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Villa vacation rentals in San Gimignano

Find and book unique villas on Airbnb

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Popular amenities for San Gimignano villa rentals

Villa rentals with a pool

Guest favorite
Villa in Palaia
4.92 out of 5 average rating, 12 reviews

Villa La Gemma

ImaneRating, 5 stars3 weeks ago
Es war für uns als kleine Familie mit einem kleinkind ein sehr schöner Urlaub. Unsere Tochter liebte das Haus und die Umgebung. Trotz kurzen Aufenthalt fühlten sich die Tage wie zwei Wochen Ferien an. Wir kommen auf jeden Fall wieder. Die Gastgeberin war proaktiv und hat uns in allem was wir benötigt hatten unterstützt. Es hat uns an nichts gefehlt. Wir können es wärmstens weiterempfehlen.
Top guest favorite
Villa in Panzano
4.93 out of 5 average rating, 75 reviews

Luxury Villa on Chianti Wine Estate

StevenRating, 5 stars1 month ago
Wonderful stay at the Villa among the vineyards in Panzano. Vicky, the host, is the owner of Le Fonti winery with the villa surrounded by their vineyards and olive groves. The view from the villa is absolutely stunning. The town of Panzano is very cute. We bought groceries at the Coop and made breakfast each morning, gathering in the cozy well equipped kitchen. There is a courtyard immediately outside the doors of the villa with a large table, and again amazing views. Our time in the villa was so relaxing! Though we went to several wineries, a highlight was a very personal tour of the winery, wine making process and wines by Vicky at Le Fonti. She spent time discussing/pouring the different wines, even bringing over the same wine from different years to show us the difference the weather/grape stress influences the final taste. Overall exactly what we wanted from a Tuscan experience and really enriched by an extremely friendly and knowledgeable host.
Guest favorite
Villa in Gaiole in Chianti
5 out of 5 average rating, 6 reviews

Casanova di Bricciano

JacquesRating, 5 stars1 month ago
Nous avons découvert un endroit incroyable avec une vue et un décor fééerique typiquement de la Toscane. Les hôtes Andréa et Fabio sont très accueillants et disponibles, et la maison était impéccable et identique aux photos. C'est plus qu'un 5 étoiles! Nous sommes des fervents de la location par AIrbnb, et ce fut le plus bel endroit que nous avons connu, un coup de coeur! Nous avons pu également profiter d'une dégustation de vin à leur vignoble familial, et ce fut une très belle et enrichissante expérience. Nous avons passé des moments mémorables en Toscane et c'est beaucoup à cause de cette location. De plus, il y a un petit village à proximité, et nous avons découvert de délicieux restaurants. Cette villa est également près de Florence et Sienne. Nous vous recommandons très fortement cet endroit.
Top guest favorite
Villa in Rignano sull'Arno
5 out of 5 average rating, 15 reviews

villa "La Fonticina"

KathyRating, 5 stars2 weeks ago
Incredible host and property. We feel fortunate to have had the opportunity to stay here. Cesare was beyond helpful with recommendations and flexible with our check in. Secluded, peaceful and a great place for making memories during our travels around Italy.
Top guest favorite
Villa in Loro Ciuffenna
4.98 out of 5 average rating, 51 reviews

The Lazy Oak

JordanRating, 5 stars2 weeks ago
The Lazy Oak Villa is everything we dreamed of and more for our honeymoon. The house is beautiful, well furnished and feels so homely and comfortable. The surroundings are simply stunning; the view from the house and pool never get old! Mario and Alessandro were super helpful, offering to help us book restaurants and vineyards if needed. Mario keeps to himself so still feels very private but is happy to help with anything and it was nice to see him around (with his cute little dog!) and know he was about if we needed anything. Couldn’t recommend the Lazy Oak Villa more, and we’re already talking about when we could come back!! Thank you Mario and Alessandro!
Guest favorite
Villa in Buonconvento
5 out of 5 average rating, 12 reviews

Beautiful tuscan country house

LukasRating, 5 stars1 month ago
Das Haus ist schön und sehr gross. Es liegt etwas ausserhalb von Buonconvento und bietet absolute Privatsphäre. Ein Auto ist von Vorteil. Die Zimmer sind grosszügig, es gibt Mückennetze über allen Betten und genügend Badezimmer und WCs für alle. Generell ist das Haus sehr gut ausgestattet, sowohl in der Küche als auch sonst. Der Pool ist etwas erhöht, schön, gross, mit natürlichem Schatten rundherum und bietet eine herrliche Aussicht auf die umliegende Landschaft. Im riesigen Garten kann man Essen, Verweilen, Spielen... Es gibt sogar einen kleinen Basketball-Court. Aber Achtung: Gleich nebenan gibt es wilde Brombeeren und der Ball kann verloren gehen :) In Buonconvento gibt es einen Coop, eine feine Gelateria und eine gutes Caffé mit den berühmten und feinen Produkten von Le Dolcezze di Nanni. Für eine gute Pizza lohnt sich die Fahrt ins Restaurant Mulinum etwas ausserhalb, sie haben eine eigene Mühle und verarbeiten ihr eigenes Getreide. Wir können das Haus sehr empfehlen.
Superhost
Villa in Volterra
4.95 out of 5 average rating, 22 reviews

Podere La Casetta - 2 Persone - Piscina Privata

ShemaiahRating, 5 stars10 months ago
My husband and I stayed here to celebrate our anniversary. This was our first experience in Tuscany and it did not disappoint. The house is very private, there is only 1 house behind it however from most viewpoints you cannot see it and we never saw anyone. Volterra is a beautiful medieval place that will make you feel like you are in a movie. An hour from Pisa, drivable to many many wineries in the surrounding regions, this air bnb is a perfect place to stay and we hope to return again.
Top guest favorite
Villa in Montaione
4.96 out of 5 average rating, 25 reviews

Private Villa with semi-Olympic pool and Tennis

JosephineRating, 5 stars1 month ago
absolutely amazing!! Francesca made us feel right at home. the place was amazing and we definitely want to come back. the property is beautiful and great if you want to play tennis , ping pong, or swim… super fun. Francesca was so sweet, gave us great recommendations, and helped us with all our questions. She even graciously helped our grandma get a doctor to see her when she sick. 10/10 amazing !

Family-friendly villa rentals

Top guest favorite
Villa in Bagno A Ripoli
4.98 out of 5 average rating, 128 reviews

Quite old farmhouse on the hills of Florence

TaylorRating, 5 stars5 days ago
Tommaso’s farmhouse was the perfect place for our family to stay in Tuscany! This was my dream house. We loved being able to sit and eat outside, and I never wanted to leave the beautiful living room filled with books. Everything was decorated so beautifully and the house just had the most gorgeous surroundings and character. We loved being close enough to Florence to experience all it had to offer but with the peace of being in the countryside. We hope to return one day and are so thankful for the amazing memories made here!
Top guest favorite
Villa in Panzano
4.96 out of 5 average rating, 115 reviews

Antica Dimora a Campana

JeffRating, 5 stars1 month ago
Our stay at Sonia’s place was like a week in a fairy tale. To stay in an 18th century home in Tuscany with the front door on the town square and the private rear terrace with a million dollar view was extraordinary. As for comforts & conveniences: There’s a parking space in the gated backyard, the beds are very comfortable, and the kitchen has lots of wine glasses. There’s also a well-stocked supermarket at the bottom of the backyard stairs. And if you see the food truck just below the center of town, be sure to stop for a sandwich. If you can get away from the terrace, Carolyn & Sonia recommended the restaurant Enoteca Baldi, and we do too.
Guest favorite
Villa in Montepulciano
4.91 out of 5 average rating, 126 reviews

Villa a Montepulciano con Piscina

SantiagoRating, 5 stars1 week ago
We just checked out of this wonderful villa today, and it has truly been one of the most special places we’ve ever stayed. We arrived with my husband’s parents, my husband, and our toddler, and from the moment we got there, everything exceeded our expectations. Alex greeted us warmly, gave us a tour of the villa and the property, and provided detailed printed information about nearby restaurants, supermarkets, cafés, bakeries, and wine tours. The property also produces its own wine, which was available for purchase and could be conveniently delivered to our villa during our stay. Alex shared his contact number and made himself available in case we needed anything—which we really appreciated. One of the highlights of the property was the stunning infinity pool overlooking the vineyard and offering breathtaking views. It was the perfect setting to disconnect and truly live in the moment. The air conditioning and hot water worked perfectly. Thank you Alex!
Guest favorite
Villa in San Casciano In Val di Pesa
4.94 out of 5 average rating, 171 reviews

Wheelchair accessible Villa with Jacuzzi

KristinRating, 5 stars1 week ago
This was such a beautiful stay in Tuscany. When our family arrived it was magical to them to be in Beatrice’s home and countryside. It’s full of history and breathtaking views.
Top guest favorite
Villa in Monteriggioni
4.97 out of 5 average rating, 156 reviews

Villa dei 2 Ulivi (Abbadia Isola)

LucaRating, 5 stars1 week ago
Abbiamo soggiornato una notte presso questa splendida villa. Eravamo in 14 e ognuno ha trovato comodamente i propri spazi. La casa è molto grande e ben disposta, il piano terra regala momenti di convivialità difficili da ricreare altrove. L’ampio salotto attrezzato con Ping pong e calcio balilla affaccia, insieme alla cucina (splendidamente attrezzata), sul porticato e sul giardino interno, creando un’unica, grande zona di condivisione. La casa è adatta davvero a tutti, anche ai più piccoli, il cortile interno è chiuso, sicuro e gode di molta privacy. Passare qualche giorno in questo alloggio è una di quelle esperienze che bisognerebbe fare almeno una volta al mese. La proprietaria Barbara ci ha seguito in maniera impeccabile fin dall’inizio con istruzioni accurate e ottimi consigli. Ci ritorneremo
Top guest favorite
Villa in Montespertoli
4.94 out of 5 average rating, 182 reviews

Colonica nel Chianti

DanielleRating, 5 stars3 weeks ago
Our Villa in Montespertoli was everything we could have wished for and more, full of all the modern conveniences required to cook if desired. The grounds were absolutely delightful and the hillside backdrop of grapevines etc was stunning to wake up to every morning in a secluded and peaceful place. We enjoyed many mornings having coffee around the poolside deck and afternoons sharing a glass of wine chatting with our friends after our many touring adventures. You definitely need to have a car to enjoy this Villa and surrounding areas like Pisa, Siena, hot Springs, San Gimignano to name a few. Our Caretaker Lia cooked us a delicious Sri Lankan dinner to share on our last night which we enjoyed immensely. Thankyou for hosting us in your home, we didn’t want to leave.
Top guest favorite
Villa in Siena
4.98 out of 5 average rating, 187 reviews

Virgi House

VittorioRating, 5 stars5 days ago
The place was exactly as described, we had no issues. Simone was friendly and gave us some great recommendations on where to eat and wineries to visit. The only real challenge was the three point turns required on the street when there were cars parked on both sides of the street (lol) but that’s a me problem. Thank you again Simone for everything!
Top guest favorite
Villa in Sovicille
4.95 out of 5 average rating, 73 reviews

Beautiful Country House, near Siena with jacuzzi

JohannaRating, 5 stars3 weeks ago
Unser Aufenthalt in diesem wunderschönen Haus in der Toskana war einfach traumhaft! Das Haus liegt idyllisch am Land und hat all unsere Erwartungen übertroffen – es war noch schöner als auf den Bildern. Alles war sehr geschmackvoll eingerichtet, sauber und perfekt ausgestattet, um entspannte Tage inmitten der toskanischen Natur zu genießen. Die Gastgeber waren ausgesprochen freundlich und hilfsbereit – von der unkomplizierten Ankunft bis hin zu tollen Tipps für Ausflüge in der Umgebung waren sie immer für uns da. Wir können dieses Haus wärmstens weiterempfehlen und würden jederzeit wiederkommen!

Private villa rentals

Top guest favorite
Villa in Centro Storico
5 out of 5 average rating, 41 reviews

Charming villa 15' walk to center stunning view

ChristineRating, 5 stars5 days ago
Wonderful villa with a beautiful outdoor area- fruit trees, roses, and flowers. We enjoyed the wine, snacks and fresh fruit the host had for us upon arrival. This was our last stop in Italy. Bedding, mattresses and AC has not been great in the places that we have stayed, and never was there a fan. This villa had a comfortable bed , great ac, and a ceiling fan in the bedroom. My husband said his best night sleep the entire trip. We were missing our dogs and cats and we loved having theirs visit us daily! The hosts were traveling so we didn’t get the chance to meet them. They regularly checked in on us to make sure everything was good and provided local recommendations. Given the reviews and accommodation, I’m sure they are amazing! If you’re ever in Florence, this place is worth the stay.
Guest favorite
Villa in Peccioli
4.92 out of 5 average rating, 12 reviews

Luxury villa with Pool, games room & Bocce court

KathleenRating, 5 stars8 months ago
My family and I -- six adults and a 9 month old -- spent two delightful weeks at Il Granaio. Before our arrival, Greg (the host) put me in touch with Ally, the property manager, who provided much useful information in advance and ensured we could find our way to the hidden gem that is Il Granaio. Once we arrived, Ally was available as needed, responsive to my queries as we settled in. We enjoyed the Villa and property immensely, using it as a base camp as we did day trips all around Tuscany and a longer visit to the Ligurian coast. The house was comfortable, attractive, and well-outfitted, with fantastic views from the second floor; the surrounding countryside was peaceful and beautiful; the pool was a perfect place to cool off and relax after being out and about; and the billiard table provided enjoyment for all! And having our own washer and dryer was incredibly convenient, especially when traveling with a baby. Wonderful memories were made for our family at Il Granaio!
Top guest favorite
Villa in Montecatini Terme
5 out of 5 average rating, 40 reviews

Villa Le Panteraie - situata tra Firenze e Pisa

TomRating, 5 stars3 weeks ago
A beautiful villa with exceptional views to the hills and valley. Various oudoor areas. Private location however close to sights and amenities. Cafes and restaurants not far however not walking distance, best accessed by own car. Electric bikes were available for sightseeing. Fantastic host, always responsive and helpful. Can warmly recommend.
Superhost
Villa in Capannori
4.96 out of 5 average rating, 26 reviews

Luxury Tuscany Villa on the hill with private pool

SandraRating, 5 stars2 days ago
Wir waren mit unserem Ferienhaus von Stefania sehr zufrieden. Toller, weitläufiger, uneinsehbarer Garten mit vielen Olivenbäumen. Pergola mit Sitzecke lädt zum verweilen ein. Auch die Sauberkeit der Unterkunft war ausgesprochen gut. Die Betten bzw. Matratzen waren sehr bequem und die Schlafzimmer schön eingerichtet. Stefania hat uns mit vielen Tipps und Empfehlungen versorgt. Sie hat für uns auch zweimal einen Tisch in der nahe gelegenen Osteria di Valgiano gebucht. Tolles Essen zu einem günstigen Preis mit tollem Blick über Lucca. Auf Fragen hat Stefania schnell und freundlich reagiert. Wir wären gerne noch länger geblieben und kommen bestimmt wieder!
Superhost
Villa in Colle di Val d'Elsa
5 out of 5 average rating, 10 reviews

Il Timignano

ChristelleRating, 5 stars3 weeks ago
Séjour incroyable en famille (12 adultes). Nous avons apprécié la propreté, l’espace des pièces, le calme et bien la piscine très propre avec le mobilier relax. A conseiller vivement, idéal aussi pour des familles avec des enfants encore petits.
Superhost
Villa in San Gimignano
4.81 out of 5 average rating, 27 reviews

Villa Elisa

AlexandraRating, 5 stars1 month ago
Das Haus ist schön und gut gelegen. Der Pool und der Garten ist klasse!!! Wir können die Unterkunft empfehlen. Gut zu wissen ist, dass gewisse genannte Ausstattungsmerkmale nicht vorhanden waren, wie Gewürzen oder ausreichend Toilettenpapier, des Weiteren gab es wenig Handtücher für den gebuchten Zeitraum. WLAN ist nur in der Küche und der Terrasse vorhanden und die Matratzen sind sehr durchgelegen. Ansonsten hatten wir einen tollen Aufenthalt, in einer sehr privaten Unterkunft.
Guest favorite
Villa in Buti
4.96 out of 5 average rating, 46 reviews

Villa sii felice

KristinRating, 5 stars1 week ago
We had an unforgettable stay at this villa for our bachelorette getaway! The host was incredibly responsive and made everything smooth from start to finish. The views were absolutely breathtaking — even better than in the pictures! The villa had everything we needed to set the perfect atmosphere: fully stocked kitchen with plates and glasses, plenty of towels, and thoughtful details throughout. We loved picking fresh lemons from the garden and finding peaceful spots around the property to read and relax. It’s incredibly private and serene — the perfect escape. While the drive-up can be a bit tricky at first, it quickly becomes second nature and is well worth it.This place exceeded all of our expectations. Highly, highly recommend — we'd come back in a heartbeat!
Top guest favorite
Villa in Sinalunga
5 out of 5 average rating, 45 reviews

Gli sterpi

JohanRating, 5 stars2 days ago
En mycket bra upplevelse att bo hos Sandrine och Emanuelle. Tack! Jättevänligt bemötande och en plats som vi verkligen vill tillbaka till! Utsikten, huset, poolen och tomten omgiven av oliv och- vinodlingar. 6 stjärnor om det gick att dela ut!

Quick stats about villa rentals in San Gimignano

  • Total rentals

    70 properties

  • Nightly prices starting at

    G$18,829 GYD before taxes and fees

  • Total number of reviews

    1.1K reviews

  • Family-friendly rentals

    70 properties are a good fit for families

  • Pet-friendly rentals

    20 properties allow pets

  • Rentals with a pool

    60 properties have a pool

Destinations to explore

  1. Airbnb
  2. Italy
  3. Tuscany
  4. Province of Siena
  5. San Gimignano
  6. Villa rentals