Holiday houses in San Gimignano

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Top-rated holiday rentals in San Gimignano

Guests agree: these stays are highly rated for location, cleanliness and more.

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Superhost

Farm stay in Santa Luce

5 out of 5 average rating, 11 reviews

Venere's Paradise Cabine - Le Fraine Glamping

Immerse yourself in the enchantment of the wild Tuscan hills, just 15 km from the sea. Agriturismo Le Fraine offers 4 apartments in an authentic Tuscan farmhouse and 4 elegant glamping cabins nestled in the ancient olive grove. The "Venere's Paradise" cabin disappears among the olive trees, offering breathtaking views from its veranda over the hills. With a large panoramic swimming pool and the opportunity to taste our exquisite oils and wines, the experience becomes unique and unforgettable.

Top Guest favourite

Apartment in Centro Storico

5 out of 5 average rating, 18 reviews

New MiK HoUsE 2025 with Netflix

Ciao Caro ospite, abbiamo arredato la nostra casa con tutto l'amore possibile per rendere il tuo soggiorno un sogno. Ogni cosa è pensata per il benessere dell'ospite. La zona è super accessibile e centrale ma lontana da locali notturni rumorosi e caos cittadino, parcheggio gratuito a 200 metri, possibilità di arrivare in macchina davanti alla casa, vicinissimo, anche a piedi, alla stazione ferroviaria principale della città. Scoprite tutti confort che abbiamo ideato per i nostri ospiti.

Guest favourite

Apartment in Centro Storico

4.94 out of 5 average rating, 50 reviews

David Suite [Florence Centre, Luxury]

In the heart of Florence, David Suite offers a unique experience. Located in a 15th-century historic building, next to Via Tornabuoni and a stone's throw away from the train station, Duomo, Lungarno, and Ponte Vecchio, the accommodation features a king-size bedroom, marble bathroom, modern kitchen and an elegant living room with smart TV and air conditioning. Also available washer, dryer and balcony. With the comfort and luxury of our home, you'll fully enjoy the Florentine atmosphere!

Guest favourite

Villa in Figline Valdarno

4.98 out of 5 average rating, 44 reviews

The Castellaccio of Figline

L'alloggio si trova al PRIMO PIANO di una villa immersa nel verde denominata “Il Castellaccio”, che deve il suo nome alla vicinanza con le rovine del vecchio castello appartenuto alla famiglia degli Uberti. La casa gode di una magnifica vista sulla campagna circostante ed è ideale per una vacanza rilassante per famiglie o gruppi di amici, con la possibilità di visitare città d’arte e godere degli splendidi paesaggi del Chianti, nonché delle specialità enogastronomiche della zona.

Top Guest favourite

Loft in Scandicci

4.98 out of 5 average rating, 107 reviews

Wonderful Loft in Villa with Pool in Chianti

Located on the second and top floor of the "Suites le Valline" complex, the Piazzale Michelangelo loft offers a unique style in an ideal location for exploring Tuscany, a 15-minute drive from Florence and San Casciano! Treat yourself to a moment of relaxation on the beautiful panoramic terrace overlooking Florence, or cool off in the bio pool among the olive trees... and remember that all the vegetables from the Valline vegetable garden are at your disposal!

Superhost

Condo in Centro Storico

4.84 out of 5 average rating, 45 reviews

[Free Garage] 15 Min. walk from Art

⭐ NEW LISTING! Elegant Central Apartment with BALCONY and GARAGE! &#x1F463 Perfect for exploring the UNESCO center on foot 6 min from the Garden of Gherardesca → another 6 min from the Basilica dell'Annunziata → 3 min from Michelangelo's David → 5 min to Brunelleschi's Dome, Duomo. Nearby, you'll find supermarkets, lounge bars, and typical taverns, yet enjoying a peaceful location. &#x1F9D8 The perfect balance between convenience and tranquility!

Guest favourite

Villa in Loro Ciuffenna

4.91 out of 5 average rating, 23 reviews

Villa with pool & view near Florence and Arezzo

Tuscan 1700 farmhouse in dominant position with a stunning view over the Valdarno valley. Features six separate apartments with 1 or 2 bedrooms each (total 7 bedrooms plus added beds), private gardens, private swimming pool (open May - September), common lounge and kitchen, WI-FI in every apartment. For groups up to 20 persons.

Guest favourite

Apartment in San Gimignano

4.93 out of 5 average rating, 107 reviews

"Il Nespolo" Apartment - Girasole Location

The apartment "Il Nespolo", location "Girasole", is located in the historic center of San Gimignano, just 150 meters from Piazza del Duomo, in a side street of the main street. The property is in the immediate vicinity of all points of interest and at the same time away from the noise of the busiest street in the town.

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What guests are saying

In the Heart of Florence | Elegance near Duomo

5 out of 5 average rating, 3 reviews1 week ago

Fantastic apartment in a brilliant location, so close to the Duomo and high street. The apartment had everything we needed and more, making our stay effortless. Super clean and the thoughtfully equipped. The hosts are outstanding, great at communicating and couldn’t do enough for us, even recommending local restaurants and checking in to make sure we were all settled. We stayed there with two little kids and it was perfect. We would totally recommend and will be staying here again. We have recommended to family and friends already!

Condo in Centro Storico

What guests are saying

Chic Apartment Macci

4.91 out of 5 average rating, 34 reviews1 week ago

Sergio's place is fantastic and Sergio is a great host! I almost don't want to say how wonderful our experience was, for fear it will be hard to get in the future. The location is walkable to anywhere you want to be in Florence. The apartment is spacious and having two bathrooms was convenient. Sergio was incredibly responsive and just gave you the sense he was there to make your trip great. This was our first time to Italy and it is going to be hard to find places in other locations that live up to the standard Sergio and his place set.

Apartment in Centro Storico

What guests are saying

Tuscan Villa Featured Conde Nast Best Villas Italy

4.84 out of 5 average rating, 91 reviews2 weeks ago

This is a beautiful villa! We enjoyed the easy trip into Florence each day and even happened upon a Renaissance Festival in San Casciano. We came home each night to soak in the Tuscan scenery and relax at the villa. It was a perfect stay thanks to Rose and Pier!

Home in San Casciano In Val di Pesa

What guests are saying

Il Trovatore, Casa Lama Apartments, panoramic view

4.95 out of 5 average rating, 19 reviews6 months ago

Absolutely amazing place and Elettra is ready with recommendations on everything and also offered to take on one of the trips she talked about. Cheap and really amazing place up on a small mountain. You have to drive to everything, and you don't have to get in a large SUV because the roads are small. Our Volvo XC90 had to back up and give way quite a few times.

Apartment in Castelfranco Piandiscò

What guests are saying

Cala S.Quirico-House on the beach!

4.89 out of 5 average rating, 64 reviews6 months ago

The apartment is very central and is located directly on the beach. Everything necessary is within walking distance. We felt very comfortable from the beginning. Communication with Guglielmo was always straightforward and prompt. His parents - who look after the property - are warm, loving and put a lot of effort into a pleasant stay. We all liked Case del Mare very much and made our vacation on the coast of Tuscany unforgettable. We'd love to come back. Thank you very much.

Apartment in San Vincenzo