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Holiday houses in San Gimignano

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Top-rated holiday rentals in San Gimignano

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Top Guest favourite
A rustic building is seen under a starry night sky, with a partial roof providing shelter. Soft light glows from the interior, illuminating the entrance. Lush greenery and trees surround the scene, adding depth to the serene nighttime landscape.
Farm stay in Simignano
4.92 out of 5 average rating, 261 reviews

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!

Top Guest favourite
An aerial view captures Podere Vergianoni nestled in the Chianti hills, surrounded by lush vineyards. The property features a clear blue pool, shaded terraces, and carefully landscaped gardens. Rolling hills and rows of grapevines create a serene backdrop, highlighting the natural beauty of the Tuscan countryside.
Condo in Noce
5 out of 5 average rating, 324 reviews

Podere Vergianoni nestled in Chianti with a pool

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.

Top Guest favourite
An aerial view showcases the expansive grounds of La settecentesca Villa di Geggiano, surrounded by manicured gardens and lush vineyards. The main villa is prominent, with a circular driveway leading to it, while gentle hills extend into the background.
Cottage in Geggiano
4.99 out of 5 average rating, 151 reviews

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.

Top Guest favourite
The image showcases a vibrant town square surrounded by historic buildings, including the prominent Torre Salvucci Maggiore. The sky is expansive, featuring soft clouds scattered across a blue backdrop. The texture of the stone architecture provides a glimpse into the medieval influence of the area.
Tower in San Gimignano
4.94 out of 5 average rating, 126 reviews

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.

Top Guest favourite
The image showcases a view of the Torre del Diavolo framed by lush greenery. Two bottles of wine are positioned in the foreground, enhancing the peaceful garden setting. Historic buildings with textured stone facades are visible, complementing the charming medieval atmosphere.
Apartment in San Gimignano
4.98 out of 5 average rating, 165 reviews

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 is available in a private garage at a cost of €9.00 per day.

Top Guest favourite
An aerial view of the property reveals a charming red house surrounded by lush greenery. Tall cypress trees and vibrant bushes create a tranquil landscape, while an expansive lawn features relaxing loungers, inviting guests to enjoy the serene atmosphere of the Tuscan countryside.
Home in Gambassi Terme
5 out of 5 average rating, 211 reviews

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.

Top Guest favourite
A bright bedroom features a spacious bed with crisp white linens and a decorative pillow. A vivid landscape painting hangs above, while a window with wooden frames reveals a scenic view of the Tuscan hills, complemented by soft natural light filtering through sheer curtains.
Holiday home in San Gimignano
4.98 out of 5 average rating, 150 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.

Top Guest favourite
The image showcases a refreshing pool surrounded by lounge chairs and umbrellas, enhancing the outdoor relaxation area. The pool is framed by lush greenery and a stone wall, with the charming rustic house visible in the background under a clear blue sky.
Home in Barberino Tavarnelle
5 out of 5 average rating, 122 reviews

Infinity pool in Chianti area

On the Chianti hills, portion of an old stone farmhouse from the 1800s, located in S. Filippo, a small hamlet of Barberino Tavarnelle, halfway between Florence and Siena, a 30-minute drive from Florence airport, 1 hour from Pisa airport. Three bedrooms, two bathrooms, large living room with fireplace, eat-in kitchen and dining room. Magnificent view of the hills from every window! Beautiful infinity pool with whirlpool area, unheated and open from April to October.

Top Guest favourite
The image showcases the exterior of an ancient stone building within the historical walls of San Gimignano. Sunlight illuminates the textured facade, highlighting the charming architectural details, including windows and balconies. A quiet pathway leads to the entrance, surrounded by greenery.
Home in San Gimignano
4.97 out of 5 average rating, 115 reviews

Casa Maurino

"Casa Maurino", in the historic center of San Gimignano, is a delightful apartment nestled in the ancient city walls. Ideal place to spend short stays, immersing yourself in the evocative atmosphere of the medieval village. Located in a quiet and peaceful position with a panoramic terrace overlooking the Tuscan hills to indulge in romantic moments of relaxation. Independent entrance from a characteristic stone staircase, panoramic terrace. Suitable for couples.

Top Guest favourite
Apartment in San Gimignano
5 out of 5 average rating, 142 reviews

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.

Top Guest favourite
An inviting villa surrounded by lush greenery and vibrant flowers, featuring blooming rose bushes and olive trees. The gravel pathway leads to the entrance, showcasing a two-story structure with balconies. Sunlight highlights the colorful landscape, creating a serene atmosphere.
Villa in Impruneta
5 out of 5 average rating, 171 reviews

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.

Guest favourite
The rustic stone building is surrounded by vibrant pink flowers in planters, creating a natural and welcoming setting. Tall trees provide shade, while a clear blue sky adds to the serene atmosphere of the outdoor space.
Farm stay in San Gimignano
4.88 out of 5 average rating, 127 reviews

ECOLOGICAL FARMHOUSE "THE OLD OAKS"

A big apartment consisting of a kitchen and dining room at the entrance; from here you climb to the upper floor where there is a livingroom with sofa and two armchairs, a TV equipped with a DVD player. From the living room a corridor leads to a first double bedroom with private bathroom, followed by a small hallway serving two other double bedrooms with a common bathroom.

Popular amenities for San Gimignano holiday rentals

When is the best time to visit San Gimignano?

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Avg. price$250 NZD$242 NZD$235 NZD$233 NZD$233 NZD$245 NZD$269 NZD$269 NZD$250 NZD$238 NZD$235 NZD$253 NZD
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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 holiday rentals in San Gimignano

  • Total holiday rentals

    Explore 950 holiday rentals in San Gimignano

  • Nightly prices starting at

    San Gimignano holiday rentals start at $51 NZD per night before taxes and fees

  • Verified guest reviews

    Over 36,280 verified reviews to help you choose

  • Family-friendly holiday rentals

    510 properties offer extra space and kid-friendly amenities

  • Pet-friendly accommodation

    Find 460 rentals that welcome pets

  • Holiday rentals with a pool

    520 properties feature pools

  • Rentals with dedicated workspaces

    350 properties have a dedicated workspace

  • Wi-Fi availability

    910 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!

Destinations to explore

  1. Airbnb
  2. Italy
  3. Tuscany
  4. Siena
  5. San Gimignano