
Holiday Homes in San Gimignano
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Top-rated Holiday Homes in San Gimignano
Guests agree: These holiday homes are highly rated for location, cleanliness and more.

Casa al Gianni - Oak
Hi, we're Cristina and Carmelo! We look forward to welcoming you to “Casa al Gianni,” our agritourism facility located in the woods of the Montagnola Senese, just 20 minutes from Siena. Here, life slows down: There is only the scent of the earth, the song of the birds, and the companionship of our animals. It is an invitation to rediscover the beauty of the little things, surrounded by the greenery of the most authentic Tuscany. It's not just a vacation; it's a return to our roots. This peaceful haven will stay with you in your heart. We look forward to welcoming you!
4.93 out of 5 average rating, 244 reviews
[Florence Hills] Tuscan house with parking space
Our B&B offers a peaceful and quiet corner, quick and easy to reach, in a renovated, characteristic Tuscan house just 7 km (25 minutes) from the parking lot in the historic center of Florence. At Borgo Le Palaie, you can immerse yourself in the landscape of the Florentine hills among cypresses and olive trees, enjoy the view, and visit important vineyards and wineries just a short distance away. You can easily get there by car (including a reserved parking space for guests) or by bus, which is 300 meters away.
4.92 out of 5 average rating, 145 reviews
San Gimignano, Montagongolfi SIX
Wonderful apartment in the country side of San Gimignano, at about 3Km and 5min from town center by car, far from noise, but close to all you may need. The apartment is suited for 4 people with 2 bedrooms each one with its en-suite bathroom. Bedrooms have an high privacy, splitted by the living room with kitchen, featured by the huge fireplace where our ancient farmer used to sleep over a FIAT 500 seat. First floor, 20 steps, no elevator. Side view on San Gimignano city and towers on the right
4.78 out of 5 average rating, 248 reviews
Vittoria Chianti Vacations 🍇🍷
Vittoria Chianti Vacations is the ideal solution for those seeking peace and tranquility in the heart of Chianti, close to all comforts. Typical Tuscan farmhouse halfway between Florence and Siena, is located in a strategic position to quickly reach Florence, Siena, San Gimignano, Monteriggioni, Volterra and the Chianti hills. Siena Eye Laser Clinic 2 min. Private parking, two bedrooms, equipped kitchen, private bathroom, Wi-Fi, private garden, barbecue, a wonderful view of the Chianti hills.
4.94 out of 5 average rating, 205 reviews
Podere La Castellina - No. 1 COTTAGE
Independent stone and brick cottage inside the "Podere la Castellina" (former 13th century convent), in the magnificent natural park of Montagnola Senese. The cottage can comfortably accommodate 5 people and includes: - large living room with TV and fireplace - kitchen with oven - master bedroom - bedroom with three single beds - bathroom with shower Guests have access to a panoramic swimming pool, solarium and terrace with breathtaking views, equipped with a wood-burning oven and barbecue.
4.97 out of 5 average rating, 160 reviews
Chianti Craft House Badia a Passignano
Ancient house in the historic village of Badia a Passignano, completely and finely restored in 2022. The house is located exactly in the center of the village of Badia a Passignano, overlooking the abbey castle and the Chianti vineyards. The house consists of 2 bedrooms air-conditioned: 1 double bedroom with service bathroom and 1 with 2 single beds and the possibility of a third with sofa chair; a full bathroom with shower, a full kitchen with washing machine and dishwasher, dining area
5.0 out of 5 average rating, 121 reviews
Breathe in Tuscany: 180° view of the hills
Please note that the second bedroom is divided from the hallway by a curtain and not by a door. Experience San Gimignano with a splendid view of the Tuscan hills! In the heart of San Gimignano, experience the city with a separate entrance, second floor and breathtaking views of the Tuscan hills. Private parking is available upon request. Entrance, living room, 2 double bedrooms, kitchen and large bathroom. city tax to be added to the price, €2.50 per person per night.
4.98 out of 5 average rating, 163 reviews
La Casa dei Ricordi - car/motorcycle garage at 650m
Welcome to La Casa dei Ricordi, a 17th-century home full of soul: this is where I was born and raised. Today, it opens its doors to offer you an authentic experience. Located in an incredibly quiet and peaceful area, it’s the perfect place to relax just steps away from Piazza del Duomo and Piazza della Cisterna. A charming retreat in the heart of the historic center, where history meets the peace of a true family home.
4.96 out of 5 average rating, 139 reviews
[Authentic StoneHouse]Jacuzzi & Viewpool Apartment
Nestled in a medieval village in the heart of Chianti, this exclusive historical apartment blends Tuscan charm with refined contemporary design. Enjoy a panoramic pool overlooking the hills, multiple terraces, and a unique hot tub Jacuzzi suite and bathroom carved in travertine. Designed for two, it’s the perfect place to slow down, reconnect, and experience Tuscany in total peace.
4.89 out of 5 average rating, 320 reviews
Michelangelo: entire space in the heart of Tuscany
Come and take a vacation at our beautiful apartment in Peccioli, Tuscany! Enjoy a renovated space, beautifully decorated, with new appliances and furniture, Air conditioner in all spaces, high-speed internet, and all you need to enjoy your time in Italy. Peccioli is a gem in the heart of Tuscany, near all the big cities and touristic attractions.
4.89 out of 5 average rating, 259 reviews
White lily with a view of Siena
Caggiolo is a completely renovated farm consisting of several apartments, with a panoramic view of Siena. Located 1 km from Ville di Corsano, just 14 km from the city. An ideal place to spend days in total relaxation and enjoy the wonders that this area offers (Chianti, Val d'Orcia, Crete Senesi etc).
4.92 out of 5 average rating, 112 reviews
San Gimignano, Tuscany
Set inside the walls of historic San Gimignano, this medieval (but fully refurbished) apartment will stir your senses. San Gimignano is right at your door. Step out into a World Heritage City 45 minutes from Florence, 35 minutes from Siena. Enjoy
4.8 out of 5 average rating, 117 reviewsPopular amenities for San Gimignano holiday homes
Family-Friendly holiday homes

Charming farmhouse with garden, views & pool
4.92 out of 5 average rating, 232 reviews
House of Poggio al Vico
4.91 out of 5 average rating, 186 reviews
Stunning Tuscan apartment for 2
4.9 out of 5 average rating, 130 reviews
1-Coral House with private parking
4.9 out of 5 average rating, 31 reviews
Tuscan House with Private Jacuzzi in Chianti
4.95 out of 5 average rating, 92 reviews
The Cottage
4.85 out of 5 average rating, 41 reviews
Apartment La Roccaia
4.94 out of 5 average rating, 48 reviews
Lo Scrigno Dei Sogni San Gimignano Apartment
5.0 out of 5 average rating, 25 reviewsHoliday home rentals with a patio

I Rosai apartment on the Florentine hills
4.9 out of 5 average rating, 270 reviews
Il Toscano - New with terrace in downtown Greve
4.93 out of 5 average rating, 104 reviews
La Selva , Country house, 130 mq, Stunning views
4.93 out of 5 average rating, 28 reviews
Tuja
5.0 out of 5 average rating, 35 reviews
Tuscan Cottage - I' Cipresso di Mirro
5.0 out of 5 average rating, 17 reviews
Glicini 1, holiday home and pool 30' from Florence
5.0 out of 5 average rating, 6 reviews
Tuscany Country House, Central Chianti, Pano Views
4.98 out of 5 average rating, 46 reviews
Casa Camelia - Your authentic Tuscan getaway
4.93 out of 5 average rating, 14 reviewsHoliday home rentals with a washing machine and dryer

Chianti Panorama | House with 3 En-Suite Bathrooms
4.95 out of 5 average rating, 146 reviews
4BR • Luxury Palazzo • Iconic Views • Pitti Palace
4.97 out of 5 average rating, 144 reviews
Zen Island downtown Florence, new apartment for 6
4.94 out of 5 average rating, 100 reviews
Tuscan Nature Views From Casa Gave
4.95 out of 5 average rating, 308 reviews
Melarancio Residence
4.91 out of 5 average rating, 356 reviews
Podere Docciolino Vacation Home
4.98 out of 5 average rating, 165 reviews
SMN Luxury Secret Garden View
4.95 out of 5 average rating, 114 reviews
Duomo Charme – A few steps from the Duomo
4.74 out of 5 average rating, 144 reviewsWhen is the best time to visit San Gimignano?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sept | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $188 NZD | $190 NZD | $275 NZD | $244 NZD | $277 NZD | $246 NZD | $277 NZD | $300 NZD | $299 NZD | $239 NZD | $185 NZD | $300 NZD |
| Avg. temp | 7°C | 8°C | 11°C | 14°C | 18°C | 23°C | 25°C | 25°C | 21°C | 16°C | 11°C | 7°C |
Destinations to explore
- House rentals San Gimignano
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- Luxury rentals San Gimignano
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- Holiday home rentals Siena
- Holiday home rentals Tuscany
- Holiday home rentals Italy
- Cathedral of Santa Maria del Fiore
- Santa Maria Novella
- Santa Maria Novella
- Ponte Vecchio
- Basilica of Santa Maria Novella
- Piazza del Duomo (Pisa)
- Cala Violina
- Stazione Santa Maria Novella
- Mugello Circuit
- Mercato Centrale
- Spiagge Bianche
- Parco Nazionale delle Foreste Casentinesi, Monte Falterona e Campigna
- Pisa Centrale Railway Station
- Uffizi Gallery
- Gulf of Baratti
- Fortezza da Basso
- Piazza della Repubblica
- Parco delle Cascine
- Del Chianti
- Piazzale Michelangelo
- Palazzo Vecchio
- Piazza della Signoria
- Pitti Palace
- Boboli's Garden
- Things to do San Gimignano
- Tastings San Gimignano
- Cooking San Gimignano
- Outdoors San Gimignano
- Food tours San Gimignano
- Things to do Siena
- Art workshops Siena
- Tastings Siena
- Museums Siena
- Food tours Siena
- Dining Siena
- Cultural tours Siena
- Outdoors Siena
- Landmarks Siena
- Wildlife Siena
- Cooking Siena
- Things to do Tuscany
- Water sports Tuscany
- Flying Tuscany
- Cooking Tuscany
- Wildlife Tuscany
- Landmarks Tuscany
- Galleries Tuscany
- Outdoors Tuscany
- Food tours Tuscany
- Dining Tuscany
- Museums Tuscany
- Performances Tuscany
- Shopping and fashion Tuscany
- Art workshops Tuscany
- Cultural tours Tuscany
- Tastings Tuscany
- Workouts Tuscany
- Things to do Italy
- Workouts Italy
- Shopping and fashion Italy
- Cooking Italy
- Food tours Italy
- Flying Italy
- Cultural tours Italy
- Wellness Italy
- Tastings Italy
- Wildlife Italy
- Museums Italy
- Performances Italy
- Art workshops Italy
- Dining Italy
- Galleries Italy
- Outdoors Italy
- Architecture Italy
- Water sports Italy
- Landmarks Italy







