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Holiday houses in San Carlo

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Top-rated holiday rentals in San Carlo

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Top Guest favourite
An aerial view captures Podere Vergianoni nestled in the Chianti hills, surrounded by lush vineyards. The property features a clear blue pool, shaded terraces, and carefully landscaped gardens. Rolling hills and rows of grapevines create a serene backdrop, highlighting the natural beauty of the Tuscan countryside.
Condo in Noce
5 out of 5 average rating, 319 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
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
A stone house is positioned on a hillside overlooking the deep blue sea. Lush green terrain surrounds the structure, and a large umbrella provides shade near the entrance. The coastline and distant boats can be seen in the background under a clear sky.
Home in Rio Marina
5 out of 5 average rating, 102 reviews

Captain's House | Monte Grosso, Elba

The Casa del Capitano is located on the top of Monte Grosso in the National park of the tuscan archipelago. The location is unique on the island and from here you have a fantastic view of the city of Portoferraio, Piombino, Corsica, Capraia and Gorgona. The house was restored during a project lasting several years, in close collaboration with the National Park and was designed to be self-sufficient and ecological. Here you use purely the energy of the sun, without having to renounce luxury.

Top Guest favourite
The image features a rustic stone house surrounded by lush greenery, with a wooden door and shuttered windows. A set of stairs leads to a raised outdoor area, partially enclosed by a stone wall, providing a serene view of the surrounding nature.
Holiday home in San Gimignano
4.97 out of 5 average rating, 63 reviews

Peaceful tuscan house with pool in Tuscany

An oasis of peace located in the heart of Tuscany on the wine roads! -A strategic area between Certaldo, San Gimignano, Siena and Florence. -Casa Valentina is hidden in a grove where you will enjoy fresh air, a stream with the chirping of birds -A newly renovated house that meets the historicity of the property, the comfort and the contemporaneity that makes it unique in its style - The warmth of the wood-burning fireplace - Heated whirlpool tub embraced by your own private garden.

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, 207 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 spacious living area features exposed brick walls, wooden beams, and warm lighting. A comfortable sofa and a mid-century modern coffee table sit invitingly, while a dining table and chairs are positioned nearby. Large windows enhance the natural light, which complements the earthy tones of the room.
Condo in San Gimignano
5 out of 5 average rating, 39 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
Two individuals are seated in comfortable chairs on a wooden deck, enjoying a serene moment as the sun sets. A bottle of wine and two glasses are placed on a small table nearby, surrounded by lush greenery and vibrant flowers.
Home in Greve in Chianti
4.99 out of 5 average rating, 70 reviews

Relaxation and comfort in the hills of Florence

Apartment in a typical Tuscan stone farmhouse: measuring 160 square meters, it is finished with typical Tuscan materials, pietra serena and terracotta. It consists of a large living room at the entrance, dining room, kitchen, 2 bathrooms, storage room, 3 bedrooms, and a study area. Arranged in an east-west position thanks to a large terrace, a patio and a large private garden, it allows you to enjoy the sunrise for your breakfast and the sunset for a pleasant aperitif.

Guest favourite
A spacious living area is highlighted by an inviting sofa and a unique decorative coffee table. Large glass doors open to a terrace, allowing natural light to flow in. Indoor plants add a touch of greenery, enhancing the relaxed atmosphere.
Apartment in San Vincenzo
5 out of 5 average rating, 17 reviews

Luxury penthouse - 100 sqm 2 bedrooms 2 bathrooms

Located in the heart of San Vincenzo, a small tourist village on the Tuscan coast, a 5-minute walk from the sea and a few minutes by car from one of the most famous wine areas (Bolgheri, Castagneto Carducci..) The apartment is NEW (completed in early July 2024) and measures 100 square metres. It is composed of: 2 double rooms with a king-size bed 1 Living room with TV, table and sofa 1 Kitchen complete with everything 2 Bathrooms 2 terraces with table, sun loungers

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, 255 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
Castle in Tignano
5 out of 5 average rating, 14 reviews

Luxury Medieval Tower • Exclusive Chianti Stay

Benvenuti in una delle residenze più esclusive del Chianti: una torre medievale trasformata in un raffinato luxury retreat con vista sulle colline toscane. Design contemporaneo, arredi iconici, opere d’arte e comfort di lusso si fondono in un’esperienza unica. Un’oasi di quiete con giardino privato, dependance vetrata, Wi-Fi, area smart working. Servizi extra: chef privato, degustazioni in cantina, trattamenti benessere e tour tra i borghi più belli della Toscana.

Top Guest favourite
A spacious terrace is surrounded by lush greenery, featuring terracotta pots filled with plants. Comfortable wooden chairs are positioned to invite relaxation, overlooking scenic hills in the distance. A soft canopy provides shade, enhancing the tranquil atmosphere of this outdoor space.
Home in Peccioli
4.99 out of 5 average rating, 137 reviews

House with a breathless view in Tuscany

Halfway between Pisa and Florence, this dreamy Tuscan house is your perfect escape. Lounge on the panoramic terrace with sun-kissed views, sip your morning coffee, or enjoy al fresco dinners under the golden sunset. Nestled in the heart of a charming village turned open-air contemporary art museum, every corner feels like a picture-perfect moment. Peccioli is your gateway to Tuscany’s art cities or a serene hideaway to savor the magic of authentic local life.

Top Guest favourite
Home in Barberino Tavarnelle
5 out of 5 average rating, 60 reviews

Enjoy Amazing View in Tuscany in Our Country House

An amazing experience between nature, flavor and relax in the heart of Chianti. Situated between Barberino Tavarnelle, San Gimignano, Greve in Chianti, and Florence, Belvedere 27/A overlooks the Santa Maria Novella Castle, amidst olive groves and vineyards with an amazing view. A countryside Tuscan home, surrounded by olive’s fields And greenery, equipped with every comfort. Reconnect in this serene, one-of-a-kind stay, for a cozy and relaxing holiday.

Popular amenities for San Carlo holiday rentals

  1. Airbnb
  2. Italy
  3. Tuscany
  4. Livorno
  5. San Carlo