
Vacation rentals in Pienza
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Top-rated vacation rentals in Pienza
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Other great vacation rentals in Pienza
Superhost

Villa in Poppi
4.8 out of 5 average rating, 5 reviewsVilla for 22 people w/private pool
Marie-ClaireRating, 5 stars7 months ago
This little hamlet was ideal for a group of several families wanting a Tuscan holiday. Christina was a very responsive host, always available for help and suggestions. One down side was the distance from many of the Tuscan attractions such as Florence and Sienna. The hamlet is reasonably remote so is ideal for those who want a secluded holiday rather than those who want to see the sights of Tuscany.
Guest favourite

Cottage in Volterra
4.9 out of 5 average rating, 179 reviewsPodere Grignano, beautiful Tuscany
MarkRating, 5 stars2 months ago
Stefano and Roberta are two of the most absolute intrepid souls you will ever encounter. Their hospitality and generosity is without equal. Smartly appointed and expertly renovated, this exquisite example of an ancient farmhouse sits atop a stunning ridge line with vast views and expansive mountain scenery inspiring and enchanting at every turn. Right in the heart of Tuscany, this spectacular piece of the Italian wonderland does not disappoint!
Top guest favourite

Farm stay in Camucia
5 out of 5 average rating, 7 reviewsThe Garden of Olives | Casa Ippocastano
ViktorijaRating, 5 stars7 months ago
Everything was perfect! Nice place to rest with a wonderful chill lounge and a pool. Federica and Enrica were responsive and helpful hosts. Thanks for the time and all the recomendations.
Superhost

Villa in Radicondoli
4.94 out of 5 average rating, 18 reviewsA Romantic Villa in the heart of Tuscany
AmandaRating, 5 stars7 months ago
We are 2 couples in our early 60s. We adored the home. The surrounds and views sublime. We cooked and loved sitting in kitchen as sun set. Ahhhh. We enjoyed a drink in village at a little store. Our favourite meal was at Nazionale (book or you won’t get in). The lady there is areal character you will get to like her. The agricento restaurant also good. Coop had groceries. The village of Radicondolli is just beautiful. We drove to many places from there. Siena, san Gin, the Terma Antica ….. ( warm mineral waters with spa) nice to be spoilt. Try the other small villages around Radicondoli, we did better than larger ones, like castle d’elsa. Fabulous museum. Our hosts Francesca and Lorenzo were welcoming and met us on arrival. Each room was well separated with ensuite each room. Kitchen fully appointed. Italian coffee pot (buy you ground coffee at coop in town), some basic condiments. Roomy showers, one bath, lots of room to spread out. Herbs in garden.
Guest favourite

Villa in Asciano
4.95 out of 5 average rating, 76 reviewsPodere on the Crete Senesi
ChulaRating, 5 stars6 months ago
We spent a glorious and relaxing week at Sarchianello and could not recommend it more. The location was perfect for day trips to local places like Siena and Montalcino, and it was the ideal place to return to for an evening of eating and drinking. We loved our stay and were sorry to leave! It truly felt like a home away from home.
Guest favourite

Farm stay in Roccatederighi
4.92 out of 5 average rating, 129 reviewsHoliday in antique farm, Belvedere
JessicaRating, 5 stars3 weeks ago
This place is an absolute gem! It was so breathtakingly beautiful, that we tried to delay our flights and stay longer! Every single family member was lovely! It truly did feel like home. My husband and I cannot wait to come back and bring family with us too. There simply aren't any words to describe how much we loved our time at Peruzzo!
Superhost

Cottage in San Gimignano
4.78 out of 5 average rating, 32 reviewsGlicine romantic cottage in country
BartRating, 5 stars19 months ago
Concetta is the most lovely host! And the house provided everything we needed. Beautiful, remote area! Would gladly return.
Guest favourite

Farm stay in Greve in Chianti
4.87 out of 5 average rating, 192 reviewsThe Bartaline Hut
OmerRating, 5 stars1 week ago
Just book it! It was extraordinary
Quick stats about vacation rentals in Pienza
Total rentals
60 properties
Nightly prices starting at
$111 CAD before taxes and fees
Total number of reviews
2.7K reviews
Family-friendly rentals
20 properties are a good fit for families
Pet-friendly rentals
30 properties allow pets
Rentals with dedicated workspaces
20 properties have a dedicated workspace
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- Marina di Grosseto beach
- Kite Beach Fiumara
- Santa Maria della Scala
- Avignonesi Winery Fattoria Le Capezzine
- Terme Dei Papi
- Cala Di Forno
- Podere La Marronaia, Sosta alle Colonne
- Tenuta Le Velette
- Basilica of St Francis
- Cala Violina
- Cantina de' Ricci
- Cantina Stefanoni
- Madonna del Latte
- Castiglion del Bosco Winery
- Golf Club Toscana
- Cantina Winery, Cellar and Farm Fattoria Santa Vittoria
- Ugolino Golf Club
- Cantina di Montefiascone Soc.Coop.Agr. - Punto di Vendita
- Casa Del Cioccolato Perugina
- Pubblico Palace
- Podere Il Cocco
- Cantina Contucci