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Cottage vacation rentals in Montepulciano

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Popular amenities for Montepulciano cottage rentals

Cottage rentals with a hot tub

Top guest favorite
A stone cottage is surrounded by lush greenery, featuring a rustic facade with wooden accents. Potted plants are placed near the entrance, and the roof is topped with a small chimney. A pathway of stones leads to the door, inviting guests to explore.
Cottage in San Gimignano
4.97 out of 5 average rating, 66 reviews

Romantic House in Tuscany with jacuzzi

RobertRating, 5 stars5 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
A spacious area of well-kept grass is seen in the foreground, with a rustic Tuscan farmhouse in the background. The building features a tiled roof and multiple windows. Bare trees and some greenery surround the property, under a clear blue sky with scattered clouds.
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.
Top guest favorite
The jacuzzi is featured outdoors, illuminated with blue lights, creating a calming atmosphere at night. The surrounding stone walls provide privacy, and a dining table can be seen nearby. Steam rises, indicating the water is warm and inviting.
Cottage in San Casciano In Val di Pesa
4.95 out of 5 average rating, 141 reviews

Il Fienile, Cottage in the country with Jacuzzi

MagdalenaRating, 5 stars1 week ago
Our family loved this cottage. Plenty of space for the kids to stretch their legs and the recommendations for a private chef were amazing. Easy drive to lots of lovely places in the Chianti region.
Superhost
A private jacuzzi is situated in a serene outdoor space, surrounded by lush greenery. Olive and other trees provide shade, while a distant view of rolling hills complements the tranquil setting. The bubbling water invites relaxation amidst the peaceful landscape.
Cottage in Colle di Val d'Elsa
4.86 out of 5 average rating, 49 reviews

Cottage in the greenery with private jacuzzi and pool

AlexandraRating, 5 stars2 months ago
2 Nights of Dreams! We were greeted by Niccolò, perfect in everything, he gave us many tips on both places to see and where to go to eat, we followed them all and we stayed with God! The very nice cottage, has everything you need even for longer stays, the view is wonderful ,and the hot tub is a treat , both day and night . They welcomed us with a bottle of sparkling wine and red petals, which was not at all obvious, everything was perfect , thank you very much Natasha and Niccolò 😊
Guest favorite
The exterior of the property features a rustic stone façade complemented by wrought iron details. A spacious terrace is equipped with a large umbrella and an outdoor dining area, surrounded by lush greenery, enhancing the natural setting.
Cottage in Radicondoli
4.92 out of 5 average rating, 132 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
A glass-enclosed veranda offers a view of the private garden and pool area. A round dining table with decorative tiles is surrounded by iron chairs. Light filters through the glass, enhancing the rustic charm of the exposed stone walls.
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
Guest favorite
A modern stone house is surrounded by lush greenery, nestled against a hillside. Large glass windows provide ample natural light, showcasing the inviting interior. The roof has a gentle slope, reflecting a blend of traditional and contemporary architecture.
Cottage in Seggiano
4.95 out of 5 average rating, 86 reviews

EcoLodge – modern design in quiet panoramic location

EricRating, 5 stars1 month ago
Beautifull quite and lovely place. Good location to visit surroundings by car on day trips.

Pet-friendly cottage rentals

Superhost
A rustic stone building is set amidst a large, green lawn dotted with olive trees. The facade features multiple windows with arched tops, reflecting the characteristic Tuscan architecture. Natural scenery and gentle hills in the background suggest a peaceful, rural atmosphere.
Cottage in Fungaia, Monteriggioni
4.83 out of 5 average rating, 271 reviews

Countryside, 10 min from Siena

RobRating, 5 stars2 weeks ago
a beautiful house, lovely garden among the olive trees. and a very nice host. the location is more spacious than it looks in the pictures. you get a good description to get there and you do need it because is wonderfully quiet secluded in nature
Top guest favorite
A stone house features a rustic charm, framed by lush greenery. In the foreground, a clear, inviting pool reflects the sky. Sun loungers are positioned around the pool area, providing space for relaxation while enjoying the serene landscape.
Cottage in Lucardo
4.99 out of 5 average rating, 245 reviews

Best view ever & private pool

JennaRating, 5 stars1 day ago
This stay exceeded our expectations. It is actually nicer than pictured, from the attention to detail to the friendly greeting and responsiveness we cannot say enough about how much we enjoyed our stay here. The location is great for both privacy and ease to get to many places in Tuscany. Massimo and his son were beyond gracious hosts. We absolutely plan to come back!
Superhost
A spacious pool is framed by wooden decking, with sun loungers positioned nearby. The view includes a charming stone building with green shutters and lush greenery surrounding the area, creating a serene environment perfect for relaxation.
Cottage in Montespertoli
4.9 out of 5 average rating, 52 reviews

Cottage with panoramic view

PriskaRating, 5 stars7 months ago
We, 2 couples a baby and a dog, enjoyed our week at this lovely location. After a quite rocky and adventurous road, the house is situated in the midst of the beautiful tuscan landscape with wine hills and olive trees. From the lovely pool which was only for us we enjoyed those lovely views. The rooms are spacious and the kitchen is fully equipped, including a nice barbecue ourside. Florence is reachable within about 45 minutes by car and there are two little towns about 10-15 minutes away with big grocery stores, restaurants and gelaterias. Andrea and Gianni were super helpful, responsive and lovely hosts. We would highly recommend Le Spugne.
Guest favorite
Two lounge chairs with cushions are positioned beside a private pool, overlooking rolling hills at sunset. A small table holds a bottle of sparkling beverage, enhancing the serene atmosphere. Lush greenery and trees frame the view, creating a sense of tranquility.
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!
Top guest favorite
An aerial view of the historic Monteriggioni Castle showcases its medieval architecture surrounded by lush countryside. The fortified walls encircle the village, which is dotted with trees and buildings, while rolling hills extend into the distance under a sunset sky.
Cottage in Monteriggioni
4.96 out of 5 average rating, 234 reviews

Monteriggioni Castello, holiday house in Tuscany

SusanRating, 5 stars1 week ago
If you get a chance to stay here, do it! Matteo is a superb host who demonstrates knowledge and caring. He goes the extra mile without being asked and it really helped us when our car rental fell through. The cottage is very well stocked with anything you might need. It is especially nice to stay on site in the Monteriggioni Castle because after the day tripping tourists leave, the castle is mellow and beautiful. Because we have been away from home a long time, we needed to do laundry. The washing machine is in a small shed next to the cottage and a drying rack was provided. We tried two of the restaurants within the castle and felt both had excellent food and the service was attentive and friendly. The best thing I can say about this booking is that we would love to stay there again if our travels bring us back to Toscana.
Guest favorite
Cottage in San Casciano In Val di Pesa
4.82 out of 5 average rating, 157 reviews

Chianti Independent barn

AriannaRating, 5 stars6 months ago
Beautiful little cottage! My young daughters (5 & 2) loved being around Daniella’s dog and the beautiful surroundings of olive trees and being able to disconnect with electronics. We even got to see how olives were harvested early in the morning. We were even given a bottle of wine to enjoy during our stay. Daniella was very helpful! And out of all the Airbnbs I’ve stayed in, the beds were very comfortable!! It is very secluded and the road is very curvy so if you get car sick, take your motion sickness meds. Other than that, I would stay here again! My 5 year old loved our stay here and didn’t want to leave. Thank you Daniella!
Superhost
A well-lit living area features a round wooden dining table surrounded by classic chairs. Soft curtains frame the window, and a door opens to a small balcony. A television stands on a wooden stand, while a decorative lamp and a vase of dried flowers add to the ambiance.
Cottage in Montespertoli
4.77 out of 5 average rating, 243 reviews

Barn in Chianti

AntonioRating, 5 stars5 months ago
Beyond all expectations, the view from the windows over the Chianti vineyards is priceless, comfortable and clean apartment, the photos do not do justice, Paola is really kind and responsive. We will definitely be back, highly recommended
Guest favorite
A cozy bedroom features a large bed framed by elegant wrought-iron headboards. Textured stone walls complement the cream-colored backdrop. A small table displays travel brochures and decorative elements, providing a homely touch.
Cottage in Pari
4.95 out of 5 average rating, 152 reviews

La Casa del Frantoiano - Pari -

MauraRating, 5 stars2 months ago
Beautiful location! Wonderful stay.

Private cottage rentals

Superhost
An outdoor scene depicts a sunlit area featuring mature olive trees and a green grassy landscape. A stone path leads into the view, which includes a distant panorama of a valley and nearby town against a partially cloudy sky.
Cottage in Sinalunga
4.86 out of 5 average rating, 78 reviews

Rustic retreat in the Tuscan hills

ErikaRating, 5 stars1 month ago
Beautiful accommodation, well maintained and very clean. The only flaw was the very small hair dryer and there was no paper towels in the kitchen. Everything else is well-stocked and very quiet.
Superhost
A rustic stone building is framed by lush greenery and seasonal flowers. Outdoor seating is arranged on a grassy area, including a table and chairs. A swimming pool partially visible in the background invites relaxation. The sky is clear, suggesting a bright day.
Cottage in Fabro
4.88 out of 5 average rating, 83 reviews

dependance mandriola

AndreaRating, 5 stars8 months ago
The annex is very nice and welcoming, with an "old" style but with modern amenities, thoughtful, beautiful and functional decor. We had a very good time and felt welcomed by the owners, who, living a few meters away, invited us to not hesitate to bother them in case of anything. The location is excellent, with 360-degree views of the surrounding hills, just a few minutes from the highway toll booth, although it is impossible to say from the house. Obviously the outdoor jacuzzi, great for evening relaxation after shooting all day. We enjoyed having the visit while we were on the porch of the various 4-legged friends who were very cuddly! If it happens, I'll be back!
Guest favorite
Cottage in San Martino in Grania
5 out of 5 average rating, 41 reviews

Crete Senesi - Asciano Cavoni Hut

ChristophRating, 5 stars7 months ago
perfect place in Tuscany we stayed 7 days and it was perfect to explore Tuscany and to relax at the pool side. The house is very charming in Tuscany style Laura even left us coffee water and Prosecco. One if the best stays during our Italy trip
Top guest favorite
A large swimming pool is surrounded by a well-maintained stone patio and lush greenery, including olive trees. Sun loungers are positioned nearby, inviting relaxation. The clear water reflects the bright sky, creating a tranquil atmosphere perfect for unwinding amidst nature.
Cottage in Pergine Valdarno
4.77 out of 5 average rating, 57 reviews

Holiday Casa Vacanze Tuscan countryside with swimming 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 favorite
A serene outdoor area features a rectangular pool surrounded by a grassy lawn. Sun loungers are positioned along the poolside. An umbrella provides shade near the pool, with rolling hills and lush greenery visible in the background under a clear blue sky.
Cottage in Pratovecchio
4.79 out of 5 average rating, 39 reviews

HOUSE IN TUSCANY, WITH POOL

JagodaRating, 5 stars7 months ago
The place is wonderful ! The cottage had everything you need, a great space in front of the cottage - a private grill, a table with chairs, sun loungers, an umbrella and a grill. The nearest store is about 10 minutes by car, there are several great restaurants in pratovecchio and Stia. The pool area is great- the pool is clean, the sun loungers are comfortable, and the view is AMAZING. Definitely recommend for shorter and longer stays !
Guest favorite
An infinity pool reflects the clear blue sky, creating a seamless view with the surrounding Tuscan hills. Tall cypress trees frame the space, alongside lush greenery that adds to the serene atmosphere.
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.
Superhost
A shared swimming pool is surrounded by lush greenery and olive trees, offering a serene space for relaxation. Sun loungers and shaded areas are present, providing comfortable options for enjoying the outdoors. The scenic views of the valley enhance the tranquil environment.
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 favorite
A covered veranda provides shaded seating with a table and chairs, overlooking expansive green hills dotted with trees and shrubs. A soft breeze can be imagined flowing through the open space, enhancing the serene countryside atmosphere.
Cottage in Osteria delle Noci
5 out of 5 average rating, 87 reviews

Your Tuscan oak tree house, enchanting Val d'Orcia

MikeRating, 5 stars3 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.

Destinations to explore

  1. Airbnb
  2. Italy
  3. Tuscany
  4. Province of Siena
  5. Montepulciano
  6. Cottage rentals