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Holiday Homes in Province of Siena

Find and book unique holiday homes on Airbnb

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Popular amenities for Province of Siena holiday homes

Family-Friendly holiday homes

Superhost
Holiday home in Poggibonsi
4.5 out of 5 average rating, 40 reviews

Poggiarello - Royal Mail

MelinaRating, 5 stars20 months ago
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.
Holiday home in Barberino Val d'Elsa
4.87 out of 5 average rating, 102 reviews

Ancient Barn in Chianti with Pool

CatherineRating, 5 stars1 day ago
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.
Guest favourite
Holiday home in Panzano
4.95 out of 5 average rating, 56 reviews

Antico Chianti Residence

DaveRating, 5 stars2 weeks ago
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.
Superhost
Holiday home in Villa Parigini
4.89 out of 5 average rating, 9 reviews

Near Siena (6 km), swimming pool and terrace

KennethRating, 5 stars1 week ago
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!
Superhost
Holiday home in Rapale
5 out of 5 average rating, 8 reviews

Borgo Rapale – Jacopo

LaurenRating, 5 stars13 months ago
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.
Superhost
Holiday home in Radicofani
4.8 out of 5 average rating, 50 reviews

17th century farmhouse Val d'Orcia private pool

ZairaRating, 5 stars1 month ago
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
Guest favourite
Holiday home in Buonconvento
4.91 out of 5 average rating, 55 reviews

farm in the countryside for groups

FrançoiseRating, 5 stars1 month ago
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.
Top Guest favourite
Holiday home in Monticiano
5 out of 5 average rating, 27 reviews

Relax near the Tuscan Spa Petriolo Siena

CindyRating, 5 stars6 days ago
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

Superhost
Holiday home in Torrita di Siena
4.83 out of 5 average rating, 18 reviews

Pian'D'olmo, an ancient farmhouse in the heart of Tuscany

LauraRating, 5 stars1 week ago
We had a great stay and Frederic was always reachable. The house and garden are beautiful and it’s perfect for 4 people.
Guest favourite
Holiday home in Torrenieri
5 out of 5 average rating, 5 reviews

Orchid apartment with terrace

ErikRating, 5 stars3 weeks ago
good stay for 1 night. Amazing balcony
Top Guest favourite
Holiday home in Monticiano
5 out of 5 average rating, 40 reviews

Casa Dani with private pool

PhilippeRating, 5 stars1 week ago
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!
Top Guest favourite
Holiday home in Petrignano del Lago
4.98 out of 5 average rating, 81 reviews

Fontarcella, H&R- mediterranean home with jacuzzi

MelissaRating, 5 stars3 days ago
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!
Top Guest favourite
Holiday home in Monticchiello
5 out of 5 average rating, 20 reviews

Elegant farmhouse overlooking Pienza

CherylRating, 5 stars5 days ago
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.
Superhost
Holiday home in Radda in Chianti
5 out of 5 average rating, 31 reviews

Tuscany Country House, Central Chianti, Pano Views

KyleRating, 5 stars1 month ago
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.
Top Guest favourite
Holiday home in Pienza
4.95 out of 5 average rating, 79 reviews

Pienzalettings

EllenRating, 5 stars5 days ago
Lovely suave in the historic section.
Guest favourite
Holiday home in Roccastrada
5 out of 5 average rating, 18 reviews

Apartment in a wine estate in Tuscany

JulianeRating, 5 stars3 weeks ago
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

Guest favourite
Holiday home in Casole d'Elsa - Siena
4.97 out of 5 average rating, 30 reviews

Elegant farmhouse surrounded by nature, Terra

EdytaRating, 5 stars1 month ago
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!
Top Guest favourite
Holiday home in Chianciano Terme
5 out of 5 average rating, 95 reviews

The Eagle and the Olive Tree

PatrickRating, 5 stars2 weeks ago
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! ❤️❤️❤️
Superhost
Holiday home in Laterina
4.73 out of 5 average rating, 11 reviews

Apartment with pool and restaurant

StefaniaRating, 5 stars1 month ago
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.
Guest favourite
Holiday home in Monteroni d'Arbia
4.91 out of 5 average rating, 74 reviews

White lily with a view of Siena

ShufanRating, 5 starstoday
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.
Superhost
Holiday home in Ulignano
4.73 out of 5 average rating, 11 reviews

★ Romantic apartment & stunning view of Tuscany ★

AndrewRating, 5 stars12 months ago
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.
Superhost
Holiday home in Lilliano
4.83 out of 5 average rating, 6 reviews

Cosy house with private pool

LucasRating, 5 stars10 months ago
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.
Superhost
Holiday home in Colle di Val d'Elsa
4.76 out of 5 average rating, 37 reviews

Tower House of the 1000

GaspareRating, 5 stars2 weeks ago
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.
Guest favourite
Holiday home in Gaiole in Chianti
4.96 out of 5 average rating, 28 reviews

The Piccola Villa of Borgo Argenina

MeghanRating, 5 stars4 weeks ago
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