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Vacation home rentals in San Gimignano

Find and book unique vacation home rentals on Airbnb

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Popular amenities for San Gimignano vacation home rentals

Family-friendly vacation home rentals

Guest favorite
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
Vacation home in Siena
4.85 out of 5 average rating, 78 reviews

"Lisa" apartment with fireplace

BerinRating, 5 stars4 weeks ago
The place is just breathtaking. Lisa was very sweet and had prepared us a little gift. I would definitely recommend! There are lovely dogs which we got used to so much 🥹🧡
Guest favorite
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
Top guest favorite
Vacation home in Siena
4.97 out of 5 average rating, 60 reviews

Apartment in historic Villa in Siena_"LE CONTRADE"

PaulRating, 5 stars1 month ago
Located a long walk or very short (5 min) drive outside of Siena. Upon arrival, we had a little difficulty locating the apartment parking lot (small entrance off street), but once we knew where it was it was very easy after that. The apartment was wonderful, big for us, and cozy. Cristina was very communicative with us, and recommended many wineries and restaurants in Siena. We really enjoyed our stay and would stay here again.
Superhost
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
Vacation home in Montespertoli
4.95 out of 5 average rating, 136 reviews

Tuscan Orchard

MaryseRating, 5 stars2 months ago
Our host was really warm. and attentive. We had a chance to try their products. She gave us some good recommendations. She was very responsive to our late arrival due to our delayed flight. We would highly recommend this beautiful home and will definitely come back. Thanks for your hospitality. ❤️
Top guest favorite
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.
Guest favorite
Vacation home in Figline e Incisa Valdarno
4.94 out of 5 average rating, 358 reviews

Romantic stay at a bio-agritourism in Florence

MariaRating, 5 stars1 month ago
Amazing place and the place offered by Francesca is totally great. She was so kind and helpful. Totally recommended!

Vacation home rentals with a patio

Guest favorite
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
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
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
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 .
Top guest favorite
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.
Guest favorite
Vacation home in Certaldo
4.93 out of 5 average rating, 15 reviews

La Selva , Country house, 130 mq, Stunning views

LindaRating, 5 stars1 month ago
Staying with Carmine is top. We have been to Carmine and Alessandra in Certaldo for a month (mid-April / mid-May) and we can recommend that to everyone. Not only the reception ( in our case very late) was incredibly warm, but throughout our stay we felt very comfortable, this host is always open to questions, is proactive with giving information, tips about everything like where it is nice / tasty/ beautiful to visit. In addition, the house is very nice, it is great in the Tuscan hill country, between the wine and olive farmers, nice beds (we always find important especially if you are staying there longer) and really good Wi-Fi which was important for us to be able to work from here. The location is perfect. You are close to Florence, Siena, Pisa, and many special other villages/towns that are more than worth visiting. The month was over too soon! If we visit Tuscany again for sure with Carmine and Alessandra!
Superhost
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
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.

Vacation home rentals with a washer and dryer

Top guest favorite
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!
Guest favorite
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
Vacation home in Pistoia
4.99 out of 5 average rating, 134 reviews

Podere Docciolino Vacation Home

CsabaRating, 5 stars3 days ago
Perfect accommodation, everything was as described. Almost all the equipment was new, everything was spotless. Nice, well-equipped, sophisticated house. The host was helpful and kind.
Superhost
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.
Top guest favorite
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
Vacation home in Bagni di Lucca
4.88 out of 5 average rating, 200 reviews

Hausbe Room, Vacation Home

RachaelRating, 5 stars3 weeks ago
This was a fantastic place with a great view. The host was hospitable more than he even needed to be. I enjoyed our stay and would definitely stay again!
Guest favorite
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!

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