
Holiday houses in Sassetta
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Top-rated holiday rentals in Sassetta
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Casa al Gianni - The Simignano Barn
Transformed from a historic barn, this luxurious retreat offers 5 bedrooms, 4 bathrooms, a large, fully equipped kitchen, a spacious living area, and 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, with relaxation in the hot tub and outdoor dinners. A memorable getaway awaits you in this little slice of paradise!

House in Tuscany with fenced garden and mini pool
A townhouse in authentic Tuscan style (exposed walls, beams, and harmonious colors), is a fairytale place. This villa, surrounded by a large fenced garden, is the ideal oasis for couples, families, and pet-friendly guests. The true beating heart of the property is the embrace of the Tuscan countryside, the perfect backdrop for a vacation. The setting is further enhanced by a mini pool for enjoying the view of the valley, and a gazebo with barbecue, ideal for unforgettable dinners and aperitif.

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.

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.

Luxury Medieval Tower • Exclusive Chianti Stay
Welcome to one of the most exclusive residences in Chianti: a medieval tower transformed into a refined luxury retreat overlooking the Tuscan hills. Contemporary design, iconic furnishings, works of art and luxury comforts come together in a unique experience. An oasis of tranquility with a private garden, glass annex, Wi-Fi, and smart working area. Extra services: private chef, tastings in the cellar, wellness treatments and tours of the most beautiful villages in Tuscany.

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.”

Suvereto Suite with private roof top terrace
Suite apartment with private roof top terrace. Charming little Suite fro couples, situated in the heart of Suvereto in a tranquil, natural and highly private setting. Unique panorama with stunning postcard views, overlooking vineyards, olive groves and the ocean in the distance. Secure Bike Storage for Cyclists in Suvereto's Historic Center For a small fee of €10 per day, you can safely store your bike and enjoy your ride without worrying about your vehicle's security.

Authentic Tuscany Experience in our Country House
An amazing experience between nature, flavour 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 vineyards and olive groves 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.

Green Dome @ The Land Before Time Retreats
Nestled among Tuscan olive groves between Volterra and San Gimignano, The Land Before Time – Quad & Saddle Retreats offers 4 Green Domes with private jacuzzi, en-suite bathroom, air conditioning and Wi-Fi. Enjoy breakfast each morning in the Cupola Lounge with stunning views. During your stay, experience horseback rides through scenic trails, quad tours to discover hidden Tuscany, or simply relax under the starry sky.

Casa Samanda with a beautiful view
Casa Samanda is a Tuscan-style three-room apartment in the middle of the medieval old town of Sassetta. It is a great starting point for a wide variety of vacation activities. The many magical cities of Tuscany, such as San Gimignano, Siena, Volterra and Massa Marittima, are not far away and the sea with its long sandy beaches can be reached in less than half an hour.

Get-away apartment in Sassetta
Amazing little town, 20 min from beaches and 10 from best thermal baths of Tuscany (‘La Cerreta Terme’). The perfect 'get-away' apartment in La Bella Italia. The apartment combines beautiful design and modern comfort. And in Sassetta there are great restaurants. Next door you will find a little grocery store.
Popular amenities for Sassetta holiday rentals
Other great holiday rentals in Sassetta

La Mignola Apartment

Tuscan Farmhouse with Pool & Panoramic View

Herons Superior Apartment - Splendid view!

Lorenzo Charme in Chianti

Antea Blu: beach house in Tuscany - 2 bedrooms

"Lo Stollo" Farm (Stollo 1) - Sassetta - Tuscany

Luxury Medieval Tower - Penthouse

Luxury Residence in the Heart of San Gimignano
Destinations to explore
- Elba
- Piazza del Duomo (Pisa)
- Parco Regionale Della Maremma
- Cala Violina
- Pisa Centrale Railway Station
- Spiagge Bianche
- Gulf of Baratti
- Del Chianti
- Spiaggia Di Sansone
- Gorgona
- Capraia
- Pianosa
- Spiaggia di Marina di Campo
- Spiaggia di Capo Bianco
- Spiaggia Di Barbarossa
- Porta Elisa
- CavallinoMatto
- Antinori nel Chianti Classico
- Piazza dei Cavalieri
- Siena Cathedral
- Palazzo Pubblico
- Quercetano
- Spiaggia di Fetovaia
- Rimigliano Natural Park





