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Vacation home accommodations in Province of Siena

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Popular amenities for Province of Siena vacation houses

Family-friendly vacation houses

Top guest favourite
Vacation home in San Donato In Poggio
4.98 out of 5 average rating, 134 reviews

Chianti Penthouse with panoramic View & Pool

Jens & KatjaRating, 5 stars4 weeks ago
Our stay in Tuscany was absolutely unforgettable! The peaceful surroundings and stunning views made it the perfect getaway. The small village nearby was charming, with some fantastic restaurants and a supermarket just a short walk away. The scenery all around was simply breathtaking. Giada was super friendly and incredibly responsive — they even helped us rent bikes, which made exploring the area even more special. Everything was clean, well-equipped, and comfortable. We had a wonderful time and would love to come back!
Superhost
Vacation home in Siena
4.84 out of 5 average rating, 76 reviews

"Lisa" apartment with fireplace

DonRating, 5 stars2 days ago
We loved our stay! Were there for our honeymoon and couldn’t have been more pleased. It’s a very historic, rural setting with beautiful views. It’s a working vineyard, olive farm and horse breeding farm and we enjoyed seeing the farming activities going on each day. There are dogs roaming the property which added to the ambience for us (we loved Robert, the little black dog especially!). Lisa was great and we’d definitely recommend the location if you visit Siena area. In 15 min you could be right in center city parking but great feeling of being removed from the busy city and escaping to your own historic villa on the hillside. Perfect for us.
Superhost
Vacation home in Asciano
4.88 out of 5 average rating, 99 reviews

Charming home Crete Senesi

NadezhdaRating, 5 stars2 weeks ago
The house and the location are amazing! Emiliano is super nice host. I strongly recommend it.
Guest favourite
Vacation home in Panzano
4.94 out of 5 average rating, 54 reviews

Antico Chianti Residence

LinaRating, 5 stars4 months ago
Nice and clean apartment. Good beds. In the middle of Panzano
Superhost
Vacation home in Villa Parigini
4.88 out of 5 average rating, 8 reviews

Near Siena (6 km), swimming pool and terrace

Paul LudvigRating, 5 stars8 months ago
Great location close to Siena and good size for a large family
Superhost
Vacation home in Rapale
5 out of 5 average rating, 8 reviews

Borgo Rapale – Jacopo

LaurenRating, 5 stars12 months ago
Nice relaxing place off the beaten path, beautiful views. Well cared for. You can walk around their vineyards and Olive Grove, and even buy local wine from the host.
Top guest favourite
Vacation home in San Gimignano
4.91 out of 5 average rating, 228 reviews

Appartamento Margherita Tuscan home

CarloRating, 5 stars2 days ago
Stefania was extremely kind and welcoming. The place is super comfortable and within walking distance of the main attractions. It's also very convenient to be able to leave the car in a private parking lot.
Superhost
Vacation home in Siena
4.86 out of 5 average rating, 14 reviews

Borgo dei Fondi, Apt. Loggia

KimRating, 5 stars10 months ago
David and Vittoria take great care to ensure a positive experience at their beautiful Tuscany home. David welcomed us after our harrowing day in Pisa and we felt at ease and welcomed immediately. Borgo dei fondi is the quintessential Tuscany home, peaceful, beautiful, surrounded by nature, with relaxing and fun amenities like the pool, bbq and outdoor patio. It was the perfect place to come home to and relax after day trips to Florence and Siena and equally wonderful to just stay put for a day and enjoy the tranquility. We highly, highly recommend staying here.

Vacation home rentals with a patio

Superhost
Vacation home in Torrita di Siena
4.81 out of 5 average rating, 16 reviews

Pian'D'olmo, an ancient farmhouse in the heart of Tuscany

AnnieRating, 5 stars7 months ago
We had a vision and dream of staying in a Tuscan villa in the country and it exceeded all our expectations.
Guest favourite
Vacation home in Monticiano
5 out of 5 average rating, 37 reviews

Casa Dani with private pool

LorenzoRating, 5 stars2 days ago
Great location to visit the Abbey of San Galgano and the hermitage, even on foot in just halfanhour through a beautiful forest, and also convenient to Siena (30/40 min by car). Fantastic private pool and outdoor courtyard!
Superhost
Vacation home in Lilliano
4.83 out of 5 average rating, 6 reviews

Cosy house with private pool

LucasRating, 5 stars9 months ago
Very nice house. Very nice welcome from our host's in-laws. They were always available and thoughtful although they only speak Italian. The location of the accommodation is ideal between Siena and Florence. Lots of pretty villages nearby.
Top guest favourite
Vacation home in Petrignano del Lago
4.97 out of 5 average rating, 67 reviews

Fontarcella, H&R- mediterranean home with jacuzzi

CristinaRating, 5 stars2 days ago
We stayed here 3 nights! We live in Florence and we chose this place to escape the chaos of the city and I have to say that we spent 3 days in complete relaxation! Very clear check-in instructions and everything related to the use of the accessories of the house, including a jacuzzi! The Host has always been ready to give us advice both before and during our stay! Nothing to complain about!
Top guest favourite
Vacation home in Poggibonsi
4.97 out of 5 average rating, 39 reviews

Ellerone 20, an old barn in Chianti

yamiRating, 5 stars6 months ago
In one word amazing ! in two words highly recommend ! we where 5 adults and the place was warm and welcome . full kitchen , absolutely amazing view and private . Thanks sara for all your help !
Top guest favourite
Vacation home in Monticchiello
5 out of 5 average rating, 17 reviews

Elegant farmhouse overlooking Pienza

KrisRating, 5 stars2 weeks ago
Gorgeous home in Monticchiello with breathtaking views. Pictures do not do it justice! Truly one of the most beautiful properties and homes we’ve ever stayed in. There was plenty of space for our group of 5 to spread out and relax. Enjoyed amazing nights together cooking in the beautiful farmhouse kitchen. There was everything we needed to feel right at home. Laura was an excellent host and greeted us with a warm welcome. She checked in throughout our stay to make sure we were comfortable and answered all our questions in a timely manner. You must follow her exact instructions for getting to the house as GPS can take you down some bad roads if you are not paying attention. Still dreaming of this home and cannot wait to return!

Vacation home rentals with a washer and dryer

Guest favourite
Vacation home in Chianciano Terme
5 out of 5 average rating, 88 reviews

The Eagle and the Olive Tree

Michael RobertRating, 5 stars1 week ago
Amazing place to spend time. Great hosts and fantastic location
Superhost
Vacation home in Laterina
4.73 out of 5 average rating, 11 reviews

Apartment with pool and restaurant

StefaniaRating, 5 stars1 week ago
the stay was perfect. The attention to detail distinguishes it. The possibility of bringing the puppy was super appreciated. The restaurant deserves a great applause. I highly recommend it.
Top guest favourite
Vacation home in Monteroni d'Arbia
4.9 out of 5 average rating, 69 reviews

White lily with a view of Siena

RonRating, 5 stars4 days ago
The white lily was the perfect location for us to explore Tuscany’s towns and wineries and to return in the evenings to a lovely villa with breathtaking views. The sunrises were spectacular and the apartment was very clean and well equipped with everything we needed. Close to a small village for grabbing a few groceries if needed and the patio was a great place to sit and relax with some morning coffee or an evening wine while fully appreciating the Tuscan countryside. Thank you Marta for such a wonderful holiday we enjoyed our stay immensely. Ron
Superhost
Vacation home in Ulignano
4.73 out of 5 average rating, 11 reviews

★ Romantic apartment & stunning view of Tuscany ★

AndrewRating, 5 stars10 months ago
A great peaceful location with excellent pool area and gardens, but also well placed to visit Florence, Siena and San Gimignano. A car is necessary and it is easy to get around the Tuscan hills from here. Giorgia greeted us on arrival and responded very quickly to our questions during the week. Bug spray is essential. All in all we had a wonderful holiday.
Guest favourite
Vacation home in Vitignano
5 out of 5 average rating, 28 reviews

Podere Vittoria Apartment: Heart of Chianti

AmandaRating, 5 stars2 weeks ago
Magical place! It was even better that imagined. It felt like an idyllic Toscana movie and it was so peaceful with the nature. The interior and furniture felt like a luxury countryside house. Edoardo was amazing and really helpful with recommendations for local goods. Thank you so much for the stay! We will definitely be back.
Guest favourite
Vacation home in Siena
4.9 out of 5 average rating, 40 reviews

Apartment in historic Villa in Siena_"IL MANGIA"

YuRating, 5 stars1 month ago
This was such a wonderful experience, enjoyed the beautiful courtyard for 4 days, clean rooms, quaint and textured furnishings and set up, it does have a warm home feel.Many times I want to be lazy in the room, enjoy the sunshine of the courtyard, and enjoy all the amenities provided in the room.I highly recommend this homestay, take a bus at the door for a few minutes to the ancient city of Siena, we go up each time to the ancient city on foot, you can enjoy the pastoral scenery of Tuscany all the way, thank you Cristina and her brother for their warm and thoughtful service, and the opportunity to come back here later.
Superhost
Vacation home in Campagnatico
4.86 out of 5 average rating, 14 reviews

Cozy Cottage with a beautiful view - Casa Luciano

ThomasRating, 5 stars1 month ago
We had a very nice time at Casa Luciano! Unfortunately, we could not use the great pool in March (although ice bathing is becoming more and more popular;-)). The area is very nice and quiet. We were able to hike, explore Campagnatico and other places. Once we were able to enjoy the good food at Vecchia Oliviera. (Attention: Pizza is only available from about May) We also supported the village shop properly. It has a decent selection for the size. Thank you Mel for the always timely assistance with questions and problems! We will recommend the accommodation and may also be able to vacation here during the pool time.
Superhost
Vacation home in Colle di Val d'Elsa
4.76 out of 5 average rating, 33 reviews

Tower House of the 1000

KatherineRating, 5 stars3 days ago
We really enjoyed staying at Marta’s apartment! It was so beautiful and spacious, and it had such a great view of the city. Marta was very responsive and helpful!

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