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

Check out our pick of great holiday rentals in Pienza

  • Scored out of 10, guest rating 9.8
    Exceptional - What previous guests thought, 482 reviews
    From
    US$148
    1 night, 2 adults
  • Scored out of 10, guest rating 9.8
    Exceptional - What previous guests thought, 292 reviews
    From
    US$182
    1 night, 2 adults
  • Scored out of 10, guest rating 9.5
    Exceptional - What previous guests thought, 165 reviews
    From
    US$122
    1 night, 2 adults
  • Scored out of 10, guest rating 9.8
    Exceptional - What previous guests thought, 208 reviews
    From
    US$153
    1 night, 2 adults
  • Scored out of 10, guest rating 9.5
    Exceptional - What previous guests thought, 141 reviews
    From
    US$128
    1 night, 2 adults
  • Scored out of 10, guest rating 9.3
    Superb - What previous guests thought, 262 reviews
    From
    US$115
    1 night, 2 adults
  • Scored out of 10, guest rating 9.5
    Exceptional - What previous guests thought, 764 reviews
    From
    US$249
    1 night, 2 adults
  • Scored out of 10, guest rating 9.5
    Exceptional - What previous guests thought, 641 reviews
    From
    US$136
    1 night, 2 adults
  • Scored out of 10, guest rating 9.0
    Superb - What previous guests thought, 866 reviews
    From
    US$233
    1 night, 2 adults
  • Scored out of 10, guest rating 9.3
    Superb - What previous guests thought, 234 reviews
    From
    US$214
    1 night, 2 adults
  • Scored out of 10, guest rating 9.3
    Superb - What previous guests thought, 516 reviews
    From
    US$185
    1 night, 2 adults
  • Scored out of 10, guest rating 9.9
    Exceptional - What previous guests thought, 60 reviews
    From
    US$159
    1 night, 2 adults
  • Scored out of 10, guest rating 9.3
    Superb - What previous guests thought, 24 reviews
    From
    US$291
    1 night, 2 adults
  • Scored out of 10, guest rating 8.6
    Fabulous - What previous guests thought, 513 reviews
    From
    US$159
    1 night, 2 adults
  • Scored out of 10, guest rating 8.8
    Fabulous - What previous guests thought, 105 reviews
    From
    US$117
    1 night, 2 adults
  • Scored out of 10, guest rating 8.9
    Fabulous - What previous guests thought, 360 reviews
    From
    US$85
    1 night, 2 adults
  • Scored out of 10, guest rating 8.7
    Fabulous - What previous guests thought, 671 reviews
    From
    US$141
    1 night, 2 adults
  • Scored out of 10, guest rating 7.5
    Good - What previous guests thought, 235 reviews
    From
    US$100
    1 night, 2 adults
  • Scored out of 10, guest rating 9.5
    Exceptional - What previous guests thought, 110 reviews
    From
    US$204
    1 night, 2 adults
  • Scored out of 10, guest rating 9.7
    Exceptional - What previous guests thought, 230 reviews
    From
    US$247
    1 night, 2 adults

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

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

  • Affittacamere del Corso

    Pienza
    Free cancellation options available
    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$93.96 per night
  • Agriturismo Barbi

    Monticchiello
    Free cancellation options available
    Scored out of 10, guest rating 9.1
    Superb - What previous guests thought, 292 reviews

    Overlooking Val d'Orcia and 8 km from the town of Pienza in southern Tuscany, Azienda Agricola Barbi offers 2 stone farmhouses that still maintain its original features.

  • Le Maribelle

    Monticchiello
    Free cancellation options available
    Scored out of 10, guest rating 8.4
    Very good - What previous guests thought, 112 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$225.50 per night
  • La Casa nel Borgo

    Monticchiello
    Free cancellation options available
    Scored out of 10, guest rating 9.3
    Superb - What previous guests thought, 137 reviews

    Set 44 km from Mount Amiata, La Casa nel Borgo in Monticchiello offers rooms with air conditioning and free WiFi. There is a private entrance at the holiday home for the convenience of those who stay.

    From US$123.32 per night
  • Agriturismo Riposati

    Monticchiello
    Free cancellation options available
    Scored out of 10, guest rating 9.7
    Exceptional - What previous guests thought, 296 reviews

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

    From US$140.94 per night
  • Agriturismo Zampugna

    Montefollonico
    Free cancellation options available
    Scored out of 10, guest rating 8.4
    Very good - What previous guests thought, 130 reviews

    Agriturismo Zampugna is set in Montefollonico and features a pool with a view and pool views. There is a private entrance at the farm stay for the convenience of those who stay.

    From US$475.44 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$243.12 per night
  • VINO SUITE

    San Quirico dʼOrcia
    Free cancellation options available
    Scored out of 10, guest rating 9.1
    Superb - What previous guests thought, 42 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$183.22 per night

Enjoy breakfast in Pienza and nearby

  • L'Olmo

    Monticchiello
    Breakfast options
    Scored out of 10, guest rating 9.8
    Exceptional - What previous guests thought, 171 reviews

    Offering a heated outdoor pool, L'Olmo is located in Pienza, in the heart of Val d 'Orcia. Free WiFi access is available. The suites here offer air conditioning and parquet floors.

    From US$633.06 per night
  • Scored out of 10, guest rating 9.6
    Exceptional - What previous guests thought, 185 reviews

    Villa Poggiano is a 6-hectare estate in the heart of the peaceful Tuscan countryside. It offers an outdoor pool and luxurious guest rooms with free internet access and panoramic views.

  • Lupaia

    Montepulciano
    Breakfast options
    Scored out of 10, guest rating 9.7
    Exceptional - What previous guests thought, 117 reviews

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

  • Scored out of 10, guest rating 9.0
    Superb - What previous guests thought, 46 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$129.19 per night
  • Scored out of 10, guest rating 9.0
    Superb - What previous guests thought, 83 reviews

    Offering an outdoor pool and garde, the Locanda in Tuscany is 5 km from Castiglione d'Orcia. Guests enjoy free WiFi and a restaurant. Rooms at the farm stay feature wood-beamed ceilings.

    From US$324.16 per night
  • Il Tosco

    Montepulciano
    Breakfast options
    Scored out of 10, guest rating 9.7
    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$691.55 per night
  • Scored out of 10, guest rating 9.3
    Superb - What previous guests thought, 210 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$577.85 per night
  • Scored out of 10, guest rating 9.3
    Superb - What previous guests thought, 87 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.

Highly rated holiday rentals in Pienza and nearby

  • Scored out of 10, guest rating 9.6
    Exceptional - What previous guests thought, 125 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$147.65 per night
  • Scored out of 10, guest rating 9.4
    Superb - What previous guests thought, 40 reviews

    Featuring air-conditioned accommodation with a balcony, Residence Hill is located in San Quirico dʼOrcia. Built in 2018, the property includes hot tub and spa centre.

    From US$393.08 per night
  • Scored out of 10, guest rating 9.0
    Superb - What previous guests thought, 142 reviews

    Located within 41 km of Mount Amiata and 44 km of Piazza del Campo, Acquerello provides rooms with air conditioning and a private bathroom in San Quirico dʼOrcia.

    From US$140.94 per night
  • Scored out of 10, guest rating 9.3
    Superb - What previous guests thought, 143 reviews

    Set just 40 km from Mount Amiata, Affittacamere Casa Mac & Rose features accommodation in San Quirico dʼOrcia with access to a garden, a shared lounge, as well as a housekeeping service.

  • Scored out of 10, guest rating 8.7
    Fabulous - What previous guests thought, 15 reviews

    Located in San Quirico dʼOrcia in the Tuscany region, Molino della Tuoma provides accommodation with free WiFi and free private parking, as well as access to a hot tub.

    From US$240.77 per night
  • Scored out of 10, guest rating 9.3
    Superb - What previous guests thought, 126 reviews

    La Chiusa dei Monaci, a property with a garden and barbecue facilities, is situated in Castelmuzio, 49 km from Piazza Grande, 21 km from Parco dei Mulini, as well as 23 km from Terme di Montepulciano.

    From US$129.19 per night
  • Scored out of 10, guest rating 9.2
    Superb - What previous guests thought, 27 reviews

    Featuring mountain views, La terrazza da Barbara offers accommodation with balcony, around 16 km from Terme di Montepulciano. This property offers access to a terrace and free private parking.

  • Scored out of 10, guest rating 9.0
    Superb - What previous guests thought, 38 reviews

    Situated in Montefollonico and only 16 km from Terme di Montepulciano, 15 min da Montepulciano - Villa Chiara features accommodation with garden views, free WiFi and free private parking.

    From US$234.90 per night

FAQ about holiday rentals in Pienza

Holiday rentals that guests love in Pienza

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  • Scored out of 10, guest rating 9.5
    Exceptional - What previous guests thought, 267 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
  • Scored out of 10, guest rating 9.7
    Exceptional - What previous guests thought, 257 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
  • Scored out of 10, guest rating 9.3
    Superb - What previous guests thought, 516 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
  • Avg. price/night: US$258.39
    Scored out of 10, guest rating 9.2
    Superb - What previous guests thought, 387 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
  • Avg. price/night: US$563.17
    Scored out of 10, guest rating 9.0
    Superb - What previous guests thought, 866 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
  • Scored out of 10, guest rating 9.6
    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
  • Scored out of 10, guest rating 9.8
    Exceptional - What previous guests thought, 59 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