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Holiday rentals in Colle di Val d'Elsa

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Top-rated holiday rentals in Colle di Val d'Elsa

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

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Guest favourite
A panoramic view of an ancient Tuscan village is depicted, showcasing stone buildings and a prominent clock tower. The landscape features rolling hills in the background, with trees partially obscuring the view. The warm tones of the architecture contrast with the blue sky.
Flat in Colle di Val d'Elsa
4.78 out of 5 average rating, 382 reviews

Ancient Apartment Steeped in History 052012LTN0001

Hi, I'm Laura. I furnished my apartment with the grace and love of those who were born there, to allow those who come to breathe the familiar and peaceful atmosphere of an ancient Tuscan village. From the attic, you can admire the battlements of the Castle, which welcomes you with the grandeur of its walls, the Civic Tower, the Cathedral and the Palazzo del Campana, and the view of the green countryside. The high ceilings, the huge walls, the chandeliers that fall from above, testify to the ancient heritage.

Guest favourite
Home in Asciano
4.96 out of 5 average rating, 132 reviews

Palazzo Monaci - Pool in the Crete Senesi

Welcome to Palazzo Monaci! An oasis of nature and unique beauty, in the heart of the Crete Senesi, in Tuscany. A residence with a pool and a breathtaking view of the Crete Senesi. Perfect for couples or families looking for a relaxing vacation. The location is perfect for exploring the surrounding areas. You can hike in the Tuscan countryside, visit the characteristic medieval villages, taste the delicious local wines, and immerse yourself in the culture and history of this fascinating region.

Top guest favourite
Home in Colle di Val d'Elsa
4.96 out of 5 average rating, 281 reviews

Casa per la Costa – Colle di Val d'Elsa

In the center, a completely renovated, cozy and quiet historic house from the 1300s, equipped with every comfort. Independent entrance, kitchen, living room and bathroom and upstairs double bedroom and bathroom. Located 100 meters from Piazza Arnolfo and 200 meters from the historic center, for those traveling by bus the stop is just 200 meters away. Convenient location for visiting Siena, Florence, San Gimignano, Volterra, Chianti and for walking the Via Francigena or taking the Elsa Trail.

Guest favourite
A modern kitchen is shown, featuring a gas stove, oven, and minimalistic cabinetry. A stone wall adds rustic charm, while soft lighting enhances the warm ambiance. A table is set with glasses and a bottle of wine, inviting a relaxed dining experience.
Flat in Colle di Val d'Elsa
4.92 out of 5 average rating, 112 reviews

Il Poggino Apartment

Strategic location with beautiful view of the highest part of the village. The apartment, recently renovated while maintaining the original rustic architecture and furnished in a modern style, has 1 living room with equipped kitchen, TV, air conditioning, and 2 bedrooms, 1 double and 1 triple, each equipped with private bathroom with shower, Wi-Fi connection and air conditioning. Private parking, a separate entrance with a covered courtyard and a small garden are also available to our guests.

Top guest favourite
A stone structure with a tiled roof is framed by greenery, surrounded by rolling hills. A spacious outdoor area features a wooden table, inviting relaxation. Large trees and thriving shrubs enhance the tranquil setting, with a backdrop of a serene sunset illuminating the landscape.
Home in San Casciano In Val di Pesa
4.98 out of 5 average rating, 234 reviews

Sunset on Chianti Classico

Se cercate una location idilliaca nel cuore del Chianti classico, immersi nei vigneti e oliveti delle splendide colline toscane, nel podere di una Villa storica del ‘500, allora venite nel nostro fienile!! Ha una posizione dominante con una vista strepitosa, dove è possibile godersi tramonti mozzafiato. La totale indipendenza della casa, l'accogliente giardino, il grande loggiato permettono di trascorrere soggiorni in totale tranquillità. Le nostre recensioni sono la vostra migliore garanzia.

Top guest favourite
The living area features polished wooden floors and a cozy sofa. A painting is displayed above a brick fireplace, while a television is placed on a small cabinet. A staircase with a wooden handrail leads to the upper level, illuminated by soft wall lights.
Apartment in Colle di Val d'Elsa
4.98 out of 5 average rating, 238 reviews

DorminColle - Tuscan-style apartment

Appartamento luminoso e spazioso, composto da confortevole camera matrimoniale con tv, condizionatore portatile, con al suo interno bagno completo di doccia e servizi igienici. Terzo posto letto situato in caratteristica area soppalcata con travi in legno dotato di letto. Ampia cucina dotata di lavastoviglie, macchina del caffè, microonde, erogatore acqua filtrata, Salone con tv e divano, sala da pranzo con vista sul Borgo Antico. Parcheggio gratuito a 150 mt visibile dell’appartamento.

Top guest favourite
A medieval stone tower stands tall against a clear blue sky, showcasing its historic architecture. The narrow road lined with greenery leads to the entrance, with the texture of the stonework and windows highlighted, inviting guests to explore its unique charm.
Tower in San Quirico d'Orcia
5 out of 5 average rating, 110 reviews

Luxurious Medieval Tower & Private Concierge

It’s rare to find a place that’s not only romantic but also historic & truly one of a kind. La Torretta is part of Toscana a Due—a medieval tower with a huge garden & olive trees, right in the heart of San Quirico, overlooking the Val d’Orcia. The 1000-year-old building has been redesigned as a blend of heritage & antique luxury. With our unique tailored concierge service and a warm welcome into our family’s life, we share our traditions, history, and Tuscany’s hidden treasures with you.

Guest favourite
Apartment in Colle di Val d'Elsa
4.97 out of 5 average rating, 69 reviews

La Torre di Canonica

Enchanting Historic Home in the Center of Colle di Val d'Elsa. Welcome to living history! This charming historic residence, located in the heart of the historic center of Colle di Val d'Elsa, is a unique opportunity for those looking for a living experience in a tower house dating back to 1300. The structure is located in a strategic point on the Via Francigena, offers an unforgettable panorama and is very close to major cities like Siena, Casole d'Elsa, San Gimignano, Firenze

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, 218 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
Apartment in San Gimignano
5 out of 5 average rating, 50 reviews

AnticaVista, Luxury Apartment with Tower Views

A hidden gem nestled within the ancient walls of a 14th-century tower house, right in the heart of San Gimignano, a UNESCO World Heritage Site. This one-of-a-kind apartment is where history meets contemporary elegance. Look out the window and you’ll feel like you can almost touch the medieval towers. The view is breathtaking: unforgettable glimpses of the majestic Torre Grossa, framed by the iconic skyline that earned San Gimignano its nickname, the “Medieval Manhattan.”

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, 269 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 favourite
An elegant medieval castle is surrounded by lush olive trees, showcasing its stone façade and characteristic towers. Soft lighting emanates from the windows, creating a warm ambiance as dusk approaches. The castle is set against a backdrop of gently rolling hills, enhancing its historic charm.
Castle in Barberino Tavarnelle
4.89 out of 5 average rating, 124 reviews

Suite in Castello di Valle

A unique experience in a historical dwelling located in the Chianti region. This medieval castle is situated in a strategic position, surrounded by the major Tuscan touristic attractions. The suite is at the entrance floor level: double bedroom with bathroom, sofa bed for two people, kitchenette, fireplace.

Popular amenities for Colle di Val d'Elsa holiday rentals

When is the best time to visit Colle di Val d'Elsa?

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Avg. price$126 SGD$121 SGD$121 SGD$121 SGD$118 SGD$118 SGD$121 SGD$130 SGD$121 SGD$122 SGD$118 SGD$130 SGD
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Frequently Asked Questions

  • What are the best places to stay in Colle di Val d'Elsa?

    Stay in the historic upper town for a medieval atmosphere or choose modern apartments near the main piazza for easy access to cafés and shops. Agriturismos around the outskirts are often suggested for travelers seeking a countryside setting.

  • What are the best things to do in Colle di Val d'Elsa with kids?

    Families can try interactive workshops at the crystal museum, picnic in Elsa River Park, or enjoy gelato while wandering old town lanes. Many green spaces nearby are suitable for relaxed outdoor games and exploration.

  • What are some of the best things to do in Colle di Val d'Elsa?

    Stroll the Via della Misericordia in the old town, enjoy tastings at artisan gelaterias, and explore exhibits in the crystal museum. Art walks, handicraft shopping, and exploring local cafés are popular ways to connect with the town’s traditions.

  • How is the weather in Colle di Val d'Elsa?

    Colle di Val d'Elsa typically has mild winters around 36–53°F (2–11°C), with wetter months in autumn and winter. Summers are often warm and dry, with daytime highs near 90°F (32°C); spring and fall have pleasant temperatures for exploring outdoors.

  • When is the best time to visit Colle di Val d'Elsa?

    Late spring and early autumn are often recommended for mild weather, fewer crowds, and countryside colors. Summer brings warm, dry days ideal for outdoor exploring and local festivals, while winter visits reveal a quieter town atmosphere.

  • What are the best places to visit in Colle di Val d'Elsa?

    Colle di Val d'Elsa has the Museo del Cristallo, which highlights the area’s glassmaking tradition, and the upper town with its medieval gate and narrow lanes. Piazza Arnolfo is often recommended for its lively atmosphere, and the historic city walls draw those interested in architecture and history.

  • What are some hiking trails in Colle di Val d'Elsa?

    Colle di Val d'Elsa has scenic walking paths along the Elsa River Park, where visitors can enjoy natural pools and woodland trails. Trails often wind past mills, historic bridges, and open countryside landscapes.

  • What are some family activities we can do in Colle di Val d'Elsa?

    Families can explore the upper town’s medieval streets, visit hands-on crystal workshops, or picnic near the Elsa River Park’s natural pools. Interactive museums and local parks are popular for children to play and learn.

  • What are some of the best day trip ideas from Colle di Val d'Elsa?

    Explore nearby hill towns known for wine and olive oil, or visit historic sites such as castles and Roman roads in the surrounding region. Countryside villages and scenic vineyard tours are also frequently suggested.

  • Are there any pet friendly accommodations available in Colle di Val d'Elsa?

    Many accommodations in Colle di Val d'Elsa welcome pets, including countryside stays and town apartments with outdoor space. Hosts often highlight proximity to walking trails, parks, and pet-friendly cafés.

  • What are some local tips for visiting Colle di Val d'Elsa?

    Explore the historic upper town for stone streets and artisan shops, and try local gelato in the main piazza. Visiting early in the day often means fewer crowds, while nearby countryside trails can offer quiet nature walks.

  • What is Colle di Val d'Elsa known for?

    Colle di Val d'Elsa is known for its crystal glass production, well-preserved medieval architecture, and vibrant artisan community. Visitors often explore its historic core for local shops, museums, and food traditions.

  • What are the best hidden gems to explore in Colle di Val d'Elsa?

    Art studios tucked in the historic center, quiet viewpoints over the Elsa Valley, and bakeries known for traditional pastries are often recommended. Small contemporary galleries and artisan workshops can also be found around the upper town.

  • What are the best foods to try in Colle di Val d'Elsa?

    Tuscany’s flavors shine here, with pici pasta, wild boar ragù, and wood-fired breads often recommended. Look for local pastries such as ricciarelli and cantucci, and enjoy fresh gelato in town squares.

  • What should I bring for a trip to Colle di Val d'Elsa?

    Comfortable walking shoes are useful for cobblestone streets and hilly paths, and a light jacket is helpful as evenings can be cool. Bringing a refillable water bottle makes it easy to stay hydrated, especially in summer.

  • What is the nightlife in Colle di Val d'Elsa like?

    Colle di Val d'Elsa has a relaxed nightlife scene centered around wine bars, osterias, and cafés, especially in the main piazza and upper town. Occasional live music nights and open-air gatherings often bring a lively, welcoming atmosphere.

  • What are the most popular events or festivals in Colle di Val d'Elsa?

    Colle di Val d'Elsa has seasonal celebrations such as summer concerts, outdoor cinema, and local markets highlighting Tuscan crafts and food. Folkloric celebrations and art events are often suggested during the spring and summer months.

  • Are there family friendly vacation rentals in Colle di Val d'Elsa?

    Colle di Val d'Elsa has a range of family-friendly vacation rentals, including homes with spacious gardens, kitchens, and multiple bedrooms. Many hosts in the area share local tips for exploring nearby parks and enjoying town traditions together.

Quick stats about holiday rentals in Colle di Val d'Elsa

  • Total holiday rentals

    Explore 160 holiday rentals in Colle di Val d'Elsa

  • Nightly prices starting at

    Colle di Val d'Elsa holiday rentals start at $26 SGD per night before taxes and fees

  • Verified guest reviews

    Over 6,090 verified reviews to help you choose

  • Family-friendly holiday rentals

    60 properties offer extra space & child-friendly amenities

  • Pet-friendly holiday rentals

    Find 50 rentals that welcome pets

  • Holiday rentals with a pool

    10 properties feature pools

  • Rentals with dedicated workspaces

    50 properties have a dedicated workspace

  • Wifi availability

    140 of Colle di Val d'Elsa holiday rentals include wifi access

  • Popular amenities for guests

    Guests love Kitchen, Wifi and Pool across Colle di Val d'Elsa rentals

  • 4.8 Average rating

    Colle di Val d'Elsa stays are highly rated by guests – averaging 4.8 out of 5!

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