Vacation rentals in Sassetta

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Top-rated vacation rentals in Sassetta

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

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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 in Simignano

Casa al Gianni - Hut

Hi, we’re Cristina and Carmelo! We look forward to welcoming you to “Casa al Gianni,” our agritourism property nestled in the woods of the Montagnola Senese, just 20 minutes from Siena. Here, life slows down: There is only the scent of the earth, the song of the birds, and the companionship of our animals. It is an invitation to rediscover the beauty of the little things, surrounded by the greenery of the most authentic Tuscany. It’s not just a vacation; it’s a return to our roots. This peaceful haven will stay in your heart. We look forward to welcoming you!

FamilyValueSleep quality

4.93 out of 5 average rating, 295 reviews

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 in Rio Marina

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.

LocationValueHospitality

5.0 out of 5 average rating, 118 reviews

Guest favourite

Home in Montescudaio

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

FamilyValueGetting around

4.96 out of 5 average rating, 137 reviews

Superhost

The outdoor patio features a spacious lounge area, adorned with comfortable seating and illuminated by soft lighting. Stone walls and wooden beams create a rustic charm. Sheer curtains gently billow in the evening breeze, enhancing the inviting atmosphere of the space.

Home in Castagneto Carducci

Villa Siloral a jewel in the Etruscan Coast

Our cozy and elegant Villa Siloral Blu is nestled among the vineyards overlooking Bolgheri, a village well known to lovers of wine and literature. The park where the villa is located is bordered by a line of olive trees Under the large outdoor patio there is a lounge area and veranda for unforgettable summer dinners. Given the thick walls and its position, the temperature is always pleasantly cool even during the hot summer months. It comfortably accommodates 8 persons.

LocationFamilyComfort

4.89 out of 5 average rating, 18 reviews

Top guest favourite

Apartment in Suvereto

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.

LocationCleanlinessAmenities

5.0 out of 5 average rating, 21 reviews

Top guest favourite

A large swimming pool surrounded by a brick patio and manicured lawns is highlighted in this image. Sun loungers are positioned along the pool's edge, with lush greenery and trees creating a serene backdrop. The villa's charming structure is visible in the distance under a partly cloudy sky.

Villa in Barberino Tavarnelle

Podere Tignano, 4-bedroom villa in the Chianti!

Nestled among the rolling hills of Chianti between Florence and Siena, Podere Tignano offers breathtaking views over vineyards, olive groves, and golden grain fields. This charming Tuscan stone villa blends authentic rural character with modern comfort and welcomes up to 8 guests in 4 bedrooms. Surrounded by peaceful countryside and featuring a private swimming pool, it is the perfect retreat for those seeking relaxation, nature, and the true spirit of Tuscany.

FamilyValueCondition

4.98 out of 5 average rating, 108 reviews

Guest favourite

A serene garden area features two lounge chairs positioned on lush green grass, overlooking the sea in the distance. White lilies bloom in the foreground, complemented by a rustic shade structure nearby, providing a tranquil setting for relaxation.

Farm stay in Castagneto Carducci

Casa del Poggio, with a beautiful sea view

The Casa del Poggio (house at the hill) is located in the hills of Castagneto Carducci and is part of our organic farm. It is immersed in a peaceful countryside surrounded by olive groves, vineyards and woodland and enjoys a beautiful view of the sea and the castle of Castagneto Carducci. At the same time its position allows you to reach the village in just 10 minutes by foot and the beaches of Marina di Castagneto in 10 minutes by car or bus.

LocationFamilyGetting around

4.95 out of 5 average rating, 165 reviews

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 in Suvereto

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.

LocationFamilyBeach

5.0 out of 5 average rating, 18 reviews

Top guest favourite

Vacation home in Lajatico

Rosa: Tuscan Views & Pool, Walk to Town

Welcome to La Lunaria di Lajatico, an elegant residence in the Tuscan hills, just a 7-minute walk from the village of Lajatico, hometown of Andrea Bocelli. With two pools, panoramic terraces overlooking rolling hills, olive groves, BBQ, and full modern comfort, it offers four rustic-chic apartments—ideal for families, couples, or groups seeking authentic Tuscany close to town.

LocationValueCondition

5.0 out of 5 average rating, 41 reviews

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.

Apartment in Sassetta

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.

LocationFamilyIndoor spaces

4.86 out of 5 average rating, 69 reviews

Top guest favourite

An outdoor terrace is presented with a circular stone table set for dining, featuring plates and drinks. Comfortable chairs are adorned with striped cushions. A light curtain gently drapes, while a scenic view of the sea is visible in the background.

Apartment in San Vincenzo

Antea Blu: beach house in Tuscany - 2 bedrooms

98 sqm apartment, on the beach and 200 metres from the pedestrian street with shops. Private garage 2 minutes' walk from the house (€12/night) The house has: -a large living room with large sofa and 55-inch SMART TV - a beautiful and bright kitchen/dining area -2 bedrooms -2 baths -1 terrace with outdoor stone table and iron chairs, sea view

LocationValueAccess

4.95 out of 5 average rating, 93 reviews

Superhost

Apartment in Sassetta

Tuscany between Sea and Hills with pool

Welcome to your peaceful retreat in the Tuscan hills. At Locanda degli Alberi in Sassetta, nature, silence, and a pool surrounded by greenery await you. Perfect for couples and families seeking relaxation, amidst medieval villages, scenic trails, and the nearby Tuscan coast. Comfort, authenticity, and a slow pace for a rejuvenating break in Tuscany.

ValueFamilyAccuracy

4.82 out of 5 average rating, 60 reviews