| Montepulciano Central Villa – Sauna & Jacuzzi | Luxury Villa Rentals in Montepulciano, Tuscany | villa | 4 | 9 | €765 |
| Apartments at Poggiolo - Borgo - Montepulciano | Luxury Villa Rentals in Montepulciano, Tuscany | apartment | 2 | 4 | €137 |
| Casa la Stadera | Luxury Villa Rentals in Montepulciano, Tuscany | farmhouse | 2 | 4 | €139 |
| Celeste – The color of the summer sky in Tuscany | Luxury Villa Rentals in Montepulciano, Tuscany | farmhouse | 2 | 4 | €150 |
| La Limonaia Delightful Apartment in Montepulciano | Luxury Villa Rentals in Montepulciano, Tuscany | apartment | 2 | 5 | €176 |
| Colombi Palace Montepulciano | Luxury Villa Rentals in Montepulciano, Tuscany | farmhouse | 2 | 4 | €178 |
| Wi-Fi Fiber Large Apartment in Montepulciano | Luxury Villa Rentals in Montepulciano, Tuscany | apartment | 2 | 6 | €179 |
| Casa Olivieri Tuscany House in the Center | Luxury Villa Rentals in Montepulciano, Tuscany | house | 2 | 5 | €192 |
| "Hortus Conclusus" House | Luxury Villa Rentals in Montepulciano, Tuscany | house | 2 | 4 | €214 |
| La Piazzetta - Cozy open space in the historic center of Montepulciano | Luxury Villa Rentals in Montepulciano, Tuscany | villa | 6 | — | €236 |
| Stunning Tuscan apartment in 14 Century Palazzo 2 | Luxury Villa Rentals in Montepulciano, Tuscany | apartment | 1 | 2 | €248 |
| Casale Santa Barbara - Exclusive Apartment | Luxury Villa Rentals in Montepulciano, Tuscany | apartment | 1 | 2 | €255 |
| Vicolo delle Mura, ancient home with a view | Luxury Villa Rentals in Montepulciano, Tuscany | house | 2 | 4 | €285 |
| Piana - owned by Sant' Antonio Country Resort | Luxury Villa Rentals in Montepulciano, Tuscany | farmhouse | 3 | 4 | €310 |
| Luxurious Medieval Tower & Private Concierge | Luxury Villa Rentals in Montepulciano, Tuscany | villa | 1 | 2 | €401 |
| Elegant farmhouse overlooking Pienza | Luxury Villa Rentals in Montepulciano, Tuscany | farmhouse | 3 | 6 | €448 |
| Luxury Villa with Private Pool | Luxury Villa Rentals in Montepulciano, Tuscany | villa | 6 | 11 | €719 |
| Luxury Attic in Tuscany+Incredible view and A/C | Luxury Villa Rentals in Montepulciano, Tuscany | villa | 4 | 10 | €857 |
| Nice double room in a charming B&B | Luxury Villa Rentals in Montepulciano, Tuscany | villa | 1 | 2 | €179 |
| Amazing view 3 bdr villa with pool & A/C in Pienza | Luxury Villa Rentals in Montepulciano, Tuscany | villa | 3 | 6 | — |
| ERAMO Wine House • Design, Parking & AC | Luxury Villa Rentals in Montepulciano, Tuscany | house | 3 | 6 | — |
| Flat, terrace, pool, Spa resort,restaurant, A/C,S1 | Luxury Villa Rentals in Montepulciano, Tuscany | farmhouse | 2 | 6 | — |
| Flat, terrace, pool,Spa resort,restaurant, A/C, G1 | Luxury Villa Rentals in Montepulciano, Tuscany | villa | 1 | 4 | — |
| Fontarcella, H&R- mediterranean home with jacuzzi | Luxury Villa Rentals in Montepulciano, Tuscany | house | 1 | 3 | — |