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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 ancient stone farmhouse with a rustic red-tiled roof is surrounded by lush greenery. The building sits within a mountainous landscape, framed by trees. The open sky above reveals soft clouds and sunlight, hinting at the serene atmosphere of the rural environment.
Vacation home in Chiusi della Verna
4.96 out of 5 average rating, 135 reviews

Experience rustic off-grid life in the wilderness

RalfRating, 5 stars2 months ago
amazing place with some amazing hosts.... beautiful nature and some nice hikes right from the house. make sure to go eat at Il Sassone. thank you again for sharing your place.
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 stars4 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 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 stars4 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 scenic view captures rolling hills in the Valdarno valley, with a private swimming pool set amidst olive trees. A farmhouse with a terracotta roof can be seen in the distance, complemented by lush greenery and a clear blue sky.
Vacation home in Loro Ciuffenna
4.93 out of 5 average rating, 30 reviews

"Gelso" (Mulberry) 2/4p, pool, garden, view

AnnaRating, 5 stars1 week ago
We had a wonderful stay! Information and check-in were super easy with Simone. The property is beautiful! The great pool and the cool house did very well. I can recommend it 100%!
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

Superhost
An aerial view showcases a sprawling estate nestled in a lush, green hillside. The property features multiple buildings, a swimming pool, and cultivated terraces. Surrounding greenery and winding roads enhance the sense of seclusion and tranquility in this rural landscape.
Vacation home in Castelfranco di sopra
4.74 out of 5 average rating, 39 reviews

House in the heart of Tuscany

AlexRating, 5 stars1 month ago
The property and location is absolutely idyllic. The views are stunning, and the food is fantastic. Oscar is extremely helpful. Would highly reccomend.
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.
Top guest favorite
A serene garden area features a manicured landscape with various shrubs and plants. White outdoor furniture is positioned on a stone pathway, surrounded by lush greenery, providing a peaceful view of the rolling hills and trees in the background.
Vacation home in Chianni
5 out of 5 average rating, 42 reviews

5*Casa Serena,Fab 1 bed with aircon,parking garden

RobertRating, 5 stars6 days ago
Great place to stay to sample Tuscan village life. Only Walking distance for several very good restaurants in an idyllic setting. Very informative and welcoming hosts who have an abundance of information to share in order to make your stay more complete .
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.
Superhost
An aerial view captures a restored farmhouse nestled in the green landscape of Tuscany. Surrounding hills are visible, with patches of trees and a glimpse of the swimming pool. The winding road leads to the property, enhancing the tranquility of the rural setting.
Vacation home in Montaione
4.84 out of 5 average rating, 32 reviews

Podere Sant'Anna | Fiordaliso House

KamilaRating, 5 stars4 weeks ago
A wonderful place, everything you need on site. The best balcony view in the world. We have already been to Tuscany, but we will return to this place with great pleasure.
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 traditional kitchen features wooden beams on the ceiling and terracotta tiles on the floor. A rustic wooden table is surrounded by four chairs. Kitchenware is neatly arranged on shelves, and a large window offers natural light and scenic views.
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!

Vacation home rentals with a washer and dryer

Top guest favorite
A tranquil swimming pool is framed by a sun terrace, featuring rolling green hills in the background. A straw hat rests on white linen, while sunlight casts soft shadows across the scene, creating a serene atmosphere for relaxation.
Vacation home in Serravalle Pistoiese
4.93 out of 5 average rating, 45 reviews

Il Glicine @ Casa d'Olival

PatrickRating, 5 stars8 months ago
Gioia’s little piece of Tuscan paradise exceeded all expectations. The apartment was lovely, the scenery gorgeous and the pool perfect for lounging amongst the lavender and olive trees, not to mention hanging out with Wolfy. Do not miss an opportunity to take the pasta making class with Graziella as she helped us craft one of the best Italian meals we’ve had! This was one of the highlights of our weeks in Europe and we can’t wait to return.
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
A clean and modern bathroom is displayed, featuring a sleek sink with a minimalist faucet. Two neatly rolled white towels rest on a stylish countertop, complemented by a large mirror above. A door in the background leads to the rest of the apartment.
Vacation home in Centro Storico
4.98 out of 5 average rating, 49 reviews

Appartamento Donizetti24 (D24)

WesleyRating, 5 stars2 weeks ago
One of the best Airbnb’s I’ve stayed at during this trip. Sara was very helpful and responsive. It was very peaceful. The bus station is right around the corner and easy to get anywhere. Very pleased!
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!
Guest favorite
Vacation home in Casole d'Elsa - Siena
4.91 out of 5 average rating, 23 reviews

Elegant farmhouse surrounded by nature, Air

YanaRating, 5 stars2 months ago
We enjoyed staying at this beautiful accommodation, surrounded by nature and just outside a small village. Romina and Ricardo were fantastic hosts, kind and helpful. The accommodation is new, very clean and beautifully decorated. The area is secluded, you need to drive everywhere. We will come again!

Destinations to explore

  1. Airbnb
  2. Italy
  3. Tuscany
  4. Province of Siena
  5. Siena
  6. Vacation home rentals