
Holiday houses in San Gimignano
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Quick stats about holiday rentals in San Gimignano

Total holiday rentals
Explore 900 holiday rentals in San Gimignano

Nightly prices starting at
San Gimignano holiday rentals start at $52 NZD per night before taxes and fees

Verified guest reviews
Over 36,760 verified reviews to help you choose

Family-friendly holiday rentals
500 properties offer extra space and kid-friendly amenities

Pet-friendly accommodation
Find 460 rentals that welcome pets

Holiday rentals with a pool
490 properties feature pools

Rentals with dedicated workspaces
350 properties have a dedicated workspace

Wi-Fi availability
860 of San Gimignano holiday 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!
Top-rated holiday rentals in San Gimignano
Guests agree: these stays are highly rated for location, cleanliness and more.

Casa al Gianni - Hut
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!

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.Parking available in a private garage at a cost of €9.00 per day,6 min walk.

Florence Sunset Hills • Giogoli
Escape to the peaceful hills of Giogoli where authentic Tuscan charm meets breathtaking views of Florence.Just 15 minutes from the city center and the Chianti countryside, this elegant home is the perfect base for exploring Tuscany while enjoying quiet mornings, unforgettable sunsets, and the beauty of the surrounding landscape. Surrounded by nature but close to the region's most iconic spots, it's the ideal retreat for anyone looking for comfort, tranquility, and a genuinely Tuscan experience
Medieval Tower experience with Panoramic Rooftop
If you are looking for a unique experience in the heart of San Gimignano, this is the place for you! With its 42 mt of height, Torre Salvucci Maggiore is one of the medieval town's famous towers and today the only one turned into a vertically-spread accommodation divided into 11 floors for a total of 143 steps. A magical setting unlike any other. The tower can hosts couples or small groups of up to 3 people. At the top, the panoramic terrace awaits for you with an axtraordinary 360° city view.

Villa di Geggiano – Guesthouse
PLEASE NOTE THAT BEING IN THE COUNTRYSIDE WITH FEW PUBLIC TRANSPORTATION OTHER THAN TAXI, THE BEST WAY TO ENJOY YOUR STAY AND TO VISIT THE BEAUTIFUL SURROUNDINGS IS TO HAVE A CAR. The 18th century Villa di Geggiano, surrounded by vineyards and lovingly cared gardens, is located in the Chianti area near Siena, one of the most beautiful regions of Italy which will provide an idyllic and enchanting backdrop to your vacation. Our guesthouse is located in one of the garden pavilions of the villa.

Podere Vergianoni nestled in Chianti with a pool
Podere Vergianoni is a family-run, historic property dating back to the 1600s, located in the beautiful hills of Chianti in Tuscany. Our family can arrange a private shuttle and local experiences directly. The apartment is available for 2 adults with the option of adding a sofa bed for 2 children under 12 years of age. In the large outdoor courtyard you'll find a saltwater pool with a relaxation area on a panoramic terrace overlooking the castle and vineyards with unique sunsets.

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.

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.

The Tuscan Dream-modern in the center of San Gimignano
The Tuscan Dream, an exclusive apartment in the historic center of San Gimignano! This 100 m² apartment, located a few steps from the famous medieval towers, is the ideal base for exploring the UNESCO heritage village. The apartment has large bright spaces, a fully equipped kitchen, a living room with panoramic views of the Tuscan hills, two elegant bedrooms and two spacious bathrooms. Enjoy a spectacular view and relax at sunset with a good glass of local wine.

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.

A Big Dream in a Little Tower.
The Tower was created in the late 1800s by an illustrious Englishman, Sir John Temple Leader, in one of the oldest and most important stone quarries belonging to the Medici family. From the same quarry were extracted many important works such as the columns of the Medici chapels, the steps of the Laurenziana library .. all just 5 km from the historic center of Florence.

Romantic Garden in Historic San Gimignano
Enjoy a romantic stay in the heart of San Gimignano, inside the medieval walls.The apt features a private garden, a rare and peaceful corner where you can have breakfast, relax after exploring the town or enjoy a glass of wine in the evening. Perfect for couples looking for charm, history and quiet retreat in one of Tuscany's most beautiful villages.
Popular amenities for San Gimignano holiday rentals
Other great holiday rentals in San Gimignano

AnticaVista, Luxury Apartment with Tower Views

Private Courtyard | 3BR/3BA | Garage

The Penthouse of Dreams

Luxury Medieval Tower • Exclusive Chianti Stay

Tuscan House with Private Jacuzzi in Chianti

Experience Real Tuscany from our Country Home

Cipressini 2 - pool and amazing views

Fabulous 3Br Villa with 360° Views!
When is the best time to visit San Gimignano?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sept | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $253 NZD | $244 NZD | $237 NZD | $235 NZD | $235 NZD | $247 NZD | $272 NZD | $272 NZD | $253 NZD | $240 NZD | $237 NZD | $256 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 |
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.
Destinations to explore
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- 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
- Uffizi Gallery
- Pisa Centrale Railway Station
- Spiagge Bianche
- Parco Nazionale delle Foreste Casentinesi, Monte Falterona e Campigna
- Fortezza da Basso
- Piazza della Repubblica
- Gulf of Baratti
- Parco delle Cascine
- Piazzale Michelangelo
- Del Chianti
- Pitti Palace
- Boboli's Garden
- Palazzo Vecchio
- Piazza della Signoria
- Medici Chapel
- Stadio Artemio Franchi
- Things to do San Gimignano
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