A town with terracotta-roofed buildings and a distant church.

Piancastagnaio Vacation Rentals

Check prices for these dates

In two weeks
Oct 30 - Nov 1
In two months
Dec 11 - Dec 13
In three months
Jan 8 - Jan 10
In four months
Feb 5 - Feb 7

Our top choices for Piancastagnaio vacation rentals

A covered outdoor seating area with brick pillars, potted plants, and a view of trees and mountains.

1. Holiday Home 'Casale I Cascetti' with Pool, Garden and Wi-Fi

Holiday Home 'Casale I Cascetti' with Pool, Garden and Wi-Fi
Siena
10.0 out of 10, Exceptional, (1 review)
"Bellissime camere, dotate di ogni confort, immerse nel verde della campagna toscana. Camere spaziose, comode, luminose e attrezzate di tutto. Proprietari ospitali e gentili, sempre pronti a fornire indicazioni. Grazie di tutto , torneremo senz'altro!"
United States
Annarosa m.
$727 nightly
The price is $732
Oct 16 - Oct 17
Total with taxes and fees
Holiday Home 'Casale I Cascetti' with Pool, Garden and Wi-Fi
A terrace with a table set for dining, overlooking a scenic landscape with a castle in the distance.

2. FonteLiving

FonteLiving
San Casciano dei Bagni
10.0 out of 10, Exceptional, (20 reviews)
"Fabulous apt., elegant, clean lines, quiet, pool and wonderful staff"
Italy
Dauray
$81 nightly
The price is $92
Oct 15 - Oct 16
Total with taxes and fees
FonteLiving
A room with a curved ceiling, a hot tub, and a glass door leading outside.

3. Chalet Il Cristallo

Chalet Il Cristallo
Castel del Piano
7.6 out of 10, Good, (4 reviews)
"Camera impeccabile, personale cortese e disponibile, colazione ottima ,come la cena. Struttura molto accogliente. Ottima per famiglie."
Italy
Federico
$45 nightly
The price is $53
Oct 21 - Oct 22
Total with taxes and fees
Chalet Il Cristallo
An open door leading to a balcony with a view of a forested hillside.

4. La Dimora di Dida

La Dimora di Dida
Seggiano
$74 nightly
The price is $81
Nov 3 - Nov 4
Total with taxes and fees
La Dimora di Dida
A stone building with a wooden door, steps leading to a balcony, and potted plants.

5. The Old Washhouse

The Old Washhouse
Radicofani
10.0 out of 10, Exceptional, (2 reviews)
"What a wonderful stay! This apartment was absolutely perfect for the two of us. It was impeccably clean, warm, cozy, and spacious enough for a couple. The bed and furniture was so comfortable, and the attention to detail was simply spot on. Everything was absolutely perfect!We were so touched by the thoughtful complimentary coffee, tea, and breakfast items. The bathroom was just as equipped with shampoo and soaps. Every little detail made us feel right at home.The gorgeous private garden was a...
Canada
Chantale M.
$137 nightly
The price is $142
Oct 20 - Oct 21
Total with taxes and fees
The Old Washhouse
A natural hot spring with multiple pools and people swimming.

6. Il Cantuccio

Il Cantuccio
Manciano
9.2 out of 10, Wonderful, (62 reviews)
"The breakfast was good, they had a few different kinds of options of breads, pastries, coffee, toppings for bread, and other things."
United States
Mara
$74 nightly
The price is $84
Oct 25 - Oct 26
Total with taxes and fees
Il Cantuccio
A modern bedroom with a wooden headboard, a large bed with a textured blanket, bedside tables with lamps, and a mirror.

7. Terme bagni san filippo La Balena Bianca a due passi: Casa Nuova con Terrazza

Terme bagni san filippo La Balena Bianca a due passi: Casa Nuova con Terrazza
Bagni San Filippo
$153 nightly
The price is $157
Oct 20 - Oct 21
Total with taxes and fees
Terme bagni san filippo La Balena Bianca a due passi: Casa Nuova con Terrazza
A pool with a waterfall feature and a stone sculpture.

8. Villaggio Le Querce

Villaggio Le Querce
4.0 star property
Sorano
9.0 out of 10, Wonderful, (64 reviews)
"The smaller, children, pool is further away and down many stairs. There are many comfortable seats by the main pool. I wish the main pool had a variation in depth.Breakfast is heavenly. All the staff we encountered were very friendly."
United States
Nathan
$81 nightly
The price is $95
Oct 21 - Oct 22
Total with taxes and fees
Villaggio Le Querce
A patio area with outdoor seating, potted plants, and a view of the landscape.

9. Affitacamere Maria Gabriella

Affitacamere Maria Gabriella
Pienza
9.8 out of 10, Exceptional, (71 reviews)
"A very pleasant and homey place to stay"
Germany
Janine und Thomas
$116 nightly
The price is $132
Oct 14 - Oct 15
Total with taxes and fees
Affitacamere Maria Gabriella
A stone building with a tiled roof, a staircase leading to a lower level, and a garden with various plants.

10. Double bedroom with private bathroom, private access, garden and swimming pool

Double bedroom with private bathroom, private access, garden and swimming pool
Radicofani
$89 nightly
The price is $94
Nov 6 - Nov 7
Total with taxes and fees
Double bedroom with private bathroom, private access, garden and swimming pool
A hotel room with a bed, a desk, a chair, a lamp, and a mirror.

11. Hotel San Gregorio

Hotel San Gregorio
3.0 star property
Pienza
9.4 out of 10, Exceptional, (162 reviews)
"Great location. Clean and quiet with good breakfast"
United States
Michael
$128 nightly
The price is $147
Nov 8 - Nov 9
Total with taxes and fees
Hotel San Gregorio
A stone archway leading to a dining area with a table set for two, overlooking a lush green landscape.

12. Agriturismo Poggio Monte

Agriturismo Poggio Monte
Manciano
9.8 out of 10, Exceptional, (14 reviews)
"A special place—quiet, clean, and cozy. Best of all, are the amazing people in charge of the place, who were very attentive and always made sure that everything ran smoothly."
United States
jason
$98 nightly
The price is $111
Oct 20 - Oct 21
Total with taxes and fees
Agriturismo Poggio Monte
A rectangular pool with a metal ladder, surrounded by wooden lounge chairs and a stone deck.

13. Corte Francigena - Apartments

Corte Francigena - Apartments
Montalcino
9.8 out of 10, Exceptional, (19 reviews)
"The unit is very clean, awesome breakfast, beautiful view"
Canada
Ivan
$98 nightly
The price is $117
Nov 5 - Nov 6
Total with taxes and fees
Corte Francigena - Apartments
A bedroom with a large bed, a chandelier, a wall-mounted lamp, and a round mirror.

14. Km 0 dal Centro

Km 0 dal Centro
Pitigliano
10.0 out of 10, Exceptional, (82 reviews)
"Very friendly wonderful hosts and fabulous breakfast"
United States
Laura
$110 nightly
The price is $124
Oct 21 - Oct 22
Total with taxes and fees
Km 0 dal Centro
A stone house with a tiled roof, surrounded by dense greenery and a clear sky.

15. Le Roghete

Le Roghete
Acquapendente
9.4 out of 10, Exceptional, (3 reviews)
"The address of the hotel was wrong on the Hotels.com web site. After an anxious hour or so our host was kind enough to come and get us, we were on foot walking the Via Francigena and the additional 4 miles back would have been a killer. Our host arranged for a cab the next morning so we were back on schedule. Worth the cab expense to keep on schedule. Wonderful evening meal and a great hotel. I would visit it again."
United States
Mark
$81 nightly
The price is $89
Oct 19 - Oct 20
Total with taxes and fees
Le Roghete
A stone building with a tiled roof, a small window, and a door. There is a garden with various plants and flowers in front of the building.

16. Apartment with garden in old farmhouse with swimming pool

Apartment with garden in old farmhouse with swimming pool
Radicofani
10.0 out of 10, Exceptional, (1 review)
"Podere Pietreta è un luogo magico, comodo da raggiungere, ma immerso in un paesaggio della campagna tipicamente toscana, che non ci si stanca mai di contemplare. Appartamento estremamente accogliente ed arredato con gusto in linea con la bellezza del podere, ottima pulizia ed accoglienza. Torneremo in estate per godere anche della piscina, e continuare il tour in Val d'Orcia. Grazie di tutto Silvia & friends"
Italy
SILVIA T.
$156 nightly
The price is $161
Nov 4 - Nov 5
Total with taxes and fees
Apartment with garden in old farmhouse with swimming pool
A stone building with a courtyard, outdoor seating, and a warm light setting.

17. Sarna Residence

Sarna Residence
San Quirico d'Orcia
9.4 out of 10, Exceptional, (40 reviews)
"We enjoyed our stay. The room was very clean. The staff was helpful."
United States
Bokang
$111 nightly
The price is $127
Nov 3 - Nov 4
Total with taxes and fees
Sarna Residence
A stone-walled room with a large bathtub, a fireplace, and a set of stone steps leading to the tub.

18. Borgo San Quirico d'Orcia B&B - Capitano Collection - Albergo diffuso

Borgo San Quirico d'Orcia B&B - Capitano Collection - Albergo diffuso
San Quirico d'Orcia
9.0 out of 10, Wonderful, (50 reviews)
"Our stay was great. "
United States
Elena
$123 nightly
The price is $140
Nov 1 - Nov 2
Total with taxes and fees
Borgo San Quirico d'Orcia B&B - Capitano Collection - Albergo diffuso
A poolside area with two glasses of water, candles, and a stone pathway.

19. Casanova - Panoramic Rooms and Suites

Casanova - Panoramic Rooms and Suites
3.0 star property
San Quirico d'Orcia
9.2 out of 10, Wonderful, (101 reviews)
"Great location and lovely pool. Rooms were large but the place is definitely dated. Breakfast was decent with a lot of options. Parking wasn’t all that great but nevertheless on the property itself"
Canada
Sunil
$170 nightly
The price is $191
Oct 18 - Oct 19
Total with taxes and fees
Casanova - Panoramic Rooms and Suites
A wooden door with a metal handle, a brick archway, a staircase, and a flower pot on the wall.

20. Idolina Guest House

Idolina Guest House
Montalcino
9.6 out of 10, Exceptional, (118 reviews)
"Felt like home. The central kitchen / coffee area felt like home."
United States
Bradley
$94 nightly
The price is $113
Nov 2 - Nov 3
Total with taxes and fees
Idolina Guest House
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.
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Top Piancastagnaio Hotel Reviews

Hotel San Gregorio

Hotel San Gregorio

10/10 Excellent
"Great location. Clean and quiet with good breakfast"
Michael 1-night trip
Posted 1 day ago
Hotel San Gregorio

Find out more about Piancastagnaio

Everything you need to know about Piancastagnaio vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Piancastagnaio vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. The list goes on, and on …and on.

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Piancastagnaio vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Piancastagnaio vacation rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Piancastagnaio. If you’re looking for a little peace, consider booking during the quieter low season months. For more hustle and bustle, you may prefer to visit Piancastagnaio in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $72 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Piancastagnaio rentals

At Expedia, we put the best Piancastagnaio vacation rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia.

To find some top Piancastagnaio rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Piancastagnaio vacation.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Piancastagnaio. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.

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Frequently asked questions

Are there vacation rentals in Piancastagnaio?

Yes, there are vacation rentals near popular local attractions in Piancastagnaio, or you can select a secluded option if you want a relaxing place to stay.

What are some of the best vacation home rentals that Piancastagnaio has to offer?

Tuscan villa pool spa Siena Montepulciano Perugia Pienza Florence 2 hours from Rome: This vacation home rental near Piancastagnaio is located in a rural location and has an outdoor pool, a fireplace, and a barbecue grill to put you at ease in your new surroundings. It has 4 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. It offers a patio, a garden, and a selection of games so you can immerse yourself in your vacation.

How many vacation rentals will I find in Piancastagnaio?

Choose from 5 Expedia vacation rentals in Piancastagnaio for a memorable vacation.

What’s there to see and do in Piancastagnaio?

Explore the area and family-friendly sights such as Villa Acquaviva - La Fattoria, or get out into nature at a spot like Monte Amiata. In the larger area, you’ll find Abbazia di San Salvatore and Baths of San Filippo.

What’s a vacation rental in Piancastagnaio like?

Vacation rentals are privately owned properties you can book for a few weeks or just a few days in Piancastagnaio. Vacation rentals feature amenities such as WiFi and washers and dryers so you'll have all the comforts of home. If you're concerned about a clean environment, a vacation rental can offer a sense of safety away from shared hotel elevators and busy front desks while still allowing you the experience of travel. You'll also find more space in a vacation rental than in a standard hotel, which makes a vacation rental a popular option for family gatherings.