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Apartment holiday rentals in Province of Siena

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Popular amenities for Province of Siena apartment rentals

Weekly apartment rentals

Top guest favourite
Apartment in Siena
5 out of 5 average rating, 9 reviews

Stylish and Tuscany home 360° view Piazza Il Campo

CaterinaRating, 5 stars1 week ago
We had the most wonderful experience staying at this beautiful apartment in Siena. From the moment we arrived, we were warmly welcomed by our incredible host, who went above and beyond to make our stay special and at ease. The apartment itself is absolutely stunning—immaculately clean, incredibly spacious, and tastefully decorated with a charm that perfectly complements the magic of Siena. Every detail was just right, making us feel comfortable and relaxed from the start. If you're looking to enjoy the full experience of Siena, this is definitely the place to stay. It felt like a true home away from home, and we honestly can’t wait to come back! Grazie Martina!
Guest favourite
Apartment in Siena
4.87 out of 5 average rating, 38 reviews

Rinuccini Cecco Palace

AnnetteRating, 5 stars3 weeks ago
Fabulous place and amazing location
Guest favourite
Apartment in Siena
4.93 out of 5 average rating, 72 reviews

[NEW] Modern Central Studio with parking space

KarinaRating, 5 stars2 days ago
This apartment was absolutely wonderful! The location couldn't be better — we were right across the street from Siena’s historic city walls, making it easy to walk into the heart of the city and explore everything it has to offer. The apartment itself was impeccable: ultra clean, fresh-smelling, and beautifully decorated with thoughtful touches throughout. It felt like a true home away from home. We absolutely loved our time here. Tommaso was amazing host— responsive, welcoming, and made everything smooth from check-in to check-out. I will definitely come back and will be recommending this property to my friends. We had a fantastic time in Siena thanks to this lovely place!
Top guest favourite
Apartment in Siena
5 out of 5 average rating, 72 reviews

Casa Manori - refined and cozy two-room apartment

MatthewRating, 5 stars6 days ago
Nora’s apartment is simple wonderful. Located just a stone’s throw outside the Siena old city wall, the location is perfectly quiet but walkable to the entire town, and affords much more space than average. This is a very large one bedroom, with plenty of lounge space, plus an actual washer plus separate dryer! The bed was super comfortable and the Nespresso machine was lovely. Nora was a fantastic host, helping answer questions before arrival and during the trip. Would definitely stay here again on our next trip to Siena.
Top guest favourite
Apartment in Colle di Val d'Elsa
4.98 out of 5 average rating, 180 reviews

DorminColle - Tuscan-style apartment

NunoRating, 5 stars2 weeks ago
This place is great, I strongly recommend it. The hosts are also amazing. We stayed while doing a bike trip around Tuscany and the hosts allowed us to store our bikes in their garage.
Guest favourite
Apartment in Siena
4.91 out of 5 average rating, 82 reviews

•Il Chiostro• A gem in the heart of Siena

EmilyRating, 5 stars2 weeks ago
Julia’s place was a wonderful stay. Very convenient to the sites in Siena; the piazza del campo and the duomo or less than five minute walk. The apartment interior is very spacious and well equipped. Will stay again when we return to Siena!
Top guest favourite
Apartment in Monteriggioni
4.92 out of 5 average rating, 122 reviews

Il Vecchio Noce

JuliaRating, 5 stars1 week ago
A super nice place to stay. The way there is a bit adventurous and not recommended for low-riding vehicles, but otherwise quite doable if you drive slowly. But it is also totally quiet there. The cottage is nicely furnished. Everything important was available and Alessandro even greeted us with a bottle of wine. The bed and pillows are extremely comfortable. Somewhat annoying is the squeaky gas heater and the fact that the water temperature in the shower fluctuated quite a bit. Maybe it can still be repaired. But that's already whining at a high level. All in all, a great place to stay with a very nice and accommodating host.
Superhost
Apartment in Siena
4.96 out of 5 average rating, 182 reviews

Elegant and Bright Central Loft

NickRating, 5 stars8 months ago
Fantastic location and easy arrival.

Pet-friendly apartment rentals

Guest favourite
Apartment in Monte San Savino
4.96 out of 5 average rating, 49 reviews

La Foresteria | Granary House

LynneRating, 5 stars2 weeks ago
Such a beautiful, peaceful place to spend a few days! It was central to many tours and activities, great for exploring! Luca was a wonderful host and ensured we were happy and had everything we needed. The restaurant was great! I can’t think of anything that would have made our stay better! Completely exceeded our expectations!
Guest favourite
Apartment in San Gimignano
4.95 out of 5 average rating, 130 reviews

Adalberto Apartment inside the Manor of Fulignano

KevinRating, 5 stars2 weeks ago
A beautiful apartment with stunning views. Easy access to many beautiful places to visit such as San Gimignano, Florence and Sienna. The apartment was clean and comfortable with amenities as listed. The views from the communal terrace were stunning and there was plenty of space to sit without being on top of other guests. We would highly recommend.
Guest favourite
Apartment in Montepulciano
4.89 out of 5 average rating, 121 reviews

La Civetta - Stylish Retreat in Historic Center

JaneRating, 5 stars2 weeks ago
We loved Montepulciano and the Casa di Design / La Civetta was the perfect place to stay. The apartment is a creative and beautifully renovated space with everything needed for a short stay. The showers were powerfull and the beds very comfortable with lovely sheets. Everywhere in the centre of Montepulciano is within walking distance and there was even a bar at the end of the road! Check in was easy with helpful photos to help us find our way. Thanks
Top guest favourite
Apartment in Siena
4.96 out of 5 average rating, 47 reviews

A casa di Luca - entire apartment with balcony

SusanRating, 5 stars3 weeks ago
Barbara’s place was perfect for exploring Siena on foot . Her apartment was immaculate and she had left tea and coffee for guests. We were able to drop our bags off before check in time . Also walking distance from train station. Would definitely recommend. 😊
Superhost
Apartment in Siena
4.91 out of 5 average rating, 33 reviews

Traditional Apartment next to Piazza del Campo

KathyRating, 5 stars1 day ago
This was the most amazing apartment right in the middle of everything! Literally just behind the Piazza del Campo we walked out our door and had everything right there. And the apartment was so cool! Everywhere you look there’s cool features. It was so unique and charming. We loved having the windows open to the view of a restaurant below and the rolling hills beyond. Fabio was very helpful as well. We would definitely stay here again.
Guest favourite
Apartment in San Gimignano
4.83 out of 5 average rating, 236 reviews

Historic centre - cozy apartment

ArcadiaRating, 5 stars4 days ago
We loved staying at Helga and Federico’s apartment! The place was very clean and nearby one of the main gates, with many restaurants, parking options, and things to do. Federico gave us recommendations for places to go, and it is clear he loves this town!
Guest favourite
Apartment in Pienza
4.91 out of 5 average rating, 99 reviews

Amazing view of Val d'Orcia Pienza

AnneRating, 5 stars3 weeks ago
Very comfortable accommodations and gorgeous property and views
Superhost
Apartment in Siena
4.88 out of 5 average rating, 26 reviews

[Porta Camollia] Sam's House

MoranRating, 5 stars3 weeks ago
amazing department !!

Apartment rentals with a pool

Superhost
Apartment in Cavriglia
4.88 out of 5 average rating, 150 reviews

Chianti La Pruneta, Michelangelo apartment.

TomRating, 5 stars1 day ago
Lovely stay in this rural location. Comfortable, scenic, friendly hosts! Nice pool!! Clean and everything we needed! Massimo made us feel as comfortable as possible down to the details!! We loved Iris the dog too (and we think she loved us!) Recommend the meal which helped make my wife’s birthday very special.
Top guest favourite
Apartment in Buonconvento
5 out of 5 average rating, 24 reviews

Beautiful cottage surrounded by greenery,pool,relaxation

NaumanRating, 5 stars8 months ago
Had an amazing time with Sara & Simone - truly the best hosts we've come across. The place was fantastic, amazing views by the pool, great room, clean and all the amenities needed are available. Sara & Simone are great hosts, they made us breakfast one day which was amazing, fresh organic food with the best view. And all their local recommendations and reservations made our trip in Tuscany much nicer. Can't wait to come back again 👌
Top guest favourite
Apartment in Castellina in Chianti
4.95 out of 5 average rating, 38 reviews

Il Giaggiolo – Chianti with a view

AmeliaRating, 5 stars1 week ago
We stayed in Monica’s home for five nights and four days, and it was incredible. The second we checked in Monica sent me an extensive list of instructions and places to visit during our stay. My favorite list was restaurants and local food shops in the area she recommends as a local. The house had all the amenities you could need/want, comfortable beds, and a really nice patio area. We are a few meals outside and enjoyed the stunning view. We saw some of the most beautiful sunsets as well. The pool was really well kept. There were many wineries the were nearby. The location was also great for taking day trips to Florence and Siena. The nearest town was so cute and had a lot of nice shops and restaurants. We are so appreciative of Monica’s food recommendations and suggestions of things to do. Overall we had an amazing time, and we highly recommend staying here!!
Superhost
Apartment in Castelnuovo Berardenga
5 out of 5 average rating, 5 reviews

San Rocco – Bellavista – Castello di Bossi

GaiaRating, 5 stars9 months ago
The property is wonderful, surrounded by greenery and with a pool with an incredible view. The room was super clean and with all possible comforts. We interacted a lot with a very kind lady at the reception, very friendly and helpful. The wine we tasted was also exceptional , it's worth staying there for just one night! Extremely recommended
Top guest favourite
Apartment in Cinigiano
5 out of 5 average rating, 90 reviews

Spinosa Apartment in Podere Capraia

StellaRating, 5 stars1 week ago
We had an amazing time at Alberto & Laura's. The place was quiet, spacious, exactly like in the pictures. On arrival we were welcomed by our hosts and got some great recommendations on what to do in the area. They even shared some homemade food with us, which was so good and thoughtful. Also, the swimming pool and outside space we could use was amazing and private. Would definitely go back again, 10/10!
Top guest favourite
Apartment in Montieri
5 out of 5 average rating, 46 reviews

Podere Cupiano "La Costa"

SimonRating, 5 stars1 week ago
We could go on forever about what we liked. We especially want to highlight the great hospitality of Francesco and his family. Not only the building and the pool, but also the plants and the lawn garden were provided with a lot of attention to detail. We can't wait to see you next time!
Top guest favourite
Apartment in Castellina in Chianti
4.91 out of 5 average rating, 58 reviews

Apartment with terrace and stunning view

AlexRating, 5 stars1 week ago
The apartment was lovely. We stayed there for 6 days from end of May into start of June. The view is incredible and the fact there is a nice balcony and a swimming pool that look over it are a bonus. Raisa was very helpful with suggestions for the area, and they let us do our own thing on the land peacefully. The dogs are very adorable and friendly too! For anyone looking for a peaceful getaway with the occasional trip into Castelina in Chianti (would recommend there are many lovely spots to eat), this is a perfect getaway.
Top guest favourite
Apartment in Castelnuovo Berardenga
4.96 out of 5 average rating, 69 reviews

Castello di Orgiale Charme Residenz

ShellRating, 5 stars1 month ago
Property is amazing, host so friendly and helpful… Honestly we spent very little time on the property as we were exploring so much of Tuscany during our stay with the lovely location as our home base. But it was so beautiful to wake to every day and come “home” to late every evening :) During our 6 days, we explored Florence, hung out in Siena, hiked Chianti trails, visiting all over from Monteriggioni to San Gimignano to Volterra… and throughout Val d’Orcia from Montepulciano to Pienza , Pitigliano to Serano… and north to Lucca & Pisa. Just wonderful location :) Thank you so much!

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