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Holiday houses in Pignano

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Top-rated holiday rentals in Pignano

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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, 124 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
A charming cottage is shown with a terracotta facade and a tiled roof. A small table with two chairs is set on a patio, surrounded by potted plants. Lush greenery and trees can be seen in the background under a clear blue sky.
Guesthouse in Macciano
4.97 out of 5 average rating, 207 reviews

Tuscan cottage with an heavenly view

Heaven's Window takes your breath away. As our only guests, you will be surrounded by infinite views, endless tranquility, sounds of singing birds and calling deer. Down the valley and on your walks you may spot foxes ferrets and wild boar. Collect porcupine quills. Breathe! Halfway between Rome and Florence. Close to Siena, Val d’Orcia and countless hot springs . A private paradise surrounded by divine dining and hilltop jewels of antiquity like Montepulciano and Montalcino of sublime wines.

Top Guest favourite
A panoramic view showcases a 17th-century farmhouse surrounded by lush greenery and sprawling fields. An infinity pool is visible in the foreground, complemented by sun loungers and shaded areas. The bright blue sky is adorned with fluffy white clouds, enhancing the serene atmosphere.
Villa in Volterra
5 out of 5 average rating, 27 reviews

Luxury Villa + Annex with Jacuzzi + Pool, Chef

Exclusive stay in restored 17th-century Casale + luxury Dépendence with A/C and whirlpool tub. 24-hour assistance, personalized services on request: private chef for Tuscan, Italian, international, vegan, pizza menus, Michelin-starred chef, sommelier, grocery delivery, massages, cooking, yoga, handpan sessions. Outdoors: 5,000m² garden, infinity pool, 360° views, wood-fired oven, BBQ, patio, hammock, private parking, EV charging station. Indoors: 6 bedrooms, 3 equipped kitchens, laundry room.

Top Guest favourite
The elegantly structured Villa di Geggiano is set amidst lush vineyards and well-maintained gardens. Its classic stone facade and terracotta roof harmonize with the surrounding greenery, while neatly manicured pathways and symmetrical garden beds create a picturesque landscape under a partly cloudy sky.
Apartment in Siena
4.99 out of 5 average rating, 164 reviews

Villa di Geggiano – Alfieri Suite

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 idilic and enchanting backdrop to your vacation. Our guesthouse is located in one of the garden pavilions of the villa. 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.

Superhost
The villa features large glass doors that open to a grassy area, creating a seamless connection between indoor and outdoor spaces. Sun loungers placed on the lawn invite relaxation, while greenery surrounds the property, emphasizing its tranquil environment.
Holiday home in Campiglia
4.93 out of 5 average rating, 45 reviews

Villa Marcella

USO ESCLUSIVO della Villa dalla quale si gode uno splendido panorama sulla vallata sottostante caratterizzata dalla campagna toscana con vista in lontananza su San Gimignano. Composta da un grande soggiorno con cucina a vista, tre camere e tre bagni, e' circondata da un vasto giardino con piscina, campo da tennis e campo da basket. Tutta la villa e le strutture sono ad USO ESCLUSIVO degli ospiti in quanto viene affittata ad un nucleo per volta. Al CHECK-IN RICHIESTO DOCUMENTO OSPITI.

Top Guest favourite
An aerial view captures a natural swimming pool, surrounded by lush greenery and various lounging areas. The pool features a sandy beach-like entryway and is complemented by spaces for relaxation beneath the shade of trees.
Villa in Tavarnelle Val di Pesa
5 out of 5 average rating, 20 reviews

Luxury Chianti Villa•Natural Pool•Total Privacy

Tenuta Virgilio nel Chianti è una villa privata luxury immersa tra le colline toscane, circondata da oltre 3 ettari di uliveto. La proprietà offre una suggestiva piscina naturale con spiaggia, ampi spazi esterni e totale privacy, in un contesto autentico e panoramico nel cuore del Chianti. Da aprile piscina naturale con spiaggia privata e chiringuito. Jacuzzi e bagno turco per momenti di puro relax. Posizione strategica: 20 min Firenze, 30 Siena, 5 km San Gimignano, 8 km Certaldo.

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, 204 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 lush green garden is framed by a rustic pergola made of wooden beams. Grassy paths lead deeper into the garden, where vibrant flowers and trees provide a natural backdrop. Rolling hills and a clear blue sky are visible in the distance, creating a serene outdoor setting.
Home in Castellina in Chianti
4.98 out of 5 average rating, 127 reviews

StageROOM03 - Idyllic Chianti cottage near Siena

Set in a picturesque hamlet, overlooking the Chianti hills, this charming country house is just 10 minutes from Siena and Castellina in Chianti. Recently renovated, it blends authentic Tuscan charm with modern comforts. The house features two bedrooms, two bathrooms, a cozy living area and a fully equipped kitchen with a dishwasher, two fridges, and a washing machine. Outside, enjoy a beautiful garden and relax in the outdoor marble hot tub, soaking in the breathtaking views.

Superhost
A charming stone villa is situated amidst lush greenery, featuring a private pool in the foreground. Sunloungers are positioned beside the pool, while tall cypress trees frame the scene, creating a serene atmosphere against a backdrop of rolling hills and a blue sky with scattered clouds.
Villa in Radda in Chianti
4.89 out of 5 average rating, 9 reviews

Fienile al Corno

Fienile al Corno is a charming holiday home in the Chianti Classico, ideal for a relaxing break with family or friends. Surrounded by olive groves, vineyards, and gently rolling hills, it offers sweeping views of the typical Chianti landscape dotted with cypress trees. A well-kept garden and a private pool create the perfect setting for peaceful days immersed in nature. The house is quietly located yet perfectly positioned for exploring the region.

Top Guest favourite
A large swimming pool surrounded by a brick patio and manicured lawns is highlighted in this image. Sun loungers are positioned along the pool's edge, with lush greenery and trees creating a serene backdrop. The villa's charming structure is visible in the distance under a partly cloudy sky.
Villa in Barberino Tavarnelle
4.98 out of 5 average rating, 86 reviews

Podere Tignano, 4-bedroom villa in the Chianti!

Nestled among the rolling hills of Chianti between Florence and Siena, Podere Tignano offers breathtaking views over vineyards, olive groves, and golden grain fields. This charming Tuscan stone villa blends authentic rural character with modern comfort and welcomes up to 8 guests in 4 bedrooms. Surrounded by peaceful countryside and featuring a private swimming pool, it is the perfect retreat for those seeking relaxation, nature, and the true spirit of Tuscany.

Guest favourite
Condo in Greve in Chianti
5 out of 5 average rating, 5 reviews

Poggio ai Pianacci – Flo Apartments

Just 2 km from Greve in Chianti, the warm and familiar hospitality of Poggio ai Pianacci, composed by two indipendent apartments, welcomes you to the idyllic Chianti countryside Newly renovated, the apartment, that is part of a countryhouse, is on two levels, with a private patio in front of the living, and can comfortably accommodate up to 5 people. Garden and swimming pool are shared with the owners who live beside.

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
4.91 out of 5 average rating, 243 reviews

Casa al Gianni - Hut

Hi, we're Cristina & Carmelo! We invite you to live an authentic experience in our farmhouse “Casa al Gianni” located 20 minutes from Siena. Our hallmark is simple life in close contact with nature and the animals of our farm. Immersed in the woods and the beautiful Tuscan countryside, you will spend an unforgettable vacation. This slice of paradise will remain in your heart!

Popular amenities for Pignano holiday rentals

  1. Airbnb
  2. Italy
  3. Tuscany
  4. Pisa
  5. Pignano