
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 $84 AUD per night before taxes and fees

Verified guest reviews
Over 1,000 verified reviews to help you choose

Family-friendly holiday rentals
50 properties offer extra space and kid-friendly amenities

Pet-friendly accommodation
Find 30 rentals that welcome pets

Rentals with dedicated workspaces
20 properties have a dedicated workspace

Wi-Fi availability
40 of Castiglione della Pescaia holiday rentals include Wi-Fi access

Popular amenities for guests
Guests love Kitchen, Wi-Fi and Pool across Castiglione della Pescaia rentals

4.7 Average rating
Castiglione della Pescaia stays receive an average rating of 4.7 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.

Domus Nannini - Loggia Salimbeni SPA
Apartment of 200 sqm furnished with precious classical furniture and very spacious rooms: 13 windows overlooking the old town, each window offers a unique view of the city. Big and spacious lounge with peerless view on the begin of Banchi di Sopra, Piazza Salimbeni and the headquarter of the Monte dei Paschi, formed by the noble palaces Tantucci, Salimbeni and Spannocchi. Second lounge with library, sofa-bed and the same exclusive view. 2 large bedrooms with city-views and king-size beds. 3 bathrooms one with jacuzzi and one with shower. A long corridor that crosses the apartment, spacious entrance and private terrace on the internal courtyard. Third lounge with sofa-bed and city-view. Dining room with panoramic views of the Duomo of Siena and Basilica of San Domenico which stand out over the medieval roofs of Siena a few meters from us. Fully equipped kitchen with laundry area. It occupies the entire second floor our 1600's palace and offers unique and privileged views of Siena and its architectural wonders. We are on Banchi sopra Sopra, the main course of the historical center of Siena, below the house you will find the best shops in the center with all the brands of high fashion, lots of restaurants; Wineries, Bars and Supermarkets with typical Tuscan products.
4.96 out of 5 average rating, 156 reviews
Casa al Gianni - The Simignano Barn
Transformed from a historic barn, this luxurious retreat offers 5 bedrooms, 4 bathrooms, a large, fully equipped kitchen, a spacious living area, 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 looking for a unique experience, it combines rustic charm with modern comforts. Perfect for families or groups, it promises magical evenings under the stars, with relaxation in the hot tub and outdoor dinners. A memorable getaway awaits you in this little slice of paradise!
4.97 out of 5 average rating, 198 reviews
LECCIONE RESIDENCE
Characteristic country house with exposed wooden beams, 2 double bedrooms, 1 bedroom with bunk bed and a double sofa bed in the living room. The 2 bathrooms with shower. Large and well-equipped kitchen. Dishwasher, wood-burning and electric oven, espresso machine. Large garden with barbecue, swimming pool and a hot tub. Expenses to be paid on-site based on consumption: wood €8 per box, LPG €6 per cubic meter, electricity €0.36 per kW. Wood will be provided for a barbecue and a hot bath in the hot tub for free.
4.93 out of 5 average rating, 145 reviews
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.
4.96 out of 5 average rating, 142 reviews
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.
5.0 out of 5 average rating, 118 reviews
Open space surrounded by nature
Casa Namaste is a small stone cottage with well-kept interiors 1 km from the medieval village of Montescudaio. The house is completely surrounded by woods and centuries-old oaks. 150 meters away flows the Cecina river. In the 5000 square meter garden there is a natural spring with a large stone tub to cool off and an outdoor hot shower surrounded by greenery. We have a Vodafone adsl line with download 33 and upload 1.4. Smart TV and air conditioning are also available starting this spring
4.96 out of 5 average rating, 137 reviews
Charming Salicornia near beach and town centre
Bright and brand new, this apartment is in a quiet location close to both the sea and the town centre, so you can forget about your car—everything is just steps away. This fully equipped 2-bedroom apartment has it all: a modern kitchen, mosquito nets, comfortable air conditioning, and even a cot and high chair for your little one. We’ve thought of every detail, including beach toys for added fun. Everything you need for a carefree stay is already here; just bring your personal belongings.
5.0 out of 5 average rating, 58 reviews
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.
4.9 out of 5 average rating, 135 reviews
Frontemare house with exclusive sea access
Casa Frontemare is a completely renovated property with direct access to the sea, from which you can enjoy a panoramic view of the sea, the Tuscan islands and wonderful sunsets. It is a perfect place for those who love a relaxing and private vacation. The proximity to the Tuscan art cities and the small typical villages means that it is also possible to discover new places and discover the flavors of Italian cuisine.
4.95 out of 5 average rating, 111 reviews
Beach villa with parking
Exclusive villa in Castiglione della Pescaia, just 500 meters from the sea. It boasts private parking on site, designer kitchen, a large garden with refined outdoor furnishings. It offers 4 comfortable beds divided into 2 bedrooms, air conditioning and Wi-Fi connection. Ideal for families or couples looking for a charming stay. Just a short drive to gourmet restaurants and lively locals.
4.9 out of 5 average rating, 10 reviews
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.
4.98 out of 5 average rating, 181 reviews
Cosy house in Porto Azzurro
Porto Azzurro, the house, with beautiful view, has been renovated now in 2026. The house has good place for 4 persons. The beach, "Golfo della Mola", that is very close to our house, is perfect for who has a kayak or a small boat. To bath we recommend sand beaches that is 1-2 km away.
4.9 out of 5 average rating, 106 reviewsPopular amenities for Castiglione della Pescaia house rentals
House rentals with a pool

Collina Power
4.93 out of 5 average rating, 203 reviews
Explore Chianti from a Charming Stone House
4.98 out of 5 average rating, 123 reviews
Private Chianti Cottage, Garden & Vineyard Views
4.99 out of 5 average rating, 137 reviews
Podere Scorno country house with swimming pool
4.93 out of 5 average rating, 146 reviews
Casa Sofema seaside home with Wi-Fi
4.88 out of 5 average rating, 130 reviews
Design loft with private SPA in Tuscany
5.0 out of 5 average rating, 77 reviews
Vetulonia farmhouse with a relaxing pool
4.95 out of 5 average rating, 60 reviews
Podere La Fornace is a small Ferienparadies
4.91 out of 5 average rating, 22 reviewsWeekly house rentals

La Casa di Alvino
5.0 out of 5 average rating, 3 reviews
Lovely seasidehouse with new air condition !
4.66 out of 5 average rating, 97 reviews
Casa Vista Sea and Maremma
5.0 out of 5 average rating, 24 reviews
The garden by the sea
5.0 out of 5 average rating, 21 reviews
Comfortable house and terrace by the sea
4.87 out of 5 average rating, 31 reviews
Country house short distance from the sea
4.94 out of 5 average rating, 48 reviews
Villa Simonetta, Poggio le Trincee, Castiglione
4.91 out of 5 average rating, 11 reviews
Maremma farmhouse by the sea LA NORD
4.89 out of 5 average rating, 36 reviewsPrivate house rentals

Beachfront Tuscany
5.0 out of 5 average rating, 48 reviews
The House in the Castle and the Terrace overlooking the Village
5.0 out of 5 average rating, 18 reviews
Sensational semi-detached villa - Astonishing view
4.98 out of 5 average rating, 91 reviews
Casa Lucrezia with garden overlooking the sea on the hill
4.96 out of 5 average rating, 27 reviews
VILLA LILLA on the Beach of San Vincenzo LUXURY
4.9 out of 5 average rating, 58 reviews
Casa Il Leccio – Relax and nature in Tuscany
5.0 out of 5 average rating, 36 reviews
The House of Paintings
5.0 out of 5 average rating, 13 reviews
Casale Renieri – Petronilla
5.0 out of 5 average rating, 10 reviewsWhen is the best time to visit Castiglione della Pescaia?
| Month | Jan | Feb | Mar | Apr | May | June | July | Aug | Sept | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $246 AUD | $219 AUD | $211 AUD | $202 AUD | $205 AUD | $229 AUD | $245 AUD | $295 AUD | $211 AUD | $212 AUD | $211 AUD | $277 AUD |
| 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
- Apartment rentals Castiglione della Pescaia
- Condo rentals Castiglione della Pescaia
- Beachfront rentals Castiglione della Pescaia
- Villa rentals Castiglione della Pescaia
- Rentals with beach access Castiglione della Pescaia
- Family-friendly rentals Castiglione della Pescaia
- Pet-friendly rentals Castiglione della Pescaia
- Beach house rentals Castiglione della Pescaia
- Waterfront rentals Castiglione della Pescaia
- House rentals Grosseto
- House rentals Tuscany
- House rentals Italy
- Elba
- Giglio Island
- Giannutri
- Cala Violina
- Parco Regionale Della Maremma
- Feniglia
- Spiagge Bianche
- Gulf of Baratti
- Spiaggia Di Sansone
- Le Cannelle
- Pianosa
- Spiaggia di Marina di Campo
- Spiaggia di Capo Bianco
- Mount Amiata
- Cascate del Mulino
- Siena Cathedral
- CavallinoMatto
- Vulci
- Palazzo Pubblico
- Saturnia Thermal Park
- Rimigliano Natural Park
- Riserva Naturale Diaccia Botrona
- Terme San Filippo
- Abbey of Sant'Antimo





