
Holiday houses in Montepescali
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Top-rated holiday rentals in Montepescali
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Casa al Gianni - The Simignano Barn
Transformed from a former barn, this luxurious retreat offers 5 bedrooms, 4 bathrooms, a large, fully equipped kitchen, a spacious living room, 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 seeking a unique experience, it combines rustic charm with modern comforts. Perfect for families or groups, it promises magical evenings under the stars, complete with relaxation in the hot tub and al fresco dining. A memorable getaway awaits you in this slice of paradise!
FamilyLocationOutdoor spaces
4.97 out of 5 average rating, 198 reviews
LECCIONE RESIDENCE
Characteristic country house with exposed wooden beams, 2 double bedrooms, 1 bedroom with bunk bed and a double sofa bed in the living room. The 2 bathrooms with shower. Large and well-equipped kitchen. Dishwasher, wood-burning and electric oven, espresso machine. Large garden with barbecue, swimming pool and a hot tub. Expenses to be paid on-site based on consumption: wood €8 per box, LPG €6 per cubic meter, electricity €0.36 per kW. Wood will be provided for a barbecue and a hot bath in the hot tub for free.
FamilyValueWi-Fi
4.93 out of 5 average rating, 145 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.
ValueLocationSolo travel
5.0 out of 5 average rating, 118 reviews
Wp Relais Borgo Vignalunga
Discover Borgo Vignalunga by WP Relais, an charming hamlet set in a 46-hectare estate in the heart of the Val D'Orcia, a UNESCO World Heritage Site. Surrounded by woodland, pastures, a lush vegetable garden, cultivated fields and three olive groves with 1,500 olive trees, Borgo Vignalunga is the ideal place to experience the true essence of Tuscany. The property is close to historical villages, evocative architecture, unspoilt natural landscapes and renowned restaurants, bars and wineries.
LocationValueRiver
4.95 out of 5 average rating, 146 reviews
Podere Vergianoni nestled in Chianti with a pool
Podere Vergianoni is a family-run, historic property dating back to the 1600s, located in the beautiful hills of Chianti in Tuscany. Our family can arrange a private shuttle and local experiences directly. The apartment is available for 2 adults with the option of adding a sofa bed for 2 children under 12 years of age. In the large outdoor courtyard you'll find a saltwater pool with a relaxation area on a panoramic terrace overlooking the castle and vineyards with unique sunsets.
ValueLocationEV charging
5.0 out of 5 average rating, 352 reviews
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.
LocationValueBackyard
4.98 out of 5 average rating, 107 reviews
Villa Casale "Il Diaccio" with views of the Maremma
Villa Casale with large garden partly in grass and partly in stone slabs. Immersed in nature and lying on a comfortable sunbed, the town of Roccatederighi divides the horizon, on one side the view of the sea with the Gulf of Follonica and beyond the Island of Elba and Corsica, on the other the Maremma plain and the island of Giglio. You can walk in nature, admire the local fauna, go by bike, relax by taking a bath in the mini pool or reach the cities of art.
ValueFamilyGetting around
4.94 out of 5 average rating, 18 reviews
Agriturismo Marrucheti 82 South Apartment
An 88sqm apartment, it consists of a large living room with an open space kitchen, two bedrooms, two bathrooms (one with a shower and one with a bathtub). Ideal for large families or a group of friends. It includes: A sofa bed in the living room, which can be used as an extra bed. Bed linen, bathroom towels and beach towels Cleaning services, bed linen and towels replacement halfway through the week.
FamilyLocationBathroom
5.0 out of 5 average rating, 46 reviews
Castel Brunello - 2 doublebed rooms + terrace
Located in amidst the Tuscan countryside, Castel Brunello is offers an outdoor swimming pool and a garden. This self-catering accommodation features rustic-style furnishings, air condioning and free Wi-Fi. They also offer a satellite TV, and a fully equipped kitchenette with a refrigerator and a dining table. Each apartment has a terrace with an outdoor seating area.
ValueLocationHospitality
4.99 out of 5 average rating, 118 reviews
Poggio Bicchieri Holiday Farm - Poesia apartment
Overlooking the Val d 'Orcia, our holiday farm consists of 2 apartments each with a kitchen, bedroom, and bathroom. Large equipped garden. Surrounded by silence, close to Pienza, Montalcino, Bagno Vignoni, and the natural thermal baths of Bagno San Filippo. Getting here is very easy; the last km of the road is unpaved but accessible for all.
LocationFamilyHospitality
4.95 out of 5 average rating, 577 reviews
La Stallina - Perfect retreat from the city rush
Recently restored, La Stallina, was my grandfather's horse stable at the beginning of last century. Now it is a charming apartment perfect for a couple and suitable for 2+2 guests. One living room with kitchen in a conservatory, double bed and mezzanine with bed. Bathroom with large shower box, kitchen equipped with dish-washing and oven.
ValueFamilyAir conditioning
4.98 out of 5 average rating, 181 reviews
Spacious Flat just 15 Minutes from the Sea
Discover the perfect combination of modern Scandinavian comfort and Tuscan charm in this private flat located in the village of Tirli. The flat offers modern yet cosy interiors, two bathrooms, a fully equipped kitchen, two bedrooms and a balcony with all the amenities you need for a relaxing holiday away from the stress of everyday life.
FamilyValueCondition
5.0 out of 5 average rating, 35 reviewsPopular amenities for Montepescali holiday rentals
Other great holiday rentals in Montepescali

Luxury Penthouse with a View of Piazza del Campo
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5.0 out of 5 average rating, 21 reviews
Podere Raspollino | Maremma 10 people
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Design loft with private SPA in Tuscany
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XIII Century Tower with Private Panoramic Pool
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4.8 out of 5 average rating, 296 reviews
Golden View - Dream Farmhouse in Tuscany
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4.97 out of 5 average rating, 65 reviews
Podere Cavone Villa Vigna A breathtaking view
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5.0 out of 5 average rating, 17 reviews
Stone villa with pool
LocationFamilyGetting around
5.0 out of 5 average rating, 23 reviews
Tuscany countryhouse with pool: 10 beds apartment
FamilyLocationOutdoor spaces
4.93 out of 5 average rating, 15 reviewsDestinations to explore
- Elba
- Giglio Island
- Lake Bolsena
- Giannutri
- Cala Violina
- Parco Regionale Della Maremma
- Feniglia
- Spiagge Bianche
- Gulf of Baratti
- Spiaggia Di Sansone
- Le Cannelle
- Del Chianti
- Spiaggia di Marina di Campo
- Spiaggia di Capo Bianco
- Mount Amiata
- Cascate del Mulino
- Siena Cathedral
- CavallinoMatto
- Avignonesi Winery Fattoria Le Capezzine
- Vulci
- Val di Chiana
- Quercetano
- Palazzo Pubblico
- Valdichiana Outlet Village





