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Vacation home rentals in Siena

Find and book unique vacation home rentals on Airbnb

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Popular amenities for Siena vacation home rentals

Family-friendly vacation home rentals

Guest favorite
A glass of white wine rests on a stone railing, overlooking a tranquil scene of Lake Trasimeno. Lush green cypress trees frame the view, with the calm waters reflecting the sky’s hues and two distant islands visible in the background.
Vacation home in Passignano sul Trasimeno
5 out of 5 average rating, 25 reviews

Antico Casale Tiravento - Apartment with balcony

Marcel SarahRating, 5 stars1 week ago
Antonella, Andreas and not to forget Lullu are perfect and so relaxed hosts. They sweetened our mornings with fresh bread, croissants & coffee. The apartment is well equipped and of high quality. We felt very comfortable right away. The garden invites you to linger and is particularly well maintained. Thank you for this special stay!
Guest favorite
A swimming pool is set within a lush green landscape, bordered by a stone path. Sun loungers are arranged around the pool, with a shaded gazebo nearby. The surrounding area features trees and a fence, offering scenic views of the valley in the distance.
Vacation home in Matraia
4.91 out of 5 average rating, 106 reviews

"IL FIENILE" rustic stone house

SandraRating, 5 stars2 weeks ago
Our stay at Marina and Paolo’s hilltop home in the Tuscan hills was nothing short of magical. The house is a true piece of paradise, immaculately clean, with breathtaking views that left us in awe every day. Marina and Paolo were incredibly kind hosts, making us feel completely at home. The swimming pool was fantastic, and the entire experience immersed us in the charm of Tuscan life. We highly recommend this gem to anyone looking for an unforgettable getaway!
Guest favorite
An outdoor area is presented, featuring a stone-paved patio with several potted plants. The entrance to the house is framed by arched doors, which open to a cozy seating arrangement. Views of the surrounding landscape are visible in the background.
Vacation home in Faella
4.93 out of 5 average rating, 112 reviews

Historic apartment Il Prato in Castelfranco

AnneRating, 5 stars5 days ago
Fab pool! Very comfortable accommodation with friendly host. We really enjoyed our family time there. Train station 10 minutes away with free parking. Very good coop near also
Superhost
The exterior of a two-story terraced apartment features warm, rustic brickwork, a private terrace adorned with potted plants, and a wooden dining table surrounded by seating. Lush greenery and scenic hills are visible in the background under a clear blue sky.
Vacation home in Asciano
4.87 out of 5 average rating, 101 reviews

Charming home Crete Senesi

TaraRating, 5 stars1 week ago
We had the most wonderful time here, the host was very kind snd helpful, we even met a few of the neighbours, all really friendly and helpful. The views and peacefulness of this house/area made it so special. Waking up to birdsong and roosters everyday. Everything was perfect, thank you.
Guest favorite
A sparkling swimming pool is surrounded by sun loungers and umbrellas, offering a relaxing space for guests. The rustic farmhouse, with its stone exterior, is visible in the background, amidst lush greenery and trees under a partly cloudy sky.
Vacation home in Castelnuovo Berardenga
4.9 out of 5 average rating, 78 reviews

PIERFANTINI private Chianti house ♿️ 🏊‍♂️ 🐶

KellyRating, 5 stars1 day ago
The home is beautiful, clean, peaceful. We loved the pool! The location was a bit challenging to get to, things that are close in kilometers take a long time to get to because of narrow, twisty roads. The upstairs apartment had AC, but the bottom one did not. We stayed cool anyway with all the windows open! All five of us loved the water pressure in the showers! eating our breakfast out on the pergola each morning, watching the birds swoop in for drinks in the pool was delightful! It felt safe and peaceful!
Top guest favorite
An outdoor pool is set amidst olive trees, with sunbeds arranged around it, offering a picturesque view of the rolling hills and the Valdarno valley. The distant mountains create a serene backdrop under a clear blue sky, enhancing the tranquil atmosphere.
Vacation home in Loro Ciuffenna
4.95 out of 5 average rating, 37 reviews

"Loggiato" (Porch) 2/4p, terrace, pool, garden

MaximilianRating, 5 stars1 week ago
We had a wonderful stay! The place was absolutely perfect – clean, beautifully furnished, and equipped with everything we needed. The peaceful location in the middle of the Tuscan countryside was ideal for relaxing. Communication with the host was smooth and friendly. We’d love to come back – 100% recommended!
Guest favorite
A spacious living area features exposed wooden beams and a terracotta floor. A sectional sofa, adorned with decorative pillows, faces a wooden coffee table. A dining area with a simple table is visible, along with stairs leading to the upper level and large windows allowing ample natural light.
Vacation home in Porto
4.95 out of 5 average rating, 130 reviews

La Dimora del Lago - Lake views of Tuscany and Umbria

MurrayRating, 5 stars5 days ago
Jan's place could not have been better! As advertised..and even better..and Jan was incredibly responsive to everything..INCLUDING being proactive before checkin. She anticipated everything and even when I had one question, she was immediately responsive. Of all my Air Bnb experiences, this was probably my best. She made local recommendations for restaurants, stories and services...all turned out to be accurate. We met Jan and (her husband Emilio--a Doctor--and good to know) and felt more like good friends in their home rather than "tenants." And as a bonus, Jan has researched her property history and has documentation to prove that Leonardo DaVinci -that one--had a role in the areas development. Just a nice touch. Am VERY happy.
Top guest favorite
A swimming pool is framed by well-maintained stone walls and lush greenery. The surrounding area showcases rustic stone buildings with terracotta roofs, enhancing the serene atmosphere. Clear blue skies reflect on the water's surface, creating a peaceful ambiance in the outdoor space.
Vacation home in Rignano sull'Arno
4.89 out of 5 average rating, 345 reviews

Holiday Tuscany in the Strettoio

CamillaRating, 5 stars2 weeks ago
Absolutely beautiful air bnb. The views and surroundings are breathtaking, we loved swimming in the pool whilst looking over the Italian countryside. Leonardo was a great host, always responded quickly and made us feel welcome. We will definitely come back for another stay.

Vacation home rentals with a patio

Top guest favorite
Aerial view of the farmhouse complex surrounded by lush fields and vineyards. The property includes a swimming pool and is framed by olive and cypress trees, with rolling hills and the countryside visible in the distance.
Vacation home in Cantagallina
4.98 out of 5 average rating, 63 reviews

Il Gelsomino, apartment between Tuscany and Umbria

SuedaRating, 5 stars5 days ago
I cannot recommend this place enough!! We stayed here for a couple of nights and the location is absolutely amazing. It was so quiet, peaceful and being surrounded by beautiful views and nature was just the best feeling. This place is run by Valentina and her parents Rosi and Stefano who are just the sweetest people. They made us feel right at home and were so kind and welcoming. Thank you all so much for having this amazing place! We cannot wait to return one day.
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
The aerial view captures a serene landscape surrounding the property, with lush greenery and mature trees. A rectangular pool is visible, surrounded by sun loungers, while the rustic building features a terracotta roof, blending with the natural setting. Pathways connect various outdoor areas.
Vacation home in Greve in Chianti
4.9 out of 5 average rating, 20 reviews

Cuculo - Rifugium

KlioRating, 5 stars2 months ago
Beautiful apartment in the countryside. Spacious and clean. The access by car was a little difficult but definitely recommended.
Superhost
A serene outdoor pool area is surrounded by lush greenery and tall cypress trees. Sun loungers and umbrellas provide shaded seating options, with a stone wall framing the space. The clear blue sky enhances the tranquil ambiance, creating a relaxing atmosphere for guests.
Vacation home in Ulignano
4.72 out of 5 average rating, 18 reviews

★ Relaxing apartment & stunning view of Tuscany ★

Anna-LenaRating, 5 stars10 months ago
We went there for the second time and it was just perfect as the first time. Diego's property is beautiful overlooking San Gimignano, it is quiet and very idyllic so you can really unwind. The apartment was great, is well equipped with everything you need. We felt very comfortable and would love to come a third time next year. Thanks to Giorgia for the good communication and flexible check-in.
Top guest favorite
An airy living space features a high wooden beamed ceiling, enhancing the openness. Large glass doors offer views of the Toscan landscape. A round dining table is centered in the room, accompanied by a light-colored sofa and a modern kitchen area equipped with sleek appliances.
Vacation home in Chianni
5 out of 5 average rating, 19 reviews

Villa Sottosopra - Il Limone

TinaRating, 5 stars1 week ago
We had a wonderful time at Lena's. The apartments are very high quality and the view over Tuscany at breakfast is simply breathtakingly beautiful. Those who have the chance to stay with Lena and her beloved 4-legged friends will feel right at home and have a wonderful, very special time, so that you don't want to leave at the end.
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 stars1 week 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.
Guest favorite
A spacious kitchenette and dining area is presented, featuring wooden cabinets and a gas stove. A wooden table with four chairs occupies the center, while a green sofa sits against the wall. Natural light filters through a nearby window, illuminating the terracotta floor.
Vacation home in Roccastrada
5 out of 5 average rating, 18 reviews

Apartment in a wine estate in Tuscany

AnnikaRating, 5 stars1 day ago
We felt very comfortable during our stay at the end of June. The hosts were very friendly, helpful and gave good tips for activities. We particularly liked the relaxed atmosphere, the beautiful pool and the good wines ☀️

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
Vacation home in Figline e Incisa Valdarno
5 out of 5 average rating, 43 reviews

Farmhouse in the countryside with swimming pool Solatìo

ArnoRating, 5 stars2 weeks ago
We absolutely loved our stay at Marco’s beautiful place! The apartment is stylish, comfortable, and fully equipped with everything you might need. The swimming pool and stunning views of the Tuscan countryside created the perfect setting to relax, read a book, or enjoy a glass of wine. What truly made our stay exceptional, though, was Marco himself—his warm personality and genuine hospitality made us feel incredibly welcome. We highly recommend staying at Marco’s and would love to come back someday!
Superhost
The exterior of a charming building features a light-colored facade adorned with green shutters. A landscaped garden with neatly trimmed hedges and vibrant flower pots is visible. Two umbrellas provide shade by the entrance, enhancing the inviting atmosphere of the property.
Vacation home in Crespina
4.91 out of 5 average rating, 11 reviews

Poggio al Casone - Barrique basic apartment

PaulRating, 5 stars13 months ago
Micheal & Ottavia were excellent hosts, gracious, kind & always nearby to answer any questions.
Guest favorite
A compact kitchen countertop is displayed, featuring a white espresso machine and a sleek black ventilation hood. Soft lighting illuminates the area, highlighting the natural wood grain of the countertop. A striped fabric curtain adds a subtle touch to the space.
Vacation home in Centro Storico
4.91 out of 5 average rating, 275 reviews

Melarancio Residence

TasneemRating, 5 stars3 weeks ago
We enjoyed our stay at this apartment. Having an elevator was a blessing on days we were exhausted and air conditioning in every room meant we didn’t have to melt the few days we had really hot weather. Location is super convenient with the Mercato Centrale, Firenze SMN station, and the Medici chapel just around the corner from us. The grocery store downstairs was well stocked and there’s also a dollar store, pharmacy, and gym nearby.
Top guest favorite
The dining area features a round table set for a meal, complemented by colorful chairs. Sunflowers in a vase add a lively touch. Large glass doors open to a private outdoor space filled with greenery, enhancing the connection between indoor and outdoor settings.
Vacation home in Centro Storico
4.96 out of 5 average rating, 49 reviews

RED into the heart of Florence

NeilRating, 5 stars1 month ago
Casasafer is a modern AirBnB with all that you need for a memorable stay in Florence. Step out the door, walk for a few mins in any direction, and you'll likely find yourselves in one of Florence's many wonderful must-see places. The duplex apartment we stayed in was very pleasant, opening into a cozy dining room with an adequate kitchen on the side, an open air sit-out for sunny days, and a mezzanine loft with a comfortable large double bed that fit two adults and two lite kids. There was also a sofa-bed in the dining room we could've used. The common basement area is also another zone that one can spend time in, especially if you are a frazzled parent who needs to maybe read a book far from the madding kids. Overall, the sort of place you can always safely recommend. Our special thanks also to Claudia, whose care for the little details like a bit of a snack and a good bottle of local wine to welcome us, and helpful tips for places to visit, food to try, gave our trip a local touch.
Guest favorite
A narrow hallway is depicted with warm terracotta tiles underfoot and soft lighting provided by large lanterns. The walls feature a mix of smooth finish and exposed brick, leading to a wooden door at the end adorned with elegant windows.
Vacation home in Centro Storico
4.93 out of 5 average rating, 179 reviews

TOSCANELLA RUBY STUDIO

BilbaoRating, 5 stars1 month ago
We had an excellent stay at this apartment in Florence! The space is simple yet very practical, comfortable, and equipped with everything needed. The building is old, charming, and authentic — a true piece of the city’s history. Having an elevator was a big plus. The apartment is cozy, well laid out, and perfect for relaxing after a day of exploring. The neighborhood is wonderful, full of life, with many art galleries, bars, and cozy cafes. The neighbors are friendly and the street is especially beautiful — ideal for peaceful walks. Everything combined made our experience in Florence truly special. Highly recommend!
Superhost
Vacation home in Sovicille
5 out of 5 average rating, 6 reviews

SienaEntire TuscanProperty PoolHottub OutdrKitchen

MadelineRating, 5 stars20 months ago
My family came from the UK, Germany, and the US to Liesbeth's place for a grand reunion. We had three young children and they absolutely loved the property, the pony, Polly, the swings, the pond, and the trampoline. Even though it was too cold to swim, we loved hanging around and wandering through the olive groves. I think if it was warmer, we would have had a tough decision whether to stay and enjoy all the outdoor cooking and swimming opportunities or venture out to Siene and other areas. The three apartments were great though it was tough to pick a central kitchen and living room to congregate. The beds were comfy and there were tons of bathrooms and showers. We explored Siene three times because it was only a 30 minute drive. The Etruscan necropoli close by was a cool hike as well as walking along the river near Colle D'Elsa. It was the perfect home base for all the area offers as well as a great spot to stay home and spend time together; a long stay is highly recommend.
Guest favorite
Vacation home in Poggibonsi
4.93 out of 5 average rating, 54 reviews

App.Cavallo - Megognano,2/A

XinyiRating, 5 stars5 days ago
Flaminia and Luigi are very welcoming! The view of the place is fantastic. Room is very clean and spacious, we enjoyed our stay here!

Destinations to explore

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