
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.

Casa al Gianni - The Simignano Barn
Converted from an old barn, this luxurious retreat offers 5 bedrooms, 4 bathrooms, a large fully equipped kitchen, a spacious living room, a large private garden with parking, a hot tub, a patio with sofas, a BBQ, a fire pit, and an outdoor kitchen. Ideal for those looking for a unique experience, it combines rustic charm with modern comforts. Perfect for families or groups, it promises magical evenings under the stars, including relaxation in the hot tub and outdoor dinners. A memorable getaway awaits you in this slice of paradise!

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.

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.

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.

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.”

Florida Apartments - Cinque
La nostra suite al piano primo caratterizzata da un esclusiva terrazza privata di 40 mq sul mare vi farà godere dall'alba al tramonto la brezza marina. Si compone di due zone, cucina soggiorno con divano letto e zona notte con bagno con possibilità di aggiungere un terzo letto. Può ospitare comodamente coppie, famiglie con massimo 2 bambini e viaggiatori singoli. Ogni alloggio include il servizio spiaggia allo stabilimento balneare Florida con ombrellone e due lettini.

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.

Podere Tignano, 4-bedroom villa in the Chianti!
Nestled among the rolling hills of Chianti between Florence and Siena, Podere Tignano offers breathtaking views over vineyards, olive groves, and golden grain fields. This charming Tuscan stone villa blends authentic rural character with modern comfort and welcomes up to 8 guests in 4 bedrooms. Surrounded by peaceful countryside and featuring a private swimming pool, it is the perfect retreat for those seeking relaxation, nature, and the true spirit of Tuscany.

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.
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

Apartment in country house with panoramic view

Open Space Piscina e Giardino

Frontemare house with exclusive sea access

Casa Giorgiana in Bolgheri, Tuscany

[Relax] Modern suite with garden, A/C and Wi-Fi

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





