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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.

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Top guest favourite
An outdoor patio area features rustic furnishings and is framed by gracefully draping curtains. The space is adorned with comfortable seating and a communal dining table, set against a backdrop of tall cypress trees and a clear blue sky, inviting relaxation in a serene environment.
Home in Simignano
4.98 out of 5 average rating, 174 reviews

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!

Guest favourite
Home in Asciano
4.96 out of 5 average rating, 131 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.

Top guest favourite
A stone house is positioned on a hillside overlooking the deep blue sea. Lush green terrain surrounds the structure, and a large umbrella provides shade near the entrance. The coastline and distant boats can be seen in the background under a clear sky.
Home in Rio Marina
5 out of 5 average rating, 107 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.

Guest favourite
An outdoor terrace features a wooden deck furnished with comfortable seating, including two armchairs and a small table. Reclining sun loungers are positioned nearby, surrounded by lush greenery and offering a peaceful setting for relaxation.
Home in Castiglione della Pescaia
4.89 out of 5 average rating, 9 reviews

Villa Simonetta, Poggio le Trincee, Castiglione

Welcome to Villa Simonetta, recently renovated, located in Castiglione della Pescaia, just 7 minutes from the sea and the historic center. It has a modern kitchen, a living area with a sofa bed and a panoramic terrace, 2 double bedrooms with a smart TV and 2 private bathrooms. Outside, equipped terraces, garden, barbecue and independent annex. Equipped with air conditioning, video-monitored parking and a cellar-laundry. Strategic location and breathtaking views of the Tuscan islands.

Top guest favourite
A lush green garden is framed by a rustic pergola made of wooden beams. Grassy paths lead deeper into the garden, where vibrant flowers and trees provide a natural backdrop. Rolling hills and a clear blue sky are visible in the distance, creating a serene outdoor setting.
Home in Castellina in Chianti
4.98 out of 5 average rating, 130 reviews

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.

Guest favourite
A scenic view features a tranquil landscape with rolling hills in the distance. Tall trees frame the image, providing shade to a stone patio. The outdoor area includes comfortable seating, inviting guests to relax while enjoying the surrounding natural beauty.
Home in Castiglione della Pescaia
5 out of 5 average rating, 17 reviews

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.

Top guest favourite
A view from the window reveals a serene landscape of rolling hills and valleys bathed in soft morning light. The garden below is adorned with colorful flowers and greenery, enhancing the tranquil atmosphere of the Tuscan countryside.
Home in San Quirico d'Orcia
4.99 out of 5 average rating, 226 reviews

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.

Guest favourite
A serene bedroom features a spacious bed with a simple white coverlet. A wooden chair with a striped cushion is placed beside a bench. Natural light filters through the two wooden windows, revealing views of the lush vineyards outside.
Home in Castelnuovo Berardenga
4.9 out of 5 average rating, 122 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.

Top guest favourite
A charming stone house is surrounded by lush greenery and colorful flowers. The exterior features a thatched roof and several wooden windows, with a seating area adorned with potted plants. Mature trees provide shade, creating a peaceful outdoor atmosphere.
Home in Pancole
4.99 out of 5 average rating, 149 reviews

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

Top guest favourite
A light-filled living area features large glass windows, offering views of the surrounding nature. An orange armchair and a minimal dining table are visible, complemented by wooden cabinetry and kitchen appliances. Natural light illuminates the space, enhancing the warm tones of the decor.
Home in Marrucheti
4.98 out of 5 average rating, 172 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.

Top guest favourite
A modern kitchen is presented with sleek gray cabinetry and a stylish countertop. Stainless steel appliances, including an oven and induction cooktop, are incorporated. Ambient lighting enhances the workspace, while a wall-mounted TV is visible, offering convenience and entertainment options.
Home in Castiglione della Pescaia
5 out of 5 average rating, 48 reviews

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.

Top guest favourite
A cozy bedroom is highlighted with a floral wallpaper featuring vibrant colors. A bedside table made of wood stands beside a spacious bed dressed in pink bedding. A modern lamp provides warm lighting, enhancing the inviting details of the room.
Home in Pievescola
4.95 out of 5 average rating, 195 reviews

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

When is the best time to visit Castiglione della Pescaia?

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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
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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

  • 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

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  3. Tuscany
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  5. Castiglione della Pescaia
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