
Holiday Homes in Province of Siena
Find and book unique holiday homes on Airbnb
Top-rated Holiday Homes in Province of Siena
Guests agree: These holiday homes are highly rated for location, cleanliness and more.
Holiday rentals for every style
Get the amount of space that is right for you
Popular amenities for Province of Siena holiday homes
Family-Friendly holiday homes

Poggiarello - Royal Mail
We spent 5 days at this charming Airbnb property in October. The breathtaking landscape and panoramic views added an extra layer of beauty to our stay. The outdoor facilities, including a swimming pool, sauna, jacuzzi, grill, and a spacious table, were top-notch, enhancing our overall experience. The location was ideal, providing easy access to San Gimignano, Siena, and some wonderful wineries. t's worth noting that there is a 2km dirt road leading to the property. Our family thoroughly enjoyed our time here, making it an enjoyable getaway.

Ancient Barn in Chianti with Pool
Stefania was extremely friendly and helpful. The apple cake on arrival was delicious and a welcome touch. The gardens and pool were exceptionally well tended and the views were stunning. Stefania gave us a number of wonderful recommendations of restaurants and towns to visit. We had a wonderful, relaxing holiday.

Antico Chianti Residence
Lucia was so kind and helpful getting us checked in. Her insights of local history and the beautiful spaces inside the location was very helpful. An excellent experience and an enjoyable Airbnb.

Near Siena (6 km), swimming pool and terrace
Beautiful apartment over 3 floors with a lovely patio, spacious common spaces and a beautiful shared pool, conveniently located just a few minutes from Siena. Great base for exploring Tuscany!

Borgo Rapale – Jacopo
Nice relaxing place off the beaten path, beautiful views. Well cared for. You can walk around their vineyards and Olive Grove, and even buy local wine from the host.

17th century farmhouse Val d'Orcia private pool
Agostina was right away, and I mean January when we booked, available and kind to any of our questions and requests. the farmhouse was super clean, bathrooms, kitchens, rooms, sheets, towels and dishes. Everything was in great condition. Agostina responded and welcomed us on the phone and her door even late in the evening. Check-in and check-out instructions are always very clear from the beginning. The house is complete with everything, for example, there was salt, sugar, oil, vinegar to buffer the arrival, in the pantry there was even a mini primer, a blender, a spinner and plates, glasses, pots and saladers at will. Until now I never saw such a thing. 100% recommended. There were 11 of us and we occupied the entire farmhouse with the possibility of another 3 places. Truly satisfied. Kindness, reliability and expertise, three rare qualities to find all together. Thank you Agostina

farm in the countryside for groups
We had a great time in Tuscany. The house is in the countryside, quiet and peaceful. We just regretted that there is not a basic kit (salt, pepper, oil, sugar and laundry detergent ) for the first day because we hadn't thought of everything and the shops are not all ready. Other than that, everything was good.

Relax near the Tuscan Spa Petriolo Siena
We loved it! It’s quiet and calm! Was an amazing experience! The hosts were AMAZING! The grounds were amazing and walkable and foliage was a dream! The home was quite comfortable and has everything you need for short or long term stays! If you rent a car there is private parking. You can reach the property without a car via bus or taxi … the last bus leaves at 230 at the Autostazione in Siena, bus 116 monticiano and review the driving directions to see where to get off, but it is the last stop before Tocchi, let the bus driver know and they can help you! It is a half mile walk from the bus stop to the house, so be prepared for a little walk. (We enjoyed the walk and adventure each time we went intosiena whichwas usuallytwice a week. A taxi will run you about 90euros from the train/bus station. The bus runs daily from the airbnb at 630am sharp(bus 116 at the end of the road) and can take you to Siena for amazing sightseeing, shopping and food! Enjoy and love the nature there!
Holiday home rentals with a patio

Pian'D'olmo, an ancient farmhouse in the heart of Tuscany
We had a great stay and Frederic was always reachable. The house and garden are beautiful and it’s perfect for 4 people.

Orchid apartment with terrace
good stay for 1 night. Amazing balcony

Casa Dani with private pool
We had a wonderful stay at Daniela's place The apartment is extremely well maintained, well located for visiting the surroundings of Tuscany and Umbria. The magnificent swimming pool is a real plus when you come back from a walk and want to cool off. The small downside, the house is not well soundproofed, the slamming of the front door because of the comings and goings of the residents is the only inconvenience of this pleasant Airbnb. Great place to share with friends!

Fontarcella, H&R- mediterranean home with jacuzzi
The place was a 10/10! We felt incredibly comfortable, the communication was great and very friendly. We would 100% recommend it. We were able to relax a lot, it was very clean and the kitchen was perfectly equipped. Thank you for everything!

Elegant farmhouse overlooking Pienza
Apart from the stunning location and beautiful well equipped house, Laura was a delight to deal with. She was responsive and informative. Our guests loved it as much as we did. Thank you Laura.

Tuscany Country House, Central Chianti, Pano Views
We found Peggy’s place to be the perfect spot for exploring Tuscany. The instructions made it for easy to find & only a few short minutes drive from Panzano where we had lunch at Dario’s (a must in our opinion). Also highly recommend Montese Cooking Experience in San Gimignano.

Pienzalettings
Lovely suave in the historic section.

Apartment in a wine estate in Tuscany
Our apartment was rustic and cosily furnished. The entire building was also very beautiful, the large garden well maintained. There is a pool area with loungers and also shaded areas, which was also very well maintained. There are several seating options outside, so you can enjoy your food or a glass of wine in the evening outside. The location is in the middle of the vineyards, very quiet and idyllic. During our stay, we had the opportunity to enjoy a 4-course meal one evening. The food was extraordinarily delicious! Chiara and her team were always available and very friendly. We felt very comfortable and enjoyed the time very much.
Holiday home rentals with a washing machine and dryer

Elegant farmhouse surrounded by nature, Terra
We stayed ar Romina's and Riccardo with a couple of friends. We enjoyed our lovely apartment and beautiful peaceful property surrounded by olive trees and herbs. Our hosts were super friendly and helpful, especially since airline lost one of our friends' luggage. Romina helped us communicate with DHL and went above and beyond to make sure it was delivered. Riccardo gladly explained the kind of plants they were growing and harvesting for essential oils. We enjoyed the company of Luna the cat who came visit but was politely staying outside. Wildlife is abundant and nature unspoiled - truly a magical place! The area is quite remote so it may not be convenient to everyone. The closest little town is Casole d'Elsa where you can find 2-3 restaurants and a pharmacy, larger supermarkets are within 20min drive. It's a great starting point to visit Siena, San Gimignano, Volterra. The apartment is well equipped with small stove, dishwasher, fridge and microwave. Highly recommend!

The Eagle and the Olive Tree
We had the absolute pleasure of spending three unforgettable days at Paolo and Monica’s 800-year-old farmhouse — and it was hands down the best Airbnb experience we’ve ever had. The home itself is stunning: full of history, character, and comfort, with every amenity thoughtfully provided. Each morning, Paolo and Monica prepared a beautiful, fresh breakfast spread complete with homemade cakes and warm, delicious options that started our days off with so much care and joy. The hospitality was truly beyond compare — Paolo and Monica are salt-of-the-earth people with hearts of gold. One of the highlights of our stay was visiting with the many animals they lovingly care for. From eagles and owls to donkeys, horses, peacocks, ducks, and sheep — it felt like something out of a storybook. Monica’s passion for rescuing and training animals is inspiring, and added such a special, personal touch to the experience. Thier home is filled with beauty, warmth, and heart. Coming back soon! ❤️❤️❤️

Apartment with pool and restaurant
the stay was perfect. The attention to detail distinguishes it. The possibility of bringing the puppy was super appreciated. The restaurant deserves a great applause. I highly recommend it.

White lily with a view of Siena
It’s a nice quiet rural place up in a hill. The bedrooms upstairs are more updated, comfortable and the kitchen downstairs is more outdated. Laundry machine and dishwasher are older, same as stove took some time to fully boil eggs like 25-30 minutes. But the location is great if you have a car to go around the places and a nice experience to stay in the area. There are no walkable groceries or restaurants so you need to plan ahead. The host communicates well and responds quickly, also flexible which is great for a more relaxing environment. Would definitely recommend if you would like to stay around Siena area.

★ Romantic apartment & stunning view of Tuscany ★
A great peaceful location with excellent pool area and gardens, but also well placed to visit Florence, Siena and San Gimignano. A car is necessary and it is easy to get around the Tuscan hills from here. Giorgia greeted us on arrival and responded very quickly to our questions during the week. Bug spray is essential. All in all we had a wonderful holiday.

Cosy house with private pool
Very nice house. Very nice welcome from our host's in-laws. They were always available and thoughtful although they only speak Italian. The location of the accommodation is ideal between Siena and Florence. Lots of pretty villages nearby.

Tower House of the 1000
Beautiful apartment located in the middle of a historic village. We were a group of 5 people and we used all the services indicated (kitchen, bathrooms, spaces,...) without any problems. The location of the village is very strategic for visiting the surrounding cities and winery areas. Thanks Marta, see you soon.

The Piccola Villa of Borgo Argenina
This was our favorite place we stayed in Italy and we went to three other locations. The view is unbeatable and so much to do nearby. We went to a few wineries and ate at Malborghetto (Highly recommend for an authentic experience and small town feel!). We hope to come back! Communication with hosts was great. amenities such as the pool, breakfast, the kitchen, were awesome. Thanks so much for a wonderful stay!
Destinations to explore
- Kid-friendly rentals Province of Siena
- Rentals with a fireplace Province of Siena
- Rentals with a hot tub Province of Siena
- Apartment rentals Province of Siena
- Luxury rentals Province of Siena
- Rentals with a fire pit Province of Siena
- Tiny house rentals Province of Siena
- Rentals with a kayak Province of Siena
- Nature eco lodge rentals Province of Siena
- Serviced apartment rentals Province of Siena
- Rentals with breakfast Province of Siena
- Rentals with a balcony Province of Siena
- Guesthouse rentals Province of Siena
- Barn rentals Province of Siena
- Boutique hotel rentals Province of Siena
- Private suite rentals Province of Siena
- Hotel rentals Province of Siena
- Family-friendly rentals Province of Siena
- Rentals with pools Province of Siena
- Castle rentals Province of Siena
- Condo rentals Province of Siena
- Rentals with a sauna Province of Siena
- Smoking-friendly rentals Province of Siena
- House rentals Province of Siena
- Townhouse rentals Province of Siena
- Farmstay rentals Province of Siena
- Rentals with an EV charger Province of Siena
- Loft rentals Province of Siena
- Rentals with an accessible height bed Province of Siena
- Rentals with a patio Province of Siena
- Villa rentals Province of Siena
- Cottage rentals Province of Siena
- Rentals with a home theatre Province of Siena
- Pet-friendly rentals Province of Siena
- Waterfront rentals Province of Siena
- Rentals with outdoor seating Province of Siena
- Fitness-friendly rentals Province of Siena
- Rentals with a washing machine and dryer Province of Siena
- Rentals with lake access Province of Siena
- Bed and breakfasts Province of Siena
- Holiday home rentals Tuscany
- Holiday home 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
- Food and drink Province of Siena
- Tours Province of Siena
- Art and culture Province of Siena
- Nature and outdoors Province of Siena
- Things to do Tuscany
- Nature and outdoors Tuscany
- Entertainment Tuscany
- Wellness Tuscany
- Sports activities Tuscany
- Sightseeing Tuscany
- Art and culture Tuscany
- Tours Tuscany
- Food and drink Tuscany
- Things to do Italy
- Wellness Italy
- Sports activities Italy
- Food and drink Italy
- Tours Italy
- Entertainment Italy
- Nature and outdoors Italy
- Art and culture Italy
- Sightseeing Italy