Pienza Vacation Rentals

    calendar shield illustration

    Change your mind

    Book hotels with free cancellation
    deals illustration

    Treat yourself

    Sign in to save 10% or more on thousands of hotels
    bed illustration

    Be picky

    Search almost a million properties worldwide

Check prices for these dates

Vacation Rentals in Pienza

Hotel San Gregorio

3.0 star property
9.2 out of 10, Wonderful, (122)
"Cozy and welcoming hotel in a perfect location near Pienza’s historic center. I could only stay one night out of three due to personal reasons, but I’ll definitely come back on my next visit"
The price is CA $278
CA $315 total
includes taxes & fees
Aug 26 - Aug 27
Hotel San Gregorio

Casanova - Panoramic Rooms and Suites

3.0 star property
9.0 out of 10, Wonderful, (65)
"My fiancée and I enjoyed ourselves! It’s a beautiful place and I adored walking around in the nearby town. "
The price is CA $253
CA $285 total
includes taxes & fees
Aug 24 - Aug 25
Casanova - Panoramic Rooms and Suites

Il Casale Di Manuele 12, Emma Villas

10.0 out of 10, Exceptional, (3)
"We loved this home - everything was perfect and it was easy to find and enjoy. I highly recommend the next time you are wanting to stay in Tuscany! "
Il Casale Di Manuele 12, Emma Villas

Bosco della Spina

9.6 out of 10, Exceptional, (162)
"We enjoyed the scenery and service! Clean and comfortable. "
The price is CA $190
CA $222 total
includes taxes & fees
Aug 25 - Aug 26
Bosco della Spina

Abbadia Sicille Relais

4.0 star property
8.8 out of 10, Excellent, (159)
"An amazing place with a luxury feel. Comfy, welcoming and peacefully relaxing "
The price is CA $261
CA $292 total
includes taxes & fees
Aug 31 - Sep 1
Abbadia Sicille Relais

Residenza Fabroni

8.8 out of 10, Excellent, (89)
"We had a wonderful stay, the staff was extremely friendly and helpful. Restaurants and shops were right at our doorstep."
The price is CA $124
CA $142 total
includes taxes & fees
Aug 25 - Aug 26
Residenza Fabroni

Tuscasì Aparthotel

9.4 out of 10, Exceptional, (18)
"Very clean and comfortable accommodations. Beautiful view of the countryside!"
The price is CA $125
CA $137 total
includes taxes & fees
Aug 17 - Aug 18
Tuscasì Aparthotel

Sun-Soaked Private View Terrace in the Historical Centre of Cortona.

9.6 out of 10, Exceptional, (69)
"My husband and I loved our stay here! It was so close to town and the terrace was absolutely stunning. Would definitely stay here again! "
Sun-Soaked Private View Terrace in the Historical Centre of Cortona.

Il Tosco

10.0 out of 10, Exceptional, (111)
"The people here are authentic and welcoming! The building, rooms and facilities are gorgeous! One of our most beautiful stays in our many trips to Italy "
The price is CA $403
CA $450 total
includes taxes & fees
Aug 19 - Aug 20
Il Tosco

Porta Pispini Residence

2.0 star property
9.6 out of 10, Exceptional, (17)
"That’s not a hotel room, that’s small apartment with guest room and kitchen with washer and dishwasher Amazing window view Free parking Very clean 3 minutes walk from the city wall More than reasonable price "
Porta Pispini Residence

Villa in Montalcino, exclusive for you, stunning view!!!

10.0 out of 10, Exceptional, (82)
"Luigi was very helpful. We had a chef 3 nights that he helped facilitate. Beautiful location. "
Villa in Montalcino, exclusive for you, stunning view!!!

Corte Francigena

9.8 out of 10, Exceptional, (6)
"Loved everything about my stay"
The price is CA $264
CA $310 total
includes taxes & fees
Sep 7 - Sep 8
Corte Francigena

Hilltop house in the heart of Tuscany with private pool

9.8 out of 10, Exceptional, (89)
"The location and property are beautiful."
Hilltop house in the heart of Tuscany with private pool

Private and cozy retreat in Montalcino with private pool surrounded by vineyards

9.4 out of 10, Exceptional, (61)
"We wanted to enjoy the Tuscany area and this house checked all the boxes for us. The photos can’t actually capture the true beauty of this place. The host, Camilla was so gracious and kind. Comfortable bed, kitchen well stocked with the dishes we needed. Full size refrigerator was nice too! It’s a little bit of a drive to the property but oh so worth it! "
Private and cozy retreat in Montalcino with private pool surrounded by vineyards

Gite Montemirello, with garden and swimming pool

9.8 out of 10, Exceptional, (54)
"Great property,only 30 mins from Siena, very peaceful large garden and large private pool. Just what we needed after doing 9 days touring Tuscan cities, highly recommend this property."
Gite Montemirello, with garden and swimming pool

Osteria del Borgo

9.2 out of 10, Wonderful, (147)
"Jacopo and his family were super friendly, the restaurant is the best in Montepulciano and the views are breathtaking. If we come back we will stay at Osteria del Borgo again without a doubt. "
Osteria del Borgo

Il Poggio dell'Eremita

10.0 out of 10, Exceptional, (53)
"Located in a peaceful location, the house is charming and homey. The hosts are very kind and accommodating, and we had a wonderful stay. The view from the bedroom balcony is spectacular."
The price is CA $211
CA $244 total
includes taxes & fees
Sep 12 - Sep 13
Il Poggio dell'Eremita

Your dream home! In harmony with nature! Priv. Pool - fantastic views!

10.0 out of 10, Exceptional, (16)
"Tolles Haus, wahnsinnig schöner Ausblick, super Urlaub"
Your dream home! In harmony with nature! Priv. Pool - fantastic views!

Montalcino Villa - Breathtaking Views of the Val d'Orcia

9.8 out of 10, Exceptional, (43)
"We had a wonder stay at the villa. Gave a true Tuscan countryside experience in a luxurious, comfortable and convenient location."
Montalcino Villa - Breathtaking Views of the Val d'Orcia

LA CASINA CANTINI - Panoramic apartment in Montepulciano in the historic center

9.6 out of 10, Exceptional, (48)
"Wonderful home away from home!"
LA CASINA CANTINI - Panoramic apartment in Montepulciano in the historic center
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.
Save an average of 15% on thousands of hotels when you're signed in

Top Pienza Hotel Reviews

Frequently asked questions

Can I find a vacation rental in Pienza?

Yes, we give you a choice of vacation rentals in Pienza close to RI Crea RE, or you can go with a secluded option if you want a relaxing stay. Pienza is known for its churches and wineries. Make sure you have time to check out the temples while you're in the area.

What are some of the best vacation home rentals in Pienza?

The House of Alice, charm and relaxation: This vacation home rental near Pienza is located in a rural location and has a fireplace, a terrace, and air-conditioning to put you at ease in your new surroundings. Kitchen amenities include a fridge, a stovetop, and kitchenware. Kick off your shoes and enjoy yourself with a garden and a selection of books.

How many vacation rentals are there in Pienza?

Expedia has 28 vacation rentals for your stay in Pienza.

What’s there to see and do in Pienza?

Cultural attractions include Palazzo Borgia and Artemisia Gallery, whereas Historic Centre of Pienza and Val di Chiana are a couple of picturesque spots to enjoy the outdoors. Other places in town to visit include Palazzo Piccolomini and Pienza Cathedral.

What’s a vacation rental in Pienza like?

Vacation rentals are private properties you can book for a long or short time in Pienza. Vacation rentals feature amenities like WiFi and washers and dryers to help you enjoy your stay. If you're concerned about a clean environment, a vacation rental can provide a sense of security away from public hotel elevators and bustling concierge desks while still allowing you the enjoyment of travel. You'll also have more space in a vacation rental than in a hotel, which is another reason why a vacation rental is a great choice for a small group gathering.