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Holiday rentals in Sassetta

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Top-rated holiday rentals in Sassetta

Guests agree: these stays are highly rated for location, cleanliness and more.

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Guest favourite
The image features a rustic stone house surrounded by lush greenery, with a wooden door and shuttered windows. A set of stairs leads to a raised outdoor area, partially enclosed by a stone wall, providing a serene view of the surrounding nature.
Holiday home
4.94 out of 5 average rating, 79 reviews

Tuscan House with Private Jacuzzi in Chianti

An oasis of peace in the heart of Tuscany, along the wine route! - Exclusive Jacuzzi in your own private garden - Strategic location between the medieval towns of Certaldo, San Gimignano, Siena, and Florence - A 700 sqm private garden filled with the sweet sound of birds singing - A newly renovated home where history meets modern comfort and unique design - The warmth of a wood-burning fireplace to heat your beautiful winter dreams - The perfect place to regenerate and completely unplug

Top guest favourite
Home
5 out of 5 average rating, 107 reviews

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.

Top guest favourite
Apartment
5 out of 5 average rating, 51 reviews

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.”

Top guest favourite
The rustic building features a warm ochre facade and a classic tiled roof. An expansive oak tree provides shade to the outdoor seating area, which includes wooden chairs and a small table. Lush greenery surrounds the property, contributing to the tranquil rural setting.
Farm stay
4.92 out of 5 average rating, 272 reviews

Casa al Gianni - Fig

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!

Superhost
Apartment
4.71 out of 5 average rating, 7 reviews

Tuscan Nature & Relax: Panoramic Terrace

La Terrazza 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.

Top guest favourite
Castle
5 out of 5 average rating, 22 reviews

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.

Top guest favourite
Home
5 out of 5 average rating, 72 reviews

Live the Tuscany Experience in Our Country House

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 amazing 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 relaxing and peaceful holiday.

Top guest favourite
A stone farmhouse in Tuscan style is depicted, featuring a two-story structure with terracotta roofing. Lush greenery surrounds the building, with potted plants and shrubs enhancing the landscape. Balconies adorn the upper level, and the entrance is accentuated by a stone staircase leading to the garden.
Holiday home
5 out of 5 average rating, 79 reviews

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.

Guest favourite
Home
5 out of 5 average rating, 6 reviews

Open Space Piscina e Giardino

La mia casa è immersa nella campagna toscana, tra olivi e vigne, nel cuore del Chianti. Intorno, panorami meravigliosi e un’atmosfera di pace e relax. Il giardino è uno spazio speciale, ideale per momenti da vivere all’aperto. Per chi lo desidera, è possibile – su richiesta – condividere esperienze legate alla cucina e alla convivialità, come cene preparate con cura, da gustare insieme, anche a lume di candela, in un contesto intimo e accogliente.

Top guest favourite
Home
5 out of 5 average rating, 28 reviews

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.

Top guest favourite
Casa particular
5 out of 5 average rating, 44 reviews

Palazzina Maresa - Loft 4

Palazzina Maresa is a 1920s building carefully restored to host eight independent apartments, each shaped by the vision of a different young local designer. The project reflects on early 20th-century aesthetics through a contemporary lens, blending architecture, design, and artistic research. Located in a quiet residential area with private and shared gardens, the building is just a short walk from Florence’s historic center.

Top guest favourite
A charming entrance greets guests with terracotta pots filled with greenery along a stone path. The inviting door, framed by green shutters, opens to the home. A small table and chairs are positioned on the terrace, perfect for enjoying the outdoor view.
Home
5 out of 5 average rating, 13 reviews

The House in the Castle and the Terrace overlooking the Village

Our house, fresh from a renovation in 2024, combines the charm of history with modern comfort in 90 m2 all on one level. Every detail has been designed to give you a warm and welcoming atmosphere, where tradition meets well-being: exposed wooden beams, ancient decorations patiently brought to light by me... and the principles of Feng Shui guide the design, colors and arrangement of the furnishings and rooms.

Popular amenities for Sassetta holiday rentals

  1. Airbnb
  2. Italy
  3. Tuscany
  4. Sassetta