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Holiday houses in Province of Siena

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Popular amenities for Province of Siena holiday rentals

Other great holiday rentals in Province of Siena

Top Guest favourite
Farm stay in Camucia
5 out of 5 average rating, 7 reviews

The 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.
Home in Cetona
5 out of 5 average rating, 6 reviews

La Macina di Modì

JudithRating, 5 stars9 months ago
Our stay was in the magnificent city of Cetona. We felt so lucky to be in the old part of the City. The decor was picked with an artist’s care. The space was elegant and we loved our vacation!
Superhost
Villa in Radicondoli
4.94 out of 5 average rating, 18 reviews

A Romantic Villa in the heart of Tuscany

AmandaRating, 5 stars6 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, 75 reviews

Podere 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
Home in Tavarnelle Val di Pesa
4.93 out of 5 average rating, 138 reviews

Nada Home

JamesRating, 5 stars2 days ago
We had a lovely holiday in Tuscany. The villa is surrounded by beautiful scenery with lots of day trip options nearby. We added on a cooking class with Raimondo and Viola (Nada's daughter) and learnt so much. We will definitely be making fresh pasta from now on! The villa is well equipped, and nicely furnished.
Top Guest favourite
Home in Campagnatico
5 out of 5 average rating, 7 reviews

Beautiful bright villa with view - Casa Luca

RafiRating, 5 stars1 month ago
We stayed at Mel's Casa Luca in March 2025 for over a week. Tucked away yet near medieval Campagnatico, it’s 5 minutes from the E78 to Grosseto/Siena, 15-20 minutes to Grosseto, and 30 minutes to the sea. Casa Luca, one of three stone farmhouses on what is essentially an olive farm, offers resort-like amenities which are shared with the guests of the other 2 houses: a trampoline, large pool, and ample walking space. Casa Luca is a single-storey house with two bedrooms with plenty of storage, comfy beds, an open-plan kitchen/dining/living area with Netflix, a big bathroom, and a well-equipped kitchen. Outside, there’s a private garden, terrace, BBQ. There is also a shared bakehouse with a pizza oven and huge dining table. We loved it and highly recommend it!
Superhost
Apartment in Arezzo
4.5 out of 5 average rating, 4 reviews

Pozzale Apartment 2+2 | 50m

KatrienRating, 5 stars9 months ago
We loved this place. The grandmother welcomed us and she was such a nice lady! There is a lot of space for the kids to play and the view from the swimming pool with the sunsets is amazing! It’s an ideal place to visit some villages in the neighborhood during the day and to relax at the end of the day at the pool. We would love to come back a bit longer!
Top Guest favourite
Villa in Roccatederighi
4.97 out of 5 average rating, 33 reviews

Villa Il Diaccio with view of the Tuscan Maremma

AleahRating, 5 stars4 days ago
This house is perfect for a family vacation with so many different amenities. We got the most out of the jacuzzi, pool table, living room campfire and beautiful views down to Roccatederighi along with the mountains and sea in the far distance. The host, Riccardo is so sweet, welcoming and very helpful and responsive to questions I had asked. Experiencing this place is even better in person and all we wanted in a relaxing vacation.

Destinations to explore

  1. Airbnb
  2. Italy
  3. Tuscany
  4. Province of Siena