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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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Top guest favourite
A stone house is positioned on a hillside overlooking the deep blue sea. Lush green terrain surrounds the structure, and a large umbrella provides shade near the entrance. The coastline and distant boats can be seen in the background under a clear sky.
Home
5 out of 5 average rating, 112 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.

Guest favourite
Home
4.96 out of 5 average rating, 131 reviews

Open space surrounded by nature

Casa Namaste is a small stone cottage with well-kept interiors 1 km from the medieval village of Montescudaio. The house is completely surrounded by woods and centuries-old oaks. 150 meters away flows the Cecina river. In the 5000 square meter garden there is a natural spring with a large stone tub to cool off and an outdoor hot shower surrounded by greenery. We have a Vodafone adsl line with download 33 and upload 1.4. Smart TV and air conditioning are also available starting this spring

Top guest favourite
An aerial view of the property reveals a charming red house surrounded by lush greenery. Tall cypress trees and vibrant bushes create a tranquil landscape, while an expansive lawn features relaxing loungers, inviting guests to enjoy the serene atmosphere of the Tuscan countryside.
Home
5 out of 5 average rating, 226 reviews

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.

Top guest favourite
A spacious living area features exposed brick walls, wooden beams, and warm lighting. A comfortable sofa and a mid-century modern coffee table sit invitingly, while a dining table and chairs are positioned nearby. Large windows enhance the natural light, which complements the earthy tones of the room.
Apartment
5 out of 5 average rating, 61 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
Flat
5 out of 5 average rating, 15 reviews

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.

Top guest favourite
A rustic building is seen under a starry night sky, with a partial roof providing shelter. Soft light glows from the interior, illuminating the entrance. Lush greenery and trees surround the scene, adding depth to the serene nighttime landscape.
Farm stay
4.93 out of 5 average rating, 281 reviews

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!

Guest favourite
Castle
5 out of 5 average rating, 25 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.

Superhost
A spacious bedroom features a canopy bed draped in rich red curtains, complemented by intricately designed wooden ceilings. Traditional furnishings include a vintage writing desk and a wooden wardrobe, while natural light enters through a small window adorned with a decorative grill.
Castle
4.93 out of 5 average rating, 54 reviews

Medieval Tower in the Tuscan Countryside

On request, a delicious sweet and/or savory breakfast, a rich dinner with seasonal products and cooking class Have you ever lived like a King and Queen among armor, frescoed ceilings and four-poster beds? From the top of the wonderful panoramic terrace, Torre Sassa will show you all of Tuscany up to the sea. Discover the history of this small but wonderful village just a stone's throw from the most iconic areas of the region

Guest favourite
Dome
4.97 out of 5 average rating, 141 reviews

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.

Guest favourite
A living area features exposed wooden beams and terracotta tiled flooring. A stone fireplace is located on one side, while a circular dining table with pastel-colored chairs occupies the center. A compact kitchen area is visible to the right, with modern appliances and wooden cabinetry.
Flat
4.84 out of 5 average rating, 64 reviews

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.

Guest favourite
Tent
4.98 out of 5 average rating, 64 reviews

Glamping on a farm in Tuscany - Nature

Glamping set in the woods of the Tuscan countryside. Our accommodation options are designed for those seeking tranquillity, open spaces and simplicity: a back-to-basics experience, far removed from mass tourism and traditional hotel services. Here, time slows down, the nights are quiet, and nature is an integral part of your stay.

Guest favourite
The kitchen area features rustic wooden ceiling beams and terracotta floor tiles. A dining table with chairs is set for meals, while modern appliances, including an oven and a refrigerator, are visible in the background. Natural light streams through the window, enhancing the inviting space.
Flat
5 out of 5 average rating, 22 reviews

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