
House holiday rentals in Castiglione della Pescaia
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Top-rated house rentals in Castiglione della Pescaia
Guests agree: these houses are highly rated for location, cleanliness and more.

Casa al Gianni - The Simignano Barn
Transformed from a former barn, this luxurious retreat offers 5 bedrooms, 4 bathrooms, a large, fully equipped kitchen, a spacious living room, and a large private garden with parking, a hot tub, a patio with sofas, a BBQ, a fire pit, and an outdoor kitchen. Ideal for those seeking a unique experience, it combines rustic charm with modern comforts. Perfect for families or groups, it promises magical evenings under the stars, including relaxation in the hot tub and outdoor dinners. A memorable getaway awaits you in this slice of paradise!

Palazzo Monaci - Pool in the Crete Senesi
Welcome to Palazzo Monaci! An oasis of nature and unique beauty, in the heart of the Crete Senesi, in Tuscany. A residence with a pool and a breathtaking view of the Crete Senesi. Perfect for couples or families looking for a relaxing vacation. The location is perfect for exploring the surrounding areas. You can hike in the Tuscan countryside, visit the characteristic medieval villages, taste the delicious local wines, and immerse yourself in the culture and history of this fascinating region.

Captain's House | Monte Grosso, Elba
The Casa del Capitano is located on the top of Monte Grosso in the National park of the tuscan archipelago. The location is unique on the island and from here you have a fantastic view of the city of Portoferraio, Piombino, Corsica, Capraia and Gorgona. The house was restored during a project lasting several years, in close collaboration with the National Park and was designed to be self-sufficient and ecological. Here you use purely the energy of the sun, without having to renounce luxury.

Casale Renieri – Petronilla
Il "Casale Renieri" da secoli proprietà dei Conti Renieri, si trova nella campagna di Vetulonia, antica ed importante città etrusca, luogo ricco di storia, miti, leggende e sapori antichi. Lo sguardo spazia in un panorama immenso tra le colline, il cielo infinito e colori esuberanti. I clivi scanditi dagli argentei ulivi e orlati da filari di maestosi cipressi, incorniciano il giardino formale che si staglia davanti all' ingresso. Lo splendido mare di Castiglione della Pescaia dista 13 km

Private Chianti Cottage, Garden & Vineyard Views
Set in a picturesque hamlet, overlooking the Chianti hills, this charming country house is just 10 minutes from Siena and Castellina in Chianti. Recently renovated, it blends authentic Tuscan charm with modern comforts. The house features two bedrooms, two bathrooms, a cozy living area and a fully equipped kitchen with a dishwasher, two fridges, and a washing machine. Outside, enjoy a beautiful garden and relax in the outdoor marble hot tub, soaking in the breathtaking views.

Casa Vista Sea and Maremma
Welcome to your peaceful oasis in Castiglione della Pescaia! Located in a quiet residential area, our house offers a magnificent view of the Maremma and is just a 15-minute walk from the historic center and a 5-minute drive from the beautiful beaches. Enjoy the perfect balance between relaxing in nature and seaside adventures, with the convenience of having all the attractions of the village at your fingertips. Your ideal getaway to discover the wonders of Tuscany awaits you.

The Chianti window
A wonderful place to spend a few days in pleasant company. A large living room with fireplace where you can relax after returning from beautiful walks, bike rides, and excursions. The independent apartment is 15 km from Siena, 20 km from the Thermal Baths and 40 minutes from the villages of San Gimignano and Monteriggioni. Overall, there is a farm that produces wines and oil with the possibility of guided tours and tasting of our products with themed dinners.

La Stallina - Perfect retreat from the city rush
Recently restored, La Stallina, was my grandfather's horse stable at the beginning of last century. Now it is a charming apartment perfect for a couple and suitable for 2+2 guests. One living room with kitchen in a conservatory, double bed and mezzanine with bed. Bathroom with large shower box, kitchen equipped with dish-washing and oven.

Domus Nannini - Crossed Loggia Spa
Appartamento appena ristrutturato composto da un salotto, moderna cucina open space completamente attrezzata con sala da pranzo, due camere e due bagni. Interamente rivestito con un pregiato pavimento in parquet di Olmo, originale e restaurato, che conferisce un'atmosfera calda e accogliente.

Siena Countryside Colle Ciupi
Countryside Villa apartment. Located in the nearby of Siena (Colle Ciupi, 10 kms away) Ground floor: Kitchen, living room with fireplace, bathroom with shower. First Floor: 3 Double Bedrooms and 2 bathrooms, outdoor with courtyard and huge garden

Borgo Ripostena – No. 8 Casa Vecchia
Charming cottage in the heart of Tuscany on a peaceful property surrounded by 5 hectares of private gardens and forest. The apartment has stunning views over San Gimignano and the Chianti Hills. One of the two bedrooms has air conditioning.

Secret Garden Siena
A beautiful house located inside the city walls of Siena. The house develops on two floors has three bedrooms and two toilets. The real strong point of this location is the private garden. Walking distance to all the main attractions.
Popular amenities for house rentals in Castiglione della Pescaia
House rentals with a pool

Podere Scorno country house with swimming pool

Family Forest - Pool in the Crete Senesi

Podere Cavone / Villa Oliva

Relax in the countryside near the sea( Lavanda )

Charming estate with views. A/C in the bedrooms

Country chic house in a village,private pool,wiFi

Country House in the Crete Senesi

Collina Power
Weekly house rentals

La Casa di Carla

Sensational semi-detached villa - Astonishing view

Villino Orchidea

The garden by the sea

Stunning loft in Montalcino.

Le Porrine V

Barn of Vignanova in Alta Maremma (Montieri)

Tosco Suite "Solis"
Private house rentals

Villa "alla vigna"

Villa Berenice

Monte Regio

Luxury 4BR Chianti Tuscany Home Pool Ensuite Baths

Capezzuolo 33

Casa nel Bosco in Seccheto, an oasis of peace

3 bedrooms, near the pool – Fonte di Sotto

City Center Palazzo: 4 King BR 6 Bath and Garage
When is the best time to visit Castiglione della Pescaia?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sept | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $225 SGD | $201 SGD | $193 SGD | $189 SGD | $188 SGD | $188 SGD | $224 SGD | $271 SGD | $193 SGD | $195 SGD | $193 SGD | $254 SGD |
| Avg. temp | 8°C | 8°C | 11°C | 13°C | 18°C | 22°C | 25°C | 25°C | 21°C | 17°C | 12°C | 9°C |
Quick stats about house rentals in Castiglione della Pescaia

Total holiday rentals
Explore 70 holiday rentals in Castiglione della Pescaia

Nightly prices starting at
Castiglione della Pescaia holiday rentals start at $52 SGD per night before taxes and fees

Verified guest reviews
Over 930 verified reviews to help you choose

Family-friendly holiday rentals
40 properties offer extra space & child-friendly amenities

Pet-friendly holiday rentals
Find 30 rentals that welcome pets

Rentals with dedicated workspaces
20 properties have a dedicated workspace

Wifi availability
40 of Castiglione della Pescaia holiday rentals include wifi access

Popular amenities for guests
Guests love Kitchen, Wifi and Pool across Castiglione della Pescaia rentals

4.6 Average rating
Castiglione della Pescaia stays receive an average rating of 4.6 out of 5 from guests
Destinations to explore
- Pet-friendly rentals Castiglione della Pescaia
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- Flat rentals Castiglione della Pescaia
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- Rentals with a washing machine and dryer Castiglione della Pescaia
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- House rentals Grosseto
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- House rentals Italy
- Elba
- Giglio Island
- Giannutri
- Cala Violina
- Feniglia
- Spiaggia Di Sansone
- Spiagge Bianche
- Spiaggia Di Barbarossa
- Spiaggia di Capo Bianco
- Gulf of Baratti
- Le Cannelle
- Spiaggia di Marina di Campo
- Pianosa
- Cascate del Mulino
- Parco Regionale Della Maremma
- Palazzo Pubblico
- Siena Cathedral
- CavallinoMatto
- Abbey of Sant'Antimo
- Santa Maria della Scala
- Vulci
- Mount Amiata
- Terme San Filippo
- Abbey of Monte Oliveto Maggiore





