Title: Pienza Vacation Rentals from CA $119: Short-Term Rentals for 2025 | Expedia.ca

  

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# Pienza Vacation Rentals

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## Check prices for these dates

In two weeks

[Nov 21 - Nov 23](https://www.expedia.ca/Hotel-Search?regionId=6023645&startDate=2025-11-21&endDate=2025-11-23&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In two months

[Jan 2 - Jan 4](https://www.expedia.ca/Hotel-Search?regionId=6023645&startDate=2026-01-02&endDate=2026-01-04&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In three months

[Jan 30 - Feb 1](https://www.expedia.ca/Hotel-Search?regionId=6023645&startDate=2026-01-30&endDate=2026-02-01&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In four months

[Feb 27 - Mar 1](https://www.expedia.ca/Hotel-Search?regionId=6023645&startDate=2026-02-27&endDate=2026-03-01&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

## Vacation Rentals in Pienza

![Breakfast, lunch, dinner served; local cuisine ](https://images.trvl-media.com/lodging/3000000/2700000/2692200/2692135/9fda43a3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Seasonal outdoor pool, open 8:00 AM to 8:00 PM, pool umbrellas](https://images.trvl-media.com/lodging/3000000/2700000/2692200/2692135/4a89a1fb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fountain](https://images.trvl-media.com/lodging/3000000/2700000/2692200/2692135/2d2d56ec.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Breakfast buffet](https://images.trvl-media.com/lodging/3000000/2700000/2692200/2692135/cd7670ac.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Hotel San Gregorio

Pienza

9.4/10

Exceptional

(131)

"Excellent property! Very elegant and the service was wonderful. The breakfast was also excellent. The location could not be any better - the entry to the old town is just across from the hotel. Wish we could have stayed longer."

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

DEBORAH

CA $280

CA $318 total

includes taxes & fees

Dec 5 - Dec 6

[](https://www.expedia.ca/Pienza-Hotels-Hotel-San-Gregorio.h2692135.Hotel-Information)

![Outdoor pool](https://images.trvl-media.com/lodging/34000000/33740000/33736700/33736684/7a01fd7b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/34000000/33740000/33736700/33736684/16ad62df.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Outdoor dining](https://images.trvl-media.com/lodging/34000000/33740000/33736700/33736684/f2e30cfa.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![9 bedrooms, iron/ironing board, WiFi, bed sheets](https://images.trvl-media.com/lodging/34000000/33740000/33736700/33736684/2c20aa4b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

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

Pienza

9.6/10

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!"

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

julie l.

[](https://www.expedia.ca/Pienza-Hotels-Whole-Big-Tuscan-Villa-With-Pool-Vineyards-In-The-Heart-Of-Tuscany.h33736684.Hotel-Information)

![View from room](https://images.trvl-media.com/lodging/11000000/10660000/10653000/10652908/80de574a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Billiards](https://images.trvl-media.com/lodging/11000000/10660000/10653000/10652908/cd3bbebf.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Billiards](https://images.trvl-media.com/lodging/11000000/10660000/10653000/10652908/a6535507.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Front of property - evening/night](https://images.trvl-media.com/lodging/11000000/10660000/10653000/10652908/38f51959.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Abbadia Sicille Relais

Trequanda

8.8/10

Excellent

(162)

"We stayed there for 1 night our our way to Rome. BEAUTIFUL. Bed was very comfortable as well. 10/10 will recommend to everyone "

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Brittnay

CA $103

CA $119 total

includes taxes & fees

Dec 9 - Dec 10

[](https://www.expedia.ca/Trequanda-Hotels-Abbadia-Sicille.h10652908.Hotel-Information)

![Front of property - evening/night](https://images.trvl-media.com/lodging/52000000/51830000/51829000/51828901/7dd03bcb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Superior Room, Terrace, Valley View](https://images.trvl-media.com/lodging/52000000/51830000/51829000/51828901/2f810565.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Free daily continental breakfast](https://images.trvl-media.com/lodging/52000000/51830000/51829000/51828901/ce312570.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Rooftop terrace](https://images.trvl-media.com/lodging/52000000/51830000/51829000/51828901/7a16fc61.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Casanova - Panoramic Rooms and Suites

San Quirico d'Orcia

9.0/10

Wonderful

(78)

"Delightful stay. The room was lovely, and the view from our private terrace was wonderful. Dinner was first rate. Easily walkable into San Quirico, short drive to Montalcino, Pienza, and Montalcino. Nice massage and spa. A very good value."

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Charles

CA $263

CA $296 total

includes taxes & fees

Nov 13 - Nov 14

[](https://www.expedia.ca/San-Quirico-DOrcia-Hotels-Resort-Casanova-Panoramic-Rooms-And-Suites.h51828901.Hotel-Information)

![Deluxe Apartment, 2 Bedrooms, Balcony](https://images.trvl-media.com/lodging/120000000/119060000/119052900/119052871/18007833.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Superior Apartment, 2 Bedrooms](https://images.trvl-media.com/lodging/120000000/119060000/119052900/119052871/4add3036.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/120000000/119060000/119052900/119052871/8e818071.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Deluxe Apartment, 2 Bedrooms, Balcony](https://images.trvl-media.com/lodging/120000000/119060000/119052900/119052871/302bfcfc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Bellarmino Boutique Apartments

Montepulciano

CA $111

CA $129 total

includes taxes & fees

Nov 9 - Nov 10

[](https://www.expedia.ca/Montepulciano-Hotels-Bellarmino-Boutique-Apartments.h119052871.Hotel-Information)

![Royal Apartment | View from room](https://images.trvl-media.com/lodging/106000000/105580000/105570300/105570206/8b57b476.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Royal Apartment | Private kitchen](https://images.trvl-media.com/lodging/106000000/105580000/105570300/105570206/1808f82b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![1 bedroom, premium bedding, down comforters, pillowtop beds](https://images.trvl-media.com/lodging/106000000/105580000/105570300/105570206/7fe98579.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Elite Apartment | Terrace/patio](https://images.trvl-media.com/lodging/106000000/105580000/105570300/105570206/c89c2c15.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Tuscasì Aparthotel

Sovicille

9.0/10

Wonderful

(24)

"Newly built property featuring large modern accommodation. Safe and easy parking on property, excellent breakfast. "

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Sergey

CA $105

CA $120 total

includes taxes & fees

Nov 9 - Nov 10

[](https://www.expedia.ca/Sovicille-Hotels-Tuscasi-Aparthotel.h105570206.Hotel-Information)

![Outdoor pool](https://images.trvl-media.com/lodging/91000000/90310000/90300100/90300061/b96fbe26.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![5 bedrooms, in-room safe, iron/ironing board, travel crib](https://images.trvl-media.com/lodging/91000000/90310000/90300100/90300061/ea7982e4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Dining](https://images.trvl-media.com/lodging/91000000/90310000/90300100/90300061/691c226c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Outdoor dining](https://images.trvl-media.com/lodging/91000000/90310000/90300100/90300061/c550d6f9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

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

Montalcino

10/10

Exceptional

(86)

"We were a group of 4 couples and found there was plenty of room for all of us. The property as better in person than we had expected. We had a car so it was really easy to get around and see all the towns nearby. Very beautiful property with great vistas. So relaxing to hang out at the pool or the deck."

![Canada](https://a.travel-assets.com/egds/marks/flags/ca.svg)

Elfrieda S.

[](https://www.expedia.ca/Montalcino-Hotels-Villa-In-Montalcino.h90300061.Hotel-Information)

![Pool](https://images.trvl-media.com/lodging/36000000/35330000/35330000/35329902/822e6f62.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/36000000/35330000/35330000/35329902/0dd7cc53.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/36000000/35330000/35330000/35329902/3fbaa990.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/36000000/35330000/35330000/35329902/2f21d9f2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

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

Siena

9.4/10

Exceptional

(67)

"Just did a 2 week trip In Italy and this was by far our favorite place to stay. Ready to go back already. Don’t think twice….JUST BOOK IT!"

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Blake R.

[](https://www.expedia.ca/Montalcino-Hotels-Private-And-Cozy-Retreat-In-Montalcino-With-Private-Pool-Surrounded-By-Vineyards.h35329902.Hotel-Information)

![Lobby](https://images.trvl-media.com/lodging/9000000/8210000/8204400/8204306/093ed3b4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Classic Suite, 2 Bedrooms](https://images.trvl-media.com/lodging/9000000/8210000/8204400/8204306/c477a48b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Breakfast area](https://images.trvl-media.com/lodging/9000000/8210000/8204400/8204306/17ae36fc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property entrance](https://images.trvl-media.com/lodging/9000000/8210000/8204400/8204306/124b8b86.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Residenza Fabroni

Montepulciano

8.8/10

Excellent

(93)

"We had a great stay! Beautiful on the roof top terrace!"

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Jennifer

CA $119

CA $137 total

includes taxes & fees

Nov 12 - Nov 13

[](https://www.expedia.ca/Montepulciano-Hotels-Residenza-Fabroni.h8204306.Hotel-Information)

![Outdoor dining](https://images.trvl-media.com/lodging/19000000/18770000/18764200/18764107/7dffae86.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Outdoor banquet area](https://images.trvl-media.com/lodging/19000000/18770000/18764200/18764107/ce0b1bfb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/19000000/18770000/18764200/18764107/d2c33991.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/19000000/18770000/18764200/18764107/660dd65a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

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

chiusi

10/10

Exceptional

(53)

"Our group of 15 thoroughly enjoyed our stay. The communication prior to and during the visit was excellent. The villa is stunning and HUGE and the grounds are magnificent. One day of our trip was spent just relaxing on the property and it was precious time well spent. "

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Mindy K.

[](https://www.expedia.ca/Chiusi-Hotels-PRIVATE-TUSCAN-VILLA-WITH-HEATED-SWIMMING-POOL-JACUZZI-SPA-SAUNA-EVENTS.h18764107.Hotel-Information)

![Outdoor pool](https://images.trvl-media.com/lodging/19000000/18770000/18768900/18768895/06ac7272.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Outdoor dining](https://images.trvl-media.com/lodging/19000000/18770000/18768900/18768895/15e9955b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![TV](https://images.trvl-media.com/lodging/19000000/18770000/18768900/18768895/5c9fc364.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/19000000/18770000/18768900/18768895/632252a3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Gite Montemirello, with garden and swimming pool

Casciano di Murlo - Siena

9.8/10

Exceptional

(60)

"Very nice stay and very nuce Host :)"

![Germany](https://a.travel-assets.com/egds/marks/flags/de.svg)

Timo

[](https://www.expedia.ca/Murlo-Hotels-Gite-Montemirello.h18768895.Hotel-Information)

![Property entrance](https://images.trvl-media.com/lodging/7000000/6310000/6309600/6309554/3e489ee1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior entrance](https://images.trvl-media.com/lodging/7000000/6310000/6309600/6309554/e6496db8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![View from property](https://images.trvl-media.com/lodging/7000000/6310000/6309600/6309554/6fa7b9db.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Family Suite, 2 Queen Beds, City View](https://images.trvl-media.com/lodging/7000000/6310000/6309600/6309554/fe06c21c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Il Tosco

Montepulciano

10/10

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 "

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Michael

CA $330

CA $370 total

includes taxes & fees

Nov 12 - Nov 13

[](https://www.expedia.ca/Montepulciano-Hotels-Il-Tosco.h6309554.Hotel-Information)

![Exterior detail](https://images.trvl-media.com/lodging/19000000/18980000/18976500/18976420/8def11f2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/19000000/18980000/18976500/18976420/5d163297.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/19000000/18980000/18976500/18976420/7d70a4e6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/19000000/18980000/18976500/18976420/8e2d77d7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### The House of Alice, charm and relaxation

Montalcino (SI)

9.8/10

Exceptional

(66)

"We loved our stay in this beautiful apartment. The town was so quiet and peaceful. Definitely a spot we’d like to visit again"

![Canada](https://a.travel-assets.com/egds/marks/flags/ca.svg)

Nathan E.

CA $260

CA $344 total

includes taxes & fees

Nov 9 - Nov 10

[](https://www.expedia.ca/Montalcino-Hotels-The-House-Of-Alice.h18976420.Hotel-Information)

![Outdoor dining](https://images.trvl-media.com/lodging/35000000/34030000/34024200/34024116/e5c35199.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior detail](https://images.trvl-media.com/lodging/35000000/34030000/34024200/34024116/4108e65d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/35000000/34030000/34024200/34024116/b43cefc1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, oven, stovetop, dishwasher](https://images.trvl-media.com/lodging/35000000/34030000/34024200/34024116/049b00fd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Hilltop house in the heart of Tuscany with private pool

Montisi

9.8/10

Exceptional

(94)

"Wonderful, quiet, beautiful. Everything you could want in country stay near a small village."

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Timothy C.

[](https://www.expedia.ca/Montalcino-Hotels-Hilltop-House-In-The-Heart-Of-Tuscany-With-Private-Pool.h34024116.Hotel-Information)

![Exterior](https://images.trvl-media.com/lodging/28000000/27450000/27448100/27448054/6a82a5cd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/28000000/27450000/27448100/27448054/cc976759.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/28000000/27450000/27448100/27448054/8099b959.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Dining](https://images.trvl-media.com/lodging/28000000/27450000/27448100/27448054/f6eed317.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Il Poggio dell'Eremita

Sinalunga

10/10

Exceptional

(57)

"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."

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Vivian K.

CA $192

CA $224 total

includes taxes & fees

Nov 9 - Nov 10

[](https://www.expedia.ca/Sinalunga-Hotels-Il-Poggio-Delleremita.h27448054.Hotel-Information)

![Outdoor pool](https://images.trvl-media.com/lodging/38000000/37010000/37008400/37008383/a46cc114.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/38000000/37010000/37008400/37008383/dc13bcf3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/38000000/37010000/37008400/37008383/e5339cc6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/38000000/37010000/37008400/37008383/53805381.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

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

Siena

10/10

Exceptional

(9)

"We were a group of 12 retired friends staying at Villa Santa Chiara for a few nights. The entire checkin/out process was very easy. Anna and Mario allowed us a late checkout which was very helpful. The location is a short but uphill walk to the city center. The accommodations were perfect for us and we especially enjoyed sitting outside by the pool or by the gazebos. All 12 of us loved the location, the quality of the accommodations and especially the helpfulness of the owners. This would be our...

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Michael O.

[](https://www.expedia.ca/Siena-Hotels-Villa-Santa-Chiara-Apartments-To-Rent-With-Pool.h37008383.Hotel-Information)

![Aerial view](https://images.trvl-media.com/lodging/2000000/1210000/1206200/1206161/46c3ab32.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Comfort Room](https://images.trvl-media.com/lodging/2000000/1210000/1206200/1206161/007eaefe.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Front of property](https://images.trvl-media.com/lodging/2000000/1210000/1206200/1206161/f58a3308.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Superior Room | Terrace/patio](https://images.trvl-media.com/lodging/2000000/1210000/1206200/1206161/e9ec6f1a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Bosco della Spina

Murlo

9.6/10

Exceptional

(169)

"We enjoyed the scenery and service! Clean and comfortable. "

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Sanaz

[](https://www.expedia.ca/Murlo-Hotels-Bosco-Della-Spina.h1206161.Hotel-Information)

![Outdoor dining](https://images.trvl-media.com/lodging/29000000/28850000/28840500/28840420/73d0cc6c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Outdoor pool, a heated pool](https://images.trvl-media.com/lodging/29000000/28850000/28840500/28840420/7b5bc062.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV, fireplace, DVD player, books](https://images.trvl-media.com/lodging/29000000/28850000/28840500/28840420/7484c9c1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/29000000/28850000/28840500/28840420/2dd1cad0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Luxury Cortona view hilltop Villa

cortona

10/10

Exceptional

(50)

"Perfect location for day trips covering so many of the hilltop towns. Perfect accommodation for a group of 12 friends as each bedroom has it’s own bathroom.Perfect Villa for relaxing at home coffee every morning, lying by the pool and dinner watching the incredible sunsets.Perfect hosts. Denise takes care of everything while you are at the villa including cooking us a wonderful dinner. Mieke answered all our questions prior to our arrival very promptly. She has set the villa up perfectly and...

![Australia](https://a.travel-assets.com/egds/marks/flags/au.svg)

Belinda P.

[](https://www.expedia.ca/Cortona-Hotels-Luxury-Cortona-View-Hilltop-Villa.h28840420.Hotel-Information)

![Exterior](https://images.trvl-media.com/lodging/34000000/33610000/33602800/33602782/ea1c471d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/34000000/33610000/33602800/33602782/018eac3e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/34000000/33610000/33602800/33602782/b1f88f9c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/34000000/33610000/33602800/33602782/90-e4732e09.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Casina in authentic Tuscany

Cortona

9.8/10

Exceptional

(68)

"We had a lovely stay at the Casina, thank you to the family for such a welcome."

![United Kingdom](https://a.travel-assets.com/egds/marks/flags/uk.svg)

David B.

[](https://www.expedia.ca/Cortona-Hotels-Casina-In-Authentic-Tuscany.h33602782.Hotel-Information)

![Outdoor pool](https://images.trvl-media.com/lodging/19000000/18780000/18772500/18772459/3729a37b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/19000000/18780000/18772500/18772459/23454ac9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Dining](https://images.trvl-media.com/lodging/19000000/18780000/18772500/18772459/717b04bd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Outdoor dining](https://images.trvl-media.com/lodging/19000000/18780000/18772500/18772459/a76f358b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Montalcino: Private villa in the heart of Tuscany, private pool,panoramic view!

Montisi

10/10

Exceptional

(58)

"This was a stunning property and we thoroughly enjoyed our time enjoying the pool and the beautiful yard. Luigi was very helpful and quick to respond with any questions we had. The little village of Montisi is cute and we enjoyed walking there in the mornings. The location is a short drive to other towns and some of the best wines in Tuscany. It was very hot the week we were there - a few nights we found it difficult to sleep. Overall it is a beautiful location and Luigi was a fabulous host....

![Canada](https://a.travel-assets.com/egds/marks/flags/ca.svg)

Neysa D.

[](https://www.expedia.ca/Montalcino-Hotels-Montalcino-Private-Villa-In-The-Heart-Of-Tuscany-With-Private-Pool.h18772459.Hotel-Information)

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

![Villa di Piazzano - Small Luxury Hotel of the World](//images.trvl-media.com/lodging/1000000/980000/972000/971985/473f66a9_y.jpg)

### Villa di Piazzano - Small Luxury Hotel of the World

10/10 Excellent

"Room was wonderful, bathroom spacious and well appointed. Staff amazing and so friendly "

[](https://expedia.ca/Cortona-Hotels-Villa-Di-Piazzano-Small-Luxury-Hotel-Of-The-World.h971985.Hotel-Information)

![Monastero di Cortona Hotel & Spa](//images.trvl-media.com/lodging/24000000/23270000/23264500/23264410/cea3a0e9_y.jpg)

### Monastero di Cortona Hotel & Spa

10/10 Excellent

"What a unique place. Near the top of the hill. Staff service and amenities were all great. Not an easy place to drive to. The taxis drive-in backwards the last eighth of a mile."

[](https://expedia.ca/Cortona-Hotels-Monastero-Di-Cortona-Hotel-Spa.h23264410.Hotel-Information)

![Nuovo Etruria Resort](//images.trvl-media.com/lodging/114000000/113750000/113748300/113748275/5960f205_y.jpg)

### Nuovo Etruria Resort

10/10 Excellent

"Friendly and efficient desk clerk. Beautifully designed rooms. "

[](https://expedia.ca/Montepulciano-Hotels-Nuovo-Etrurua-Resort.h113748275.Hotel-Information)

![Hotel Relais II Chiostro di Pienza](//images.trvl-media.com/lodging/1000000/900000/893100/893017/ef61d192_y.jpg)

### Hotel Relais II Chiostro di Pienza

10/10 Excellent

"The room was beautiful and very clean. Breakfast staff was very kind."

[](https://expedia.ca/Pienza-Hotels-Hotel-Relais-II-Chiostro-Di-Pienza.h893017.Hotel-Information)

![Precise Tale Poggio Alla Sala](//images.trvl-media.com/lodging/91000000/90890000/90888700/90888666/8fbdd5cc_y.jpg)

### Precise Tale Poggio Alla Sala

10/10 Excellent

"Fantastic hotel in an incredible setting. Staff were extremely helpful, attentive and understanding. The perfect location for a relaxing break and a centre for exploring Tuscany"

[](https://expedia.ca/Montepulciano-Hotels-Precise-Tale-Poggio-Alla-Sala.h90888666.Hotel-Information)

![Castello di Velona Resort Thermal SPA & Winery](//images.trvl-media.com/lodging/2000000/1040000/1037900/1037832/87359911_y.jpg)

### Castello di Velona Resort Thermal SPA & Winery

10/10 Excellent

"Everything was 5 star. It’s like living in a castle in the sky with hot thermal pools everywhere and amazing food. We loved our outdoor patio with the sunset view of the panorama."

[](https://expedia.ca/Montalcino-Hotels-Castello-Di-Velona-Resort-The-Leading-Hotels-Of-The-World.h1037832.Hotel-Information)

![Fonteverde Lifestyle & Thermal Retreat](//images.trvl-media.com/lodging/1000000/910000/909000/908918/f6fb188e_y.jpg)

### Fonteverde Lifestyle & Thermal Retreat

10/10 Excellent

"Best resort I’ve ever stayed in! So clean, bathroom is refreshing, the many thermal pools, the views, I’ll be going back every year."

[](https://expedia.ca/San-Casciano-Dei-Bagni-Hotels-Fonteverde.h908918.Hotel-Information)

![Hotel San Gregorio](//images.trvl-media.com/lodging/3000000/2700000/2692200/2692135/9fda43a3_y.jpg)

### Hotel San Gregorio

10/10 Excellent

"Super convenient location steps to the historic center. Possibly the only hotel with its own dedicated secure / covered parking. Well decorated and breakfast was great!"

[](https://expedia.ca/Pienza-Hotels-Hotel-San-Gregorio.h2692135.Hotel-Information)

![Hotel Corsignano](//images.trvl-media.com/lodging/3000000/2530000/2525700/2525690/e0c5b2be_y.jpg)

### Hotel Corsignano

10/10 Excellent

"Perfect stay"

[](https://expedia.ca/Pienza-Hotels-Hotel-Corsignano.h2525690.Hotel-Information)

## Find out more about Pienza

**Everything you need to know about** **Pienza** **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 Pienza vacation rental for you. At Expedia, you can take your pick from [private vacation homes](https://www.expedia.ca/aa/PrivateVacationHomes), [apartments](https://www.expedia.ca/aa/Apartments), cottages, [cabins](https://www.expedia.ca/aa/Cabins), villas... 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 Pienza vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search. 

**Pienza vacation rentals: An excellent choice for every season**

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

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Pienza vacation rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a vacation rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Pienza vacation rentals we have selected for you start as low as CA $119 per night. Entering your travel dates in the search wizard you might find even better deals!

**How to find incredible deals on Pienza rentals**

At Expedia, we put the best Pienza 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 Pienza 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 Pienza 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 Pienza. 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

### 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?

> [Villa I Cipressini Tuscany Private luxury pool spa](https://www.expedia.ca/Pienza-Hotels-Villa-I-Cipressini-Tuscany-Private-Luxury-Pool-Spa.h26681929.Hotel-Information): Visitors give good reviews to this Pienza vacation home rental, which offers a fireplace, a balcony, and a barbecue grill to help you feel perfectly comfortable in your new surroundings. It has 5 bedrooms as well as a kitchen with a dishwasher, a fridge, and an oven, so you can cook with friends or family. It offers a garden, a selection of games, and a hot tub so you can immerse yourself in your vacation.

### How many vacation rentals are there in Pienza?

> Expedia has 33 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.

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Save on select hotels and earn double points when you book on the app. Our app deals help you to save on trips so you can travel more and manage it all on the go.

Scan the QR code with your device camera and download our app

![QR code to download the app](data:image/png;base64,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)