
House holiday rentals in Castiglione della Pescaia
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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

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

Charming converted Hayloft overlooking the Chianti Hills
Inspired by the rustic Tuscan style, this gorgeously refurbished hayloft features ceilings with exposed beams and bricks and thoughtful touches for a stylish and comfortable decor. From the relaxing hammock and the stone made barbecue in a panoramic garden to the cozy fireplace, every space feels open and inviting. Immersed in total peace and tranquillity with a breathtaking view over the Chianti hills, halfway between Florence, Arezzo and Siena, the barn is a perfect homebase to visit Tuscany. The accommodation has 2 floors. The upper floor spaces 2 double bedrooms with wonderful views of the olive trees and a bathroom with window and large masonry shower. On the ground floor a cozy and spacious living area with fireplace and a kitchenette with gas stove a large fridge and oven. The barn has ceilings with exposed beams and bricks. Outside there is a panoramic garden set on its own where, in the shade of a walnut trees, you can relax on a hammock or grill your meal (included an authentic local Fiorentina steak :-) on the stone made barbecue. A garden table is there for romantic dinners 'al fresco'. Immersed in total peace and tranquility halfway between Florence, Arezzo and Siena the barn is a perfect homebase to visit Tuscany. To find the exact location of the house type the following code in GMaps: 8FMHGG25+QV The house is in the countryside. The closest towns are Cavriglia and the small Medioeval villages of Moncioni and Montegonzi. In each town you can find great local restaurants and a small grocery shop. Moncioni is 3 km far away. A big supermarket is located in Montevarchi and you can reach it in 8 minutes by car ( exactly 7 km far away). In Montevarchi you can also find one of the best farmer markets in Tuscany! The station of Montevarchi is 8 km away from the barn. From there you can take train to Florence and Arezzo. Siena can be reached in 30 minutes by car. The easy access to the motorway A1/E35 Milan-Florence-Rome (the Valdarno exit is only at 13 km) allows you to reach numerous interesting spots within a short time, both in Tuscany and Umbria, while few kilometres south of Cavriglia you enter the suggestive territory of the Crete Senesi. Out in the countryside, the home offers an authentic experience of Tuscany. Small towns and villages are a short drive away providing acces to exceptional local restaurants and fantastic farmers markets. A big supermarket is located in Montevarchi (7 km far away). The railway station is 8 km away from the barn. From there you can take train to Florence and Arezzo. Cities of interest like Siena, Montepulciano, Pienza and Monteriggioni can be reached in 40 minutes by car The only way to reach the house is by car. A taxi service is active from Montevarchi You will be provided of blankets and towels. The kitchen is equipped with and kind of pots, pans, bowl, plates and silverware. You are welcome to use them. Free Netflix available

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.

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.

Alma Vignoni - Vignoni Val d 'Orcia - Bagno Vignoni
Alma Vignoni is an elegant and exclusive holiday house in Vignoni Alto that recalls Tuscan style and is enriched by unusual and personal details. The house consists of an open-space with fireplace in the center. On the one hand the room with stunning views over the surrounding hills (Pienza, Monticchiello and Montepulciano) on the other the kitchen area. Two cozy rooms overlook the ancient Via Francigena and the Orcia river valley. The bathroom has a large shower.

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.

The Bandita dei Bovi
The cottage is located 4 km from Castell'Azzara, surrounded by the greenery of an olive grove consisting of 38 olive and fruit trees and surrounded by wooded land and pastures, overlooking the valley offering a breathtaking 180° view starting north with the Fortress of Radicofani until descending towards the west to get lost on the horizon among the Sibillini Mountains. 300 meters from the provincial road, it can be reached by a dirt road.

Casa Dante – Authentic Chianti Stay | Views & Relaxation
Wake up to breathtaking views over the rolling hills of Chianti and enjoy a glass of wine at sunset from your private terrace. This peaceful home offers the perfect mix of privacy, comfort, and authentic Tuscan charm. Located just minutes from the center of Radda in Chianti, the house is ideally positioned to explore wineries, charming villages, and the surrounding countryside—while still feeling quiet.

Casa Pancole
Beautiful stone house completely and tastefully renovated, surrounded by nature, ideal for privacy, close to places of interest such as Grosseto, Terme di Saturnia, Alberese, Parco dell'Uccellina, Marina di Grosseto (in the cold periods there is a pellet stove that heats the rooms, the pellet is an additional cost to be requested, thank you) tourist tax to be paid directly on site

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.

Alluring Elicriso a few steps from beach & centre
New, cozy, fully equipped, with a private entrance, at the foot of a verdant hill, close to the sea and shops, in a quiet location. Forget about your car because everything is within walking distance. Private terrace surrounded by a charming communal garden. Pets allowed. Accommodates up to 4 people.
Popular amenities for house rentals in Castiglione della Pescaia
House rentals with a pool

Podere Scorno country house with swimming pool

Podere Cavone / Villa Oliva

Luxury 4BR Chianti Tuscany Home Pool Ensuite Baths

Charming estate with views. A/C in the bedrooms

Explore Chianti from a Charming Stone House

Collina Power

House Rigomagno Siena

Vetulonia farmhouse with a relaxing pool
Weekly house rentals

Country house short distance from the sea

Monte Regio

Sensational semi-detached villa - Astonishing view

Villino Orchidea

Casa San Ripa: Relax Oasis with Private Pool

Poggiolo

Tosco Suite "Solis"

La Bandita Dependance
Private house rentals

Private Cottage with Plunge Pool in Tuscan Estate

casa LU e JO

City Center Palazzo: 4 King BR 6 Bath and Garage

3 bedrooms, near the pool – Fonte di Sotto

Stunning loft in Montalcino.

Country chic house in a village,private pool,wiFi

CasAgata - Valley view

Domus Antiqua
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 | $226 SGD | $201 SGD | $194 SGD | $190 SGD | $188 SGD | $188 SGD | $224 SGD | $271 SGD | $194 SGD | $195 SGD | $194 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 |
Destinations to explore
- Smoking-friendly rentals Castiglione della Pescaia
- Rentals with outdoor seating Castiglione della Pescaia
- Apartment rentals Castiglione della Pescaia
- Waterfront rentals Castiglione della Pescaia
- Beachfront rentals Castiglione della Pescaia
- Flat rentals Castiglione della Pescaia
- Rentals with a washing machine and dryer Castiglione della Pescaia
- Rentals with beach access Castiglione della Pescaia
- Rentals with a firepit Castiglione della Pescaia
- Rentals with a fireplace Castiglione della Pescaia
- Family-friendly rentals Castiglione della Pescaia
- Pet-friendly rentals Castiglione della Pescaia
- Villa rentals Castiglione della Pescaia
- Beach house rentals Castiglione della Pescaia
- Rentals with a patio Castiglione della Pescaia
- House rentals Grosseto
- House rentals Tuscany
- House rentals Italy
- Elba
- Giglio Island
- Giannutri
- Cala Violina
- Feniglia
- Spiaggia Di Sansone
- Spiagge Bianche
- Spiaggia Di Barbarossa
- Gulf of Baratti
- Spiaggia di Capo Bianco
- Le Cannelle
- Spiaggia di Marina di Campo
- Cascate del Mulino
- Siena Cathedral
- Parco Regionale Della Maremma
- Pianosa
- Palazzo Pubblico
- CavallinoMatto
- Terme San Filippo
- Abbey of Sant'Antimo
- Santa Maria della Scala
- Mount Amiata
- Saturnia Thermal Park
- Abbey of Monte Oliveto Maggiore





