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

Enchanting Tuscan Villa / Private Estate / Heated Pool / Panoramic Views

Enchanting Tuscan Villa / Private Estate / Heated Pool / Panoramic Views

Castelnuovo Berardenga Tuscany
Guests staying at this villa enjoy an outdoor pool, a terrace, and laundry facilities. Staff members can help with accommodation requests, and provide concierge services. Additional amenities include barbecue grills and 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
Beautiful private villa for 4 people with WIFI, pool, A/C, TV and terrace

Beautiful private villa for 4 people with WIFI, pool, A/C, TV and terrace

Asciano Tuscany
Guests staying at this villa have access to laundry facilities, barbecue grills, and a garden.
Kitchen
Washer
Il Poggio dell'Eremita

Il Poggio dell'Eremita

Sinalunga Tuscany
$183 nightly
The price is $185 total per night
$185 total
Jul 4 - Jul 5
Total with taxes and fees
Guests staying at this villa have access to barbecue grills and a garden. Staff members can help with accommodation requests, and provide luggage storage.
Kitchen
Free WiFi
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 a garden. Transportation is made easy with limo/town car service. This family-friendly villa also has barbecue grills.
Pool
Kitchen
Villa with swimming pool and large garden, nestled in the hills of Maremma

Villa with swimming pool and large garden, nestled in the hills of Maremma

Elmo Provincia di Grosseto
At this villa, guests have access to an outdoor pool, laundry facilities, and a garden.
Pool
Kitchen
Big house

Big house

Castiglione del Lago Umbria
Guests staying at this villa enjoy a gym, laundry facilities, and local meal delivery service. Transportation is made easy with limo/town car service. Staff members can help with accommodation requests, and provide concierge services. Additional amenities include barbecue grills and a garden.
Pool
Kitchen
Villa Podere Belvedere

Villa Podere Belvedere

Pienza Tuscany
This villa features free WiFi in public areas, a terrace, and laundry facilities. This smoke-free villa also has barbecue grills.
PRIVATE LUXURY VILLA WITH HEATED SWIMMING POOL AND JACUZZI

PRIVATE LUXURY VILLA WITH HEATED SWIMMING POOL AND JACUZZI

Città della Pieve PG
Guests of this villa enjoy features like an outdoor pool, a hot tub, and an arcade/game room. Staff members can answer questions about accommodations, and also provide concierge services. Other amenities at this family-friendly villa include laundry facilities, a garden, and barbecue grills.
Pool
Hot Tub
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 Corsignano

    Hotel Corsignano

    Via Della Madonnina 11 Pienza SI
    $134 nightly
    The price is $154 total per night from Jun 21 to Jun 22
    $154 total
    Jun 21 - Jun 22
    Total with taxes and fees
    9.4/10 Exceptional! (361 reviews)
    Hotel San Gregorio

    Hotel San Gregorio

    Via Della Madonnina 4 Pienza SI
    $196 nightly
    The price is $222 total per night from Jun 30 to Jul 1
    $222 total
    Jun 30 - Jul 1
    Total with taxes and fees
    9.4/10 Exceptional! (147 reviews)
    Tenuta Santo Pietro

    Tenuta Santo Pietro

    Localita Santo Pietro 29 Pienza SI
    $215 nightly
    The price is $241 total per night from Jul 19 to Jul 20
    $241 total
    Jul 19 - Jul 20
    Total with taxes and fees
    9.6/10 Exceptional! (126 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
1490 Villas
Lowest Price
$154
Highest Price
$241
Popular accommodation
Enchanting Tuscan Villa / Private Estate / Heated Pool / Panoramic Views, Montalcino: Private villa in the heart of Tuscany, private pool, A/C, Beautiful private villa for 4 people with WIFI, pool, A/C, TV and terrace, Il Poggio dell'Eremita, Private and cozy retreat in Montalcino with private pool surrounded by vineyards, Villa with swimming pool and large garden, nestled in the hills of Maremma, Big house, Villa Podere Belvedere, PRIVATE LUXURY VILLA WITH HEATED SWIMMING POOL AND JACUZZI

More to Explore