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Browse Select Pienza Villas

Outdoor pool
Tuscan villa pool spa Siena, Montepulciano Montalcino Pienza Florence
10.0 out of 10, Exceptional, (95)
"Stayed at this home for 4 nights and wish we stayed longer. Perfect Tuscan home and great hosts. Just do it!"
Tuscan villa pool spa Siena, Montepulciano Montalcino Pienza Florence
Outdoor pool
Tuscan stone villa with private pool surrounded by greenery
10.0 out of 10, Exceptional, (82)
"My family and I had been planning a trip to Tuscany for over 10 years, then one day we just decided it was time to go, so after much research, I found this gorgeous villa in Arcidosso, and booked it. I have never looked back. From the moment I booked the villa, it just felt right. Margo and Marco met us in Arcidosso where they escorted us to the villa. I fell in love with it from the moment I saw it. It was better to look at in real life than the pictures. It was absolutely perfect. The villa...
Tuscan stone villa with private pool surrounded by greenery
Pool
Villa Calcinaio - Holiday Country Villa with swimming pool in Cortona
9.4 out of 10, Exceptional, (39)
"Just on the slope nestled between Cortona city and the Calcinaio church, the location was perfect for us. We enjoyed the serenity of no one immediately around us while only being a very short drive from the city walls. (Admittedly, we could have walked, but driving was easier!) Taking day trips to various Tuscan cities and sights was wonderfully served by the central location."
Villa Calcinaio - Holiday Country Villa with swimming pool in Cortona
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Outdoor pool
Villa with private pool, air conditioning, 4km from town, 30km Siena & Arezzo
10.0 out of 10, Exceptional, (20)
"Our stay at this house surpassed all our expectations. Everything was very clean and well stocked with many little amenities and personal touches. The grounds have the most amazing views, especially in springtime. Mrs Rossella was a most gracious host. She was attentive to any of our needs. We had a wonderful experience with a chef as well. The hosts recommended her, and our dinner was unique and delicious! We will definitely come back to this house and would recommend it to anyone."
Villa with private pool, air conditioning, 4km from town, 30km Siena & Arezzo
Outdoor dining
Magnificent Leopoldian Villa for 10p (+option. 4p) with private pool and garden
10.0 out of 10, Exceptional, (17)
"Villa Gagnoni is a well restored authentic Tuscan farmhouse in a superb, tranquil "away from it all" natural setting. It is an excellent, well located base for exploring central Tuscany with many of the top attractions anywhere from a short drive to an easy day trip away. The nearby village of Lucignano is charming. The quality of the architectural restoration is of a high standard. The furnishings include some impressive antique sideboards and wardrobes and is otherwise comfortably...
Magnificent Leopoldian Villa for 10p (+option. 4p) with private pool and garden
Pool
Wonderful private villa for 4 people with pool, WIFI, A/C, TV, terrace and parking
9.8 out of 10, Exceptional, (27)
"Nice house suitable for a family of 3-4. Two bed rooms, one with a double bed. Living room and well equipped kitchen. Very cozy property a kilometer or so from the town center. The host family lives in another house on the same property, and are very nice and hospitable, while not being intruding in any way. The private church on the property is worth a visit, it was built in 710 a.d. and has frescos from the 1500s inside. The pool is very nice, and there is a nice playground for children. We...
Wonderful private villa for 4 people with pool, WIFI, A/C, TV, terrace and parking
Pool
Villa Scopetello with Pool and Tennis court near Montepulciano and Siena
10.0 out of 10, Exceptional, (98)
"We were group of 16 adults and three children under the age of three. Sonja and Diego could not have been better hosts! They are truly lovely people! Everything was absolutely perfect! The villa is stunning and very child friendly! We opted to have Sonja cook breakfast and dinner for us each day, and her food was absolutely delicious! You must try their pizza and bbq! We enjoyed the tennis court, feeding the horses, and day trips to Siena, Florence, and Montepulciano. The villa location is...
Villa Scopetello with Pool and Tennis court near Montepulciano and Siena
Pool
A private luxury retreat in Montalcino
9.4 out of 10, Exceptional, (47)
"We loved this place. Beautiful pool, facilities and views"
A private luxury retreat in Montalcino
Outdoor pool
Enchanting Private Villa in Chianti Rolling Hills:Free WiFi,AC,Garden,Pool,View!
9.8 out of 10, Exceptional, (90)
"We had the most amazing time at Il Poggio! The property is well maintained, Roberta and Marina were incredible, and the location could not be beat. We took day trips (by car) to Siena, Arezzo, Florence, Orvieto, and Montalcino, all of which were easily and quickly accessible. Each of our five guests (two couples, one single!) had their own floor and bathroom. We cooked in the well-stocked kitchen, drank wine while watching the sunrise on the patio, and were transported to the past walking...
Enchanting Private Villa in Chianti Rolling Hills:Free WiFi,AC,Garden,Pool,View!
Outdoor pool
Recently restored Villa in Tuscany, sleeps 12, sw.pool, big garden, olive grove.
10.0 out of 10, Exceptional, (2)
"The property is extremely well maintained and feels brand new. The location is perfect for exploring wine country and villages! The property manager is extremely responsive and helpful, and went as far as stocking groceries prior to our arrival and preparing dinner for us the first night. We were very happy with our experience."
Recently restored Villa in Tuscany, sleeps 12, sw.pool, big garden, olive grove.
Outdoor pool
Villa with private pool and panoramic view in beautiful Val d'Orcia
10.0 out of 10, Exceptional, (3)
"Enjoyed 10 relaxing days at Villa Montisi, a very clean and comfortable property with a lovely pool and garden. Also an excellent base to explore the local towns and stunning scenery (with Pienza, Montalcino, Montepulciano and Siena all within easy reach) and to enjoy the wonderful food and wine the region has to offer. Thoroughly recommend."
Villa with private pool and panoramic view in beautiful Val d'Orcia
Pool
La Torretta 10, Emma Villas
9.0 out of 10, Wonderful, (6)
"The villa was lovely, and our property manager was very attentive. The villa itself was very comfortable, bedrooms were clean and neat. The bathrooms were adequate with clean towels and great hot water. The kitchen was well equipped, definitely could use a larger coffee pot. The outdoor space is beautiful, the pool is well maintained.There is a washer but no dryer.The property is a bit remote, on the side of a mountain you need to drive everywhere. The house was not equipped with flashlights or...
La Torretta 10, Emma Villas
Pool
House with Modern Design, Pool, Views of the Sienese Countryside, Air Conditioning
9.4 out of 10, Exceptional, (22)
"The house is nice but doesn’t have the Tuscany view that we all dream about it with a lot of tree around it. The driveway is not paved is very rough, if you have a sport car definitely you can’t drive in with out scratches or damage the car. Inside everything is very cheap (look like all IKEA stores) the beds are good and comfortable, the showers very small and i fell In twice special if you are 6.3 F or 193 cm . Is not luxury is just above average. Is not what I expected. Definitely not coming...
House with Modern Design, Pool, Views of the Sienese Countryside, Air Conditioning
Exterior
Villa Miralaghi: Huge Park, Private Heated Pool, Billiard, Lake, Playground,
9.4 out of 10, Exceptional, (38)
"Our group of five women thoroughly enjoyed our two-week stay at Miralaghi. We were in the main house (old hunting lodge) with 4-bedrooms, 3 baths, huge living space, kitchen, carport, and private pool. Miralaghi is a unique property, located between Paciano and Moiano, high up on a hillside. It is very peaceful, quiet and provides lovely hiking trails on the huge, 750 acre property. It's a perfect retreat at the end of a day of visiting nearby hill towns. Our host, Mausi, was a delight and so...
Villa Miralaghi: Huge Park, Private Heated Pool, Billiard, Lake, Playground,
Fridge, microwave, oven, stovetop
Vintage Villa Vagnucci - Cortona
10.0 out of 10, Exceptional, (1)
"Have stayed in area before, but not Cortona. We were taken around the property by Nonna and her grandson. A great team. They bogg live on siteNonna was attentive but not intrusive, and always left us tomatoes and basil from her garden, but spoke no english - more of a comment about us than her as it would have been great to talk to her more fully. A lovely lady. Stefano was great as translator, go to guy for info - taxi firms, air con specialists, bar to watch womens footy final! Etc A great...
Vintage Villa Vagnucci - Cortona
Pool
Villa Este
9.0 out of 10, Wonderful, (2)
Villa Este
Fridge, microwave
Villa Pozzonovo is an old stone farmhouse within walking distance of the centre of Castiglion Fioren
10.0 out of 10, Exceptional, (1)
"Bellissimo casolare ben tenuto con magnifico giardino e grande piscina. La padrona di casa gentilissima e molto discreta. Abbiamo soggiornato in agosto con amici e ci siamo trovati benissimo. Assolutamente consigliato!"
Villa Pozzonovo is an old stone farmhouse within walking distance of the centre of Castiglion Fioren
Outdoor pool
Beautiful intime Villa with private pool 3 Bedrooms Sleep 7
9.8 out of 10, Exceptional, (13)
"Villa Messi is located in a lovely quiet village of Casalini. The property itself is quite large, furnished with nice art and artefacts, giving it an initially opulent feel. Outside, there is an open eating area, complete with inbuilt barbeque, wood-fired pizza oven, hob, sink and even a fridge. We enjoyed using these facilities during our stay, including making and baking our own pizzas from scratch. The bedrooms are all en-suite. Messi and Dante were on hand when required during our stay and...
Beautiful intime Villa with private pool 3 Bedrooms Sleep 7
Terrace/patio
Villa "Il Fornacino" with Pool, Garden & Wi-Fi
8.0 out of 10, Very good, (2)
"This house is very nice. It is centrally located outside Siena and good location to explore all over Tuscany. It is off the beaten path so you’ll definitely need a rental car. Even just to get there. It is remote. Which is a plus but also has some drawbacks. We went in March so pool was closed. Too cold to swim. House is several levels. Kitchen and dining room are downstairs. We cooked several simple meals after going into town to grab groceries. Nearby town is nice. Not a lot of restaurant...
Villa "Il Fornacino" with Pool, Garden & Wi-Fi
Microwave, oven, stovetop, dishwasher
Porta Romana Elegant House with Private Parking!
Porta Romana Elegant House with Private Parking!
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See all available properties in Pienza
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.

Other property types in Pienza

Seasonal outdoor pool, pool loungers
Hotel San Gregorio
3.0 star property
9.2 out of 10, Wonderful, (98)
"Very nice staff, great service, super clean. Will stay again."
The price is £151
includes taxes & fees
14 May - 15 May
Hotel San Gregorio
Seasonal outdoor pool, pool umbrellas, pool loungers
Casanova - Panoramic Rooms and Suites
3.0 star property
9.2 out of 10, Wonderful, (17)
"Beautiful location convenient to many Tuscany sites."
The price is £155
includes taxes & fees
24 May - 25 May
Casanova - Panoramic Rooms and Suites
Pool | Outdoor pool
Casale Immerso nel Verde Della Campagna Toscana con Piscina Privata e Vista
9.6 out of 10, Exceptional, (38)
"The house is a beautiful old Italian house with high ceilings with wooden beams and tiled floors. Everything in the house worked pedfectly- wifi, hot water, screens on the windows, kitchen and bath. The house is set in the midst of the Tuscan hills with hikes starting right from the front door. The grounds in the nature preserve are lovely with local plantings. The hostess, Marina, was welcoming, helpful, and altogether delightful. The gravel access road is steep and curvy in places. We were...
Casale Immerso nel Verde Della Campagna Toscana con Piscina Privata e Vista
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.

Pienza Villas information

Number of reviews
376
Accommodation
1309 Villas
Lowest Price
Highest Price

Frequently asked questions

How much do villas in Pienza cost?
Rates for villas in Pienza range between and per night. No matter your budget, you’re sure to find something that suits your needs with Expedia. This price was available on Expedia within the past 7 days, for a hotel booking with a check-in date within the next year. Prices reflect current offers and availability is subject to change. Additional terms may apply.
How many villas are there in Pienza?
You’ll find 1309 villas in Pienza. No matter if you’re holidaying with the family or organising a weekend break with your pals, Expedia will help you find the perfect space for your crew.
Why book your holiday villa in Pienza with Expedia?
We think planning a holiday should be a breeze, so if you’re in search of villas at an affordable rate, Expedia has you covered. Save some cash and pick an all-inclusive stay, or splurge on a plush holiday villa to surprise your loved ones. Our handy filters make it simple to find a place in Pienza that suits you best.
How can I find cheap villas in Pienza?
The easiest way to compare cheap villas in Pienza is with Expedia’s useful filter tool. Refine your search by budget, amenities and star rating to discover unbeatable bargains in just a click or two.
What is there to do near my holiday villa in Pienza?
Pienza has enough sights to keep you going for weeks, beginning with Terme di Montepulciano Spa. Pienza Cathedral, Piscine Termali Theia and Tenuta Greppo Franco Biondi Santi are other renowned attractions. If you’re sticking around a while, Consorzio del Vino Nobile di Montepulciano and Palazzo Piccolomini are nice finishing touches to your itinerary.

Pienza Hotel Reviews
Expedia verified reviews