The 10 best holiday rentals in Pienza, Italy | Booking.com
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Holiday Rentals in Pienza

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The best holiday rentals in Pienza

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GARAGE47 Storica Officina Meccanica LOFT B&B iN PIENZA

Pienza

Set just 46 km from Mount Amiata, GARAGE47 Storica Officina Meccanica LOFT B&B iN PIENZA provides accommodation in Pienza with access to a garden, a bar, as well as a housekeeping service.

J
Jasek
From
Czech Republic
The accommodation was fantastic. Great reception, excellent communication, excellent breakfast on the terrace, comfortable and very visually and detailed room, pleasantly hard bed. Convenient parking, accommodation within sight of the beautiful city of Pienza. Thanks to the owners, we will remember only the best.
Scored out of 10, guest rating 9.7
Exceptional - What previous guests thought, 488 reviews
Price from
US$147.13
1 night, 2 adults
Check availability

Vento d’Orcia

Pienza

Vento d’Orcia, a property with a garden, is located in Pienza, 16 km from Parco dei Mulini, 19 km from Terme di Montepulciano, as well as 29 km from Bagni San Filippo.

Y
Yulia
From
France
An exceptional place with an exceptional host Ana:) Our room was very confortable, clean and beautifully decorated with great taste and attention to details. The location of the farm is ideal for visiting the many small medieval towns and tourist spots throughout the valley. Brief reference to Ana: a wonderful personne who made our stay incredibly comfortable and enjoyable. Her homemade cuisine based on fresh season farm’s products is unforgettably delicious!! We highly recommend this magic place for everyone!
Scored out of 10, guest rating 9.8
Exceptional - What previous guests thought, 290 reviews
Price from
US$180.99
1 night, 2 adults
Check availability

Pienzalettings

Pienza

Offering a terrace and inner courtyard view, Pienzalettings is set in Pienza, 45 km from Mount Amiata and 10 km from Parco dei Mulini.

Y
Yuko
From
Japan
The inn was spacious enough for two people. It was clean, simple and relaxing. It seems to have been featured in a magazine, and has a slightly unusual structure with different elevations. I came to Pienza to hike the Val d'Orcia, so I'm glad I chose this inn, which is close to the hiking trailhead. It was also close to the city center and convenient for shopping. It was raining when I arrived, but the weather miraculously improved the next day, and I enjoyed walking for six hours in the deserted Val d'Orcia. Both Val d'Orcia and this inn are great. There was coffee, but I couldn't use the espresso maker properly, so I couldn't enjoy it, but there was tea. I took rusks and other things that were left there as emergency food during the hike. There were also plenty of consumables, so it wasn't a problem.
Scored out of 10, guest rating 9.5
Exceptional - What previous guests thought, 165 reviews
Price from
US$120.92
1 night, 2 adults
Check availability

Residenza d'Epoca La Rosa

Pienza

Located 45 km from Mount Amiata, Residenza d'Epoca La Rosa in Pienza provides rooms with air conditioning and free WiFi.

F
Francesca
From
United States
The place was in a perfect location, really nicely decorated and very clean. The host was extremely helpful, providing information on where to park, and suggestions for restaurants, activities and hikes. Oh, and he dropped off warm croissants in the morning - what a treat!
Scored out of 10, guest rating 9.7
Exceptional - What previous guests thought, 209 reviews
Price from
US$151.80
1 night, 2 adults
Check availability

PienzaLettings "Casa Olivieri"

Pienza

Situated in Pienza, 45 km from Mount Amiata, PienzaLettings "Casa Olivieri" features air-conditioned rooms with free WiFi.

K
Kamila
From
Slovakia
All the instructions were perfectly clear, communication straightforward and fast. Absolutely no issues with check in, keys collection or assistance from the host.The apartment was just wonderful - located right in the centre of beautiful Pienza. Not only was the place well equipped ( shower and the welcome gift = 100% , ) it was utterly cosy and romantic. The host and the staff were very friendly and helpful - promptly answering our questions and messages. We were amazed and enjoyed our stay to the utmost. Massive thanks.
Scored out of 10, guest rating 9.5
Exceptional - What previous guests thought, 142 reviews
Price from
US$97.62
1 night, 2 adults
Check availability

PienzaLettings "Casa Gioia"

Pienza

Situated in Pienza, 45 km from Mount Amiata, PienzaLettings "Casa Gioia" features rooms with city views and free WiFi.

O
Oana
From
Romania
Wonderful, clean, quiet and spacious apartment in the heart of Pienza. Easy check in and communication.
Scored out of 10, guest rating 9.3
Superb - What previous guests thought, 262 reviews
Price from
US$114.26
1 night, 2 adults
Check availability

Agriturismo Il Casalino

Pienza

Offering a sun terrace with panoramic view over the surrounding hills, Agriturismo Il Casalino is set in a 19th-century farmhouse with olive trees and vineyards in Pienza.

A
Anna
From
Poland
Amazing place, breathtaking views. The apartment is equipped with everything you need - it is spacious, nicely decorated and spotlessly clean - the housekeeping lady is amazing, as if she read our minds :) we could stay there forever!
Scored out of 10, guest rating 9.5
Exceptional - What previous guests thought, 765 reviews
Price from
US$247.55
1 night, 2 adults
Check availability

Agriturismo Marinello

Pienza

Featuring a free outdoor pool and a farm producing its own olive oil, Agriturismo Marinello has accommodation with a patio and wrought-iron beds.

E
Erlantz
From
Spain
The place is wonderful, the greatest way to enjoy Turcany. It´s close to Pienza, about 5 minutes by car, but far enough to be a peaceful quiet place. The downs from the garden are memorable and the swimmingpool is an impressive point (I couldn´t enjoy it, but reagrding the place we would be back, for sure). It´s surrounded by olives and meadows and the sell their own olive oil. The room was spaceous with classic Tuscan furnitures, but everything was clean and in good condition.
Scored out of 10, guest rating 9.5
Exceptional - What previous guests thought, 627 reviews
Price from
US$137.56
1 night, 2 adults
Check availability

Podere Spedalone

Pienza

Offering an outdoor pool, Podere Spedalone provides country-style rooms and a large garden. It is set in the Tuscan countryside, 7 km from Pienza.

V
Vera
From
Portugal
Podere Spedalone isn't just an agriturismo, it's an experience. Nestled in the heart of Val d'Orcia, the location is simply unmatched. Peaceful tranquility reigns supreme, punctuated only by the breathtaking sunsets that paint the rolling hills in a kaleidoscope of colors. The buildings themselves are a testament to time, with a rustic charm that adds to the overall ambiance. But don't let the antique exterior fool you - our room was comfortable, providing a perfect haven to relax after a day of exploration. What truly sets Podere Spedano apart is the energy. The staff radiate warmth and create a sense of genuine connection. This energy extends to the other guests as well. We had the pleasure of sharing meals and stories with people from all corners of the globe - Portugal, Canada, Australia, Ukraine, Italy, and the USA - forging friendships that transcended borders. Speaking of meals, breakfast was a daily highlight. Fresh, local ingredients (0km products!) were transformed into delicious dishes that fueled our adventures. But the true star was the cooking class. Rodi, the chef, is an absolute gem! Her passion for Tuscan cuisine was infectious, and the hands-on experience was not only educational but incredibly enjoyable. The communal dinners that followed were the heart and soul of Podere Spedalone. Sharing a table laden with delicious food, laughter flowed freely as we swapped stories and built connections. It was an experience that made us feel like part of a big, happy family. We owe a huge shoutout to the entire Podere Spedalone team for making our stay unforgettable. Anna, David, Giuseppe, Anna, Rodi and everyone we met - thank you for the memories that will last a lifetime. We can't wait to be back!
Scored out of 10, guest rating 9.0
Superb - What previous guests thought, 883 reviews
Price from
US$231.96
1 night, 2 adults
Check availability

Tenuta Santo Pietro

Pienza

Tenuta Santo Pietro is a working farm located in Tuscan countryside, and features an outdoor swimming pool with views of Pienza, 5 km away.

B
BOJAE
From
South Korea
This place was truly amazing. It was spacious and beautiful, and the exterior of the accommodation was absolutely charming. We also had dinner here, and the food was incredibly delicious — not to mention, the portions were by far the most generous we had during our entire month-long trip. I highly recommend this place. Above all, the host lady was incredibly kind. During our stay, my wife injured her ankle. The host showed genuine concern, called the hospital to find out what we needed to do, and even contacted an ambulance for us. (In the end, we didn’t go because the hospital was too busy.) She then kept giving us ice and helped us treat the injury. We are deeply grateful — thank you once again for everything.
Scored out of 10, guest rating 9.3
Superb - What previous guests thought, 235 reviews
Price from
US$212.45
1 night, 2 adults
Check availability
All holiday rentals in Pienza

Most booked holiday rentals in Pienza and surroundings in the past month

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Highly rated holiday rentals in Pienza and nearby

  • Oliviera Camere

    Pienza
    8.0+ review score
    Scored out of 10, guest rating 8.8
    Fabulous - What previous guests thought, 106 reviews

    Set in Pienza, 46 km from Mount Amiata, Oliviera Camere offers air-conditioned rooms with free WiFi and a tour desk.

    From US$131.37 per night
  • Scored out of 10, guest rating 8.9
    Fabulous - What previous guests thought, 360 reviews

    Located in Pienza, 45 km from Mount Amiata, Affittacamere del Corso provides accommodation with a terrace, free WiFi, a shared kitchen, and luggage storage space.

    From US$87.58 per night

  • Beccofino

    Pienza
    8.0+ review score
    Scored out of 10, guest rating 8.6
    Fabulous - What previous guests thought, 511 reviews

    Offering city views, Beccofino is an accommodation located in Pienza, 46 km from Mount Amiata and 15 km from Parco dei Mulini.

    From US$157.64 per night

  • ROSSELLINO®

    Pienza
    8.0+ review score
    Scored out of 10, guest rating 8.8
    Fabulous - What previous guests thought, 349 reviews

    Housed in a historic building, the recently renovated ROSSELLINO® provides accommodation with a terrace and free WiFi.

  • Scored out of 10, guest rating 8.5
    Very good - What previous guests thought, 588 reviews

    Situated 46 km from Mount Amiata, 15 km from Parco dei Mulini and 17 km from Terme di Montepulciano, Affittacamere Dal Falco features accommodation located in Pienza.

    From US$108.60 per night

  • Le Maribelle

    Monticchiello
    8.0+ review score
    Scored out of 10, guest rating 8.5
    Very good - What previous guests thought, 116 reviews

    Set within 44 km of Mount Amiata and 11 km of Terme di Montepulciano, Le Maribelle offers rooms with air conditioning and a private bathroom in Monticchiello.

    From US$224.20 per night
  • Scored out of 10, guest rating 9.7
    Exceptional - What previous guests thought, 185 reviews

    Located within 44 km of Mount Amiata and 11 km of Terme di Montepulciano in Monticchiello, La Casa Di Adelina Monticchiello offers accommodation with seating area.

    From US$140.12 per night
  • Scored out of 10, guest rating 9.7
    Exceptional - What previous guests thought, 291 reviews

    Agriturismo Riposati features garden views, free WiFi and free private parking, located in Monticchiello, 45 km from Mount Amiata.

    From US$140.12 per night

These holiday rentals in Pienza and nearby have options with free cancellation

  • L'apparita Camere

    Pienza
    Free cancellation options available
    Scored out of 10, guest rating 7.5
    Good - What previous guests thought, 237 reviews

    Situated within 46 km of Mount Amiata and 10 km of Parco dei Mulini in Pienza, L'apparita Camere features accommodation with seating area.

    From US$98.09 per night

  • Antica Sosta

    San Quirico dʼOrcia
    Free cancellation options available
    Scored out of 10, guest rating 9.6
    Exceptional - What previous guests thought, 653 reviews

    Antica Sosta is situated in San Quirico dʼOrcia, 44 km from Piazza del Campo, 5.4 km from Parco dei Mulini, and 22 km from Bagni San Filippo.

    From US$93.42 per night

  • LA TULIPA

    San Quirico dʼOrcia
    Free cancellation options available
    Scored out of 10, guest rating 8.8
    Fabulous - What previous guests thought, 10 reviews

    Set in San Quirico dʼOrcia, 40 km from Mount Amiata and 45 km from Piazza del Campo, LA TULIPA offers air-conditioned accommodation with a balcony and free WiFi.

    From US$261.56 per night

  • VINO SUITE

    San Quirico dʼOrcia
    Free cancellation options available
    Scored out of 10, guest rating 9.1
    Superb - What previous guests thought, 41 reviews

    Set in San Quirico dʼOrcia, 41 km from Mount Amiata and 44 km from Piazza del Campo, VINO SUITE offers accommodation with free WiFi in a historic building.

    From US$158.81 per night
  • Scored out of 10, guest rating 9.6
    Exceptional - What previous guests thought, 401 reviews

    Located in San Quirico dʼOrcia, 40 km from Mount Amiata, DIMORA DEL POGGIO - Charming Historic Centre - San Quirico d'Orcia features rooms with city views and free WiFi.

    From US$157.44 per night
  • Scored out of 10, guest rating 8.9
    Fabulous - What previous guests thought, 798 reviews

    Located within 41 km of Mount Amiata and 47 km of Piazza del Campo, b&b BORGO CAPITANO COLLECTION Albergo diffuso - Centro Storico features rooms with air conditioning and a private bathroom in San...

    From US$119.11 per night

  • Dimora delle Mura

    San Quirico dʼOrcia
    Free cancellation options available
    Scored out of 10, guest rating 9.5
    Exceptional - What previous guests thought, 127 reviews

    Offering garden views, Dimora delle Mura is an accommodation situated in San Quirico dʼOrcia, 46 km from Piazza del Campo and 5.1 km from Parco dei Mulini.

    From US$142.72 per night
  • Scored out of 10, guest rating 8.4
    Very good - What previous guests thought, 287 reviews

    Situated within 40 km of Mount Amiata and 44 km of Piazza del Campo, Palazzetto del Pittore in San Quirico d'Orcia features rooms with air conditioning and a private bathroom in San Quirico dʼOrcia.

    From US$114.43 per night

Holiday Rentals with swimming pools in Pienza and nearby

  • Scored out of 10, guest rating 9.1
    Superb - What previous guests thought, 182 reviews

    SARNA Residence is situated in San Quirico d’Orcia, a 10-minute walk from the city centre. The property offers a garden with a seasonal outdoor swimming pool.

  • Lupaia

    Montepulciano
    Swimming pool
    Scored out of 10, guest rating 9.8
    Exceptional - What previous guests thought, 116 reviews

    On a hilltop in the heart of Tuscany, Lupaia, a converted stone farmhouse overlooking Montepulciano, will offer you a warm welcome.

    From US$963.35 per night
  • Scored out of 10, guest rating 9.1
    Superb - What previous guests thought, 134 reviews

    Set in Castelmuzio and only 20 km from Parco dei Mulini, Il Colombaiolo offers accommodation with pool views, free WiFi and free private parking. 23 km from Terme di Montepulciano and 34 km from Bagni...

    From US$83.95 per night
  • Scored out of 10, guest rating 9.2
    Superb - What previous guests thought, 255 reviews

    Agriturismo Belagaggio is located in Montefollonico and features a pool with a view and garden views. A hot tub and a bicycle rental service are available for guests.

    From US$197.93 per night
  • Scored out of 10, guest rating 8.3
    Very good - What previous guests thought, 79 reviews

    Situated in Castiglione dʼOrcia, 34 km from Mount Amiata, Podere le Mulina features accommodation with pool with a view, free private parking, a garden and barbecue facilities.

    From US$157.64 per night

  • Situated in Trequanda and only 48 km from Piazza Grande, Luxury Apartment in Siena Resort features accommodation with mountain views, free WiFi and free private parking.

    From US$433.45 per night
  • Scored out of 10, guest rating 8.9
    Fabulous - What previous guests thought, 367 reviews

    Located within 46 km of Mount Amiata and 2.5 km of Terme di Montepulciano, The Grapevine by MANVI provides rooms with air conditioning and a private bathroom in Montepulciano.

    From US$157.64 per night
  • Scored out of 10, guest rating 8.0
    Very good - What previous guests thought, 3 reviews

    Featuring lake views, Luxury Resort with swimming pool in the Tuscan countryside, Villas on the ground floor with private outdoor area with panoramic view provides accommodation with a seasonal...

    From US$357.30 per night

Enjoy breakfast in Pienza and nearby

  • Scored out of 10, guest rating 9.1
    Superb - What previous guests thought, 429 reviews

    La Casa di Enrico, a property with a terrace, is located in San Quirico dʼOrcia, 40 km from Mount Amiata, 45 km from Piazza del Campo, as well as 5.7 km from Parco dei Mulini.

  • Scored out of 10, guest rating 8.5
    Very good - What previous guests thought, 588 reviews

    Featuring a garden and views of pool, Locanda Il Porcellum is a guest house situated in a historic building in Bagno Vignoni, 36 km from Mount Amiata.

    From US$128.45 per night
  • Scored out of 10, guest rating 9.1
    Superb - What previous guests thought, 760 reviews

    Located in the medieval town of Bagno Vignoni, renowned for its thermal waters, the family-run B&B L’orto Delle Terme features free Wi-Fi throughout and free parking.

    From US$188 per night
  • Scored out of 10, guest rating 9.3
    Superb - What previous guests thought, 468 reviews

    Boasting a garden and views of garden, Agriturismo Cognanello is a farm stay set in a historic building in Montepulciano, 46 km from Mount Amiata.

    From US$149.47 per night
  • Scored out of 10, guest rating 9.0
    Superb - What previous guests thought, 47 reviews

    Boasting a garden and views of mountain, B&B Il Glicine is a bed and breakfast set in a historic building in Montefollonico, 15 km from Terme di Montepulciano.

    From US$136.62 per night

  • Il Tosco

    Montepulciano
    Breakfast options
    Scored out of 10, guest rating 9.8
    Exceptional - What previous guests thought, 141 reviews

    Located in Montepulciano and only 47 km from Mount Amiata, Il Tosco provides accommodation with lake views, free WiFi and free private parking.

    From US$322.29 per night
  • Scored out of 10, guest rating 9.3
    Superb - What previous guests thought, 214 reviews

    Offering mountain views, Palazzo Nobile di San Donato - Historic Experience is an accommodation located in Montepulciano, 47 km from Mount Amiata and 5.1 km from Terme di Montepulciano.

    From US$409.16 per night
  • Scored out of 10, guest rating 9.3
    Superb - What previous guests thought, 84 reviews

    Located in Montepulciano and only 47 km from Mount Amiata, Contucci Residenze d'Epoca provides accommodation with city views, free WiFi and free private parking.

    From US$216.02 per night

FAQ about holiday rentals in Pienza

Holiday rentals that guests love in Pienza

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  • Agriturismo Poggio Tobruk

    Holiday Rental in Pienza
    Scored out of 10, guest rating 9.5
    Exceptional - What previous guests thought, 265 reviews
    Beautiful location in Val d'orcia. Good place to visit the gorgeous villages and cities close by. The staff was very friendly and helpful.
    Guest review by
    Bjorn
    Family with young children

  • Poggiosalto in Toscana

    Holiday Rental in Pienza
    Scored out of 10, guest rating 9.7
    Exceptional - What previous guests thought, 268 reviews
    Idyllic setting in rural Val D'Orcia with picture postcard views, generous hosts and close to loads of scenic spots and historic villages and towns.
    Guest review by
    Rudi
    Family with young children

  • Agriturismo Il Macchione

    Holiday Rental in Pienza
    Avg. price/night: US$515.47
    Scored out of 10, guest rating 9.3
    Superb - What previous guests thought, 514 reviews
    Perfect way to enjoy the Val d’Orcia: a whole gorgeous view for ourselves, especially at sunset and sunrise. The setting is perfect, the house as well as pool and grounds just beautiful and perfectly maintained. Well located to access all the small villages. Pool was cold but great on a hot day, and it’s close to Pienza so easy to go fsck and forth for shopping etc. Staff was very friendly, especially the guy serving breakfast and the lady welcoming us.
    Guest review by
    Cecile
    Family with young children

  • Poggio ai Gelsi

    Holiday Rental in Pienza
    Avg. price/night: US$186.83
    Scored out of 10, guest rating 9.2
    Superb - What previous guests thought, 401 reviews
    Surrounded by vineyards, wheat fields, and ancient villages like Pienza and Montalcino, it offers a serene escape amidst rolling hills and stunning views of Val'd Orcia.
    Guest review by
    Thilini
    Young couple

  • Podere Spedalone

    Holiday Rental in Pienza
    Avg. price/night: US$215.97
    Scored out of 10, guest rating 9.0
    Superb - What previous guests thought, 883 reviews
    Property was charming, very beautiful, well maintained. Villa was quiet and clean, very spacious. Hosts were available and helpful. Appertivo was a unique and tasty experience and is highly recommended. Short drive to Pienza, easy half day trip to Sienna.
    Guest review by
    Zachary
    Family with young children

  • Agriturismo Castello di Spedaletto

    Holiday Rental in Pienza
    Scored out of 10, guest rating 9.7
    Exceptional - What previous guests thought, 212 reviews
    LOVED IT!!! What an amazing place! So beautiful!!! Very clean,comfortable bed, excellent breakfast. It is located just in the middle between Montalcino and Montelpuciano, which is very convenient for visiting all the beautiful villages in the area. Do not miss the tour they offer in their mill and pasta factory with a lunch with pasta, bread, and cakes made from their own flours. Highly recommended!Thank you, Laura, for your hospitality.
    Guest review by
    Gali
    Young couple

  • OgniVolta

    Holiday Rental in Pienza
    Scored out of 10, guest rating 9.8
    Exceptional - What previous guests thought, 63 reviews
    Everything. OgniVolta is a beautifully apartment - made even more so by the care and consideration of Sandra, the host/owner. The location is in the village, but still very accessible by car, with a large paid municipal parking lot close by. The apartment is clean, spacious and modern with all the facilities for a long stay - full kitchen, starter fruits, pastries and juices. Pienza (and Orvieto) were highlights of our 3 weeks in Slovenia and Tuscany. Cannot recommend more highly.
    Guest review by
    Grant
    Young couple

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