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Villa holiday rentals in Castiglione della Pescaia

Find and book unique villas on Airbnb

Quick stats about villa rentals in Castiglione della Pescaia

  • Total holiday rentals

    Explore 10 holiday rentals in Castiglione della Pescaia

  • Nightly prices starting at

    Castiglione della Pescaia holiday rentals start at $219 SGD per night before taxes and fees

  • Verified guest reviews

    Over 80 verified reviews to help you choose

  • Family-friendly holiday rentals

    10 properties offer extra space & child-friendly amenities

  • Wifi availability

    10 of Castiglione della Pescaia holiday rentals include wifi 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!

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 favourite
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, 246 reviews

Manor House - IlVillinoFarmhouse

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 favourite
A serene outdoor pool area is surrounded by lush greenery and rustic stone pathways. Lounge chairs are positioned beside the pool, creating a space for relaxation. The picturesque villa can be seen in the background, framed by trees and gentle hillside.
Villa in Castiglione d'Orcia
4.96 out of 5 average rating, 137 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 favourite
A charming stone villa is set amidst a lush green lawn. The building features wooden window shutters and a terracotta tile roof. A covered porch, adorned with flower pots, offers a welcoming outdoor space, complemented by a backdrop of blooming plants and trees.
Villa in Barberino Tavarnelle
4.97 out of 5 average rating, 102 reviews

CasaDiManuela:TotallyPrivateChiantiVilla withTub

CasaDiManuela:TotallyPrivateVilla in Chianti withTub Jacuzzi The villa, immersed in the Chianti countryside, was obtained from an old farmhouse and then renovated with extreme care and attention to detail. Original terracotta floors and ceilings with ancient exposed beams, old traditional Tuscan furniture, flowery fabrics that dress beds and armchairs, paintings, antique china and lived objects recovered from markets and junk dealers will frame your living room. Nothing here is by chance.

Top guest favourite
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, 133 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.

Top guest favourite
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, 57 reviews

Villa Il Diaccio with view of the Tuscan Maremma

Stone villa with special architectural finishes nestled in a chestnut forest. A large garden, partly paved with stone, accompanies the property from which you can admire a wonderful view of the Tuscan Maremma. Surrounded by nature, you can see the sea with the Gulf of Follonica, the island of Elba and Corsica on one side, and the island of Giglio on the other. You can take long walks in nature or reach seaside resorts or cities of art.

Guest favourite
Villa in Siena
4.89 out of 5 average rating, 300 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 favourite
Villa in Morcone
5 out of 5 average rating, 8 reviews

Luxury Villa with swimming pool ModdissiCharme Elba Island

Villa with an infinity pool, surrounded by greenery, just a few minutes from Morcone Beach. Comfortable sleeping area offers 3 double bedrooms and one with single beds, each with a full private bathroom, TV and air conditioning. In the living area there is a large equipped kitchen, dining table with relaxation area and smart TV; from here access to the outdoor terrace ideal for enjoying a great aperitif Parking lot

Top guest favourite
Villa in Monteroni d'Arbia
4.94 out of 5 average rating, 163 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).

Guest favourite
A panoramic view is presented from the villa's terrace, overlooking the azure sea and nearby islands. Lush green cypress trees line the path, which is paved with natural stone. Sun loungers are arranged thoughtfully, inviting relaxation while enjoying the surrounding nature.
Villa in Cala Piccola
4.89 out of 5 average rating, 38 reviews

Villa - Incredible View - Private Beach - Jacuzzi

In typical Tuscan style made with Vietri majolica tiles, wood and stone, it offers a breathtaking view of the Arcipelago Toscano National Park. This villa is part of one of the most beautiful and luxurious areas of Monte Argentario: Cala Piccola. Perfect for those seeking privacy and contact with nature, to relax with friends, a place to work off-site or plan family holidays.

Superhost
A private pool is surrounded by well-maintained gardens and sunloungers. Umbrellas provide shade, while the lush green vineyards stretch into the distance. The pool features clear water and a Roman step entrance, creating a relaxing outdoor space.
Villa in Civitella Paganico
5 out of 5 average rating, 3 reviews

The Passo Degli Ulivi

Il Passo degli Ulivi is a beautiful and comfortable holiday home set in the peaceful Tuscan countryside, surrounded by vineyards and olive groves. It is ideal for anyone looking to unwind in a scenic setting. The layout is particularly family-friendly as one of the bedrooms features both a double and a single bed - perfect for parents with a young child.

Top guest favourite
A solitary tree stands prominently in the foreground, framed against a vast landscape. Below, the coastline stretches toward the horizon, with the sea shimmering in the distance. The view includes a charming town nestled among the lush greenery of the surrounding hills.
Villa in Castagneto Carducci
4.99 out of 5 average rating, 116 reviews

sea view villa with private infinity pool

RENTALS ONLY FROM SATURDAY TO SATURDAY. The house is located within our farm, surrounded by forest is distance from the village of Castagneto Carducci only 3.5 km. Its unique location offers a wonderful view of the sea and the country, ensuring a pleasant tranquility, away from the heat and noise of the country.

Superhost
The villa's exterior showcases a charming Mediterranean-style design, featuring a terracotta roof and soft pink walls. The surrounding well-maintained lawn is bordered by tall trees, providing a serene backdrop, while outdoor seating is positioned on the patio, inviting relaxation.
Villa in Grosseto
5 out of 5 average rating, 25 reviews

Podere la Pompa

Villa with three bedrooms with ensuite bathroom, large kitchen and living room. External loggia for outdoor dining and possibility of using the shared swimming pool. Piccola Pompa is located a short drive from Grosseto and less than 20 minutes from the beaches of Castiglione della Pescaia

Popular amenities for villa rentals in Castiglione della Pescaia

Destinations to explore

  1. Airbnb
  2. Italy
  3. Tuscany
  4. Grosseto
  5. Castiglione della Pescaia
  6. Villa rentals