Villa vacation rentals in San Gimignano

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Top-rated villa rentals in San Gimignano

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

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Guest favourite

Villa in Castellina in Chianti

4.93 out of 5 average rating, 166 reviews

The Villino Farmhouse

Entire upper floor of the newly renovated Villa Padronale in traditional Tuscan style. High ceilings with exposed beams make it cozy and perfect for families or groups of friends. In the house there are two functional large fireplaces(in the living room and kitchen). Private accommodation, not shared. The house has a large covered terrace,garden with sofas,bbq,firepit, private parking. The pool among the olive trees and vineyards is ideal for relaxing and has a private access to the shared area

Oct. 31 – Nov. 7

$719 CAD per night

Guest favourite

Villa in Monsummano Terme

4.98 out of 5 average rating, 106 reviews

Le Maggioline : your panoramic country house

Peaceful setting surrounded by olive groves but still conveniently located for sightseeing The house is a tastefully renovated old Italian home, with modern fixtures, and 4 ensuite bedrooms with panoramic views A large terrace with a veranda for eating out, a barbecue and an outdoor panoramic pool renovated in 2023 Open from April to October Some guest say “Our favorite thing about the home was sitting out at the long table every evening, sipping local wines and enjoying majestic sunsets"

Oct. 16 – 23

$910 CAD per night

Guest favourite

Villa in Siena

4.97 out of 5 average rating, 152 reviews

Virgi House

Virgi House is a 160 sqm villa, located 3 km far from Siena’s hystorical center. The villa is distributed over three floors. On the first one there is a double bedroom with bathroom and terrace, a large open space living room, a modern kitchen and a bathroom. Downstairs a double bedroom (or 2 single beds), a large bathroom, a study and a bright living room with a loggia from which you can access the private car park and the garden. The property also provides free wifi, air conditioning.

Nov. 13 – 20

$257 CAD per night

Superhost

Villa in Siena

4.88 out of 5 average rating, 257 reviews

Fascinating Villa Senese with View!

Ancient restored barn with up to 6 bedrooms and 6 bathrooms, immersed in a historic wine estate, just 6 km from Siena. Here time passes slowly according to ancient traditions. One of the most beautiful views that the Tuscan panorama can offer, exclusive swimming pool, large triple garden, BBQ, poolside table, terrace to enjoy the sunset over the medieval towers on the horizon while sipping the organic wines of the estate, original and working fireplace, parking free, WI-FI internet.

Feb. 24 – Mar. 3

$1,092 CAD per night

Guest favourite

Villa in Monticchiello

4.98 out of 5 average rating, 111 reviews

Villa unesco heritage, Jacuzzi & garden. BB Daria

Carefully renovated and refurbished over a sustained period in order to maintain the original quality of its architecture, San Lorenzo Villa is open to guests. You are invited to enjoy the beauty, comfort and privacy of a beautiful independent villa in the centre of Monticchiello, from where you can have an incredible view on the Val d'Orcia, the UNESCO heritage! Don't forget a delicious breakfast (whatever you like) in our so close typical restaurant

Mar. 19 – 26

$890 CAD per night

Guest favourite

Villa in Capannori

4.91 out of 5 average rating, 172 reviews

La Dimora Dei Conti: Indulge in Country Farmhous

Only a Four minute drive away or 20 mins walk from the city and the Lucca train station stands La Dimora Dei Conti a superb luxury apartment located in a farmhouse villa that dates back to the 15th century and now completely and painstakingly renovated to transport you to the an era of modern beauty and traditional Tuscan feeling. As soon as you enter the foyer you will feel the special atmosphere that permeates the villa.

Oct. 19 – 26

$283 CAD per night

Guest favourite

Villa in Montespertoli

4.93 out of 5 average rating, 145 reviews

Colonica in the Chianti

Beautiful portion of farmhouse immersed in Chianti with beautiful swimming pool, surrounded by vineyards and olive trees, perfectly furnished with large garden and parking spaces. It is 20 minutes from Florence, 40 from Siena and 50 from Pisa, in a few minutes you can reach Certaldo (hometown of Boccaccio) and Vinci (hometown of Leonardo Da Vinci). the house is halfway between Montespertoli and San Casciano (7km).

Jan. 12 – 19

$309 CAD per night

Superhost

Villa in Greve in Chianti

4.86 out of 5 average rating, 136 reviews

Villa La Doccia, Greve in Chianti.

Villa la Doccia is an 8-minute drive from the center of Greve in Chianti, Località Casole, The Villa in a quiet and quiet area is located inside a small farm surrounded by vineyards and olive groves. ➡️ We want you to know that we're doing everything we can to help and protect our guests by adopting a thorough and strict cleaning approach to this emergency. We disinfect and sanitize all parts of the house.

Apr. 18 – 25

$441 CAD per night

Guest favourite

Villa in Cavriglia, Arezzo

4.99 out of 5 average rating, 110 reviews

Villa Poggio a Mandria in Chianti

Villa Poggio a Mandria is the gateway to the Chianti; it is a good base to reach the most beautiful art cities of Tuscany (Arezzo, Florence, Siena, San Gimignano, Volterra) in about one hour time. On the surrounding hills there are medieval villages, which offer visitors a charming atmosphere of the past and the opportunity to take walks in an unspoiled countryside.

May 4 – 11

$820 CAD per night

Guest favourite

Villa in Impruneta

5.0 out of 5 average rating, 114 reviews

VILLA HUGE SWIMMING POOL , TENNIS C 7 kM FLORENCE

Villa di lusso a Impruneta, vicinissima a Firenze, con spettacolare piscina privata e campo da tennis privato ed una splendida vista sulle colline fiorentine. Cucina all'aperto con forno a legna. 8 + 2 ospiti, 4 camere da letto con aria condizionata, 3 bagni e 2 bagni di servizio, parco e terreno con ulivi, alberi da frutto, vigneti.

Dec. 27 – Jan. 3

$1,372 CAD per night

Guest favourite

Villa in Bagno a Ripoli

4.97 out of 5 average rating, 102 reviews

Quite old farmhouse on the hills of Florence

Two levels 800th rustic country house, on the hills surrounding the town with original forniture and a stunning view of the facing valley, a beautiful patio and large garden. 25 min driving from center, well placed for Chianti area, Siena, San Gimignano. 1hr driving to Pisa, Lucca, Volterra, Arezzo, Cortona and much more!

Jan. 2 – 9

$410 CAD per night

Guest favourite

Villa in Tignano

4.95 out of 5 average rating, 147 reviews

The best stay in Tuscany Spring

In the Chianti's heart, independent comfortable villa on top of a sunny hill surrounded by an astonish 360° view on the Tuscan Countryside btw Siena and Florence. 2800sqm fenced private garden with pool, wi-fi indoor & outdoor, sat TV, barbecue and wood pizza oven!

Apr. 24 – May 1

$730 CAD per night