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Villa vacation rentals in Castiglione della Pescaia

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Top-rated villa rentals in Castiglione della Pescaia

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

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Top 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
4.94 out of 5 average rating, 236 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

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
4.99 out of 5 average rating, 77 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 privato, direttamente in villa, per goderti una cena toscana in tutta tranquillità. Scrivici per info!

Top guest favorite
The stone farmhouse features vibrant red shutters and a terracotta roof. A spacious patio area contains a wooden dining set, surrounded by lush green grass and tall cypress trees. The exterior is complemented by well-maintained stone pathways, inviting guests to explore the outdoor space.
Villa in San Leolino
4.99 out of 5 average rating, 119 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.

Top guest favorite
A two-story, cube-shaped villa is surrounded by greenery and tall pine trees. Large glass doors provide access to the outdoor area, enhancing the connection with nature. The well-maintained garden features a variety of plants and a lush lawn.
Villa in Marina di Castagneto Carducci
5 out of 5 average rating, 31 reviews

Villetta Il Cubo is a five-minute walk to the sea

Detached 2-story villa with garden and parking space, completely renovated in 2021. Located in the shade of the pine forest a short walk from the beach (5 min) and the promenade of Marina di Castagneto where there are shops, restaurants and other public places. The villa consists of a living-dining room, kitchen, and bathroom-laundry on the ground floor; on the first floor, 2 bedrooms and 2 bathrooms with shower. Wi-Fi, air conditioning, outdoor patio with veranda, and BBQ are available.

Top guest favorite
A modern villa with a stone exterior features strategically placed windows and a prominent porch area. The surrounding greenery includes an olive tree, while steps lead to a well-maintained garden. An ornamental planter sits at the forefront, adding a decorative touch to the entrance.
Villa in Siena
4.98 out of 5 average rating, 198 reviews

Virgi House

Virgi House is a 160 sqm villa, located 3 km far from Siena’s hystorical center. The villa is distributed over three floors. On the first one there is a double bedroom with bathroom and terrace, a large open space living room, a modern kitchen and a bathroom. Downstairs a double bedroom (or 2 single beds), a large bathroom, a study and a bright living room with a loggia from which you can access the private car park and the garden. The property also provides free wifi, air conditioning.

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, 129 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 heated mini hydro-massage pool is surrounded by greenery, featuring subtle chromotherapy lighting in shades of purple. In the background, a rustic farmhouse is set against a serene twilight sky, with tall cypress trees lining the space.
Villa in Monteroni d'Arbia
4.98 out of 5 average rating, 112 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.

Top guest favorite
A hot tub sits surrounded by trees, with water bubbling gently. The view includes rolling hills under a colorful sunset sky, offering a serene atmosphere. Natural surroundings enhance the peacefulness of the setting.
Villa in Roccatederighi
4.98 out of 5 average rating, 50 reviews

Villa Il Diaccio with view of the Tuscan Maremma

Villa in pietra con particolari rifiniture architettoniche immersa in un bosco di castagni. Un grande giardino, in parte pavimentato a pietra, correda la proprietà dal quale si può ammirare un panorama meraviglioso della maremma toscana. Immersi nella natura si nota da una parte il mare con il golfo di Follonica, l'isola d'Elba e la Corsica, dall'altra l'isola del Giglio. E' possibile fare lunghe passeggiate nella natura o raggiungere località balneari o città d'arte.

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, 32 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
Villa in Siena
4.89 out of 5 average rating, 293 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
4.98 out of 5 average rating, 42 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, 150 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).

Popular amenities for Castiglione della Pescaia villa rentals

Quick stats about villa rentals in Castiglione della Pescaia

  • Total vacation rentals

    Explore 10 vacation rentals in Castiglione della Pescaia

  • Nightly prices starting at

    Castiglione della Pescaia vacation rentals start at ﺩ.ﺇ624 per night before taxes and fees

  • Verified guest reviews

    Over 80 verified reviews to help you choose

  • Family-friendly vacation rentals

    10 properties offer extra space & kid-friendly amenities

  • Wi-Fi availability

    10 of Castiglione della Pescaia vacation rentals include wi-fi access

  • Popular amenities for guests

    Guests love Kitchen, Wifi, and Pool across Castiglione della Pescaia rentals

  • 4.8 Average rating

    Castiglione della Pescaia stays are highly rated by guests—averaging 4.8 out of 5!

Destinations to explore

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  2. Italy
  3. Tuscany
  4. Grosseto
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