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Holiday rentals in San Carlo

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Top-rated holiday rentals in San Carlo

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

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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, 72 reviews

Tuscan House with Private Jacuzzi in Chianti

An oasis of peace in the heart of Tuscany, along the wine route! - Exclusive Jacuzzi in your own private garden - Strategic location between the medieval towns of Certaldo, San Gimignano, Siena, and Florence - A 700 sqm private garden filled with the sweet sound of birds singing - A newly renovated home where history meets modern comfort and unique design - The warmth of a wood-burning fireplace to heat your beautiful winter dreams - The perfect place to regenerate and completely unplug

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, 106 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
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 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.
Apartment in San Gimignano
5 out of 5 average rating, 47 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.”

Guest favourite
Flat in Prata
5 out of 5 average rating, 24 reviews

Country Chic Tuscan Oasis, Pool, Relax & Nature

A country-chic apartment nestled in the quiet Tuscan countryside, inside a beautiful, carefully renovated farmhouse. Here, time slows down: breakfasts on the porch, relaxing by the pool, and evenings in the quiet countryside. The views of nature and the green spaces convey a sense of peace and complete harmony with the surrounding landscape. A place designed for those seeking relaxation, silence, and nature, ideal for couples and families with children aged 12 and up.

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, 267 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, 20 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, 139 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, 67 reviews

Authentic Tuscany Experience 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 greenery and olive’s fields, equipped with every comfort. Reconnect in this serene, one-of-a-kind stay, for a relaxing and peaceful holiday.

Top guest favourite
An inviting villa surrounded by lush greenery and vibrant flowers, featuring blooming rose bushes and olive trees. The gravel pathway leads to the entrance, showcasing a two-story structure with balconies. Sunlight highlights the colorful landscape, creating a serene atmosphere.
Villa in Impruneta
5 out of 5 average rating, 174 reviews

The Tower

Ancient Tuscan villa, beautiful, with exclusive private garden, completely renovated, surrounded by the beautiful and gentle Tuscan hills. The villa has a breathtaking view, is very sunny, well furnished and equipped with all amenities, quiet and not isolated. The house is located in Bagnolo, a small hamlet of Impruneta at the gates of Chianti, an area of olive groves, vineyards and peace. The house is about 10 km by car from the center of Florence.

Top guest favourite
A panoramic view depicts rolling green hills extending toward the coastline. The azure sky is adorned with scattered clouds, while the sea glistens in the distance. A sheer curtain is visible in the foreground, framing the serene landscape.
Home in Campiglia Marittima
5 out of 5 average rating, 56 reviews

Apartment in country house with panoramic view

Experience a holiday surrounded by the scents of nature, in this unique and relaxing space. Wide panoramic view of the coast and the islands of Giglio, Montecristo and Elba. You can enjoy a multitude of paths for walking, trekking and mountain biking. To reach the farmhouse from the Archaeo-mining park of San Silvestro, it is necessary to travel 1300 meters of white road, uphill with an uneven road surface.

Top guest favourite
A charming entrance greets guests with terracotta pots filled with greenery along a stone path. The inviting door, framed by green shutters, opens to the home. A small table and chairs are positioned on the terrace, perfect for enjoying the outdoor view.
Home in Suvereto
5 out of 5 average rating, 12 reviews

The House in the Castle and the Terrace overlooking the Village

Our house, fresh from a renovation in 2024, combines the charm of history with modern comfort in 90 m2 all on one level. Every detail has been designed to give you a warm and welcoming atmosphere, where tradition meets well-being: exposed wooden beams, ancient decorations patiently brought to light by me... and the principles of Feng Shui guide the design, colors and arrangement of the furnishings and rooms.

Popular amenities for San Carlo holiday rentals

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