Some info has been automatically translated. Show original language

Cottage vacation rentals in Montepulciano

Find and book unique cottages on Airbnb

0 of 0 items showing
1 of 3 pages

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.
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, 133 reviews

Beautiful renovated barn in Tuscany

EleonoraRating, 5 starstoday
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
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
The two-story villa features a rustic exterior with a tiled roof and brick accents. A private pool is visible in the foreground, surrounded by well-maintained grass. A staircase leads to the upper level, and large windows allow for natural light. Lush greenery frames the property.
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 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.
Guest favorite
A private outdoor jacuzzi is presented in the foreground, with bubbling water inviting relaxation. In the background, a rustic cottage made of stone is framed by flowering plants and a large olive tree, amidst the scenic landscape of Tuscan rolling hills.
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.

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 stars3 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
Superhost
An exterior view of a rustic stone structure is presented, featuring a covered porch with a wooden table and benches. Olive trees surround the area, providing shade. A barbecue station is visible nearby, with a pathway leading through the outdoor space.
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.
Guest favorite
An outdoor area features a tranquil pool surrounded by neatly arranged lounge chairs and umbrellas. Lush greenery and vibrant flower beds enhance the serene atmosphere, while tall cypress trees create a natural boundary. A dining table is set invitingly, offering a perfect spot for outdoor meals.
Cottage in Bagno A Ripoli
5 out of 5 average rating, 29 reviews

Borgo Spedaletto 3 – Dolcevita Holiday

MathewRating, 5 stars1 week ago
Charming little cottage perfect for a small family in the hills near Florence. Had everything we needed. About 25 minutes drive through the country to central Florence so perfect for day trips in. Lovely walks in the olive groves around the cottage.
Top guest favorite
An outdoor terrace features a rustic wooden ceiling supported by brick columns. Comfortable seating is provided by a light-colored couch and benches, alongside a dining table with chairs. The surrounding greenery and pathways lead to additional buildings, creating a serene and inviting space.
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.
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!
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 stars6 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

Private cottage rentals

Superhost
The cozy porch features a wooden table surrounded by comfortable seating, with lush greenery visible beyond. Decorative plants in terracotta pots add a touch of nature, while lanterns provide ambient lighting. The blue wooden beams create a welcoming entrance to the home.
Cottage in Castiglione della Pescaia
4.96 out of 5 average rating, 48 reviews

The Cottage

JuttaRating, 5 stars6 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
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
Guest favorite
The image captures a tranquil pool area surrounded by lush greenery, with vibrant pink flowers framing the view. A shaded lounging area is positioned adjacent to the salt-water pool, inviting relaxation under the sun.
Cottage in Cavriglia
4.92 out of 5 average rating, 38 reviews

La Loggia, cozy stone cottage for 2 with terrace

GüntherRating, 5 stars11 months ago
Vacation and relaxation from the first minute. Beautifully furnished house with two spacious rooms as well as bathroom and kitchenette. Perfect sunny terrace where you can spend your time from morning to evening. Table, chairs, armchairs and loungers are available. Easily accessible about 20 km from the highway. All shopping is 15 km away.
Guest favorite
Cottage in Pievescola
4.93 out of 5 average rating, 88 reviews

Antico Borgo Ripostena – 1 Casa Bertilla

JackRating, 5 stars7 months ago
Fantastic place to stay! A beautiful place nestled away in the countryside. We loved our honeymoon stay, thanks for the wine!
Superhost
A dining table is set outdoors, surrounded by olive trees. Plates and glasses are neatly arranged, along with green and dark bottles of wine. A slender olive tree serves as a centerpiece, blending harmoniously with the serene landscape of the Tuscan countryside.
Cottage in Cortona
4.9 out of 5 average rating, 29 reviews

Casa Gialla, Cortona-sunsets in the olive grove

Hans PeterRating, 5 stars9 months ago
We had a wonderful time. In addition to other reviews let me point this out: good matrasses, working roll-up flyscreens at bedroom windows, Lesley (or Celeste) helped very fast when WiFi was down due to power cut, comfy chairs for garden, cushions for chairs and deck chairs. Apart from that: everybody was nice, everything was as described. We would definitely like to come back.
Superhost
A refreshing swimming pool is framed by a well-maintained lawn, with two stone buildings visible in the background. The adjacent structure displays classic architecture, while the other features inviting windows and a welcoming entrance, surrounded by lush greenery and blooming flowers.
Cottage in Monteriggioni
4.75 out of 5 average rating, 58 reviews

apartment surrounded by greenery

LaurenceRating, 5 stars9 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....
Guest favorite
The exterior features a spacious garden surrounded by greenery, showcasing a variety of plants. A shaded area provides seating with lounge chairs and a large tree offers additional shade. The house structure is visible in the background, with large windows reflecting the landscape.
Cottage in Castelfranco Piandiscò
4.91 out of 5 average rating, 68 reviews

Villetta Belvedere

RicardoRating, 5 stars1 month ago
The place was very nice and well located! The garden with the view of the Tuscan hills is amazing! Simone is very responsive and helpful. The village is peaceful and idyllic with local markets and shops around the corner. The location is perfect to further explore Tuscany. Would definitely recommend Simone’s place!

Destinations to explore

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