
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 farm stay in the woods of the Montagnola Senese, just 20 minutes from Siena. Here, life slows down: just the scent of the earth, the song of the birds and the companionship of our animals. It’s an invitation to rediscover the beauty of the little things, surrounded by the greenery of the most authentic Tuscany. It’s not just a holiday; it’s a return to our roots. This haven of peace will stay with you in your heart. We look forward to welcoming you!
ValueFamilyBreakfast
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 characteristic renovated Tuscan house just 7 km (25 minutes) from the parking lot in the historic centre 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 a short distance away. You can easily get there by car (including a reserved parking space for guests) or by bus, which is 300 metres away.
FamilyLocationCleanliness
4.92 out of 5 average rating, 148 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
FamilyValueBeach
4.78 out of 5 average rating, 249 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.
FamilyLocationOutdoor spaces
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.
LocationValueAccess
4.97 out of 5 average rating, 161 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
LocationValueCheckout
5.0 out of 5 average rating, 123 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.
FamilyLocationCheckout
4.98 out of 5 average rating, 165 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.
ValueFamilyLaundry
4.96 out of 5 average rating, 142 reviews
PIERFANTINI private Chianti house ♿️ 🏊♂️ 🐶
Pierfantini is a rustic farmhouse. It is located on a hill in the middle of a natural park. Isolated from the vitta, the nearest town is the medieval village of San Gusmè. The house is renovated and the ground floor adapted for disabled people or wheelchair users There are three apartments but I never rent them separately. The house rent is for all the property
LocationFamilyBeach
4.91 out of 5 average rating, 100 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.
FamilyValueSleep quality
4.87 out of 5 average rating, 263 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).
LocationFamilyShared spaces
4.92 out of 5 average rating, 113 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
LocationValueLong stay
4.81 out of 5 average rating, 120 reviewsPopular amenities for San Gimignano holiday homes
Family-Friendly holiday homes

Charming farmhouse with garden, views & pool
FamilyValueWalkability
4.92 out of 5 average rating, 233 reviews
Stunning Tuscan apartment for 2
FamilyLocationCleanliness
4.9 out of 5 average rating, 130 reviews
Apartment - Fattoria del Turricchio
FamilyValueLaundry
4.83 out of 5 average rating, 211 reviews
[Traditional Cozy House] Garden & Viewpool Apt
ValueLocationPets
4.91 out of 5 average rating, 117 reviews
1-Coral House with private parking
LocationFamilyQuiet
4.91 out of 5 average rating, 32 reviews
Tuscan House with Private Jacuzzi in Chianti
ValueLocationHeating
4.95 out of 5 average rating, 97 reviews
Apartment La Roccaia
LocationFamilyLong stay
4.94 out of 5 average rating, 50 reviews
The Cottage
FamilyValueWalkability
4.83 out of 5 average rating, 42 reviewsHoliday home rentals with a patio

I Rosai apartment on the Florentine hills
LocationValueWalkability
4.9 out of 5 average rating, 270 reviews
Il Toscano - New with terrace in downtown Greve
FamilyLocationAir conditioning
4.93 out of 5 average rating, 106 reviews
City Centre Patio - 10 mins to Duomo
ValueLocationView
4.81 out of 5 average rating, 152 reviews
★ Romantic apartment & stunning view of Tuscany ★
FamilyValueHot tub
4.86 out of 5 average rating, 22 reviews
Tuscany Country House, Central Chianti, Pano Views
FamilyLocationHeating
4.98 out of 5 average rating, 46 reviews
HOUSE ABOVE THE CHIANTI. WITH GARDEN AND POOL
ValueFamilyBiking
4.99 out of 5 average rating, 78 reviews
Tuja
LocationFamilySleep quality
5.0 out of 5 average rating, 35 reviews
Podere le Fonti - Pet Friendly - 15 min to San Gimignano
LocationFamilyDecor
4.98 out of 5 average rating, 41 reviewsHoliday home rentals with a washing machine and dryer

Chianti Panorama | House with 3 En-Suite Bathrooms
ValueFamilyComfort
4.95 out of 5 average rating, 146 reviews
Zen Island downtown Florence, new apartment for 6
FamilyLocationAir conditioning
4.94 out of 5 average rating, 102 reviews
Tuscan Nature Views From Casa Gave
FamilyValueBackyard
4.95 out of 5 average rating, 310 reviews
Melarancio Residence
FamilyLocationAmenities
4.91 out of 5 average rating, 358 reviews
SMN Luxury Secret Garden View
FamilyValueWalkability
4.95 out of 5 average rating, 115 reviews
Podere Docciolino Vacation Home
LocationValueShared spaces
4.98 out of 5 average rating, 166 reviews
Duomo Charme – A few steps from the Duomo
ValueLocationWi-Fi
4.74 out of 5 average rating, 145 reviews
TOSCANELLA APT. AMBRA
FamilyLocationWalkability
4.91 out of 5 average rating, 248 reviewsWhen is the best time to visit San Gimignano?
| Month | Jan | Feb | Mar | Apr | May | June | July | Aug | Sept | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $156 AUD | $157 AUD | $228 AUD | $202 AUD | $229 AUD | $204 AUD | $229 AUD | $249 AUD | $247 AUD | $198 AUD | $153 AUD | $249 AUD |
| 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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- Holiday home rentals Siena
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- 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)
- Stazione Santa Maria Novella
- Cala Violina
- Mugello Circuit
- Parco Nazionale delle Foreste Casentinesi, Monte Falterona e Campigna
- Mercato Centrale
- Spiagge Bianche
- Pisa Centrale Railway Station
- Fortezza da Basso
- Gulf of Baratti
- Uffizi Gallery
- Piazza della Repubblica
- Parco delle Cascine
- Piazzale Michelangelo
- Palazzo Vecchio
- Del Chianti
- 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
- Workouts Tuscany
- Tastings Tuscany
- Galleries Tuscany
- Outdoors Tuscany
- Food tours Tuscany
- Dining Tuscany
- Museums Tuscany
- Performances Tuscany
- Shopping and fashion Tuscany
- Art workshops Tuscany
- Cultural tours Tuscany
- Things to do Italy
- Workouts Italy
- Shopping and fashion Italy
- Food tours Italy
- Cooking Italy
- Flying Italy
- Cultural tours Italy
- Wellness Italy
- Tastings Italy
- Wildlife Italy
- Landmarks Italy
- Museums Italy
- Performances Italy
- Art workshops Italy
- Dining Italy
- Galleries Italy
- Outdoors Italy
- Architecture Italy
- Water sports Italy







