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Cottage vacation rentals in Province of Siena

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Popular amenities for Province of Siena cottage rentals

Cottage rentals with a hot tub

Top guest favourite
Cottage in San Gimignano
4.97 out of 5 average rating, 65 reviews

Romantic House in Tuscany with jacuzzi

RobertRating, 5 stars4 months ago
We stayed at this lovely cottage in late November and we were delighted with every aspect of the stay. The cottage was clean and comfortable, and was well equipped. The hot-tub was wonderful and sitting there on a chilly night with a view of SG was amazing. Annalisa and Davide were really nice and friendly and very helpful- great hosts. It was about 35 minutes to walk to the town, so quite walkable, and wonderfully quiet and rural (one morning there were 3 deer walking past the window). We had a very nice day out in Sienna which was easy to drive to. I would definitely recommend this place as somewhere really special.
Superhost
Cottage in Sovicille
4.93 out of 5 average rating, 223 reviews

From Simone, podere santi Lucia and Pietro

LesleyRating, 5 stars6 months ago
Lovely, peaceful, spacious place with a kind and generous host in Simone. He met us as we arrived and used his wagon to help move our luggage into the cottage. Big rooms, lots of space, many handy supplies in the kitchen. Good shower, comfortable bed. Enough bench space in the bathroom to put your things. Simone was really helpful with local recommendations for restaurants and where to park the car. One day he made a delicious tart and bought us in half. Would recommend staying at his place.
Guest favourite
Cottage in Radicondoli
4.92 out of 5 average rating, 131 reviews

Beautiful renovated barn in Tuscany

RachelRating, 5 stars2 months ago
Beautiful spot in a peaceful setting. Gloria was a fantastic host. We had a wonderful stay.
Superhost
Cottage in Trequanda
4.74 out of 5 average rating, 141 reviews

"Rosso Poggiolo" farmhouse with swimming pool.

EliotRating, 5 stars5 months ago
Very good, it was perfect The host were so friendly Thank you very much
Cottage in Montepulciano
4.58 out of 5 average rating, 12 reviews

Tuscany Villa Girasole

ShariRating, 5 stars7 months ago
Charming home with amazing pool and a great location Massimo was so helpful and always quick to respond offering restaurant reccos as well The ac was great and the bedrooms stay completely dark if you close the shutters which was nice to sleep a little later despite the morning light There were paper towels, salt oil even some coffee and filters, many basics provided We did not hear cars or highway sounds, just owls, roosters and quiet, it truly is a special place
Guest favourite
Cottage in Seggiano
4.95 out of 5 average rating, 85 reviews

EcoLodge – modernes Design in ruhiger Panoramalage

EricRating, 5 stars1 month ago
Beautifull quite and lovely place. Good location to visit surroundings by car on day trips.
Guest favourite
Cottage in Castelmuzio
5 out of 5 average rating, 53 reviews

Panoramic view & outdoor jacuzzi - Pienza

BronwynRating, 5 stars6 months ago
We had a wonderful stay at Orto Cottage. The cottage is very comfortable, the views are divine and the surrounding area is beautiful. We were in our own private world. Frank and Phil are great hosts, very friendly, responsive to any requests and helpful with suggestions. We loved their Private Guidebook. It was packed with great suggestions of places to visit, great restaurants and activities. Orto Cottage is highly recommended if you would like a lovely place to stay in the Tuscan hills that is private and an easy drive to all that the area has to offer.
Guest favourite
Cottage in Campiglia D'orcia
4.93 out of 5 average rating, 30 reviews

Val D’Orcia Eco Cottage - Exclusive Retreat

MollyRating, 5 stars5 days ago
My husband, dogs, and I had an amazing stay at the cottage. It was peaceful and private- we enjoyed cooking dinner and eating on the patio every night. The cottage had everything we needed and my dogs loved that they could explore inside the fully fenced yard. The location is great if you like to explore all the little towns, but have peace and quiet at the end of the day. This has been our favorite place to stay in Tuscany and we hope we can come back soon!

Pet-friendly cottage rentals

Superhost
Cottage in Cinigiano
5 out of 5 average rating, 7 reviews

Cottages in Tuscan Country (Spazzacamino)

JanusRating, 5 stars9 months ago
Our stay at Gabriele's place was great and we enjoyed the week we have with him. The house has a cinematic sweeping view of the Tuscan countryside and the pool just like that. The pool is perfect for cooling off on the hot summer days. The house is beautiful, rustic, clean and cool. Air conditioning also helps. We have been a family of 4, with children of 4 and 7 years. We have enjoyed it every day! Gabriele and his wife were very friendly, welcoming and always easy to reach if needed. They helped make our stay just perfect. Thanks to them! We can only recommend a stay with Gabriele and his “Le Capannacce”.
Superhost
Cottage in Sinalunga
4.86 out of 5 average rating, 77 reviews

Rustic retreat in the Tuscan hills

ErikaRating, 5 stars1 month ago
Beautiful place, well cared for and very clean. The only flaw was the very small hair dryer and there was no hand paper in the kitchen. After all, everything is well-stocked and a very quiet place
Top guest favourite
Cottage in Pergine Valdarno
4.77 out of 5 average rating, 57 reviews

Tuscan country house with pool

Poussin Bertrand Rating, 5 stars7 months ago
We had a pleasant stay at Vito's. The house is very well arranged and offers many amenities. The place is idyllic surrounded by olive groves and high up allowing exceptional views of Tuscany. The pool is simply fantastic, spacious and extremely well maintained thanks to Vito's right-hand man who takes great care of the entire property. This is a property to remember that we highly recommend.
Superhost
Cottage in Santa Fiora
4.86 out of 5 average rating, 21 reviews

Podere di Maggio - Drying Room

AlessandroRating, 5 stars5 months ago
The Di Maggio farm is a unique place where you can regenerate, immersed in a beautiful natural setting where you can fully experience contact with Nature. The apartment is well cared for and furnished in a rustic style with ethnic touches. The outdoor veranda is priceless where you can see the farm animals and also the peacocks. The owners are very kind and helpful people with whom it is pleasant to converse and learn local news and curiosities. We fell in love.
Guest favourite
Cottage in San Casciano dei Bagni
5 out of 5 average rating, 15 reviews

Toscana, Country house with exclusive pool

JelmerRating, 5 stars7 months ago
We stayed at Leonardo's cottage for almost two weeks and we enjoyed it very much. The pool was a real highlight for us. You will have the pool all to yourselves and are privately located. The area is very quiet and the view from the cottage fantastic. However, you will have to sit in the car to visit a larger supermarket (~20 minutes) or go to a town (Sienna, Perugia for example). We enjoyed the peace and weather and privacy. There is a restaurant within walking distance, which is definitely recommended! The cottage itself was very well cleaned when we arrived and Leonardo also offered new bedding after a week if we wanted, very neat. Furthermore, the cottage is simple and it is not big, but everything you need is in it (fridge with freezer, dishwasher, good TV, good internet, etc) and if you are there on vacation, of course you are not going to sit inside... Maybe we'll come back!
Guest favourite
Cottage in Montepulciano
4.95 out of 5 average rating, 19 reviews

ELENA COTTAGE

KaliRating, 5 stars6 months ago
Cottage Elena is nothing short of a dream and the pictures don’t do justice to how beautiful and serene the views are. We are already planning our next trip back! The hospitality was truly special.
Superhost
Cottage in La Piazza
4.76 out of 5 average rating, 45 reviews

Il Cipresso

NathanRating, 5 stars7 months ago
Cozy idyllic house with a great view overlooking the Tuscany landscape. The road to the house is a bit widning and long so if you're looking to go out often maybe not the most convenient. However if you're looking for a quiet peaceful getaway, it's an amazing location.
Top guest favourite
Cottage in Osteria delle Noci
5 out of 5 average rating, 87 reviews

Your Tuscan oak tree house, enchanting Val d'Orcia

MikeRating, 5 stars2 weeks ago
What a wonderful home and location! All was exactly what we could have hoped for and more. Interior of Veronicas home is comfortable, clean and warm. We lacked for nothing. The exterior is amazing! Spent most of my time outside in awe of the view . Veronica and Antonella were so welcoming. So helpful with instructions and places to see. Thanks to both of them for sharing this beautiful place. A gift indeed for us.

Private cottage rentals

Guest favourite
Cottage in Castiglion Fiorentino
5 out of 5 average rating, 24 reviews

Charming Cottage with Pool

M.Rating, 5 stars8 months ago
The stay with Fausto and his wife (Anna's parents) was really great: a clean cottage in a great beautiful area. The kindness and helpfulness of the hosts was heartwarming. For example, we got a bunch of herbs from their own garden, they came to bring medicine when one of us was sick and they were always ready to answer our questions. After another place we booked canceled a few days before departure, Anna's place was still available and she was quick to respond. We couldn't have found a better place to stay than this one and will definitely go back.
Cottage in Bucine
4.84 out of 5 average rating, 145 reviews

Cottage in the Tuscan countryside

IvarRating, 5 stars7 months ago
Cute cottage overlooking vineyard on Ulisse's and his family's estate. Although its located on their property, there's enough privacy. Good communication, great environment. The space itself is well equipped. Recommended!
Superhost
Cottage in Villa Parigini
4.75 out of 5 average rating, 4 reviews

Restored Barn in Chianti property, pool, terrace

VeronicaRating, 5 stars32 months ago
We spent a beautiful and relaxing week of vacation in the restored barn of Villa Parigini . The house is very quiet, cozy and comfortable and is well organized. It has a nice garden and pool to cool off and relax. Great location to visit Siena and the Chianti area. Giada and her mom are very kind and helpful Hosts. We look forward to coming back.
Superhost
Cottage in Pergine Valdarno
4.3 out of 5 average rating, 10 reviews

Relaxing holiday in private house with pool

JurriaanRating, 5 stars10 months ago
We had a very nice stay with the family (5 adults) in this beautiful part of Tuscany. This beautiful cottage is part of a series of cottages managed by a cooperative. We had a villa that would have used to be a barn with its own swimming pool on the edge of a large olive grove. A breathtaking view from the living room and garden over the region. Insane. There are two restaurants at walking distance. For the rest, everything can be reached within an hour or less. The COOP and Lidl are a 20-minute drive, Siena 50 minutes away and the discovery of this holiday Arezzo is less than half an hour away. What a beautiful city with rich history and fantastic restaurant. Our neighbors from Germany who had the big villa were really friendly. It was during the European Championship so it was nice to watch the matches together. 1 evening we watched football in the ice cream parlor in the village. Was also very cozy. Very friendly people.
Cottage in Cennina
4.84 out of 5 average rating, 161 reviews

The Five Oaks Cottage

CamronRating, 5 stars5 months ago
We had a wonderful time at the cottage in Cennina. The setting was absolutely beautiful. We felt remote yet were just a few minutes from nearby Ambra and Bucine. We highly recommend this place and we hope to return soon.
Cottage in San Gimignano
4.85 out of 5 average rating, 197 reviews

Countryside Cottage With View - Le Rondini apt

ErnestoRating, 5 stars2 weeks ago
The place was great with an excellent view of the valley and San Gimignano town, which was located at a 10 min drive. Great place to relax away from all the city noise. Marco addressed all concerns in a timely manner.
Superhost
Cottage in Buonconvento
4.83 out of 5 average rating, 58 reviews

QuarterApartment for 6P Agriturismo Quarantallina

ErinRating, 5 stars1 week ago
We loved our peaceful stay at Serena’s beautiful property. The house was cozy, rustic, and spacious. She was very accommodating with a high chair and baby crib. My 1 year old especially enjoyed the horse, donkeys, dogs, and cats on the farm. She recommended fantastic local wineries, and even cooked us a delicious Florentine “farm to table” meal. Would recommend to anyone looking for a farm stay away from the bustle of the busy and crowded cities. Thanks Serena!!!
Superhost
Cottage in Gambassi Terme
4.21 out of 5 average rating, 19 reviews

Il Gelsomino 2 near San Gimignano, Siena, Firenze

DariaRating, 5 stars22 months ago
We really enjoyed our stay! Miriam and Lorenzo are great hosts, very helpfull and happy to answer all questions. House is perfect for chill holidays, very quite. Swimming pool is very refreshing in hot days!

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