Pienza Villas Rentals

A historic square with a prominent tower and statues.

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Our top choices for Pienza villas

An aerial view of a property with a large central building, a courtyard with a circular garden, and surrounding structures.

1. Elegant ground floor villa of 93 m2 consisting of a large living room with sofas and fireplace, kitchen complete with dishwasher, microwave oven, electric oven, coffee machine, kettle, fridge and freezer.Indoor and outdoor dining area, a double bedroom w

Trequanda

$215 nightly

Nov 14 - Nov 15

Total with taxes and fees

A two-story building with balconies, outdoor seating, and potted plants.

2. Artisti del Cavallo Tourism

Foiano della Chiana

Heiner

$74 nightly

Nov 8 - Nov 9

Total with taxes and fees

A stone building with multiple rooms, surrounded by lush greenery and trees.

3. WPRELAIS BORGO VIGNALUNGA

Toscana

Jeremy F.

$1,192 nightly

Nov 22 - Nov 23

Total with taxes and fees

A stone house with a sloped roof, a wooden porch, and a garden with various plants and flowers.

4. Il Poggio dell'Eremita

Sinalunga

Paul Q.

$168 nightly

Nov 6 - Nov 7

Total with taxes and fees

A stone building with a tiled roof, a small porch, and a pathway leading to it.

5. Villa "Podere Spagliarda" with Private Pool, Terrace & Wi-Fi

San Quirico d'Orcia

$1,979 nightly

Nov 3 - Nov 4

Total with taxes and fees

A stone-walled patio with wicker furniture, a table, and a view of a green landscape.

6. Wp Relais Villa Vignalunga

CASTIGLIONE D'ORCIA (SI)

Samantha L.

$715 nightly

Nov 3 - Nov 4

Total with taxes and fees

A tree, a lamp post, and a clear blue pool with a view of distant mountains.

7. Villa 'Tiberini - Casale Il Pecino' with panoramic Valdichiana view, private pool & Wi-Fi

Torrita di Siena

"Our first trip to Tuscany was made extra special by our accommodations. From the moment we arrived, our hosts Nunzia and Luca were so attentive to all our needs. They made sure we had great recommendations. We even spent a few hours at their house doing wine tasting and a tour of their operation. Make sure you get to try Day 1 wine…was my favorite!! Would highly recommend this location as a great landing spot in Tuscany. Located so close to many great little villages."

Nate D.

$2,264 nightly

Nov 3 - Nov 4

Total with taxes and fees

A patio table with a patterned tablecloth, an umbrella, and metal chairs.

8. Villa Falco-Cignella Resort Apartments in Tuscany

Trequanda

$317 nightly

Nov 3 - Nov 4

Total with taxes and fees

A patio with a table and chairs, a large umbrella, and a vase of flowers.

9. Villa Cielo- Cignella Resort Tuscany Accommodation

Trequanda

$320 nightly

Nov 3 - Nov 4

Total with taxes and fees

A large, red-roofed villa surrounded by lush green fields and rolling hills.

10. '...a delicious farmhouse in the countryside where only the wind blows...'

Campiglia d'Orcia

"We had a wonderful stay at the villa - we were a group of 10 adults and 2 children and used the villa as our home base for a week to explore the area (Pienza, Siena, Montalcino, Montelpulciano, etc). There are 4 apartments ranging from 1-3 bedrooms which were fantastic for the families, plus an additional communal kitchen and living room for everyone to gather. It was the perfect setup as it gave everyone the ability to have some privacy as well as for everyone to congregate and eat meals...

Li-Shen L.

$1,532 nightly

Nov 5 - Nov 6

Total with taxes and fees

A stone building with a garden pathway leading to it.

11. VILLA BRUNELLO - Twelve Bedroom Villa, Sleeps 24

Montalcino

$7,142 nightly

Nov 3 - Nov 4

Total with taxes and fees

A courtyard with a pathway leading to a circular garden area, surrounded by trees and a building with a tiled roof.

12. Elegant ground floor villa of 93 m2 consisting of a large living room with sofas and fireplace, kitchen complete with dishwasher, microwave oven, electric oven, coffee machine, kettle, fridge and freezer.Indoor and outdoor dining area, a double bedroom w

Trequanda

$215 nightly

Nov 6 - Nov 7

Total with taxes and fees

A stone building with a sloped roof and a chimney, surrounded by a grassy area and trees.

13. Red Heart - Relax with Your Loved Ones in Tuscany

Trequanda

$895 nightly

Nov 3 - Nov 4

Total with taxes and fees

14. Elegant and spacious two-storey villa of 142 m2 composed on the ground floor of a large living room, kitchen complete with dishwasher, microwave oven, electric oven, coffee machine, kettle, fridge and freezer.On the first floor we find a double bedroom w

Trequanda

$224 nightly

Nov 6 - Nov 7

Total with taxes and fees

A building with a red facade, green shutters, and a tiled roof.

15. Apartment In A Hotel "Villa Pesca" with Shared Pool, Private Balcony & Wi-Fi

Trequanda

$623 nightly

Nov 3 - Nov 4

Total with taxes and fees

A poolside area with lounge chairs and umbrellas, a clear view of the pool, and a pathway leading to the pool.

16. VILLA CHIGI - Seven Bedroom Villa, Sleeps 14

Siena

$6,621 nightly

Nov 3 - Nov 4

Total with taxes and fees

A building with arched windows and a hammock in the garden.

17. Villa Aquila-Cignella Resort Acommodation Tuscany

Trequanda

$533 nightly

Nov 3 - Nov 4

Total with taxes and fees

A pool with a stone border, surrounded by a well-manicured lawn and trees.

18. Apartment In A Hotel "Villa Cielo" with Shared Pool, Private Terrace & Wi-Fi

Trequanda

$623 nightly

Nov 3 - Nov 4

Total with taxes and fees

An outdoor patio with a table, chairs, an umbrella, and a lounge chair.

19. Hotel Apartment "Villa Limone" with Shared Pool & Wi-Fi

Trequanda

$623 nightly

Nov 3 - Nov 4

Total with taxes and fees

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Top Pienza Hotel Reviews

Tenuta Santo Pietro

10/10 Excellent

"This place was a Gem. The property and amenities were awesome and very homey. Very lovely and well seasoned staffed that know how to cater to their guests. I would recommend this spot to anyone who wants to be taken care of in a very special and specific manner. We had Dinner there both nights we stayed there and not only was it convenient but it was delicious. Traditional meals served simply, yet beautifully."

Fonteverde Thermal Spa Resort Tuscany

10/10 Excellent

"We travel a lot and this was our favorite hotel ever!! Natural hot springs designed into a luxurious set of pools with jets, waterfalls, and even poolside bistrot! The breakfast was the best European hot breakfast we’ve ever had as well. The rooms were beautiful too."

Agriturismo Poggio Tobruk

10/10 Excellent

"Did you ever want to say that you stayed in one of the Pope's guest houses? The Agriturismo Poggio Tobruk may be a place for you, and that is only a starter. The Poggio is a working farm (wheat, clover, olives) and it is managed by Marco, a Sardinaian, and his brother. Marco works the villa as well as running the farm with his brother. One of our group worked a wheat farm in Colorado, so a lot of time was spent looking at equipment and discussing crops. We picniked in the olive grove and basked on the lawn, both with marvelous views of the countryside and Pienza on its own hill just a few kilometers away. We bought products from the farm, and of course the friendly Marco gave us more products to take along. Poggio Tobruk is a great place to visit, and not just because the Pope once hosted guests there!"

Castello di Velona Resort Thermal SPA & Winery

10/10 Excellent

"Stayed at the hotel for our honeymoon and it was an incredible experience. The view is simply breathtaking and the castle is extremely charming. Food (breakfast and diner) and wine at the restaurants are high quality, inspired and locally sourced, though expensive. Their Brunello is VERY good. The thermal spa experience is unique in the region and is awsome, especially during the fall season when it is cooler outside. The room was super clean and the staff was very helpful throughout the entire week, and we felt welcomed at any time of day. 15 min by car from Montalcino, strongly recommend to rent a car since it is slightly remote. Overall 9.5/10, strongly recommend for a special occasion."

Podere Spedalone

8/10 Good

"The shower drain was not adequate and bath room as well as into bedroom pooled with water. Had to use shower with very low flow. No coffee machine in the room, one machine in breakfast room which staff only operated starting at 8;00am. Definitely a minus as wanted coffee earlier, and like to still be in pajamas in room. Pillows were flat and not supportive of neck or head. One mile of very bumpy road leading to property. Lots of flies around due to chickens and sheep on property. Room would be quite warm in summer"

Agriturismo Il Macchione

8/10 Good

"We stayed at the olive Farmhouse across the street from the main property. Rooms were cozy and clean with some interesting toiletries to use (made from olive oil). The property also has a range of activities (extra) to choose from. Just a note that eventhough the farmhouse is close to the main property, you have to walk uphill to get to the property for breakfast or the pool. Also it is close to Pienza but on the north side (personally I think the south side is more picturesque). But overall, a good stay and property! Staff was very professional, friendly and always courteous"

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Pienza Villas information

Number of reviews	179
Accommodation	1407 Villas
Lowest Price	$86
Highest Price	$7,142

Frequently asked questions

How much do villas in Pienza cost?

Rates for villas in Pienza range between $86 and $7,142 per night. Whatever your budget, you're sure to find a place that fits the bill with Expedia. These prices were 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?

Pack your suitcase and pick from 1407 villas in Pienza. For a family escape, a getaway with pals or anything in between, Expedia will help you find the right place in just a click or two.

Why book your villa in Pienza with Expedia?

With Expedia, it's easy to find your dream villa in Pienza. Vacationing with the kids? Use our helpful filters to search for stays with amenities like WiFi and a pool. If you have a certain budget, select how much you'd like to spend and your preferred star rating. We'll help you find the right stay in tune with your taste and style.

How can I find cheap villas in Pienza?

An excellent way to track down cheap villas in Pienza is with Expedia's user-friendly filter tool. Narrow your search results by budget, star rating and amenities to find unbeatable rates in just a click or two.

What is there to do near my villa in Pienza?

Whatever you're interested in, Pienza has plenty to keep you going. Artemisia Gallery, Pienza Cathedral and Palazzo Comunale are on many visitors' sightseeing itineraries. Don't forget about Palazzo Piccolomini, Historic Centre of Pienza and Piazza Pio II either. With Expedia's hotel deals in Pienza, you can discover more neat attractions like these with the money you save.

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Things to do in Pienza

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Our top choices for Pienza villas

1. Elegant ground floor villa of 93 m2 consisting of a large living room with sofas and fireplace, kitchen complete with dishwasher, microwave oven, electric oven, coffee machine, kettle, fridge and freezer.Indoor and outdoor dining area, a double bedroom w

2. Artisti del Cavallo Tourism

3. WPRELAIS BORGO VIGNALUNGA

4. Il Poggio dell'Eremita

5. Villa "Podere Spagliarda" with Private Pool, Terrace & Wi-Fi

6. Wp Relais Villa Vignalunga

7. Villa 'Tiberini - Casale Il Pecino' with panoramic Valdichiana view, private pool & Wi-Fi

8. Villa Falco-Cignella Resort Apartments in Tuscany

9. Villa Cielo- Cignella Resort Tuscany Accommodation

10. '...a delicious farmhouse in the countryside where only the wind blows...'

11. VILLA BRUNELLO - Twelve Bedroom Villa, Sleeps 24

12. Elegant ground floor villa of 93 m2 consisting of a large living room with sofas and fireplace, kitchen complete with dishwasher, microwave oven, electric oven, coffee machine, kettle, fridge and freezer.Indoor and outdoor dining area, a double bedroom w

13. Red Heart - Relax with Your Loved Ones in Tuscany

14. Elegant and spacious two-storey villa of 142 m2 composed on the ground floor of a large living room, kitchen complete with dishwasher, microwave oven, electric oven, coffee machine, kettle, fridge and freezer.On the first floor we find a double bedroom w

15. Apartment In A Hotel "Villa Pesca" with Shared Pool, Private Balcony & Wi-Fi

16. VILLA CHIGI - Seven Bedroom Villa, Sleeps 14

17. Villa Aquila-Cignella Resort Acommodation Tuscany

18. Apartment In A Hotel "Villa Cielo" with Shared Pool, Private Terrace & Wi-Fi

19. Hotel Apartment "Villa Limone" with Shared Pool & Wi-Fi

Find vacation rentals that suit your style

Top Pienza Hotel Reviews

Tenuta Santo Pietro

Castiglion del Bosco, A Rosewood Hotel

Fonteverde Thermal Spa Resort Tuscany

Nuovo Etruria Resort

Agriturismo Poggio Tobruk

Castello di Velona Resort Thermal SPA & Winery

Hotel Villa Ricci

Podere Spedalone

Agriturismo Il Macchione

Find out more about Pienza

Pienza Villas information

Frequently asked questions

Explore a world of travel with Expedia

Villas in Pienza

Bundle & Save

OneKeyCash

Upfront pricing

Check prices for these dates

Our top choices for Pienza villas

1. Elegant ground floor villa of 93 m2 consisting of a large living room with sofas and fireplace, kitchen complete with dishwasher, microwave oven, electric oven, coffee machine, kettle, fridge and freezer.Indoor and outdoor dining area, a double bedroom w

2. Artisti del Cavallo Tourism

3. WPRELAIS BORGO VIGNALUNGA

4. Il Poggio dell'Eremita

5. Villa "Podere Spagliarda" with Private Pool, Terrace & Wi-Fi

6. Wp Relais Villa Vignalunga

7. Villa 'Tiberini - Casale Il Pecino' with panoramic Valdichiana view, private pool & Wi-Fi

8. Villa Falco-Cignella Resort Apartments in Tuscany

9. Villa Cielo- Cignella Resort Tuscany Accommodation

10. '...a delicious farmhouse in the countryside where only the wind blows...'

11. VILLA BRUNELLO - Twelve Bedroom Villa, Sleeps 24

12. Elegant ground floor villa of 93 m2 consisting of a large living room with sofas and fireplace, kitchen complete with dishwasher, microwave oven, electric oven, coffee machine, kettle, fridge and freezer.Indoor and outdoor dining area, a double bedroom w

13. Red Heart - Relax with Your Loved Ones in Tuscany

14. Elegant and spacious two-storey villa of 142 m2 composed on the ground floor of a large living room, kitchen complete with dishwasher, microwave oven, electric oven, coffee machine, kettle, fridge and freezer.On the first floor we find a double bedroom w

15. Apartment In A Hotel "Villa Pesca" with Shared Pool, Private Balcony & Wi-Fi

16. VILLA CHIGI - Seven Bedroom Villa, Sleeps 14

17. Villa Aquila-Cignella Resort Acommodation Tuscany

18. Apartment In A Hotel "Villa Cielo" with Shared Pool, Private Terrace & Wi-Fi

19. Hotel Apartment "Villa Limone" with Shared Pool & Wi-Fi

Find vacation rentals that suit your style

Top Pienza Hotel Reviews

Tenuta Santo Pietro

Find out more about Pienza

Pienza Villas information

Frequently asked questions

Explore a world of travel with Expedia