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Holiday houses in Zona San Gregorio

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Top-rated holiday rentals in Zona San Gregorio

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

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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, 265 reviews

Casa al Gianni - Hut

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

Guest favourite
A spacious sleeping area features a large bed dressed in white linens, accented by two bedside lamps. Natural light enters through large glass doors, revealing views of the surrounding olive grove. The wooden ceiling adds warmth to the room's calming atmosphere.
Farm stay in San Vincenzo
4.78 out of 5 average rating, 37 reviews

Two bedrooms aparment in farmhouse ground floor

The apartment is located on the ground floor of our agriturismo, just 2 km from the sea and the center of San Vincenzo. It is the ideal solution for those who wish to enjoy a relaxing holiday surrounded by nature, tranquility, and beautiful views. The apartment hastwo bedrooms, a cozy living room, a bathroom, and a patio with sea view, perfect for outdoor breakfasts or for enjoying the sunset. The location is strategic: immersed in the Tuscan countryside yet close to the beaches and the town.

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.

Superhost
Tent in San Vincenzo
5 out of 5 average rating, 4 reviews

Glamping Villa Oliveta Tent l' Erica Sea view

Agriturismo Villa Oliveta offers its guests a small and charming glamping area surrounded by wild olive trees and other typical Mediterranean plants. Thanks to the elevated position of the tents, you can enjoy a panoramic view of the estate's centuries-old olive grove, the sea, and the islands that characterize this splendid stretch of the Etruscan Coast. The historic center of San Vincenzo, the sea, and its beaches are just 1.3 km away and can be reached in just a few minutes.

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, 214 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, 46 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 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

Situato nel cuore di San Vincenzo, un piccolo paese turistico sulla costa Toscana, a 5 minuti a piedi dal mare ed a pochi minuti di auto da una delle più famose aree di vino (Bolgheri, Castagneto Carducci..) L'appartamento è NUOVO (Completato a inizio Luglio 2024), ed ha una dimensione di 100 mq E' composto da: 2 Camere matrimoniali con letto king size 1 Soggiorno con tv, tavolo e divano 1 Cucina completa di tutto 2 Bagni 2 terrazzi con tavolo, lettini prendi / sole

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
Home in Barberino Tavarnelle
5 out of 5 average rating, 66 reviews

Cozy Tuscan Country House with Fantastic View

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 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.

Superhost
Home in San Vincenzo
5 out of 5 average rating, 5 reviews

The Tower

Nestled in the Tuscan countryside, 2 km from the beaches of San Vincenzo and close to the Gulf of Baratti, the apartment in the turret of a farmhouse offers an exclusive and relaxing stay. Garden view, well-kept and bright rooms, terrace and shared pool make the experience unique. Ideal for those looking for tranquility, nature and the authentic charm of Tuscany, between the sea and the hills. We're sorry, but we can't accept dogs or other pets.

Popular amenities for Zona San Gregorio holiday rentals

  1. Airbnb
  2. Italy
  3. Tuscany
  4. Livorno
  5. Zona San Gregorio