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Cottage holiday rentals in Province of Siena

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Popular amenities for cottage rentals in Province of Siena

Cottage rentals with a hot tub

Top guest favourite
Cottage in San Gimignano
4.97 out of 5 average rating, 70 reviews

Romantic House in Tuscany with jacuzzi

JosephRating, 5 stars2 weeks ago
Davide and Annalisa's cottage was absolutely gorgeous, exactly as the pictures showed. It was the perfect place for us to relax and enjoy our last week in Italy. Breakfast out on the patio with the birds chirping and surrounded by nature was a great way to start the day. Davide lit the heater for the hot tub for us and we were able to enjoy a wonderful evening relaxing. Davide and Annalisa were full of good recommendations for restaurants and local places to visit. The cottage is within driving distance of so much - Pisa, Florence, Siena and of course San Gimignano just to name a few. All the amenities we needed were included, the WIFI was great and the cottage was very comfortable. I would highly recommended staying here and if we are ever in the vicinity we would certainly stay here again.
Guest favourite
Cottage in Sovicille
4.93 out of 5 average rating, 223 reviews

From Simone, podere santi Lucia and Pietro

LesleyRating, 5 stars8 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 Seggiano
4.96 out of 5 average rating, 90 reviews

EcoLodge – modernes Design in ruhiger Panoramalage

ChrisRating, 5 stars1 week ago
Third time at this beautiful place! As always a nice surprise
Guest favourite
Cottage in Castelmuzio
5 out of 5 average rating, 60 reviews

Panoramic view & outdoor jacuzzi - Pienza

AmandaRating, 5 stars2 weeks ago
Golly where to start - my husband and I are from New Zealand and used to peace and quiet and this is 100% what we were after. We were literally blown away from the moment we arrived and walked up the path of jasmines to sitting in the spa when it cooled off and watching the fireflies and listening to the bells ringing from the local monastery and churches. It was perfect for two people. You will need to be able to cope with a fairly tight drive in! And another word of advice is make sure you have some bug spray as it’s located in an area of rich agriculture and as such the mosquitos are about not awful but they are there.
Cottage in Campiglia D'orcia
4.94 out of 5 average rating, 33 reviews

Val D’Orcia Eco Cottage - Exclusive Retreat

WilliamRating, 5 stars2 days ago
Wonderful, peaceful, quiet beautiful views, etc
Superhost
Cottage in Trequanda
4.75 out of 5 average rating, 142 reviews

"Rosso Poggiolo" farmhouse with swimming pool.

EliotRating, 5 stars7 months ago
Very good, it was perfect The host were so friendly Thank you very much
Cottage in Montepulciano
4.62 out of 5 average rating, 13 reviews

Tuscany Villa Girasole

DavidRating, 5 stars1 week ago
What a great place to stay. Everything we needed during our stay was available, from a cot for our baby to an iron and a full kitchen etc. The location was great for Tuscany, with Siena, Montelpulciano and others an easy drive away. The pool was just what we needed in the afternoons to cool down and relax after spending our mornings out and about. We hosted a dinner with family in the large dining table overlooking the pool, a lovely end to our stay at a superb family spot.
Cottage in Foiano della Chiana

Luxury Cottage Spaccasole - Sauna, Pool W/Cortona

Pet-friendly cottage rentals

Guest favourite
Cottage in Pievescola
4.93 out of 5 average rating, 91 reviews

Antico Borgo Ripostena – 1 Casa Bertilla

TroelsRating, 5 stars3 weeks ago
Beautiful place - great pool and extremely friendly host! It’s a bit of of drive of a dirt road (like 8min) to get to - but once getting there. Amazing!
Guest favourite
Cottage in San Casciano dei Bagni
5 out of 5 average rating, 16 reviews

Toscana, Country house with exclusive pool

ThomasRating, 5 stars4 weeks ago
The view is stunning. The place is very private. Leonardo is very responsive. Definitely worth visiting La Pace, a lovely restaurant 5 mins walk away. 10/10 recommend
Guest favourite
Cottage in Montepulciano
4.95 out of 5 average rating, 20 reviews

ELENA COTTAGE

TobyRating, 5 stars1 week ago
This casa is an absolutely spectacular place to stay when in Tuscany - I was amazed by the photos, but in real life the place is somehow even more beautiful and scenic! The hosting is absolutely faultless - we were made to feel right at home immediately with homemade treats, and every arrangement we needed was made super smoothly. Utterly perfect - this was our first introduction to Tuscany and we will remember it forever!
Guest favourite
Cottage in Colle di Val d'Elsa
4.8 out of 5 average rating, 61 reviews

Rustic Tuscan with swimming pool

HollyRating, 5 stars1 month ago
This is a beautiful location, ideal for a perfect relaxing break. We stayed for one week and Natasha had some excellent local recommendations of places to visit! Thank you . We had such a wonderful time and I would recommend :)
Superhost
Cottage in Buonconvento
4.83 out of 5 average rating, 60 reviews

QuarterApartment for 6P Agriturismo Quarantallina

LisaRating, 5 stars2 weeks ago
The property was beautiful amd loved the scenery and friendly animals such as the donkeys and horse which greeted us each night. Serena and Mario were exellent hosts and made us feel at home at welcomed. We enjoyed a home cooked dinner with a view and breakfast. Very comfortable rustic farmhouse accomodations. Highly recommend and would love to go back as it is close to all in Tuscany.
Top guest favourite
Cottage in Osteria delle Noci
5 out of 5 average rating, 95 reviews

Your Tuscan oak tree house, enchanting Val d'Orcia

SamRating, 5 stars1 day ago
This beautiful, private, peaceful property is a must-stay if you're in the area. Breathtaking views out of every window. Short drive to a few nearby towns with great food and wine.
Guest favourite
Cottage in Pienza
4.95 out of 5 average rating, 37 reviews

Cottage San Lorenzo

Brandon and TiffanyRating, 5 stars3 weeks ago
We stayed here with our two young adult daughters. The home and the views are just magical! The home was well stocked and provided everything we needed. It very peaceful and quiet. The grounds are stunning and well kept! Only a 15 minute drive to the town of Pienza which had some of the best local restaurants. The pool was very nice to enjoy on a hot summer day with a glass of Rose in hand. We we would stay here again in a heartbeat! You will not be disappointed!
Superhost
Cottage in Pari
4.95 out of 5 average rating, 152 reviews

La Casa del Frantoiano - Pari -

MauraRating, 5 stars4 months ago
Beautiful location! Wonderful stay.

Private cottage rentals

Cottage in Bucine
4.84 out of 5 average rating, 148 reviews

Cottage in the Tuscan countryside

CarrieRating, 5 stars1 month 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 Cinigiano
5 out of 5 average rating, 7 reviews

Cottages in Tuscan Country (Spazzacamino)

JanusRating, 5 stars11 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 Castiglione della Pescaia
4.96 out of 5 average rating, 49 reviews

The Cottage

JuttaRating, 5 stars8 months ago
The house lives from Gloria, who is a perfect host and a soul of man. She personally accompanied us to the accommodation, explained everything to us and spoiled with homemade delicacies and Tuscan specialties: homemade bread and cookies, jam, fresh fruit, water in the fridge, Tuscan olive oil and coffee. Because it sometimes got quite cool during our stay in October, she also brought us wood and lighters for the open fireplace. We had three cozy days in the blue garden house, which certainly unfolds its charm in summer even more if you can use the garden and the beautiful terraces. The sea is only a few kilometers away by bike or car. Highly recommended is also the vegetarian restaurant, which Gloria runs together with her sister, about 1 km from the house.
Superhost
Cottage in Pergine Valdarno
4.27 out of 5 average rating, 11 reviews

Relaxing holiday in private house with pool

JurriaanRating, 5 stars12 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
4.83 out of 5 average rating, 162 reviews

The Five Oaks Cottage

CamronRating, 5 stars7 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 Monteriggioni
4.75 out of 5 average rating, 58 reviews

apartment surrounded by greenery

LaurenceRating, 5 stars11 months ago
We had a great time at Antonello's place. He is very welcoming, despite the fact that he only speaks Italian, and German, if I'm not mistaken. It was very understandable that we were arriving earlier than the scheduled time. We were able to drop off our luggage and the food we brought from our previous home. When we returned, we were pleasantly surprised to see that he had transferred everything to our rental and even put our bottles in the fridge🤩. The pool is superb, at very good temperature, and the sunbeds available, are comfortable, there is even a shower, which is very good. You can eat outdoors, in the shade, there are different spaces at your disposal. In summary, we can say that we had a great stay, in a beautiful environment, quiet, tastefully furnished. You have to plan to come by car, if you want to visit....
Superhost
Cottage in Gambassi Terme
4.45 out of 5 average rating, 42 reviews

Gelsomino Cottage near Firenze,San Gimignano,Sien

MandyRating, 5 stars9 months ago
A great starting point for any excursions to Florence, Siena, Volterra, San Gimignano, Pisa and the sea Miriam and Carlo are enchantingly lovely landlords. They gave great tips for our excursion destinations. Thanks for that
Superhost
Cottage in Volterra
4.89 out of 5 average rating, 9 reviews

Indipendent barn over the Hills around Volterra

MarinaRating, 5 stars11 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.

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