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Vacation home rentals in Province of Siena

Find and book unique vacation home rentals on Airbnb

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Popular amenities for Province of Siena vacation home rentals

Family-friendly vacation home rentals

Superhost
An outdoor pool area is illuminated at dusk, surrounded by lounge chairs and umbrellas. A two-story building with multiple windows is visible in the background. Guests are seen conversing near the water, with a dog nearby, amidst the serene landscape.
Vacation 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.
Guest favorite
A hallway is presented, featuring a decorative mirror above a small wooden table adorned with a vase of red flowers. A chandelier hangs from the ceiling, casting light over the space, while a set of stairs leads towards a softly lit room in the background.
Vacation home in Panzano
4.95 out of 5 average rating, 56 reviews

Antico Chianti Residence

DaveRating, 5 stars3 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
A serene pool area is highlighted, featuring a large swimming pool surrounded by spacious stone flooring. Comfortable lounge chairs, some with light-striped patterns, are placed under shaded umbrellas. Lush greenery and tall cypress trees provide a natural backdrop, enhancing the peaceful environment.
Vacation 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
A large swimming pool is surrounded by a sun terrace featuring lounge chairs. A rustic stone building is visible in the background, complemented by a shaded seating area made of wood. Lush greenery adds to the serene outdoor space.
Vacation 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
Superhost
A stone statue is positioned near a private pool, surrounded by greenery and flowering plants. The pool reflects the blue sky, while tall trees frame the view of the lush landscape beyond. The scene offers a serene atmosphere in a secluded outdoor space.
Vacation home in Arezzo
4.73 out of 5 average rating, 55 reviews

Ancient stone farmhouse with park and pool

SimonRating, 5 stars3 weeks ago
We had a fantastic stay at this beautiful villa in Tuscany. From the moment we arrived, the owner, Stella, made us feel so welcome – she was incredibly friendly and helpful throughout our stay. The villa itself was lovely, and the highlight for us (especially the children!) was the pool. It was perfectly maintained and cleaned daily, which made it a joy to use every day. The pool area could also be shut off when not used to keep the children safe. Stella also gave us some great local restaurant recommendations, all of which served amazing food at very reasonable prices – a real bonus! We did manage to walk out to a few restaurants. Overall, we had a wonderful experience and would absolutely recommend this villa to anyone looking for a relaxing and authentic stay in Tuscany. We would definitely love to return. Thanks for all your help Stella. 👍
Guest favorite
A rustic farmhouse is depicted, featuring a warm color palette and exposed brick walls. Archways lead to a welcoming entrance, adorned with potted plants. A gravel pathway runs alongside, bordered by natural greenery, enhancing the serene countryside setting.
Vacation 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 wasn't a basic kit (salt, pepper, oil, sugar and something to make laundry) for the first day because we hadn't thought of everything and the shops aren't all ready. Other than that, everything was good.
Guest favorite
A dining area features a wooden table set with two plates, cups, and a small vase holding a single flower. A doorway leads to a spacious living area, while the kitchen includes essential appliances, blending functionality with a warm atmosphere created by wooden beams above.
Vacation home in Arezzo
5 out of 5 average rating, 12 reviews

Mivà di Più vacation homes (Rosy 1st floor)

NicoleRating, 5 stars2 months ago
This place was a gem! I’ve traveled a lot throughout Italy, and this place exceeded the usual standards. It was hotel- clean with easy to use heat and air. The bathroom is renovated and all the original charm is intact throughout the unit. The space actually feels larger than it looks in the photos, and the view from the Juliet window looks right out onto the piazza. The restaurant downstairs is delicious and convenient with plenty of cafes right around the corner. The host is very responsive and helpful. Would definitely recommend and stay again.
Top guest favorite
A rustic wooden dining table is set in a grassy area under a tree, surrounded by nature. Plates and glasses are arranged, accompanied by bottles of wine and a vase with flowers. Benches and chairs provide a comfortably inviting space for outdoor meals.
Vacation home in Monticiano
5 out of 5 average rating, 27 reviews

Relax near the Tuscan Spa Petriolo Siena

CindyRating, 5 stars1 week 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!

Vacation home rentals with a patio

Superhost
A spacious living area is highlighted by elegant brick arches and soft seating arrangements. A wooden dining table is set for a meal, complemented by stylish tableware. Natural light streams through large windows, illuminating the warm tones of the furnishings.
Vacation 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.
Superhost
A refreshing pool is set against a backdrop of rolling hills, surrounded by olive trees. Two cocktails are placed on a wooden deck, complemented by a light-colored towel nearby. The sky is clear, allowing for uninterrupted views of the serene landscape.
Vacation home in Rigomagno Scalo
5 out of 5 average rating, 5 reviews

Happy Tuscany

StefanoRating, 5 stars4 days ago
We arrived in Rigomagno Scalo by chance, traveling by motorcycle halfway between Genoa and L'Aquila and we were pleasantly impressed by the location. A Ranch immersed in olive trees and oaks with all the comforts you want, from the swimming pool with the sunbathing patio to the whirlpool. A barbecue area is also available. The house upstairs was all at our disposal and the furnishings were just refurbished with great care. Three bathrooms available (impeccable) and of course air conditioning. The two tables in the hall and the kitchen counter are of great value, suitable for hosting over 20 people for any conventions, built by Alessandro with sections of tree trunks and finished with wisdom. A heartfelt thank you to Alessandro and his wife for their hospitality! We promise to review it again.
Guest favorite
A modern kitchen area features light grey cabinetry, a turquoise refrigerator, and a small dining table surrounded by four chairs. Natural light enhances the ample space, with a simple floral tablecloth providing a subtle accent.
Vacation home in Torrenieri
5 out of 5 average rating, 5 reviews

Orchid apartment with terrace

ErikRating, 5 stars4 weeks ago
good stay for 1 night. Amazing balcony
Guest favorite
A clear view of a private salt-water pool is presented, bordered by wooden decking. Two lounge chairs are positioned nearby under a large umbrella. Lush greenery surrounds the area, complemented by a stone barbecue and covered dining space in the background.
Vacation 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 beautiful 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. Very good place to share with friends!
Top guest favorite
A spacious bedroom features a king-size bed with an intricately designed headboard. Soft lighting from two bedside lamps creates a warm glow. Natural light enters through a window with sheer curtains, offering a view of the greenery outside. A built-in wardrobe is visible in the corner.
Vacation home in Petrignano del Lago
4.98 out of 5 average rating, 81 reviews

Fontarcella, H&R- mediterranean home with jacuzzi

MelissaRating, 5 stars6 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, it was very clean and the kitchen was perfectly equipped. Thanks for everything!
Top guest favorite
A rustic stone house is set amidst lush greenery, featuring large windows that invite natural light. The structure includes a covered terrace adorned with climbing plants, providing an inviting outdoor space. The surrounding lawn is well-maintained, contributing to a peaceful rural setting.
Vacation home in Monticchiello
5 out of 5 average rating, 20 reviews

Elegant farmhouse overlooking Pienza

CherylRating, 5 stars1 week 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
The historic farmhouse is surrounded by tall, ancient cypress trees and lush greenery. A gravel patio with outdoor seating is visible in the foreground, leading to an inviting garden area. The sky is clear with scattered clouds, creating a bright and welcoming ambiance.
Vacation 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 favorite
A spacious sleeping area features a decorative bed with light-colored bedding and plush pillows. Soft towels are neatly arranged at the foot of the bed. Natural light filters through a window adorned with dark curtains, highlighting the room's rustic charm.
Vacation home in Pienza
4.95 out of 5 average rating, 79 reviews

Pienzalettings

EllenRating, 5 stars1 week ago
Lovely suave in the historic section.

Vacation home rentals with a washer and dryer

Guest favorite
Vacation 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 favorite
A close-up of a majestic bird of prey with extended wings, showcasing detailed feathers. The background features a serene landscape with rolling hills and a soft sunrise peeking through the clouds, suggesting a tranquil natural environment.
Vacation home in Chianciano Terme
5 out of 5 average rating, 95 reviews

The Eagle and the Olive Tree

PatrickRating, 5 stars3 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
A dining area is set outdoors under lush greenery, with wooden tables and metal chairs arranged for guests. Soft lighting hangs above, and a scenic view of trees and rolling hills can be seen in the background, creating a serene atmosphere.
Vacation 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 sets it apart. The possibility of bringing the puppy was super appreciated. The restaurant deserves a big round of applause. I highly recommend it.
Guest favorite
A bright bedroom features a spacious bed with light linens and a decorative throw. Natural light enters through open double windows, revealing a private terrace. A television and a small desk with a chair are present, while two bedside tables with lamps offer soft lighting.
Vacation home in Monteroni d'Arbia
4.91 out of 5 average rating, 74 reviews

White lily with a view of Siena

ShufanRating, 5 stars3 days ago
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
A serene outdoor space is featured, showcasing a swimming pool surrounded by lush greenery. Comfortable lounge chairs are positioned beside the pool, with umbrellas providing shade. Tall cypress trees and well-maintained gardens create a peaceful ambiance in the background.
Vacation 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
A sun-drenched pool area features a sparkling swimming pool surrounded by terracotta tiles. A sun lounger and an umbrella provide shaded seating, while a wooden barrel with two glasses and a wine bottle is positioned nearby, creating a serene outdoor atmosphere.
Vacation 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
A view of a charming medieval square surrounded by historic stone buildings, featuring a canopied area with potted plants. Clothes hang drying from a window, while the sky is filled with clouds and streaks of blue, enhancing the inviting atmosphere of the village.
Vacation home in Colle di Val d'Elsa
4.76 out of 5 average rating, 37 reviews

Tower House of the 1000

GaspareRating, 5 stars3 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, etc.) without any problems. The village's location is very strategic for visiting the surrounding cities and winery areas. Thanks Marta, see you soon.
Guest favorite
Aerial view of the Borgo Argenina, featuring a series of rustic stone buildings with terracotta roofs, surrounded by lush vineyards and cypress trees. A central circular driveway connects the structures, while manicured gardens enhance the tranquil atmosphere.
Vacation home in Gaiole in Chianti
4.96 out of 5 average rating, 28 reviews

The Piccola Villa of Borgo Argenina

MeghanRating, 5 stars1 month 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