
Cottage vacation rentals in Province of Siena
Find and book unique cottages on Airbnb
Top-rated cottage rentals in Province of Siena
Guests agree: these cottages are highly rated for location, cleanliness, and more.
Vacation rentals for every style
Get the amount of space that is right for you
Popular amenities for Province of Siena cottage rentals
Cottage rentals with a hot tub

Romantic House in Tuscany with jacuzzi
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.

From Simone, podere santi Lucia and Pietro
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.

EcoLodge – modern design in quiet panoramic location
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.

Panoramic view & outdoor jacuzzi - Pienza
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.

Val D’Orcia Eco Cottage - Exclusive Retreat
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!!

"Rosso Poggiolo" farmhouse with swimming pool.
Very good, it was perfect The host were so friendly Thank you very much

Tuscany Villa Girasole
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

Antico Borgo Ripostena – 1 Casa Bertilla
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!

ELENA COTTAGE
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!

Rustic Tuscan with swimming pool
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 :)

QuarterApartment for 6P Agriturismo Quarantallina
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.

Your Tuscan oak tree house, enchanting Val d'Orcia
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.

Cottage San Lorenzo
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!

La Casa del Frantoiano - Pari -
Beautiful location! Wonderful stay.

Villetta with private patio and shared pool
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

Cottage in the Tuscan countryside
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.

Cottages in Tuscan Country (Spazzacamino)
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”.

The Cottage
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.

Restored Barn in Chianti property, pool, terrace
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.

The Five Oaks Cottage
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.

apartment surrounded by greenery
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....

Countryside Cottage With View - Le Rondini apt
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!

Glicine romantic cottage in country
Concetta is the most lovely host! And the house provided everything we needed. Beautiful, remote area! Would gladly return.
Destinations to explore
- Tiny house rentals Province of Siena
- Boutique hotel rentals Province of Siena
- Rentals with a fire pit Province of Siena
- Rentals with pools Province of Siena
- Townhouse rentals Province of Siena
- Luxury rentals Province of Siena
- Kid-friendly rentals Province of Siena
- Nature eco lodge rentals Province of Siena
- Family-friendly rentals Province of Siena
- House rentals Province of Siena
- Rentals with a kayak Province of Siena
- Apartment rentals Province of Siena
- Villa rentals Province of Siena
- Rentals with a fireplace Province of Siena
- Rentals with an EV charger Province of Siena
- Bed and breakfasts Province of Siena
- Pet-friendly rentals Province of Siena
- Waterfront rentals Province of Siena
- Private suite rentals Province of Siena
- Rentals with an accessible height bed Province of Siena
- Loft rentals Province of Siena
- Guesthouse rentals Province of Siena
- Rentals with a washer and dryer Province of Siena
- Rentals with breakfast Province of Siena
- Smoking-friendly rentals Province of Siena
- Rentals with lake access Province of Siena
- Rentals with a sauna Province of Siena
- Fitness-friendly rentals Province of Siena
- Vacation home rentals Province of Siena
- Rentals with a patio Province of Siena
- Barn rentals Province of Siena
- Rentals with a hot tub Province of Siena
- Farmstay rentals Province of Siena
- Rentals with a home theater Province of Siena
- Serviced apartment rentals Province of Siena
- Rentals with a balcony Province of Siena
- Hotel rentals Province of Siena
- Castle rentals Province of Siena
- Condo rentals Province of Siena
- Rentals with outdoor seating Province of Siena
- Cottage rentals Tuscany
- Cottage rentals Italy
- Yurt Rentals United States
- Yurt Rentals United Kingdom
- Castle Rentals United States
- Houseboats United States
- Holiday Caravans United Kingdom
- Private Island Rentals United States
- Farm Houses United States
- Farm Cottages United Kingdom
- Cabin Rentals Australia
- Luxury Cabins United Kingdom
- Luxury Cabins United States
- Holiday Chalets United Kingdom
- Cottage Rentals United States
- Holiday Cottages United Kingdom
- Mansion Rentals United States
- Villa Rentals United Kingdom
- Holiday Bungalows United Kingdom
- Bungalow Rentals United States
- Condo Rentals United States
- Holiday Apartments Australia
- Holiday Houses United States
- Holiday Houses United Kingdom
- Private Holiday Rentals United Kingdom
- Big House Rentals United States
- Big Cottages Australia
- Large Villas United Kingdom
- House Rentals with a Pool United States
- Cabin Rentals with a Pool United States
- Villas with a Pool United Kingdom
- Apartments with a Hot Tub United States
- Holiday Cottages with a Hot Tub United Kingdom
- Beach Cabins United States
- Beach Condos United States
- Beachfront Rentals United States
- Beach Houses United Kingdom
- Beach Villas United Kingdom
- Coastal Cottages United Kingdom
- Pet-Friendly Vacation Rentals United States
- Pet-Friendly Beach Rentals United States
- Pet-Friendly Cabin Rentals United States
- Dog-Friendly Cottages United Kingdom
- Luxury Dog-Friendly Cottages United Kingdom
- Santa Maria Novella
- Duomo di Firenze
- Ponte Vecchio
- Lake Trasimeno
- Parco Nazionale delle Foreste Casentinesi, Monte Falterona e Campigna
- Basilica of Santa Maria Novella
- Mugello Circuit
- Cala Violina
- Fortezza da Basso
- Uffizi Gallery
- Parco delle Cascine
- Piazza della Repubblica
- Piazzale Michelangelo
- Marina di Grosseto beach
- Kite Beach Fiumara
- Mercato Centrale
- Pitti Palace
- Stadio Artemio Franchi
- Giardino Bardini
- Avignonesi Winery Fattoria Le Capezzine
- Medici Chapels
- Cavallino Matto
- Teatro Verdi
- Palazzo Vecchio
- Things to do Province of Siena
- Sightseeing Province of Siena
- Art and culture Province of Siena
- Nature and outdoors Province of Siena
- Food and drink Province of Siena
- Tours Province of Siena
- Things to do Tuscany
- Food and drink Tuscany
- Tours Tuscany
- Sports activities Tuscany
- Art and culture Tuscany
- Entertainment Tuscany
- Sightseeing Tuscany
- Nature and outdoors Tuscany
- Wellness Tuscany
- Things to do Italy
- Sports activities Italy
- Nature and outdoors Italy
- Entertainment Italy
- Sightseeing Italy
- Tours Italy
- Art and culture Italy
- Wellness Italy
- Food and drink Italy
- Family travel hub Tips and inspiration
- Family budget travel Get there for less
- Vacation ideas for any budget Make it special without making it spendy
- Travel Europe on a budget How to take the kids to Europe for less
- Outdoor adventure Explore nature with the family
- Bucket list national parks Must-see parks for family travel
- Kid-friendly state parks Check out these family-friendly hikes