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, 229 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

Guest favorite

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, 36 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

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, 117 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

The pool area is surrounded by meticulously maintained grass and features comfortable lounge chairs placed along the edge. A rustic wooden structure with open sides provides shade, and lush greenery is visible in the background, enhancing the serene setting.

Villa in Castiglione d'Orcia

4.97 out of 5 average rating, 121 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.

Top guest favorite

A historic tower rises prominently against a blue sky dotted with fluffy clouds. Surrounding greenery complements the stone structure, with trees and small buildings visible along the hillside, collectively conveying a sense of tranquility.

Villa in Montecatini Val di Cecina

4.99 out of 5 average rating, 125 reviews

Belforti Tower

Torre dei Belforti is the perfect place for people who love beauty, nature and art. Sleeping at the Tower is like traveling trough the time, between knights and princesses. The wonder of this place is enriched by a big garden, with its swimming pool, the cypresses alleys and the olive trees. The village is also a magic place well preserved and still alive. We are Emilia and Luca, we live here and our mission is to give the best to our guests, to fully enjoy this marvelous place.

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, 49 reviews

Villa with private access to the sea Castiglioncello

Independent villa surrounded by lush greenery, with private access to the sea. Spread over two levels, the ground floor features a bright living area with a fully equipped kitchen, bathroom, and a spacious lounge with fireplace. Upstairs, the sleeping area includes four bedrooms and two bathrooms. The villa was fully renovated in 2022, including most of the furnishings. The property has a private entrance with an automatic gate and offers parking for up to five cars.

Top guest favorite

A traditional Tuscan farmhouse is set against a backdrop of rolling hills. The property features a spacious pool surrounded by lush green grass and neatly trimmed hedges. Tall cypress trees provide natural framing, enhancing the serene outdoor atmosphere.

Villa in Montenero d'Orcia

5 out of 5 average rating, 30 reviews

Tuscany Villa With Pool & Magnificent Garden

This traditional Tuscan farmhouse, dating back to 1868, is situated on a small hill overlooking Castello Banfi and other large Brunello wineries and has a 360° view of the surrounding countryside of the Orcia Valley. The house is in a secluded location at the end of a well-maintained gravel road. You can use the house, garden and pool alone in an absolutely quiet location and enjoy a unique level of privacy. The sunsets are a special kind of experience!

Guest favorite

An outdoor seating area is presented, featuring colorful chairs on a wooden deck overlooking a calm bay. The landscape showcases distant mountains and shoreline, where the turquoise water meets the greenery, creating a peaceful atmosphere for relaxation.

Villa in Naregno

5 out of 5 average rating, 25 reviews

La Guardiola - Cape Pearl

In the past, La Guardiola was placed to defend the entrance to Porto Azzurro from the sea. It had two key features: an extensive and dominant view and immediate access to the sea. The view of rare beauty, the sea that pervades every environment, the peace and scents of the Mediterranean scrub, make this place magical. Currently the property, owned by our family since 1994, is a 130 sqm independent villa, surrounded by a park of over 1,000 sqm.

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, 289 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.

Top 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, 39 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.

Top guest favorite

The villa is situated in a lush landscape, surrounded by rolling hills and greenery. A private pool is framed by manicured hedges and lounging areas. The rustic stone structure features a covered patio and is complemented by nearby olive groves and trees, ensuring privacy.

Villa in Montecastelli Pisano

4.97 out of 5 average rating, 37 reviews

Exclusive villa with pool jacuzzi wifi and green

My accommodation is close to art and culture, magnificent panoramic views, restaurants and surrounded by greenery. You will like my accommodation for these reasons: the light, the outdoor spaces, the atmosphere, high level of privacy. My accommodation is suitable for couples and families (with children), romatic honeymoon and summer holiday with family. No other guest in the villa and in the surrounding area.