
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.

Lovely seasidehouse with new air condition !
Charming house with new air conditioning in the heart of Maremma on the Tuscan coast in Castiglione della Pescaia with free public parking 1-minute walk from the house. Experience the magic of an ancient medieval village away from the chaotic modern life! Choose a different beach every day (walk a few minutes downtown or drive along the coast - you'll have loads of different beaches to explore, both private and public). To get around: walk or rent a bike or drive a few minutes in Maremma.

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.

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.

Villa with a hydromassage pool
Delightful Villa 2 km from the beautiful sea of the Rocchette (choice between free beach or private bath) reachable along a flat road of the typical Maremma countryside, by bike or car. Just a 5-minute drive to the medieval village of Castiglione della Pescaia.

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.
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

Country chic house in a village,private pool,wiFi

Country House in the Crete Senesi

Collina Power

LECCIONE RESIDENCE
Weekly house rentals

Villa Berenice

Monte Regio

Capezzuolo 33

City Center Palazzo: 4 King BR 6 Bath and Garage

Casa nel Bosco in Seccheto, an oasis of peace

Domus Antiqua

Tosco Suite "Solis"

L'Uva Fragolina. House, Garden & Jacuzzi
Private house rentals

S.Ilaria - Private pool Villa with 2 bedrooms

Family Forest - Pool in the Crete Senesi

“Il Glicine” [Nature, Stars, Relaxation and Pool]

La Mignola Apartment

CountryHouse immersed in woodland

Villino Orchidea

Stunning loft in Montalcino.

The Cat Tower
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 | $200 SGD | $193 SGD | $189 SGD | $187 SGD | $187 SGD | $223 SGD | $270 SGD | $193 SGD | $194 SGD | $193 SGD | $253 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 $51 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
- Rentals with a washing machine and dryer Castiglione della Pescaia
- Apartment rentals Castiglione della Pescaia
- Family-friendly rentals Castiglione della Pescaia
- Pet-friendly rentals Castiglione della Pescaia
- Smoking-friendly rentals Castiglione della Pescaia
- Beach house rentals Castiglione della Pescaia
- Rentals with a firepit Castiglione della Pescaia
- Flat rentals Castiglione della Pescaia
- Waterfront rentals Castiglione della Pescaia
- Villa rentals Castiglione della Pescaia
- Beachfront rentals Castiglione della Pescaia
- Rentals with beach access Castiglione della Pescaia
- Rentals with outdoor seating Castiglione della Pescaia
- Rentals with a patio Castiglione della Pescaia
- Rentals with a fireplace 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
- 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





