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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 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, 70 reviews

Romantic House in Tuscany with jacuzzi

JosephRating, 5 stars1 week 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 favorite
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 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 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
4.96 out of 5 average rating, 89 reviews

EcoLodge – modern design in quiet panoramic location

TatianaRating, 5 stars1 month ago
This place is truly a 10/10. I’ve stayed at dozens of BNBs over this year and I have to say that this is one of my absolute favorites. Every detail, from the decor to the cleanliness to the nature to the spaciousness, is phenomenal. I cannot recommend this place highly enough! One thing to keep in mind is that it’s nestled quite far into the mountains so whenever we went on day trips like to Pienza or Pitigliano, it was always around an hour drive or more.
Guest favorite
A shaded pergola adorned with grapevines provides a relaxing spot for outdoor dining. A colorful table features a floral design, surrounded by wrought iron chairs. A private jacuzzi sits nearby, with lush greenery and rolling hills visible in the background.
Cottage in Castelmuzio
5 out of 5 average rating, 59 reviews

Panoramic view & outdoor jacuzzi - Pienza

JamesRating, 5 stars2 weeks ago
If you want to experience the Tuscany of your dreams, then this is the place to stay! The pictures are accurate but do not do justice to the beauty you will experience. Birds chirping and bees buzzing around the fragrant jasmine and roses bring peace and calm as you gaze out over the olive grove to the surrounding hillsides with views of Pienza, other towns and a retired monastery. Frank and Phil are incredibly gracious hosts and will not steer you wrong with recommendations, including wonderful restaurants, beautiful churches and abbeys, and wineries. The garden cottage is quite private and you will have no intrusions. Sitting on the patio with a glass of wine, some local cheese, and a good book was our favorite escape.
Guest favorite
An aerial view of the cottage reveals a spacious patio featuring a hot tub and seating area. Surrounding greenery and olive trees provide a natural backdrop, while a gravel driveway leads to the entrance of the home. The rustic roof complements the charming landscape.
Cottage in Campiglia D'orcia
4.94 out of 5 average rating, 32 reviews

Val D’Orcia Eco Cottage - Exclusive Retreat

ErwinRating, 5 stars1 month ago
What a fantastic cottage overlooking the valley (UNESCO heritage). Super quiet area, within walking distance of a nice village with various possibilities. We had a great time here and would book it again in a heartbeat!!
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 stars7 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
4.62 out of 5 average rating, 13 reviews

Tuscany Villa Girasole

DavidRating, 5 stars6 days 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.

Pet-friendly cottage rentals

Guest favorite
A charming stone house is viewed from a grassy area, framed by olive trees. Two yellow chairs sit invitingly on the lawn, while a small table is arranged on the terrace. The sky displays a mix of blue and wispy white clouds.
Cottage in Pievescola
4.93 out of 5 average rating, 91 reviews

Antico Borgo Ripostena – 1 Casa Bertilla

TroelsRating, 5 stars2 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 favorite
A bright interior is featured, with soft pink walls and two large arched windows offering expansive views of the hills. A potted plant adds a touch of greenery beside two white armchairs. A low wooden table displays decorative items, completing the inviting atmosphere.
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 favorite
A spacious outdoor area features a rustic brick patio with comfortable seating facing a breathtaking sunrise over rolling hills. Lush greenery and mature trees frame the scene, while soft morning mist envelops the valley below, creating a serene atmosphere for relaxation.
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
A rustic two-story building constructed from warm brick is surrounded by lush greenery. Large windows invite natural light, while wooden shutters add charm. The exterior features a gravel path leading to lounge chairs, creating a serene outdoor space for relaxation.
Cottage in Buonconvento
4.83 out of 5 average rating, 60 reviews

QuarterApartment for 6P Agriturismo Quarantallina

LisaRating, 5 stars1 week 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 favorite
A charming stone cottage is set within lush greenery, featuring a covered porch with outdoor seating. Olive trees surround the area, enhancing the natural beauty. A bicycle leans against the wall, inviting exploration of the peaceful countryside.
Cottage in Osteria delle Noci
5 out of 5 average rating, 94 reviews

Your Tuscan oak tree house, enchanting Val d'Orcia

LuziaRating, 5 stars1 week ago
This house with the surrounding garden, nestled in a dreamlike landscape, is an absolute paradise. The garden is huge, beautifully landscaped and very well maintained. The views are stunning and we have daily hiking trips and bike tours directly from the house. The tranquility is unbelievable, you can usually only hear birds and when it gets dark the nightingale. The house itself leaves nothing to be desired. Extremely clean, including in the cabinets and drawers. Everything you need is there, but (despite very tasteful decoration) not overcrowded. Just right and everything very high quality. Super comfortable bed & sofa and beautiful bathroom. Veronica is an outstanding host and her mother (who welcomed us) is very sympathetic. We received gifts directly from the garden and Veronica is responsive and extremely courteous in communication. You can tell from the beginning to the end how much love is in this house.
Guest favorite
A bright living area features large glass doors, inviting natural light and showcasing views of the garden. Wooden furniture, including a dining table with chairs and a cozy sofa, is accentuated by soft, light-colored curtains that gently frame the windows.
Cottage in Pienza
4.95 out of 5 average rating, 37 reviews

Cottage San Lorenzo

Brandon and TiffanyRating, 5 stars2 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
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 stars3 months ago
Beautiful location! Wonderful stay.
Superhost
A cozy outdoor patio area is featured, showcasing comfortable wicker chairs and a small table. Potted plants add greenery, while a scenic view of rolling hills and lush landscapes creates a serene backdrop.
Cottage in Casole D'Elsa -Siena
4.79 out of 5 average rating, 66 reviews

Villetta with private patio and shared pool

MarkRating, 5 stars2 weeks ago
Amazing place to relax and enjoy life. Large pool with lounge chairs, perfect outdoor seating at the each unit and a large common covered area too, Shoot a few hoops or play ping pong. Nice laundry machine with soap to reduce your suitcase size. Oh, I couldn’t believe how nice all the landscaping was perfectly manicured. Very well kept place with so much character.

Private cottage rentals

A stone entrance is framed by a wooden roof, showcasing a wooden door that opens into the home. A potted plant is positioned beside the door, and a welcome mat is laid at the threshold. The surrounding area features a grassy landscape.
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
A stone path winds through lush greenery, flanked by vibrant flowers and tall cypress trees. The landscape in the background showcases rolling hills, providing a serene atmosphere. Soft natural light filters through the trees, creating a calm and inviting scene.
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
A peaceful garden area is surrounded by lush greenery and offers a natural setting for relaxation. Several trees provide shade, while a small table and seating can be seen in the background. The ground is covered with soft earth and scattered foliage.
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
A clear blue swimming pool is surrounded by stone paving, with sun loungers arranged on one side. A wooden pergola provides shaded seating nearby. Lush greenery and rolling hills can be seen in the background, enhancing the serene outdoor environment.
Cottage in Villa Parigini
4.75 out of 5 average rating, 4 reviews

Restored Barn in Chianti property, pool, terrace

VeronicaRating, 5 stars34 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.
A medieval village is visible atop a hill, framed by blooming white flowers. The scene includes stone buildings with terracotta roofs, tall cypress trees, and a distinctive bell tower. A clear blue sky provides an unobtrusive backdrop, emphasizing the village's historical charm.
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 stars10 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....
The image captures a serene view of rolling hills, shrouded in a gentle morning mist. The landscape is dotted with vineyards and trees, stretching towards distant mountains, creating a tranquil atmosphere. The scene is framed by the edge of a stone building and lush greenery.
Cottage in San Gimignano
4.84 out of 5 average rating, 207 reviews

Countryside Cottage With View - Le Rondini apt

PeterRating, 5 stars2 weeks ago
A fabulous place in an amazing location. We sat in the garden everyday for breakfast looking at the beautiful views of Tuscany and San Gimignano. Marco was very helpful when we needed to contact him. The kitchen has all you need for 2 people if you want cook, but doesn’t have an oven just a combi microwave. Fridge Freezer was great for wine beer ice etc with plenty of space. Bathroom and shower also very good!
Superhost
An aerial view showcases the traditional Tuscan farmhouse surrounded by lush greenery. A pool is centrally located, complemented by lounge chairs. Nearby, rows of vineyards and tall cypress trees add to the serene landscape. The expansive grounds create a tranquil ambiance in the countryside.
Cottage in San Gimignano
4.78 out of 5 average rating, 32 reviews

Glicine romantic cottage in country

BartRating, 5 stars21 months ago
Concetta is the most lovely host! And the house provided everything we needed. Beautiful, remote area! Would gladly return.

Destinations to explore

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