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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, 67 reviews

Romantic House in Tuscany with jacuzzi

NickRating, 5 stars5 days ago
A simple & gorgeous cottage in its own garden with views over San Gimignano from the terrace. Davide was a perfect host.
Superhost
Cottage in Sovicille
4.93 out of 5 average rating, 223 reviews

From Simone, podere santi Lucia and Pietro

LesleyRating, 5 stars7 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
4.93 out of 5 average rating, 134 reviews

Beautiful renovated barn in Tuscany

EleonoraRating, 5 stars4 days ago
beautiful accommodation surrounded by nature and silence. Hot tub under the stars a no small plus. Impeccable cleanliness, also greatly appreciated the welcome basket. Gloria responsive, kind and helpful host. We can't wait to go back
Superhost
Cottage in Trequanda
4.75 out of 5 average rating, 142 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 stars8 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, 87 reviews

EcoLodge – modernes Design in ruhiger Panoramalage

NatalieRating, 5 stars1 week ago
The Eco Lodge is a real gem and Ulla & Ralf are very eager and helpful. Absolutely recommended!
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 stars2 weeks 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 stars10 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, 79 reviews

Rustic retreat in the Tuscan hills

SaraRating, 5 stars2 weeks ago
A nice house in the middle of the olive trees. The house was clean and tidy and had everything you need. Francesco turned on the pellet stove and so we found it warm when we arrived. great location to see the Val d 'Orcia and surroundings and with a nice walk you can get to the center of Sinalunga. thank you so much for having a good time
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 stars8 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.
Guest favourite
Cottage in Santa Fiora
4.86 out of 5 average rating, 22 reviews

Podere di Maggio - Drying Room

FrancescaRating, 5 stars3 days ago
My husband and I stayed two nights in the Chestnut Dryer of the Podere di Maggio. What can I say? A real paradise: nestled in a wonderful valley with Mount Amiata in front of it and the beautiful medieval village of Santa Fiora. We could not ask for more: wonderful structure, well cared for, in detail, priceless peace. The hosts were great, hospitable, and really made us feel at home. In short, everything is perfect, nothing is missing, of course you have to love bucolic life like us ! The only downside? Two nights were too short and we'll definitely be back . Thanks Peter , Rita and sweet Noemi. See you soon
Guest favourite
Cottage in San Casciano dei Bagni
5 out of 5 average rating, 15 reviews

Toscana, Country house with exclusive pool

JelmerRating, 5 stars8 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 stars7 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.
Guest favourite
Cottage in Colle di Val d'Elsa
4.79 out of 5 average rating, 58 reviews

Rustic Tuscan with swimming pool

TaliaRating, 5 stars7 months ago
This place is absolutely beautiful and very centrally located in Tuscany- about 20 minutes away from Siena. We spent two full days and the smaller towns and doing vineyard tastings and had a great experience! Natasha was so flexible with check in as we arrived late, left early, she sent photos of step by step instructions how to find out room. The view is as stunning as in the photos and then some! I will say be careful which way your gps takes you- I think Natasha even makes a note of it but we didn’t pay enough attention. There are two ways your gps takes you- one a very nice gravel road with a sign at the bottom that says le Ville- the other starts okay but then turns very bad with no ability to turn around! Looks for the le ville sign!
Superhost
Cottage in La Piazza
4.76 out of 5 average rating, 46 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.

Private cottage rentals

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

Charming Cottage with Pool

M.Rating, 5 stars9 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.
Guest favourite
Cottage in Bucine
4.84 out of 5 average rating, 147 reviews

Cottage in the Tuscan countryside

CarrieRating, 5 stars5 days ago
Ulisse's was really helpful as he met me at his restaurant and I followed him to the cottage. There is a coop, a butchers, a bakery and a little supermarket in Buccine and a small market on Wednesday mornings, which is really handy as there is not much around the cottage. It is in the middle of the country side surrounded by vineyards and nature, a perfect place for nature lovers. Ulisse, his wife and daughter were all really helpful and quick to resolve issues. For anyone trying to find it, have the petrol station and ristorante di ciccio on your left then continue straight on the SP540 , once you pass ristorante le bottega grassa ( a white building on your right) it is your next right turn ( the dump where you need to dispose of your rubbish from the cottage is on the right of this road) then take your next left signed "Le Mura" you continue down this road until a big yellow and white hse on the left and the big stone house on the right, the cottage is beside the stone house.
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.
Cottage in San Gimignano
4.88 out of 5 average rating, 100 reviews

Countryside Cottage With View - Le Papere apt

CarolRating, 5 stars5 days ago
For an introduction to Tuscany, Marco’s place was just incredible! With a view for miles featuring the medieval town of San Giminano, we could not have asked for better accommodation!
Superhost
Cottage in Pergine Valdarno
4.27 out of 5 average rating, 11 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 stars6 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.
Superhost
Cottage in Volterra
4.89 out of 5 average rating, 9 reviews

Indipendent barn over the Hills around Volterra

MarinaRating, 5 stars10 months ago
We spent two and a half wonderful weeks in this holiday home. Both Andrea from Be Home Services and in particular the owners Nara and Nino welcomed us warmly and were always available for questions and very helpful. We liked the secluded location of the house very much - you have a stunning panoramic view and it is largely very quiet despite the neighbors. It should be known that the nearby Villa Ulignano is used as a wedding location. On two weekends, there was live music until the early hours of the morning, which was clearly audible, but did not bother us excessively. It is worth mentioning that the lower floor shown on the exterior shots of the house cannot be used, but serves as a storage room for the owners. The drive to the house is - as already described here - quite adventurous and leads a few kilometers over unpaved, partly steep paths. If you drive slowly, this is easy to cope with.
Superhost
Cottage in Buonconvento
4.83 out of 5 average rating, 58 reviews

QuarterApartment for 6P Agriturismo Quarantallina

ErinRating, 5 stars3 weeks 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!!!

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