Pet-friendly holiday rentals in Castiglione della Pescaia

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, complete with relaxation in the hot tub and al fresco dining. A memorable getaway awaits you in this slice of paradise!

Pets · Walkability · Long stay

Apartment in Tuscan farm house.

Small, cosy apartment with independent access, consisting of charming bedroom with a beautiful view, equipped with ample closet space, a comfortable canopy bed and private bathroom and pretty living room / breakfast area, with sofa-bed. A delicious breakfast is included in the price and from April through October guests also have the option of dining on-site in our traditional farm restaurant. If dates are not available the property includes other rooms in charming cottage also on Airbnb.

Pets · Outdoor spaces · Condition

Villa di Geggiano – Guesthouse

PLEASE NOTE THAT BEING IN THE COUNTRYSIDE WITH FEW PUBLIC TRANSPORTATION OTHER THAN TAXI, THE BEST WAY TO ENJOY YOUR STAY AND TO VISIT THE BEAUTIFUL SURROUNDINGS IS TO HAVE A CAR. The 18th century Villa di Geggiano, surrounded by vineyards and lovingly cared gardens, is located in the Chianti area near Siena, one of the most beautiful regions of Italy which will provide an idyllic and enchanting backdrop to your vacation. Our guesthouse is located in one of the garden pavilions of the villa.

Pets · Outdoor spaces · Hospitality

EcoLodge – modern design in a peaceful panoramic location

The EcoLodge, modern, ecological, comfortable, is in the middle of nature in a peaceful, fertile cultural landscape on Monte Amiata in the quiet southern Tuscany. It belongs to an old farmhouse with plenty of space, beautiful views, many old fruit, chestnut, olive trees and our vineyard. It's an ideal location. From here you can explore world-famous sights, do a lot and enjoy the tranquility of Tuscan country life away from the hordes of tourists.

Outdoor spaces · Walkability · Accuracy

Claudia's House in Piazza del Campo

"The terrace overlooking Piazza del Campo" An elegant period residence, in a 13th-century building, directly overlooking Piazza del Campo, where you will be welcomed by 3 bedrooms with 5 beds, a bathroom with shower, a large living room, a kitchen and a very large living room with fully frescoed ceilings. Our guests will be welcomed in a wonderful and quiet apartment where they can enjoy the beautiful view directly on Piazza del Campo

Walkability · Pets · Kitchen

La Casetta di Brunello, very panoramic with terrace

STIAMO LAVORANDO PER VOI! ... WE ARE WORKING FOR YOU! The house is completely renovated and furnished in 2018 with classic-Tuscan style furniture. The colors are warm and enveloping to better rest during your holiday of peace and relaxation. In addition to the two double bedrooms, you have a kitchen with an equipped kitchenette, fridge, induction cooker and a furnished terrace with a beautiful view of the surrounding countryside.

Walkability · Outdoor spaces · Heating

Casetta Venere Tuscan relaxation 3 km from the sea

Casetta Venere: Sea, nature and Pet-Friendly. Just 3 km from the crystal clear sea of Castiglione della Pescaia, Casetta Venere is a small Tuscan jewel among olive trees, perfect for couples, families, and travelers with pets. The house offers well-kept spaces, a beautiful private garden and an intimate and welcoming atmosphere. We look forward to welcoming you for a slow, authentic and beautiful stay in the midst of nature.

Walkability · Outdoor spaces · Condition

"Red Rose" apartment with view of Siena.

Caggiolo is a completely renovated farm consisting of several apartments, each with an independent entrance and private garden, with a panoramic view of Siena. Located in Ville di Corsano, just 14 km from the city. An ideal place to spend days in total relaxation and enjoy the wonders that this area offers (Chianti, Val d'Orcia, Crete Senesi etc).

Walkability · Pets · Amenities

Little Jewel in the center of CDP

Typical bi-level studio right in the center of Castiglione della Pescaia with all the facilities at hand (restaurants, bars, shops, gelaterie, pharmacy ..) With stone walls, terracotta floors, beamed ceiling, wooden mezzanine and finishes, it has the typical tuscan atmosphere! Only 5 minutes walking distance from the sea

Walkability · Pets · Laundry

Cozy house at 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.

Outdoor spaces · Pets · Decor

La Pieve - the house next to the church

To the right of the Argenina church, after which it is named, it has the persuasive look of its 2 small arches facing west. Perhaps it was once the parish priest's house, or the one where cooking was done in the large wood-burning oven, who knows?

Walkability · Outdoor spaces · Access

Authentic Tuscan Country House WITH A/C

The "Pergola" apartment (75 sqm) is one of the two independent housing units that make up the Terra Rossa farmhouse, located in the heart of the Sienese countryside just a few minutes' drive from the historic center.

Walkability · Outdoor spaces · Checkout