San Casciano in Val di Pesa Vacation Rentals

There are a lot of options in San Casciano in Val di Pesa. If you plan on staying in the San Casciano in Val di Pesa area, consider making a reservation for a few nights at one of these properties as these have been rated the Top Vacation Rentals in San Casciano in Val di Pesa:

• "Villa Torre in Chianti" Vrbo Vacation Rental of the Year 2026- 8 bedrooms A/C
• Casale Tagliafune,a XV century's Country Villa near Florence with vineyards view
• Holiday home with a view, walk to restaurants and shops, car is not required
• Villa Andrei, a relaxing bath in the Tuscan countryside with private pool
• a dream vacation in Tuscany
• Archipettoli - a historical manor house with stunning panoramic views
• Casa Scopeti - Villa with private swimming pool
• Pozzo dei Desideri 1 - Apartment with swimming pool
• Cottage in Tuscany with Pool & BBQ
• Tuscany Bliss: Garden Retreat

There are 70 vacation rentals with private pools near San Casciano in Val di Pesa. Top-rated RBO homes that have access to a swimming pool include:

• Villa Salivolpe Amazing Chianti View, San Casciano VDP, Italy
• Chianti family villa, 5 bedrooms, infinity pool, A/C, BBQ, 360° view
• Stunning private villa with WIFI, hot tub, A/C, private pool, TV, panoramic view, close to Florence
• Villa Carmignani, your home in Tuscany: exlusive use of villa, grounds and pool.

If you are looking for a family-friendly vacation home in San Casciano in Val di Pesa, check out one of the following properties as all are highly-rated places to stay with excellent review for families or groups staying in San Casciano in Val di Pesa:

• Il Convento by Interhome
• Il Vichiaccio Country House
• B&B La Fonte del Machiavelli

Currently, the total number of properties listed by Rent By Owner in 2026 is over 425 in the San Casciano in Val di Pesa area, and still counting. By aggregating listings from multiple websites, Rent By Owner offers an immense amount of choice of the best RBO properties in San Casciano in Val di Pesa. 

The cancellation policy varies depending on the host and specific property. You should review the cancellation terms listed in the rental details or contact the property owner directly to understand your options and potential fees.

You can secure your stay by selecting your preferred dates, reviewing the listing details, and completing the booking through the platform. For any special requests or questions, reaching out to the property owner can help ensure a smooth reservation process.

Additional fees such as cleaning, service charges, or taxes are typically outlined in the listing. Be sure to read the full description or contact the owner for clarity on all costs before confirming your booking.

Amenities vary by property but often include essentials like Wi-Fi, kitchen facilities, and outdoor spaces. The detailed listing page will specify what each property offers, so review it carefully to match your needs.

Changes or cancellations depend on the host’s policies listed with the property. To modify your reservation or cancel, consult the listing details or contact the owner directly for guidance.