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Holiday houses in Caldana di Sopra

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Top-rated holiday rentals in Caldana di Sopra

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

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Top Guest favourite
An elegantly furnished living room features classic decor, including a chandelier and ornate details. Large windows offer views of the city's architectural highlights. Comfortable seating arrangements, including a tufted sofa and armchairs, are arranged around a glass coffee table, enhancing the room's inviting ambiance.
Home in Siena
4.96 out of 5 average rating, 156 reviews

Domus Nannini - Loggia Salimbeni SPA

Apartment of 200 sqm furnished with precious classical furniture and very spacious rooms: 13 windows overlooking the old town, each window offers a unique view of the city. Big and spacious lounge with peerless view on the begin of Banchi di Sopra, Piazza Salimbeni and the headquarter of the Monte dei Paschi, formed by the noble palaces Tantucci, Salimbeni and Spannocchi. Second lounge with library, sofa-bed and the same exclusive view. 2 large bedrooms with city-views and king-size beds. 3 bathrooms one with jacuzzi and one with shower. A long corridor that crosses the apartment, spacious entrance and private terrace on the internal courtyard. Third lounge with sofa-bed and city-view. Dining room with panoramic views of the Duomo of Siena and Basilica of San Domenico which stand out over the medieval roofs of Siena a few meters from us. Fully equipped kitchen with laundry area. It occupies the entire second floor our 1600's palace and offers unique and privileged views of Siena and its architectural wonders. We are on Banchi sopra Sopra, the main course of the historical center of Siena, below the house you will find the best shops in the center with all the brands of high fashion, lots of restaurants; Wineries, Bars and Supermarkets with typical Tuscan products.

Top Guest favourite
An outdoor patio area features rustic furnishings and is framed by gracefully draping curtains. The space is adorned with comfortable seating and a communal dining table, set against a backdrop of tall cypress trees and a clear blue sky, inviting relaxation in a serene environment.
Home in Simignano
4.97 out of 5 average rating, 194 reviews

Casa al Gianni - The Simignano Barn

Transformed from a former barn, this luxurious retreat offers 5 bedrooms, 4 bathrooms, a large, fully equipped kitchen, a spacious living room, and a large private garden with parking, a hot tub, a patio with sofas, a BBQ, a fire pit, and an outdoor kitchen. Ideal for those seeking a unique experience, it combines rustic charm with modern comforts. Perfect for families or groups, it promises magical evenings under the stars, complete with relaxation in the hot tub and al fresco dining. A memorable getaway awaits you in this slice of paradise!

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Guest favourite
Home in Siena
4.96 out of 5 average rating, 23 reviews

Private House for 4P – La Capanna Di Azzurra

Ideal for families, couples or friends looking for an elegant and welcoming home, this house is designed for those who want to experience the Tuscan countryside without sacrificing the comfort of the city. Imagine a breakfast looking at the profile of Siena, days between art, wine and nature, and the return at sunset, when the light warms the stone and the silence restores the authentic rhythm of these places. A practical, charming and scenic retreat, perfect for visiting Siena and its surroundings!

Top Guest favourite
An aerial view captures the charming layout of the property surrounded by lush greenery, showcasing a spacious pool area with sun loungers. The rustic buildings blend with the natural landscape, and rolling hills stretch into the distance, emphasizing the tranquility of the location.
Holiday home in Sovicille
4.99 out of 5 average rating, 83 reviews

Podere La Castellina - No. 6 ROSETO

Stone and brick apartment inside the "Podere la Castellina" (former 13th century convent), in the magnificent natural park of Montagnola Senese. The apartment located on the first floor can comfortably accommodate 6 people (4+2) and includes: - double living room with TV - kitchen with oven and induction stove - two double bedrooms - two bathrooms with shower Guests have access to a panoramic swimming pool, solarium and terrace with breathtaking views, equipped with a wood-burning oven and barbecue.

Guest favourite
A rustic stone house sits amidst lush greenery, surrounded by rolling hills and distant mountains. The landscape showcases varying shades of green, while a clear sky with scattered clouds adds to the serene environment. The area is spacious, offering a sense of tranquility.
Home in Pievescola
4.91 out of 5 average rating, 99 reviews

Borgo Ripostena – No. 10 Hut

Charming cottage in the heart of Tuscany on a peaceful property. It is surrounded by a big private garden and has a marvelous panoramic terrace with stunning views over San Gimignano and the Chianti Hills. PRIVACY: EACH APARTMENT HAS A PRIVATE ENTRANCE AND TERRACE FOR TOTAL PRIVACY CLEANING: APARTMENTS ARE DISINFECTED WITH CERTIFIED EQUIPMENT BEFORE EACH ARRIVAL POOL: EACH APARTMENT HAS A DESIGNATED SPACE RESERVED AT THE POOL. SMART SERVICES: WEB CHECK-IN AND GUEST ASSISTANCE VIA SMARTPHONE APP

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, 155 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 captures a tranquil outdoor area featuring a swimming pool surrounded by well-maintained grass and foliage. A shaded structure offers seating beside the pool, with steps leading into the water visible. Rolling hills and clear blue skies are seen in the background.
Home in Sovicille
4.93 out of 5 average rating, 143 reviews

Podere Scorno country house with swimming pool

Small and cozy country house ideal for couples, on a hill in the Sienese countryside. Tuscan-style stone building with a centuries-old history. The property was bought and renovated in the late '90s. With a large garden with pool, orchard, olive grove, vineyard and vegetable garden, for lovers of greenery. The pool is open from mid-May to the end of September. We don't accept pets. We would like to inform our guests that, as private hosts, we are not authorized to provide breakfast.

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Guest favourite
An aerial view captures the rustic charm of a farmhouse complex surrounded by lush greenery and neatly arranged olive groves. A rectangular swimming pool is visible near the buildings, with sun loungers positioned around it, offering a serene outdoor space.
Farm stay in Sovicille
4.98 out of 5 average rating, 99 reviews

Panoramic farmhouse with pool - Big Apartment

This confortable apartment is part of our ancient farmhouse from XVI century and it's composed of: 2 bedrooms, 2 bathrooms, 1 large livingroom with kitchen and an outside living area reserved only for you. Being the apartment very spacious it's possible to add a 5th bed! Enjoy the swimming pool and the stunning view on the Sienese countryside. Take advantage of all of our services: breakfast, typical dinner, cooking classed, picnics and more ... Siena is just 15 minutes driving!

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Top Guest favourite
Farm stay in Siena
4.98 out of 5 average rating, 218 reviews

La Villa Farmhouse - Chestnut, Pool & Garden

Immersed in the green woods of the Senese hills, the beating heart of Tuscany, lies the La Villa estate. Characterized by a large park with swimming pool, gazebo, barbecue area and relaxation area, the farmhouse stands out for its strong link with the Tuscan tradition: a suggestive path will guide you to discover the woods surrounding the farm among olive trees and fields of lavender in bloom, among which you can forget the passage of time and enjoy the charms of nature.

Guest favourite
The rustic two-story house is enveloped in lush green ivy, highlighting its stone façade. Two arched doors are framed by natural greenery, creating a harmonious appearance. An outdoor dining area with a table is partially visible under a shaded patio, providing a serene setting in the garden.
Villa in Sovicille
4.96 out of 5 average rating, 101 reviews

Beautiful Country House, near Siena with jacuzzi

Beautiful and ancient country house, located just 10 km from Siena (15 minutes by car from the city center). The house can accommodate up to 8 people. Surrounded by greenery, in a panoramic position with a beautiful garden where there is a hot tub, available, on request, even in winter. The very large property is fully fenced and offers maximum privacy. Please note: the hosts are also the owners and managers of the "Borgo dei Fondi" holiday home in Siena.

Top Guest favourite
Condo in Siena
5.0 out of 5 average rating, 20 reviews

Luxury Penthouse with a View of Piazza del Campo

There are many houses in Siena. But very few can say they've been here. Overlooking the city’s most iconic square, this penthouse offers a rare experience: Wake up to the golden light caressing the Palazzo Pubblico and fall asleep above one of the most beautiful places in the world. The location is simply one of a kind. Just outside the door, you'll find yourself immersed in history, surrounded by restaurants, wines, and a timeless atmosphere.

Guest favourite
Villa in Siena
4.89 out of 5 average rating, 307 reviews

Villa Capanna, Private Pool, Breathtaking Views

Ancient restored barn with up to 6 bedrooms and 6 bathrooms, immersed in a historic wine estate, just 6 km from Siena. One of the most beautiful views that the Tuscan panorama can offer, airconditioned bedrooms, exclusive swimming pool, large triple garden, BBQ, poolside table, terrace to enjoy the sunset over the medieval towers on the horizon while sipping the organic wines of the estate, fireplace, parking free, WI-FI internet.

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