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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
The entrance features a green door leading into the interior space, with a welcome mat visible on the tiled floor. A traditional coat rack stands beside a framed floral art piece. A small table is present, adorned with a festive decoration and a Christmas tree.
Condo in San Gimignano
4.9 out of 5 average rating, 103 reviews

Residence "La Porta Verde"

Studio apartment of about 40 square meters near the historic center, a short walk from Porta S. Matteo. Recently renovated, it is equipped with Wi-Fi and air conditioning. Entrance into the living room where we find the dining room and sofa/bed. A piece of furniture separates the sleeping area with a double bed. Kitchen with microwave, oven, dishwasher and washer-dryer. Bathroom with shower, toilet and a small closet. Parking is available nearby. Great for families! Very happy and honored to welcome you Patrizia

Top Guest favourite
Aerial view showcases the rustic property nestled among the lush vineyards. Sunlight casts a warm glow over the hills, while a sparkling pool is situated near the residences, surrounded by greenery. The tranquil landscape includes gently rolling hills and rows of grapevines.
Condo in Noce
5 out of 5 average rating, 307 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
Home in San Gimignano
4.99 out of 5 average rating, 202 reviews

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!

Guest favourite
Apartment in San Gimignano
4.96 out of 5 average rating, 244 reviews

Casa Irene

Casa Irene is a delightful Tuscan-style apartment, located on the second and top floor of a building just a 5-minute walk from the center, 50 meters to Porta San Matteo and another 50 meters to Via Francigena. Given the secluded location, it is easily reached by car to park in the immediate free parking. The apartment equipped with WiFi and air conditioning is divided into an open space living room/kitchen, bedroom and bathroom with shower and a large terrace overlooking the walls of San Gimignano

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, 156 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.Possibility of parking in a private box for a fee at a cost of € 9.00 x day.

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, 144 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
A historical square is depicted, featuring a tall stone tower and an ancient church with a circular window. Steps lead up to the church entrance, surrounded by visitors enjoying the open space. Blue sky provides a bright backdrop to the scene.
Condo in San Gimignano
4.96 out of 5 average rating, 313 reviews

Cozy Apt overlooking the Duomo, San Gimignano

Super central apartment located right in the main Piazza of San Gimignano overlooking the Duomo. Great location in the vibrant heart of the town with all services at your doorstep: chemist, cafés, restaurants, groceries, museums, tourist information office.. Walking out through Porta San Giovanni you'll find the Coop supermarket and the bus stop to Poggibonsi railway station (12km away). Car parks are also located outside the city walls, just a few minutes' walk away.

Top Guest favourite
A rustic stone staircase leads to a wooden entrance door framed by colorful potted plants. The door, featuring a decorative handle, is set against a textured stone wall, with a lantern placed on the side for soft lighting.
Home in San Gimignano
4.97 out of 5 average rating, 106 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
A bright living area features a light wooden dining table surrounded by four white chairs. A dark blue sofa is positioned against the wall, and two windows allow natural light to enhance the space. The view outside includes hints of greenery.
Apartment in San Gimignano
5 out of 5 average rating, 112 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
A serene outdoor pool area is framed by lush green grass, featuring several sun loungers and umbrellas. The clear water in the pool reflects the blue sky, while tall cypress trees provide a natural backdrop to the tranquil setting.
Farm stay in Greve in Chianti
4.99 out of 5 average rating, 447 reviews

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.

Guest favourite
Holiday home in San Gimignano
4.8 out of 5 average rating, 106 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

Guest favourite
Cottage in San Gimignano
4.84 out of 5 average rating, 235 reviews

Countryside Cottage With View - Le Rondini apt

The cottage is part of a charming traditional Tuscan farmhouse, built in stone and situated in one of the most beautiful areas of Tuscany.A lovely garden surrounds the house and has magnificent views of the medieval town with its famous towers.

Popular amenities for San Gimignano holiday rentals

When is the best time to visit San Gimignano?

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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 920 holiday rentals in San Gimignano

  • Nightly prices starting at

    San Gimignano holiday rentals start at $42 AUD per night before taxes and fees

  • Verified guest reviews

    Over 35,670 verified reviews to help you choose

  • Family-friendly holiday rentals

    500 properties offer extra space and kid-friendly amenities

  • Pet-friendly accommodation

    Find 410 rentals that welcome pets

  • Holiday rentals with a pool

    510 properties feature pools

  • Rentals with dedicated workspaces

    310 properties have a dedicated workspace

  • Wi-Fi availability

    880 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