
Vacation rentals in Zona San Gregorio
Find and book unique accommodations on Airbnb
Top-rated vacation rentals in Zona San Gregorio
Guests agree: these stays are highly rated for location, cleanliness, and more.

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!

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.

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.”

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.

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.

Casa Il Leccio – Relax and nature in Tuscany
Enjoy peace and nature in this beautiful countryside home surrounded by greenery. With a large private garden, it offers complete privacy and quiet. Just minutes from the sea, you can easily reach the beaches of Baratti, Sterpaia, and Rimigliano. Discover the wine villages of Bolgheri and Suvereto and the Etruscan sites of Populonia. Perfect all year round, with efficient heating, a cozy atmosphere, and an ideal location to explore Tuscany.

Luxury Villa with swimming pool ModdissiCharme IsolaElba
Villa with infinity pool surrounded by greenery, just a few minutes from Morcone Beach. Comfortable sleeping area offers 3 double bedrooms and one with single beds, each with a full private bathroom, TV and air conditioning. In the living area there is a large equipped kitchen, dining table with relaxation area and smart TV; from here access to the outdoor terrace ideal for enjoying a great aperitif Parking lot
Popular amenities for Zona San Gregorio vacation rentals
Other great vacation rentals in Zona San Gregorio

Luxury Medieval Tower - Penthouse

Casa Giorgiana in Bolgheri, Tuscany

casa LU e JO

Fabulous farmhouse in Chianti, panoramic garden

Relax in Tuscany Country Home with a Stunning View

The Porrine Ferienhaus IV

The House in the Castle and the Terrace overlooking the Village

Villa il Pellicano by Interhome.
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
- Siena Cathedral
- CavallinoMatto
- Palazzo Pubblico
- Antinori nel Chianti Classico
- Abbey of Sant'Antimo
- Quercetano
- Santa Maria della Scala
- Riserva Naturale Diaccia Botrona
- Rimigliano Natural Park





