
Vacation rentals in Zona San Gregorio
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Top-rated vacation rentals in Zona San Gregorio
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Podere Vergianoni immerso nelChianti con piscina
Podere Vergianoni is an ancient and historic property dating back to the 17th century, located in the beautiful hills of Chianti in Tuscany, with the possibility of organizing a shuttle service and exclusive experiences tailored to you. The apartment is available for 2 adults, with the possibility of adding a sofa bed for 2 children under 12 years of age. In the large outdoor courtyard, you'll find a saltwater swimming pool with a relaxation area on a panoramic terrace overlooking the castle, hills, and vineyards, with incomparable sunsets.

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.

[Relax] Modern suite with garden, A/C and Wi-Fi
Elegance and simplicity meet in this delightful apartment for two, nestled in a quiet area of San Vincenzo. Just 1.5 km from the beach, it offers every comfort: air conditioning, a reserved space in the garden for your moments of relaxation, and free parking on the property. Perfect for travelers from around the world looking for relaxation, a short distance from the sea and an ideal base for exploring villages, nature and local flavors. Experience the authentic magic of the Tuscan coast.

Design loft with private SPA in Tuscany
Welcome to Loft SPA, your personal refuge in the heart of Massa Marittima, an exclusive accommodation equipped with a private indoor swimming pool. This unique property offers an unparalleled stay experience, combining elegance and comfort, the accommodation has been designed with attention to detail and quality, The highlight is the indoor swimming pool with its accessories, an oasis of relaxation. This exclusive accommodation offers a stay experience you will not easily forget.

Belforti Tower
Torre dei Belforti is the perfect place for people who love beauty, nature and art. Sleeping at the Tower is like traveling trough the time, between knights and princesses. The wonder of this place is enriched by a big garden, with its swimming pool, the cypresses alleys and the olive trees. The village is also a magic place well preserved and still alive. We are Emilia and Luca, we live here and our mission is to give the best to our guests, to fully enjoy this marvelous place.

Private Courtyard | 3BR/3BA | Garage
Welcome to Casa Costarella.<br><br>Wake up in San Gimignano’s historic center and step into your own private courtyard — a rare feature within the city walls.<br><br>This 120 m² / 1,290 sqft residence spans two levels and blends preserved historic character with modern comfort.<br><br>☞ Enclosed private courtyard<br>☞ 3 bedrooms / 3 full bathrooms<br>☞ Free covered garage for 1 car (5-minute walk)<br>☞ Underfloor heating & cooling<br>☞ High-speed Wi-Fi<br>☞ Self check-in<br><br>

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.

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.

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.”

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!

Relax in Tuscany Country Home with a Stunning View
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 stunning 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 peaceful and relaxing holiday.

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 vacation rentals
Other great vacation rentals in Zona San Gregorio

Luxury Medieval Tower - Penthouse

One-Bedroom Apartment with Patio

Rosa: Tuscan Views & Pool, Walk to Town

La Mignola Apartment

Villa il Pellicano by Interhome.

Chalet i Poggetti,

Herons Superior Apartment - Splendid view!

Glamping house "Il bosco" with whirlpool
Destinations to explore
- Elba
- Piazza del Duomo (Pisa)
- Cala Violina
- Parco Regionale Della Maremma
- Pisa Centrale Railway Station
- Spiagge Bianche
- Spiaggia Di Sansone
- Gorgona
- Gulf of Baratti
- Spiaggia Di Barbarossa
- Spiaggia di Capo Bianco
- Pianosa
- Capraia
- Spiaggia di Marina di Campo
- Piazza dei Cavalieri
- CavallinoMatto
- Siena Cathedral
- Palazzo Pubblico
- Antinori nel Chianti Classico
- Abbey of Sant'Antimo
- Quercetano
- Santa Maria della Scala
- Rimigliano Natural Park
- Riserva Naturale Diaccia Botrona





