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Holiday rentals in La Cinquantina

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Top-rated holiday rentals in La Cinquantina

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

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Top guest favourite
The rustic building features a warm ochre facade and a classic tiled roof. An expansive oak tree provides shade to the outdoor seating area, which includes wooden chairs and a small table. Lush greenery surrounds the property, contributing to the tranquil rural setting.
Farm stay
4.91 out of 5 average rating, 268 reviews

Casa al Gianni - Fig

Hi, we're Cristina and Carmelo! We look forward to welcoming you to 'Casa al Gianni', our farmhouse in the woods of the Montagnola Senese, just 20 minutes from Siena. Here, life slows down: just the scent of the earth, the song of the birds, and the companionship of our animals. It's an invitation to rediscover the beauty of the little things, surrounded by the greenery of the most authentic Tuscany. It's not just a holiday; it's a return to our roots. This peaceful haven will stay in your heart. We look forward to welcoming you!

Guest favourite
A serene swimming pool surrounded by sun loungers and parasols, set against a clear blue sky. Lush greenery borders the area, enhancing the inviting space for relaxation and leisure.
Flat
4.95 out of 5 average rating, 21 reviews

Farmhouse, Tuscany Chic Flat

Charming apartment in the historic setting of the "Fattoria del Terriccio Basso" in Cecina. Large park that immerses guests in the ancient Tuscan farms, a 3-minute drive from the sea, 15 km from Bolgheri. The apartment is equipped with every comfort, renovated with fine finishes, a shared swimming pool, and a private courtyard with a gazebo. The house is well connected to Marina di Cecina and the center by bus and bike path at the end of the driveway. NB. The pool will open on 06/15 and close on 09/15

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
4.93 out of 5 average rating, 75 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
5 out of 5 average rating, 107 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.

Guest favourite
A wrought iron gate stands open, revealing a pedestrian pathway lined with stone tiles. On either side, low greenery is visible, providing a touch of nature. The blue sky above enhances the inviting entrance to the property.
Apartment
4.89 out of 5 average rating, 27 reviews

Vacation rentals in Cecina

L’appartamento è in un quartiere tranquillo e il parcheggio è libero. Il lungomare è facilmente raggiungibile in macchina, in 5 minuti, in bicicletta o a piedi attraverso una ciclabile. La casa può ospitare fino a 4 persone, la cucina è completa di accessori; la zona giorno con TV e divano. L’appartamento include una camera matrimoniale e una camera più piccola con 1 o 2 letti singoli su richiesta; un bagno con doccia. All’Esterno una terrazza per una colazione o una cena in tranquillità.

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
5 out of 5 average rating, 217 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.

Guest favourite
An outdoor area features a shaded dining table with wooden chairs, adjacent to a charcoal grill. Two white lounge chairs are positioned nearby, surrounded by well-kept plants and flowers, with the exterior of the house showcasing a traditional brick design under a bright blue sky.
Holiday home
4.92 out of 5 average rating, 39 reviews

Lovely place in Tuscany Countryside

Portion of a detached house immersed in the Tuscan countryside near the sea and all amenities. The house consists of a living room, kitchenette, bedroom, bathroom and large outdoor area that is completely fenced. Free parking on the premises. Very quiet area with little traffic, immersed in a relaxing environment in contact with nature. Nearby: Casale Marittimo (12km), Castiglioncello (13km), Bolgheri (20km), Populonia and Volterra (40km). The owners speak excellent French.

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
5 out of 5 average rating, 48 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
A single-story structure is visible, surrounded by greenery and trees. A paved pathway leads to a patio area with a few outdoor plants. The house features a warm exterior with wooden window shutters and a tiled roof, under a clear blue sky.
Home
4.86 out of 5 average rating, 147 reviews

Cottage in the Cecina countryside

In the Cecina countryside, along the road leading to the medieval village of Casale Marittimo, a private park with parking, the 30 sqm studio overlooks a veranda equipped for outdoor dining even with the use of the barbecue. Convenient to services (town and shopping center). The beautiful pine forest of Marina di Cecina and the sea can be reached by car or bicycle. Nearby are beautiful villages and very well-known locations. For additional fees, see the House Manual

Top guest favourite
Castle
5 out of 5 average rating, 22 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
4.99 out of 5 average rating, 140 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
5 out of 5 average rating, 68 reviews

Experience Real Tuscany from Our Country Home

An incredible experience between flavor, nature 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 peaceful and relaxing holiday.

Popular amenities for La Cinquantina holiday rentals

  1. Airbnb
  2. Italy
  3. Tuscany
  4. Livorno
  5. La Cinquantina