
Vacation rentals in San Gimignano
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Top-rated vacation rentals in San Gimignano
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Podere Vergianoni immerso nelChianti con piscina
Podere Vergianoni is an ancient and authentic farmhouse dating back to the 17th century located in the beautiful hills of Chianti in Tuscany. The apartment is impeccably furnished in the traditional local style of old Tuscany: ancient wooden beams, terracotta floors, and unique furniture. In the large outdoor courtyard, you'll find a large swimming pool on a panoramic terrace at your disposal, overlooking the valley with breathtaking views of vineyards and olive groves, where you can enjoy spectacular sunsets.

Garden House
"Casa del giardino" ...... a blooming oasis within the medieval walls.. The owners Mario and Donella would like to offer you a unique vacation in San Gimignano. You can enjoy the wonderful garden, an extraordinary oasis of peace and silence, in the city center, for the exclusive use of those who rent the apartment. Thus, reading a book, relaxing in the sun, sipping an excellent glass of Chianti or having breakfast surrounded by greenery and among the flowers of this garden will be a memorable experience!

Apartment at ground floor with garden
A refined and very central setting, between Piazza della Cisterna and Piazza del Duomo. The house has the rare value of combining a comfortable ground floor, with independent entrance, to a stunning view of the famous Devil's tower.The exclusive garden, equipped to dine outdoors, read or stay between flowers and towers, is an extraordinary oasis of peace and silence, just around the corner of the two lively main squares.Possibility of parking in a private box for a fee at a cost of € 9.00 x day.
Medieval Tower experience with Panoramic Rooftop
If you are looking for a memorable experience this is the right place for you! With its 42 mt high, the Salvucci Tower is one of the famous towers of San Gimignano and today the only one turned into a vertically-spread apartment divided into 11 floors, for a total of 143 steps. A unique and timeless place, ideal to experience something never tried before. The tower can hosts couples or small groups up to 3 people. Its panoramic rooftop boasts an incredibly breathtaking view all over the town.

Il Fienile, Luxury Apartment in the Tuscan Hills
‘Il Fienile’ is in an enchanting position immersed in the beauty of the Tuscan hills, with a breathtaking view of the surrounding countryside. It is located in the hamlet of Catignano in Gambassi Terme, just a few kilometres from San Gimignano. The house sits in a protected oasis surrounded by a beautiful private park with olive trees, a pond, pine trees and woods, where you can walk, relax and enjoy the pleasures of unspoilt nature. A unique experience entirely to be enjoyed.

The Chianti Classico Sunset
If you are looking for an idyllic location in the heart of the classic Chianti, immersed in the vineyards and olive groves of the beautiful Tuscan hills, in the farm of a historic Villa of the ‘500, then come to our barn!! It has a dominating position with a stunning view, where you can enjoy breathtaking sunsets. The total independence of the house, the cozy garden, the large loggia allow you to spend stays in complete peace of mind. Our reviews are your best guarantee.

The Castle of Ferrano - Castle in Tuscany
Try the experience to stay in a real Castle! Il Castello di Ferrano offers to his hosts the chance of doing an unforgettable experiece:you will be the only guests in the castle and everythig will be for you (private pool from June to September, gardens ecc.)Historical building, surrounded by nature, finely decorated, frescoes/moulding on the ceiling, ample terrace w/ stone and terracotta floor, private outdoor pool.. Good position. Preferably come by car.

Old hayloft on the Chianti hills
Agriturismo Il Colle is located on one of the Chianti hills. The property has been completely renovated, overlooking the Chianti valleys and enjoying splendid views of the surrounding hills and the city of Florence. The apartment is completely independent, on two internally connected floors, and features a private garden lined with centuries-old oaks and Tuscan cypresses. The restoration maintained the original Tuscan architectural style of rural barns.

The Tower
Ancient Tuscan villa, beautiful, with exclusive private garden, completely renovated, surrounded by the beautiful and gentle Tuscan hills. The villa has a breathtaking view, is very sunny, well furnished and equipped with all amenities, quiet and not isolated. The house is located in Bagnolo, a small hamlet of Impruneta at the gates of Chianti, an area of olive groves, vineyards and peace. The house is about 10 km by car from the center of Florence.

Luxury Medieval Tower - Penthouse
Step into the past... San Gimignano Luxury Medieval Tower is right in the heart of the UNESCO town. You will be caught by the sight of San Gimignano's beautiful landscapes and at the same time you will be able to enjoy the luxury amenities of in-town living: walk downstairs to the cafes, bread shop, butcher, restaurants and local shops. Hear the church bells directly from your windows. Walking distance to all of San Gimignano main attractions.

Casa al Gianni - Capanna
Hi, we're Cristina & Carmelo! We invite you to live an authentic experience in our farmhouse “Casa al Gianni” located 20 minutes from Siena. Our hallmark is simple life in close contact with nature and the animals of our farm. Immersed in the woods and the beautiful Tuscan countryside, you will spend an unforgettable vacation. This slice of paradise will remain in your heart!

Tenuta Chiudendone in Tuscany
Great place in the middle of Tuscan Hills, you will be sorrounded by nature but close to all the beautiful cities of Tuscany! We rent two apartments, one on the upper floor called Balla and one on the ground floor called Modigliani. Tell us which one you prefer. PLEASE NOTE YOU WILL NEED A CAR DURING YOUR STAY.
Popular amenities for San Gimignano vacation rentals
San Gimignano house rentals

Cercis - La Palmierina

Ancient Barn in Chianti with Pool
Gorgeous Villa with Postcard Views in Historical Florence

House with a breathless view in Tuscany

Explore Chianti from a Charming Stone House

Casa Luigi Suite with exclusive pool

Secret Garden Siena

Paluffo Stillo House
Other great vacation rentals in San Gimignano

AnticaVista, Luxury Apartment with Tower Views

Romantic House in Tuscany with jacuzzi

The Tuscan-modern dream in the center of San Gimignano

Farmholiday Villino del Grillo in San Gimignano SI

TWIN TOWER unica al mondo unique in the world

Podere Tignano, 4-bedroom villa in the Chianti!

Relaxing Tuscan country home with views

Cipressini 2 - pool and amazing views
When is the best time to visit San Gimignano?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | ﺩ.ﺇ426 | ﺩ.ﺇ386 | ﺩ.ﺇ459 | ﺩ.ﺇ499 | ﺩ.ﺇ499 | ﺩ.ﺇ525 | ﺩ.ﺇ577 | ﺩ.ﺇ577 | ﺩ.ﺇ536 | ﺩ.ﺇ459 | ﺩ.ﺇ422 | ﺩ.ﺇ459 |
| 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 |
Frequently Asked Questions
What are the best places to stay in San Gimignano?
San Gimignano has unique stays near its medieval center, countryside villas surrounded by vineyards, and cozy guesthouses within historic stone buildings. Consider choosing a location near Piazza della Cisterna or around the town walls for charming local atmosphere and easy access to main sites.
What are the best things to do in San Gimignano with kids?
Families can explore the medieval towers, climb Torre Grossa for panoramic views, or discover local history at the Museo Civico. Kids often enjoy gelato shops around Piazza della Cisterna and shaded strolls along quiet lanes.
What are some of the best things to do in San Gimignano?
Explore San Gimignano’s medieval towers, tour the Duomo di San Gimignano, and discover art in the Museo Civico. The town also has artisan shops, gelato tasting, and scenic walks around its ancient walls.
How is the weather in San Gimignano?
San Gimignano has mild winters with averages from 36–52°F (2–11°C) and warmer, drier summers that typically reach 65–90°F (18–32°C). Rain is more frequent in autumn and early spring, so packing layers and a light rain jacket is helpful.
When is the best time to visit San Gimignano?
Late spring and early autumn are often recommended for mild temperatures, blooming landscapes, and local events around the medieval town. Summer draws visitors for longer daylight hours and lively piazzas, though streets can become busier during the peak of the season.
What are the best places to visit in San Gimignano?
Popular places include Piazza della Cisterna for local activity, the Duomo di San Gimignano for frescoes, and Torre Grossa for views over terracotta rooftops. Historic lane ways and the Rocca of Montestaffoli are also often suggested.
What are some hiking trails in San Gimignano?
San Gimignano has scenic trails winding through olive groves, cypress-lined paths, and gentle hills around the town. Many hikers enjoy the Via Francigena section, which is known for its countryside panoramas and quiet rural lanes.
What are some family activities we can do in San Gimignano?
Families can participate in hands-on art workshops, sample gelato, or join guided medieval town walks. The Rocca of Montestaffoli has open spaces for kids to explore and picnic with panoramic views.
What are some of the best day trip ideas from San Gimignano?
Day trips often include exploring nearby Tuscan towns, visiting local vineyards for wine and olive oil tastings, or discovering regional markets. The surrounding countryside is known for hilltop villages, medieval castles, and scenic walking trails.
Are there any pet friendly accommodations available in San Gimignano?
Many stays in San Gimignano welcome pets, especially in countryside villas or apartments near the historic center. Look for listings mentioning gardens or nearby trails for convenient walks with your pet.
What are some local tips for visiting San Gimignano?
Visit popular piazzas early or later in the day for a quieter experience, and consider sampling locally grown saffron and white wine. Comfortable shoes help with cobblestone streets, and evenings can be cooler even in summer.
What is San Gimignano known for?
San Gimignano is known for its well-preserved medieval towers, Vernaccia white wine, and local saffron traditions. The skyline and historic center are recognized for their UNESCO World Heritage status.
What are the best hidden gems to explore in San Gimignano?
Wander lesser-known lanes around the town walls, explore artisan workshops for ceramics or woodwork, and relax in the garden of the Rocca of Montestaffoli. Some visitors enjoy small frescoed chapels tucked away from the main sights.
What are the best foods to try in San Gimignano?
Frequently suggested specialties include pappardelle al cinghiale (wild boar pasta), local cheeses, and dishes featuring saffron. Sampling the town’s renowned gelato and Vernaccia di San Gimignano white wine is also popular.
What should I bring for a trip to San Gimignano?
Bring comfortable shoes for cobbled lanes and a light rain jacket for unpredictable spring or autumn showers. A reusable water bottle and a small daypack are helpful while exploring historical sites and local markets.
What is the nightlife in San Gimignano like?
San Gimignano’s nightlife has relaxed wine bars, local cafés, and outdoor seating in central piazzas. Evenings are often spent tasting regional wines or enjoying casual music events in intimate venues around the historic core.
What are the most popular events or festivals in San Gimignano?
San Gimignano hosts medieval festivals in late spring and cultural celebrations featuring traditional music and food. Local events dedicated to Vernaccia wine and saffron are often scheduled throughout the year, drawing visitors to plazas and historic venues.
Are there family friendly vacation rentals in San Gimignano?
Many homes and apartments in San Gimignano are family friendly, often with kitchens and access to outdoor spaces. Accommodations around the town’s center or quieter surrounding areas help families enjoy the local atmosphere together.
Quick stats about vacation rentals in San Gimignano

Total vacation rentals
Explore 950 vacation rentals in San Gimignano

Nightly prices starting at
San Gimignano vacation rentals start at ﺩ.ﺇ37 per night before taxes and fees

Verified guest reviews
Over 35,560 verified reviews to help you choose

Family-friendly vacation rentals
530 properties offer extra space & kid-friendly amenities

Pet-friendly vacation rentals
Find 410 rentals that welcome pets

Vacation rentals with a pool
550 properties feature pools

Rentals with dedicated workspaces
300 properties have a dedicated workspace

Wi-Fi availability
900 of San Gimignano vacation rentals include wi-fi access

Popular amenities for guests
Guests love Gym, BBQ grill, and Laptop-friendly workspace across San Gimignano rentals

4.8 Average rating
San Gimignano stays are highly rated by guests—averaging 4.8 out of 5!
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- Santa Maria Novella
- Mercato Centrale
- Piazzale Michelangelo
- Cathedral of Santa Maria del Fiore
- Basilica of Santa Maria Novella
- Spiagge Bianche
- Ponte Vecchio
- Cala Violina
- Uffizi Gallery
- Parco Nazionale delle Foreste Casentinesi, Monte Falterona e Campigna
- Piazza del Duomo (Pisa)
- Fortezza da Basso
- Gulf of Baratti
- Piazza della Repubblica
- Pitti Palace
- Parco delle Cascine
- Boboli's Garden
- Cantina Winery, Cellar and Farm Fattoria Santa Vittoria
- Spiaggia Libera
- Avignonesi Winery Fattoria Le Capezzine
- Medici Chapel
- Palazzo Vecchio
- Stadio Artemio Franchi
- Spiaggia Marina di Cecina
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