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Vacation rentals in San Gimignano

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Top-rated vacation rentals in San Gimignano

Guests agree: these stays are highly rated for location, cleanliness, and more.

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Top guest favorite
An aerial view captures the sprawling vineyards and olive groves surrounding Podere Vergianoni. The property features a salt-water pool positioned on a terrace, offering panoramic views of the lush Chianti landscape and medieval castle in the distance. Rustic buildings line the garden area.
Condo in Noce
5 out of 5 average rating, 199 reviews

Ancient 17th-century farm in Chianti, Tuscany

Podere Vergianoni is an ancient and historic property dating back to the 17th century, located in the beautiful hills of Chianti in Tuscany. The apartment is impeccably furnished in the traditional style of ancient Tuscany: wooden beams, terracotta floors, and tasteful handcrafted furnishings that will help you enjoy a pleasant stay. In the large outdoor courtyard, you'll find a saltwater swimming pool on a panoramic terrace with wonderful views of the castle, hills and vineyards, and breathtaking sunsets.

Top guest favorite
A panoramic terrace is visible, featuring a small table set with a light purple tablecloth and dark chairs. The surrounding stone wall offers views of the landscape at sunset, highlighting rolling hills and distant towers.
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 favorite
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, 216 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 favorite
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.
Vacation home in San Gimignano
4.98 out of 5 average rating, 151 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 favorite
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, 266 reviews

Casa al Gianni - Hut

Ciao, siamo Cristina e Carmelo! Vi aspettiamo a "Casa al Gianni", il nostro agriturismo tra i boschi della Montagnola Senese a soli 20 minuti da Siena. Qui la vita rallenta: Solo il profumo della terra, il canto degli uccelli e la simpatia dei nostri animali. È un invito a riscoprire la bellezza delle piccole cose, immersi nel verde della Toscana più vera. Non è solo una vacanza, è un ritorno alle origini. Questo angolo di pace vi resterà nell'anima. Vi aspettiamo!

Top guest favorite
The exterior of the castle is showcased at sunset, with vibrant orange and purple skies providing a dramatic backdrop. Stone towers rise from the landscape, surrounded by greenery and colorful flora, reflecting the historic charm of the property.
Castle in Ferrano
4.99 out of 5 average rating, 216 reviews

The Castle of Ferrano - Castle in Tuscany

Try the experience of staying in a real Castle! Il Castello di Ferrano offers to its hosts the chance of living an unforgettable experience: you will be the only guests in the castle, and everything will be for you (private pool from June to September, gardens etc..). 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.

Top guest favorite
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, 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 favorite
Apartment in San Gimignano
5 out of 5 average rating, 146 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 favorite
Apartment in San Gimignano
4.93 out of 5 average rating, 126 reviews

Apartment with panoramic garden in San Gimignano

Located close to the walls of San Gimignano, the apartment is surrounded by nature with every desirable comfort and an amazing panoramic view. The apartment consists of 1 kitchen, 1 double bedroom, 1 living-dining room, panoramic garden and reserved parking next to the house. - 2 minutes' walk from the city center, surrounded by nature - panoramic view - every desirable comfort -private parking - 1 kitchen, 1 bedroom, 1 bathroom, 2 living rooms

Top guest favorite
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, 167 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.

Guest favorite
A serene scene is presented with a stone tower beside a tranquil lagoon. Natural rock formations are reflected in the calm water, while lush greenery surrounds the area, enhancing the peaceful environment. The tower's unique architectural features add historical character to the landscape.
Tower in Fiesole
4.95 out of 5 average rating, 209 reviews

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.

Top guest favorite
Home in San Gimignano
4.99 out of 5 average rating, 209 reviews

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 vacation rentals

When is the best time to visit San Gimignano?

MonthJanFebMarAprMayJunJulAugSepOctNovDec
Avg. priceG$30,484 GYDG$29,440 GYDG$28,604 GYDG$28,396 GYDG$28,396 GYDG$29,857 GYDG$32,780 GYDG$32,780 GYDG$30,484 GYDG$29,022 GYDG$28,604 GYDG$30,901 GYD
Avg. temp7°C8°C11°C14°C18°C23°C25°C25°C21°C16°C11°C7°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 G$6,264 GYD per night before taxes and fees

  • Verified guest reviews

    Over 36,280 verified reviews to help you choose

  • Family-friendly vacation rentals

    510 properties offer extra space & kid-friendly amenities

  • Pet-friendly vacation rentals

    Find 460 rentals that welcome pets

  • Vacation 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 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!

Destinations to explore

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  3. Tuscany
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  5. San Gimignano