Pienza Vacation Rentals

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Tonight
Sep 24 - Sep 25
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Sep 25 - Sep 26
This weekend
Sep 26 - Sep 28
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Oct 3 - Oct 5

Vacation Rentals in Pienza

Hotel San Gregorio
Breakfast, lunch, dinner served; local cuisine

Hotel San Gregorio

3.0 star property
9.4 out of 10, Exceptional, (127)
"Such friendly staff, loved Pienza and the property was such a good location! "
The price is ￥26,470
￥30,163 total
includes taxes & fees
Oct 25 - Oct 26
Hotel San Gregorio
Whole big Tuscan Villa with Pool & Vineyards in the Heart of Tuscany
Outdoor pool

Whole big Tuscan Villa with Pool & Vineyards in the Heart of Tuscany

9.6 out of 10, Exceptional, (17)
"The view from the house is spectacular! What a great spot for a group of friends or a large family. Close to vineyards and shopping. We love sitting on the back patio having dinner. The dog and cats were an extra. Lily and her husband were very helpful and we really enjoyed having the meals cooked by the chef while we were there. The last night with the fish was the best!"
Whole big Tuscan Villa with Pool & Vineyards in the Heart of Tuscany
Beautiful Tuscan farmhouse in a great location near Val D'Orcia & private pool
Outdoor pool, sun loungers

Beautiful Tuscan farmhouse in a great location near Val D'Orcia & private pool

10.0 out of 10, Exceptional, (3)
"Beautiful historic villa. Loved the vibe. Would definitely stay here again! "
Beautiful Tuscan farmhouse in a great location near Val D'Orcia & private pool
Luxury Privacy in the Heart of Tuscany
Exterior

Luxury Privacy in the Heart of Tuscany

Luxury Privacy in the Heart of Tuscany
Casanova - Panoramic Rooms and Suites
Front of property - evening/night

Casanova - Panoramic Rooms and Suites

3.0 star property
9.0 out of 10, Wonderful, (66)
"My fiancée and I enjoyed ourselves! It’s a beautiful place and I adored walking around in the nearby town. "
Casanova - Panoramic Rooms and Suites
Abbadia Sicille Relais
View from room

Abbadia Sicille Relais

4.0 star property
8.8 out of 10, Excellent, (159)
"Great Historical location."
The price is ￥15,281
￥17,332 total
includes taxes & fees
Oct 22 - Oct 23
Abbadia Sicille Relais
Bosco della Spina
Aerial view

Bosco della Spina

9.6 out of 10, Exceptional, (162)
"We enjoyed the scenery and service! Clean and comfortable. "
Bosco della Spina
Private and cozy retreat in Montalcino with private pool surrounded by vineyards
Pool

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

9.4 out of 10, Exceptional, (64)
"If you like a 360-degree view from the top of the hill, this is the place. Amazing views, out in the country with little traffic (more tractors than cars). Very private. We wanted to sit on the patio all day.The house is very comfortable and a good home base for sampling Brunello and visiting the Montalcino vineyards.Camilla was easy to communicate with before and during our stay."
Private and cozy retreat in Montalcino with private pool surrounded by vineyards
Tuscasì Aparthotel
Royal Apartment | View from room

Tuscasì Aparthotel

9.2 out of 10, Wonderful, (21)
"Newly built property featuring large modern accommodation. Safe and easy parking on property, excellent breakfast. "
The price is ￥12,016
￥13,740 total
includes taxes & fees
Oct 5 - Oct 6
Tuscasì Aparthotel
Hilltop house in the heart of Tuscany with private pool
Outdoor dining

Hilltop house in the heart of Tuscany with private pool

9.8 out of 10, Exceptional, (92)
"Wonderful, quiet, beautiful. Everything you could want in country stay near a small village."
Hilltop house in the heart of Tuscany with private pool
Villa in Montalcino, exclusive for you, stunning view!!!
Outdoor pool

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

10.0 out of 10, Exceptional, (84)
"Lovely villa in a beautiful location. "
Villa in Montalcino, exclusive for you, stunning view!!!
Sun-Soaked Private View Terrace in the Historical Centre of Cortona.
Outdoor dining

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

9.6 out of 10, Exceptional, (71)
"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.
Delcorto Suites
Interior

Delcorto Suites

10.0 out of 10, Exceptional, (26)
"Exceptional service great building felt like a Medici!"
The price is ￥31,178
￥34,994 total
includes taxes & fees
Sep 29 - Sep 30
Delcorto Suites
PRIVATE TUSCAN VILLA WITH HEATED SWIMMING POOL - JACUZZI SPA - SAUNA - EVENTS
Outdoor dining

PRIVATE TUSCAN VILLA WITH HEATED SWIMMING POOL - JACUZZI SPA - SAUNA - EVENTS

10.0 out of 10, Exceptional, (53)
"We had a very nice stay and a well organized pizza night in the villa. Glad to come again:) "
PRIVATE TUSCAN VILLA WITH HEATED SWIMMING POOL - JACUZZI SPA - SAUNA - EVENTS
The House of Alice, charm and relaxation
Exterior detail

The House of Alice, charm and relaxation

9.6 out of 10, Exceptional, (64)
"Unbelievable ambience and beauty of the region and the house. Francesco was super helpful. "
The price is ￥27,904
￥37,671 total
includes taxes & fees
Oct 8 - Oct 9
The House of Alice, charm and relaxation
Gite Montemirello, with garden and swimming pool
Outdoor pool

Gite Montemirello, with garden and swimming pool

9.8 out of 10, Exceptional, (58)
"Very nice stay and very nuce Host :)"
Gite Montemirello, with garden and swimming pool
Residenza Fabroni
Lobby

Residenza Fabroni

8.8 out of 10, Excellent, (90)
"We had a wonderful stay, the staff was extremely friendly and helpful. Restaurants and shops were right at our doorstep."
The price is ￥13,065
￥15,068 total
includes taxes & fees
Oct 6 - Oct 7
Residenza Fabroni
Il Tosco
Property entrance

Il Tosco

10.0 out of 10, Exceptional, (112)
"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 ￥52,509
￥58,458 total
includes taxes & fees
Sep 29 - Sep 30
Il Tosco
Porta Pispini Residence
Terrace/patio

Porta Pispini Residence

2.0 star property
9.6 out of 10, Exceptional, (18)
"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
Siena Exclusive Luxury Villa. Private Pool, Garden, Relax, Holiday, Tuscany!
Outdoor pool

Siena Exclusive Luxury Villa. Private Pool, Garden, Relax, Holiday, Tuscany!

10.0 out of 10, Exceptional, (8)
"Fabulous place to stay with a big group of family and friends. Very easy walk to town and the beautiful treasures of Siena."
Siena Exclusive Luxury Villa. Private Pool, Garden, Relax, Holiday, Tuscany!
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 Pienza Hotel Reviews

Hotel Corsignano

Hotel Corsignano

10/10 Excellent
"Very good"
alain 1-night trip
Posted 2 days ago
Hotel Corsignano

Find out more about Pienza

Find out more about Pienza

Search for holiday rentals in Pienza on Expedia! You can easily find your home rentals, villas, holiday apartments in Pienza using one of the methods below:

  • View our selection of featured holiday rentals in Pienza
  • Use the map to find apartments and other holiday homes in the Pienza neighbourhood you prefer
  • Enter your travel dates to view the best deals on holiday rentals in Pienza while they last

Look no further and take a look at our great range of rental properties in Pienza!

Explore a world of travel with Expedia

Explore a world of travel with Expedia

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?

Agriturismo San Filippo: Located near Pienza, this vacation home rental is located in the suburbs and has a rooftop terrace, a private yard, and a barbecue grill to put you at ease in your new surroundings. It has 3 bedrooms as well as a kitchen with a fridge, a stovetop, and an espresso maker, so you can cook with friends or family.

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.