
Holiday houses in Sassetta
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Top-rated holiday rentals in Sassetta
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Podere Vergianoni nestled in Chianti with a pool
Podere Vergianoni is an ancient and authentic farmhouse dating back to the 17th century located in the beautiful hills of Chianti in Tuscany. The apartment is impeccably furnished in the traditional local style of old Tuscany: ancient wooden beams, terracotta floors, and unique furniture. In the large outdoor courtyard, you'll find a large swimming pool on a panoramic terrace at your disposal, overlooking the valley with breathtaking views of vineyards and olive groves, where you can enjoy spectacular sunsets.
Medieval Tower experience with Panoramic Rooftop
If you are looking for a memorable experience, this is the right place for you! With its 42 mt high, the Salvucci Tower is one of the famous towers of San Gimignano and today the only one turned into a vertically-spread apartment divided into 11 floors, for a total of 143 steps. A unique and timeless place, ideal to experience something never tried before. The tower can hosts couples or small groups up to 3 people. Its panoramic rooftop boasts an incredibly breathtaking view all over the town.

Villa di Geggiano – Guesthouse
PLEASE NOTE THAT BEING IN THE COUNTRYSIDE WITH FEW PUBLIC TRANSPORTATION OTHER THAN TAXI, THE BEST WAY TO ENJOY YOUR STAY AND TO VISIT THE BEAUTIFUL SURROUNDINGS IS TO HAVE A CAR. The 18th century Villa di Geggiano, surrounded by vineyards and lovingly cared gardens, is located in the Chianti area near Siena, one of the most beautiful regions of Italy which will provide an idyllic and enchanting backdrop to your vacation. Our guesthouse is located in one of the garden pavilions of the villa.

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.

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.

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!

Tuscan dwelling with pool near villages and sea
La Torretta is a green sanctuary, ideal for families and small groups seeking relaxation and nature. Enjoy two swimming pools nestled in the woods, walk along paths and through medieval villages, discover museums and natural parks, or relax at the thermal baths. The sea is only 20 minutes away. Savor the typical dishes of Tuscany and local wines in restaurants selected for you. Here, Tuscany is lived slowly, surrounded by nature, culture, and unforgettable moments.

PODERE "LO STOLLO" (Stollo 2) Sassetta - Tuscany
Vacation Home - Sassetta. "Lo Stollo" is a Tuscan-style stone farm, located in a hilly area just 15 km from the sea. The property consists of three independent apartments, each with a separate entrance: Stollo 1 – Ground floor, sleeps up to 6, ideal for families or groups of friends. Stollo 2 – First floor, sleeps 2/4, perfect for couples or small families. Stollo 3 – Independent house, sleeps 2, surrounded by greenery and perfect for a quiet holiday.

The View of Sangiorgio
In the heart of the historic center of Florence, stands this magnificent 90 m2 apartment. Thanks to the location and the splendid view overlooking Florence, you will immediately feel part of the city. The apartment is a stone's throw from the Ponte Vecchio and therefore close to every attraction in Florence. N.b. The apartment is located in an elevated position and to reach it there is a climb and two flights of stairs to climb

Tuscan Farmhouse with Pool & Panoramic View
Immersed in Tuscany's pristine nature, this elegant apartment in Podere Bagnoli offers a relaxing getaway with breathtaking views and modern comforts. Located 4 km from the medieval village of Castagneto Carducci, it is the perfect retreat for couples, wine lovers, slow travelers, and those seeking peace and authenticity.
Popular amenities for Sassetta holiday rentals
Other great holiday rentals in Sassetta

Casa La Terrazza – Le Fornaci –

Elegant 3 bedroom home inside the old castle walls

'Le Dame del Borgo' albergo diffuso – Lavinia

Medieval Tower in the Tuscan Countryside

Il Pezzo Farm by Interhome

Seaside Retreat: Borgo alla Noce

Wellness oasis in a Tuscan farmhouse, private SPA

Glamping in a farmhouse in Tuscany - Nature
Destinations to explore
- Elba
- Porta Elisa
- Marina di Cecina
- Piazza del Duomo (Pisa)
- Del Chianti
- Pisa Centrale Railway Station
- Cala Violina
- Gorgona
- Spiaggia Di Sansone
- Gulf of Baratti
- Spiaggia di Capo Bianco
- Spiagge Bianche
- Spiaggia Di Barbarossa
- Spiaggia della Padulella
- Spiaggia di Marina di Campo
- Capraia
- Palazzo Pubblico
- Arcipelago Toscano National Park
- CavallinoMatto
- Torre Guinigi
- Santa Maria della Scala
- Puccini Museum
- Castello di Verrazzano
- Siena Cathedral




