146 nightly
    The price is $168 total per night from Apr 8 to Apr 9
    $168 total
    Apr 8 - Apr 9
    Total with taxes and fees
    9.4/10 Exceptional! (339 reviews)

Luxury Villas

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

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

A top-end villa experience in Pienza 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!

Pienza Villas essential information

Accommodation
1456 Villas
Lowest Price
$91
Highest Price
$195
Popular accommodation
Casa La Fonte - Luxury Villa Rental with swimming pool in Cortona, Tuscany, Villa with private pool, air conditioning near wineries at 3km from village, Il Poggio dell'Eremita, Charming Tuscany Villa with magical Garden, shared pool, Chianti Area , Montalcino: Private villa in the heart of Tuscany, private pool, A/C, Relax in a private Tuscan Villa with pool and open hill views, Private Pool Villa near Cortona. Secluded, Perfect for Families., Stunning private villa for 4 guests with A/C, pool, WIFI, TV and terrace, Private and cozy retreat in Montalcino with private pool surrounded by vineyards

More to Explore