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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

MartinaRating, 5 stars1 week ago
Wir haben den Urlaub mit unseren drei Töchtern (13, 13, 16) sehr genossen. Besonders der Ausblick und der Pool waren fantastisch. Das Haus und die Terrasse sind sehr schön und laden zum Entspannen ein. Toll war es auch, dass wir fußläufig 2 ausgezeichnete Trattorien erreichen konnten, natürlich auf Empfehlung von Marina. Die Straße von Lucca aus ist schmal und kurvig, teilweise etwas aufregend... Wir waren mit einem großen Ford Transit unterwegs.... alles machbar. Man wird oben von der unglaublichen Aussicht belohnt, besonders nachts mit den Lichtern von Lucca, den Sternen und den Glühwürmchen. Ein schöner Ort mit hilfsbereiten Gastgebern.
Guest favorite
Vacation home in Faella
4.93 out of 5 average rating, 112 reviews

Appartamento storico Il Prato a 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 Roccatederighi
4.92 out of 5 average rating, 37 reviews

Holiday in an antique farm, Pergola

AaronRating, 5 stars2 weeks ago
If you have the chance to stay at Peruzzo, stop reading reviews and book it already! The farm is stunning, peaceful and you feel like you are staying at a friend's place rather than an Airbnb. If you have kids, Peruzzo is a perfect place for them to run around and see all of the farm animals. Giuila and Elisa were incredibly hospitable and welcoming, giving detailed and fantastic recommendations for things to do in Tuscany. The area is also a much quieter and less touristy part of Tuscany, with mostly locals. Most of the restaurants we went to were very quiet, but the food was incredible and cheap. We met many other guests that have been going to Peruzzo with their family every year for 20+ years and we can totally see why, we miss it already. We will definitely be coming back again the next time we are in Italy.
Guest favorite
Vacation home in Montespertoli
4.95 out of 5 average rating, 136 reviews

Tuscan Orchard

MaryseRating, 5 stars2 months ago
Notre hôte était vraiment chaleureuse. et à l'écoute. Nous avons eu l'occasion de goûter à leurs produits. Elle nous a donné de bonnes recommandations. Elle a été très réceptive suite à notre arrivée tardive dùe à notre vol retardé. Nous recommandons fortement cette belle maison et y reviendrons assurément. Merci pour votre accueil ❤️
Top guest favorite
Vacation home in Loro Ciuffenna
4.95 out of 5 average rating, 37 reviews

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

EmineRating, 5 stars1 month ago
Wir waren ca. 12 Tage da und als wir mit dem Auto auf dem Hügel angekommen sind, haben wir eine super Landschaft vorgefunden… eben die typische Toskana, es war herrlich. Wir waren viel mit unserem Hund unterwegs , wandern, spazieren geht, die umliegenden Städte besichtigen, wie Siena, Arezzo, Montepulciano… , loro ciuffina. Wir werden nächstes Jahr wiederkommen und etwas länger als nur 12 Tage. Highlight war, dass Simone aus seinen eigenen Olivenbäumen Olivenöl herstellt. Mussten natürlich 10 Liter Kanister mitnehmen. Das Öl ist hervorragend.Danke Simone, es war ein schöner Aufenthalt.
Top guest favorite
Vacation home in Rignano sull'Arno
4.89 out of 5 average rating, 345 reviews

Holiday Toscany nello 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

Romantico in bioagriturismo Firenze

AngelikaRating, 5 stars3 weeks ago
Wunderschöne Lage inmitten von Olivenhainen, gut ausgestattete Unterkunft, herzliche Gastgeberin. Der ideale Ort, um die Seele baumeln zu lassen & den Stress des Alltags zu vergessen. Gerne wieder *****
Guest favorite
Vacation home in Dimezzano
4.89 out of 5 average rating, 291 reviews

[Authentic StoneHouse] Garden & Viewpool Apartment

HeikoRating, 5 stars3 weeks ago
Wir hatten eine tolle Zeit! Der wunderschön gepflegte Garten, der Pool, das Haus: Alles war genau so, wie wir es uns gewünscht hatten. Ein großes Dankeschön an Lorenzo für seine tolle Beratung und seine herzliche Unterstützung. Vielen Dank für alles! Ci siamo divertiti tantissimo! Il giardino splendidamente curato, la piscina, la casa: tutto era proprio come lo si desiderava. Un grande ringraziamento a Lorenzo per gli ottimi consigli e il suo cordiale supporto. Grazie di tutto!

Vacation home rentals with a patio

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

Pian'D'olmo, antico casale nel cuore della Toscana

ClaudiaRating, 5 stars3 weeks ago
La estadía en esta casa fue realmente espectacular. Todo precioso, limpio, práctico e incluso mejor que lo que se ve en las fotos. Además la casa estaba equipada con todo lo necesario y hasta cosas extras como para cocinar, descansar, abrigarse y todo lo imprescindible para el baño y el resto de los espacios. Pasamos una increíble estadía con nuestra familia, fue el cierre ideal del viaje a Italia. Un lugar maravilloso con muchísima tranquilidad y cerca de muchos pueblos hermosos que visitar. No tuvimos ningún problema con el hospedaje y aún así Frederic estuvo siempre atento a que estuviéramos cómodos. Recomiendo este hospedaje en un 100%. De los mejores en que me he quedado. Muchas gracias por todo Frederic. De verdad estuvo todo impecable.
Guest favorite
Vacation home in Monteroni d'Arbia
4.91 out of 5 average rating, 74 reviews

White lily con vista su 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

Casa nel cuore della Toscana

OvidiuRating, 5 stars1 month ago
Foarte frumoasă locatia si peisajul, gazda deosebit de receptiva si prietenoasa, mi-a facut o deosebită placere sa-i cunosc si sa ma bucur de priveliștea mirifică, recomand tuturor.
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, 19 reviews

Villa Sottosopra - Il Limone

TinaRating, 5 stars1 week ago
Wir hatten eine wundervolle Zeit bei Lena. Die Apartments sind sehr hochwertig ausgestattet und der Blick beim Frühstück über die Toskana ist einfach atemberaubend schön. Wer die Chance hat bei Lena und ihren geliebten 4 Beinern zu übernachten - wird sich gleich wie zu Hause fühlen und eine wunderbare , ganz besondere Zeit haben, sodass man am Ende gar nicht mehr abreisen möchte.
Superhost
Vacation home in Montaione
4.84 out of 5 average rating, 32 reviews

Podere Sant'Anna | Casa Fiordaliso

KamilaRating, 5 stars4 weeks ago
Cudowne miejsce, wszystko co potrzeba na miejscu. Widok z balkonu najlepszy na świecie. Byliśmy już w Toskanii, ale do tego miejsca wrócimy z wielką chęcią.
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.
Guest favorite
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
Vacation home in Figline e Incisa Valdarno
5 out of 5 average rating, 43 reviews

Casa colonica nel verde con piscina 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
Vacation home in Crespina
4.91 out of 5 average rating, 11 reviews

Poggio al Casone - Barrique basic apartment

DanielRating, 5 stars1 week ago
Wundervolle Unterkunft mit jeglichen Möglichkeiten. Von eigens gestalteter Selbstversorgung bis hin zur Buchungsmöglichkeit aller Services für die Rundum-Versorgung. Alles vorhanden was man für einen sehr guten Entspannungsurlaub benötigt. Wir werden nochmal vorbeikommen.
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.
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.
Guest favorite
Vacation home in Sorana
4.96 out of 5 average rating, 273 reviews

Tuscan Nature Views From Casa Gave

AnkeRating, 5 stars1 month ago
Wunderschön in der Natur gelegene Unterkunft in den Bergen weit weg vom Trubel. Super sauber und sehr gut ausgestattete Unterkunft. Traumhaft schöner Garten und toller Pool. Wir haben uns sehr wohl gefühlt und kommen gerne nochmal wieder.
Top guest favorite
Vacation home in Pistoia
4.99 out of 5 average rating, 134 reviews

Podere docciolino casa vacanze

CsabaRating, 5 stars4 days ago
Tökéletes szálláshely, minden a leírásnak megfelelt. Szinte új minden berendezés, makulátlanul tiszta volt minden. Szép, jól felszerelt, igényes ház. A házigazda segítőkész és kedves volt.
Guest favorite
Vacation home in Campo
4.9 out of 5 average rating, 86 reviews

Peaceful country villa 10 far from Pisa town

RhiannonRating, 5 stars3 weeks ago
Absolutely amazing stay, Umberto and Sharif were very welcoming and couldn’t do enough for us during our stay. The villa was beautiful and rooms where incredible we each had our own space. We were a group of 8 adults and 6 children and always felt we had enough space. Would go back in a heartbeat We did trips to Pisa, Lucca, beach Pool was gorgeous and the gardens well maintained. Thank you for a wonderful holiday
Guest favorite
Vacation home in Centro Storico
4.93 out of 5 average rating, 179 reviews

TOSCANELLA STUDIO RUBINO

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!

Destinations to explore