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Condo vacation rentals in Province of Siena

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Popular amenities for Province of Siena condo rentals

Weekly condo rentals

Top guest favorite
Condo 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 favorite
Condo in Siena
4.87 out of 5 average rating, 38 reviews

Rinuccini Cecco Palace

AnnetteRating, 5 stars3 weeks ago
Fabulous place and amazing location
Top guest favorite
Condo 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.
Guest favorite
Condo 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 favorite
Condo 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 doable if you drive slowly. But it's 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 disturbing 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 whining at a high level. All in all, a great place to stay with a very nice and accommodating host.
Superhost
Condo 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.
Superhost
Condo 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.
Top guest favorite
Condo in Arbia
4.93 out of 5 average rating, 153 reviews

Il Cipresso... in the company of Franco and Lida

PamelaRating, 5 stars1 week ago
Franco is very kind, we had a great stay

Pet-friendly condo rentals

Guest favorite
Condo 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 favorite
Condo in Panzano
4.94 out of 5 average rating, 117 reviews

Apartment overlooking Panzano in Chianti

藍晒Rating, 5 stars1 week ago
Great place to stay to enjoy the vineyard canyon, I stayed here for one night and slept very comfortably, Grandma Anna took good care of us, highly recommended to everyone.
Guest favorite
Condo 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 favorite
Condo 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 favorite
Condo in Siena
4.96 out of 5 average rating, 48 reviews

A casa di Luca - entire apartment with balcony

SaskiaRating, 5 stars4 days ago
The apartment is conveniently located, but far enough from town centre to be quiet and peaceful. Barbara made extra effort with leaving milk and a few drinks, enough toilet paper, and other basics like olive oil which was helpful. We loved the small balcony looking out on a green space and found the beds comfortable and apartment clean.
Guest favorite
Condo 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 favorite
Condo 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
Condo in Siena
4.85 out of 5 average rating, 27 reviews

[Porta Camollia] Sam's House

MoranRating, 5 stars3 weeks ago
amazing department !!

Condo rentals with a pool

Superhost
Condo 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 favorite
Condo in Buonconvento
5 out of 5 average rating, 24 reviews

Beautiful cottage surrounded by greenery, swimming 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 👌
Superhost
Condo 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 favorite
Condo 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 favorite
Condo in Montieri
5 out of 5 average rating, 46 reviews

Podere Cupiano "La Costa"

PeterRating, 5 stars6 days ago
Wonderfully spacious apartment with swimming pool in a beautiful authentic village with nice restaurants, in the middle of Tuscany. Around the corner, you can find fantastic mountain bike trails and hiking trails. Siena and Florence are also almost around the corner. We have enjoyed it!
Top guest favorite
Condo 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 favorite
Condo in Castelnuovo Berardenga
4.96 out of 5 average rating, 69 reviews

Orgiale Charme Residenz Castle

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!
Guest favorite
Condo in Casole d'Elsa
4.93 out of 5 average rating, 156 reviews

La Casetta

RamRating, 5 stars3 weeks ago
Both Barbara and Andrea were very welcoming and forthcoming when we encountered a hitch in our travel plans. They are unusually friendly, and accommodating hosts. The house is a great base for exploring the surrounding area and is tastefully decorated. Highly recommended!

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