Villa vacation rentals in Castiglione della Pescaia

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Top-rated villa rentals in Castiglione della Pescaia

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Guest favorite

A spacious kitchen showcases a large stone fireplace with a wooden mantle as its centerpiece. Light streams through the window, illuminating the wooden beams overhead. A dining table is set for a meal, while traditional utensils adorn the walls, enhancing the inviting ambiance.

Villa in Castellina in Chianti

4.93 out of 5 average rating, 216 reviews

The Farmhouse Cottage

Entire upper floor of the newly renovated Manor House in traditional Tuscan style. High ceilings with exposed beams make the place cozy and perfect for families or groups of friends. In the house, there are two large functional fireplaces (in the living room and kitchen). Private, non-shared accommodation. The house has a large covered terrace, garden with sofas, BBQ, fire pit, private parking. The swimming pool among the olive trees and vineyards is ideal for relaxation and has private access to the shared area

Superhost

An outdoor pergola is nestled under tall umbrella pine trees. It features a dining area with wooden chairs and a table, a lounge space with comfortable seating, and a fully equipped kitchen. Warm, natural light filters through the trees, creating a serene ambiance.

Villa in Marina di Campo

5 out of 5 average rating, 33 reviews

Casa Pineta Elba, a short walk from the sea

Casa Pineta is submerged in umbrella pinewood trees in front of the beautiful sandy beach of Marina di Campo. The centre of the village is in walking distance while a 1min path in the woods will get you under your umbrella by the sea! Casa Pineta è immersa in un bosco di pini marittimi di fronte alla bellissima spiaggia di sabbia di Marina di Campo. Il centro del paese dista pochi minuti a piedi mentre 50 passi nella pineta priva di auto vi porteranno sotto il vostro ombrellone in riva al mare!

Top guest favorite

A private swimming pool is surrounded by vibrant flowers and lush greenery. Multiple lounge chairs are positioned under umbrellas for shade. A seating area is visible in the background, along with a well-maintained pathway and rustic stone walls, enhancing the serene outdoor setting.

Villa in Poggibonsi

4.98 out of 5 average rating, 60 reviews

Villa L'Olivo w/Private pool (Close San Gimignano)

Villa L’Olivo si trova nella campagna Toscana, a circa 10 chilometri da San Gimignano e a pochi minuti dai supermercati ed i vari servizi presenti a Poggibonsi. La nostra Villa è un ottimo punto di partenza per scoprire tutte le bellezze della Toscana, ma è anche un luogo ideale per chi ama concedersi una pausa dalla vita frenetica della città. A Villa L’Olivo, puoi prenotare una cena con chef privata, direttamente in villa, per goderti una cena toscana in tutta tranquillità. Scrivici per info!

Top guest favorite

An aerial view captures the expansive Poggio del Fattore estate, showcasing lush greenery and neatly arranged olive trees. The two main buildings, characterized by terracotta roofs, are complemented by the blue of the swimming pool, surrounded by vibrant gardens and cypress trees.

Villa in San Leolino

4.99 out of 5 average rating, 110 reviews

Poggio del Fattore-Villa with pool, hilltop, Chianti

Poggio del Fattore is situated at the eastern edge of the Chianti region in Valdambra, a green valley that joins the lands of Florence, Siena and Arezzo. The farmstead is on the top of an hill and lies at the end of a long private road through a large olive growing estate; therefore you absolutely need a car. The breathtaking landscapes and the location of the villa offer the privacy needed for a peaceful and relaxing holiday and a perfect departure point from which to explore central Tuscany.

Guest favorite

A sunlit swimming pool is situated in an expansive landscaped area, surrounded by neatly trimmed grass and lush trees. The charming building stands in the background, showcasing traditional architecture, while cypress trees line the horizon, adding to the tranquil countryside atmosphere.

Villa in Monteroni d'Arbia

4.98 out of 5 average rating, 102 reviews

San Giovanni in Poggio, villa Meriggio 95mq

Detached house, two double bedrooms, two bathrooms with shower, living room with fully equipped kitchen (dishwasher, washing machine, oven, microwave), double sofa bed, private garden with equipped pergola. Satellite TV and free Wi-Fi. Additional services at the property, upon reservation, include Focus brand Jarifa2 6.7 pedal-assisted bicycles and a wellness area with a Forest outdoor Finnish sauna and a heated mini-pool with hydromassage and chromotherapy with panoramic views.

Guest favorite

A serene setting features wooden lounge chairs positioned on a pebbled terrace, overlooking the sea. The vibrant colors of a sunset illuminate the horizon, while the gentle waves lap against the shore, creating a calming atmosphere.

Villa in Rosignano Marittimo

4.98 out of 5 average rating, 45 reviews

Villa with private access to the sea Castiglioncello

Independent villa surrounded by the greenery of a park with private access to the sea. The house is on two levels where on the ground floor we have the living area with kitchen, bathroom and a large living room with fireplace. Going upstairs we find the sleeping area with four bedrooms and two bathrooms. The villa was completely renovated and refurbished last year, including most of the furniture. The entrance to the property is served by an automatic gate and space for 5 cars.

Top guest favorite

A serene garden area features a lounging chair with a folded towel placed neatly on it. Stone planters and lush greenery surround a small hot tub, complemented by flowering plants and trees. The backdrop includes rustic architecture under a clear sky.

Villa in Monticchiello

4.98 out of 5 average rating, 154 reviews

Villa unesco heritage, Jacuzzi & garden. BB Daria

Carefully renovated and refurbished over a sustained period in order to maintain the original quality of its architecture, San Lorenzo Villa is open to guests. You are invited to enjoy the beauty, comfort and privacy of a beautiful independent villa in the centre of Monticchiello, from where you can have an incredible view on the Val d'Orcia, the UNESCO heritage! Don't forget a delicious breakfast (whatever you like) in our so close typical restaurant

Guest favorite

A rustic stone villa is surrounded by an expansive green lawn and olive trees. The structure features red window shutters and a covered terrace, enhancing the traditional charm of the property. The clear blue sky creates a bright, welcoming atmosphere.

Villa in Siena

4.89 out of 5 average rating, 286 reviews

Villa Capanna, Private Pool, Breathtaking Views

Ancient restored barn with up to 6 bedrooms and 6 bathrooms, immersed in a historic wine estate, just 6 km from Siena. One of the most beautiful views that the Tuscan panorama can offer, airconditioned bedrooms, exclusive swimming pool, large triple garden, BBQ, poolside table, terrace to enjoy the sunset over the medieval towers on the horizon while sipping the organic wines of the estate, fireplace, parking free, WI-FI internet.

Guest favorite

A two-story villa with a stone facade is set within a lush green garden. An outdoor hot tub is positioned on a tiled patio, complemented by terracotta planters. A wooden dining area is visible beneath a shaded porch, surrounded by trees and a low fence.

Villa in Basse di Caldana

4.97 out of 5 average rating, 35 reviews

Private villa in Maremma 15 minutes from the sea

Our private villa is located in the heart of the Tuscan Maremma just a few kilometres from the quiet village of Gavorrano. ‘La Quercia’ consists of a large garden with private veranda and Jacuzzi, two bedrooms, living area with fireplace and kitchen, two private and fully equipped bathrooms and a breathtaking view of the beautiful Maremma. Parking is private and free on site. Pets are allowed at an extra charge.

Guest favorite

An inviting indoor hot tub is highlighted, featuring sleek white surfaces and wooden accents. Two glasses of white wine and a tray of fresh raspberries are placed nearby, enhancing the relaxing ambiance of the space.

Villa in Monteroni d'Arbia

4.95 out of 5 average rating, 136 reviews

"Villa Daisy" overlooking Siena

Wonderful villa with independent entrance inside the "Caggiolo" farm, brought to light with careful and thorough renovation that has kept intact the typical features of a Tuscan farm. Beautiful panoramic view of Siena. Located in Ville di Corsano, just 14 km from the city. An ideal place to spend days in total relaxation and enjoy the wonders that this area offers (Chianti, Val d'Orcia, Crete Senesi etc).

Top guest favorite

The villa's rustic stone exterior is complemented by a sunlit pool area, featuring a beautifully crafted wooden pergola. Comfortable seating arrangements are provided under the pergola, surrounded by blooming flowers. A large umbrella offers shade beside the shimmering pool, enhancing the outdoor relaxation experience.

Villa in Cavriglia

4.99 out of 5 average rating, 134 reviews

Villa Poggio in Mandria in Chianti

Villa Poggio a Mandria is the gateway to the Chianti; it is a good base to reach the most beautiful art cities of Tuscany (Arezzo, Florence, Siena, San Gimignano, Volterra) in about one hour time. On the surrounding hills there are medieval villages, which offer visitors a charming atmosphere of the past and the opportunity to take walks in an unspoiled countryside.