Vacation rentals in Montepulciano
Wander Wisely with exceptional service, 24/7 support
Save an extra 10% or more on select hotels with Member Discounts
Access exclusive hotel deals, only with the Travelocity app
Vacation rentals in Montepulciano
Il Tosco
Via del Poliziano 13 Montepulciano SI
1.03 km from city centre
The price is CA $460 per night
CA $460
CA $513 total
Dec 31 - Jan 1, 2026
includes taxes & fees
Book a stay at this luxury residence in Montepulciano. Enjoy free WiFi, free parking, and room service. Popular attractions Medici Fortress and Torre del Pulcinella are located nearby.
Parking included
Free WiFi
Residenza Fabroni
Via di Gracciano nel Corso, 12 Montepulciano SI
Free cancellation
Reserve now, pay when you stay
0.51 km from city centre
The price is CA $120 per night
CA $120
CA $139 total
Jan 13 - Jan 14, 2026
includes taxes & fees
Book a stay at this historic residence in Montepulciano. Enjoy free WiFi, an attached winery, and a rooftop terrace. Popular attractions Torre di Pulcinella and Palazzo di Bucelli are located nearby.
Hot tub
Free WiFi
Bellarmino Boutique Apartments
Via di San Donato 10 Montepulciano SI
Free cancellation
Reserve now, pay when you stay
0.9 km from city centre
Stay at this apartment in Montepulciano. Enjoy free WiFi, rainfall showerheads, and air conditioning. Popular attractions Consorzio del Vino Nobile di Montepulciano and Palazzo Comunale are located nearby.
Kitchen
Pet-friendly
Osteria del Borgo
Via Ricci 7 Montepulciano SI
0.8 km from city centre
Stay at this residence in Montepulciano. Enjoy free breakfast, free WiFi, and free parking. Popular attractions Palazzo Comunale and Palazzo Ricci are located nearby.
Breakfast included
Pet-friendly
Typical villa with private pool in a panoramic position in southern Tuscany, a few kilometres from t
Montepulciano SI
4.12 km from city centre
Stay at this villa in Montepulciano. Enjoy private pools, a garden, and laundry facilities. Popular attractions Tenuta Valdipiatta and Via Ricci are located nearby.
Pool
Kitchen
INDEPENDENT HOUSE LARGE TERRACES & SPECTACULAR VIEWS in CENTER W. PARKING
Montepulciano Siena
0.99 km from city centre
Stay at this vacation home in Montepulciano. Enjoy a garden, laundry facilities, and patios. Popular attractions Medici Fortress and Torre del Pulcinella are located nearby.
Kitchen
Washer
Entire Historic Residence in Tuscany (Val d'Orcia),in the Heart of Montepulciano
Montepulciano Provincia di Siena
0.96 km from city centre
Stay at this vacation home in Montepulciano. Enjoy free WiFi, laundry facilities, and in-room jetted tubs. Popular attractions Medici Fortress and Consorzio del Vino Nobile di Montepulciano are located nearby.
Hot tub
Kitchen
montorio
Str. per Pienza 2 Montepulciano SI
1.55 km from city centre
Stay at this condo in Montepulciano. Enjoy free WiFi, free parking, and in-room massages. Popular attractions San Biagio and Torre del Pulcinella are located nearby.
Parking included
Free WiFi
Charming House in the heart of Montepulciano
Montepulciano Toscana / Italia
0.34 km from city centre
Stay at this apartment in Montepulciano. Enjoy free WiFi, laundry facilities, and in-room jetted tubs. Popular attractions Palazzo Avignonesi and Colonna del Marzocco are located nearby.
Hot tub
Kitchen
LA CASINA CANTINI - Panoramic apartment in Montepulciano in the historic center
Montepulciano (SI) Tuscany
0.96 km from city centre
Stay at this apartment in Montepulciano. Enjoy free WiFi, an in-room coffeemaker, and air conditioning. Popular attractions Medici Fortress and Consorzio del Vino Nobile di Montepulciano are located nearby.
Kitchen
Free WiFi
Panoramic villa surrounded by vineyards and olive groves, 6 km from Montepulciano. Ideal for familie
Montepulciano SI
3.99 km from city centre
Stay at this villa in Montepulciano. Enjoy private pools, a garden, and laundry facilities. Popular attractions Tenuta Valdipiatta and Colonna del Marzocco are located nearby.
Pool
Kitchen
Classic Stunning 3 Bedroom Apartment in Montepulciano with Air Conditioning,
Montepulciano Toscana
0.42 km from city centre
Stay at this apartment in Montepulciano. Enjoy laundry facilities, in-room washers/dryers, and an in-room coffeemaker. Popular attractions Palazzo di Bucelli and Torre di Pulcinella are located nearby.
Kitchen
Washer
Hotel San Gregorio
Via Della Madonnina 4 Pienza SI
Free cancellation
Reserve now, pay when you stay
9.25 km from city centre
The price is CA $257 per night
CA $257
CA $292 total
Jan 5 - Jan 6, 2026
includes taxes & fees
Book a stay at this business-friendly residence in Pienza. Enjoy free WiFi, an outdoor pool, and room service. Popular attractions RI Crea RE and Enoteca Di Ghino are located nearby.
Pool
Pet-friendly
Abbadia Sicille Relais
SP 14 Loc. Abbadia Sicille Trequanda SI
Free cancellation
Reserve now, pay when you stay
9.77 km from city centre
The price is CA $89 per night
CA $89
CA $103 total
Jan 7 - Jan 8, 2026
includes taxes & fees
Book a stay at this business-friendly residence in Trequanda. Enjoy free WiFi, free parking, and an outdoor pool. Popular attractions Monastery of Sant'Anna in Camprena and San Giovanni d'Asso Station are located nearby.
Pool
Hot tub
Casanova - Panoramic Rooms and Suites
Strada Provinciale 146 di Chianciano San Quirico d'Orcia SI
15 km from city centre
The price is CA $316 per night
CA $316
CA $354 total
Jan 2 - Jan 3, 2026
includes taxes & fees
Stay at this residence in San Quirico d'Orcia. Enjoy free breakfast, free WiFi, and an outdoor pool. Popular attractions Horti Leonini and Chapel of our Lady of Vitaleta are located nearby.
Pool
Breakfast included
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
Most popular
Hotels
Flights
