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

Villa in Castiglion d'orcia

4.95 out of 5 average rating, 77 reviews

Villa Vignalunga

Discover paintings, found art, and original sculptures from room to room in this spacious villa. Old and new worlds collide as chic bathrooms share the space with ancient beamed ceilings. Admire sweeping countryside views from a stone terrace. Villa Vignalunga has been recently, uniquely constructed with traditional materials and preserves all the architectural details of the historic Tuscan farmhouses. Furnished with extreme taste with a mix of still old and modern but always in a rustic original style The villa is surrounded by 46 hectares of picturesque land boasting olive groves, lush vineyards, plentiful orchards, and meadows for grazing horses. Go for a scenic hike or drive to a nearby town for fresh local cuisine.

Nov 13 – 20

R14,561 ZAR per night

Guest favorite

Villa in Talamone

4.91 out of 5 average rating, 44 reviews

Villa Il Molinaccio with terrace and private beach

Large villa with panoramic terrace overlooking the sea and direct access from the house to the private sassed beach. It has large outdoor and indoor spaces for dining with company, garden, deckchair, umbrella, ping-pong and barbecue. Recently purchased kitchen and furniture. A 10-minute walk from the port and downtown, it offers privacy but accessibility to all amenities, including windsurfing, diving, beaches, and boat rentals. Large private garage in front of the house on private street. Recently renovated.

Dec 24 – 31

R10,803 ZAR per night

Guest favorite

Villa in Asciano

4.96 out of 5 average rating, 57 reviews

Casa Bianca gorgeous Tuscan home, Crete Senesi

Casa Bianca si trova al centro di uno dei luoghi più affascinanti della Toscana,le Crete Senesi.A due passi dal famoso Site Transitoire di Jean Paul Philippe. Si arriva alla casa salendo una strada bianca accompagnata dai tipici cipressi e lo sguardo va ai calanchi e le biancane,brulle e lunari,facendovi subito innamorare dei suoi mille colori:dall'indaco alla terra bruciata!La casa (240mq)si apre con un parcheggio privato solo per i suoi ospiti ed un grande giardino.A solo pochi minuti da Siena

Apr 21 – 28

R6,842 ZAR per night

Guest favorite

Villa in Castellina in Chianti

4.93 out of 5 average rating, 166 reviews

The Villino Farmhouse

Entire upper floor of the newly renovated Villa Padronale in traditional Tuscan style. High ceilings with exposed beams make it cozy and perfect for families or groups of friends. In the house there are two functional large fireplaces(in the living room and kitchen). Private accommodation, not shared. The house has a large covered terrace,garden with sofas,bbq,firepit, private parking. The pool among the olive trees and vineyards is ideal for relaxing and has a private access to the shared area

Apr 13 – 20

R11,671 ZAR per night

Guest favorite

Villa in San Leolino

5.0 out of 5 average rating, 92 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.

R7,043 ZAR per night

Guest favorite

Villa in Sovicille

4.97 out of 5 average rating, 121 reviews

Podere La Castellina - N°1 COTTAGE

Independent cottage in stones and bricks inside the "Podere la Castellina" (former convent 13th century), in the magnificent natural park of Montagnola Senese. The cottage comfortably sleeps 5 people and includes: - large living room with TV and fireplace - kitchenette with oven - double bedroom - bedroom with three single beds - bathroom with shower Available for guests Guests with panoramic pool, solarium and terrace with breathtaking views, equipped with wood-burning oven and barbecue.

Oct 15 – 22

R4,479 ZAR per night

Guest favorite

Villa in Siena

4.97 out of 5 average rating, 152 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.

Nov 13 – 20

R3,436 ZAR per night

Superhost

Villa in Siena

4.88 out of 5 average rating, 257 reviews

Fascinating Villa Senese with View!

Ancient restored barn with up to 6 bedrooms and 6 bathrooms, immersed in a historic wine estate, just 6 km from Siena. Here time passes slowly according to ancient traditions. One of the most beautiful views that the Tuscan panorama can offer, 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, original and working fireplace, parking free, WI-FI internet.

Feb 15 – 22

R14,388 ZAR per night

Guest favorite

Villa in Rosignano Marittimo

5.0 out of 5 average rating, 27 reviews

Independent villa with private sea descent

Independent villa immersed in 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 a large living room with fireplace, going upstairs we find the sleeping area with four bedrooms and two bathrooms. The villa has been totally renovated and refurbished last year including most of the furnishings. The entrance to the property is served by an automatic gate and space for 5 cars.

May 23 – 30

R10,602 ZAR per night

Guest favorite

Villa in Capoliveri

5.0 out of 5 average rating, 34 reviews

Villa Orlandi Mediterranean essence

Relax in a villa in pure Mediterranean style set in an ancient olive grove on the gentle hill overlooking the most beautiful gulf on the island of Elba. Villa Orlandi offers a unique panoramic position, where you can admire the Gulf of Lacona, the Stella Gulf, the characteristic village of Capoliveri with its promontory and the island of Montecristo. A quiet and secluded place, ideal for a holiday in complete relaxation, with all the comforts, and not far from the beach.

Apr 19 – 26

R2,389 ZAR per night

Guest favorite

Villa in Monteroni D'arbia

4.97 out of 5 average rating, 93 reviews

"Villa Daisy" overlooking Siena

Wonderful villa with independent entrance inside the "Caggiolo" estate, returned to light with careful and deep renovation that has kept the typical guidelines of a Tuscan farm intact. Beautiful panoramic view of Siena. Located in the Villas of Corsano, only 14 km from the city. Ideal place to spend days in total relaxation and enjoy the wonders that this area offers (Chianti, Val d 'Orcia, Crete Senesi...).

Feb 28 – Mar 7

R5,032 ZAR per night

Guest favorite

Villa in Volterra

5.0 out of 5 average rating, 18 reviews

Podere La Casetta - 2 People - Private Pool

Volterra. Podere "La Casetta" is in the countryside of Volterra, 10 min by car from the center of Volterra. Garden and swimming pool for your exclusive use. The house is located one hour drive from Florence, Pisa and Siena. The house is located at 30 min from San Gimignano and Teatro del Silenzio, where you can partecipate at the Andrea Bocelli concert every summer.

Sep 2 – 9

R8,948 ZAR per night