Compare Vacation Rentals & Airbnb in Montepulciano

560 available vacation rental offers

7 nights
2
1
  • airbnb
  • booking
  • vrbo
  • expedia
  • priceline
  • tripadvisor
  • tripcom
  • sonder
  • homestay
  • hostelworld
  • hotelscom
  • agoda
Montepulciano vacation rentals
Choose the perfect vacation accommodation
Price per night
Accommodation type
Rating

560 Rentals and Airbnb in Montepulciano

Best family friendly Montepulciano vacation rentals

Among the 560 accommodations in Montepulciano, here are the 4 best family friendly rentals

La Colonna Di Montisi - Montepulciano
9.3 3 reviews

La Colonna Di Montisi

apartment, Montalcino
La Colonna di Montisi apartment is located in the village of Montisi, approximately 22.5km from both Bagno Vignoni and Montepulciano Terme, offering easy access to the Val d'Orcia.
This 87 square metre self-catering flat sleeps 13 guests and includes a fully equipped kitchen, air conditioning, free Wi-Fi, and private parking.
Dimora Del Corso Di Montepulciano - Montepulciano
9.2 527 reviews

Dimora Del Corso Di Montepulciano

apartment, Montepulciano
Dimora Del Corso Di Montepulciano is situated in the historic centre of Montepulciano, just 9.3 miles from the UNESCO-protected town of Pienza. The apartment is highly rated for location, cleanliness, and overall experience.
This one-bedroom apartment offers a comfortable and stylish space for a relaxing stay. Guests can enjoy modern amenities like air conditioning, free Wi-Fi, and a dishwasher, alongside a terrace, a garden, and a swimming pool.
Lovely Room In Montepulciano - Montepulciano
No reviews

Lovely Room In Montepulciano

apartment, Montepulciano
This studio apartment offers unparalleled proximity to Montepulciano's historic centre, placing you just metres from Piazza Grande and the Duomo.
The accommodation is ideal for two guests, featuring a kitchen with a fridge, microwave, and dishwasher, and benefits from on-site parking and a fitness centre.
Agriturismo Capraccioni  Family - Montepulciano
9.4 13 reviews

Agriturismo Capraccioni Family

gîte, Pienza
This Pienza farmhouse rental, situated in the Val d'Orcia countryside, is 4km from Montepulciano and 2.5km from Monticchiello, offering easy access to these historic Tuscan towns.
The 80m² ground-floor apartment sleeps four guests, comprising two bedrooms, two bathrooms, a private garden with children's play area and barbecue, plus on-site parking and Wi-Fi.

Best Montepulciano vacation rentals with a balcony

Il Vescovo, Incredible Attic In Center Of Montepulciano, Luxe - Montepulciano
9.7 11 reviews

Il Vescovo, Incredible Attic In Center Of Montepulciano, Luxe

apartment, Montepulciano
This spacious four-bedroom flat is situated in the centre of Montepulciano, just 5.3 kilometres from Montepulciano Terme and within easy reach of other Tuscan attractions like Bagno Vignoni (21 kilometres) and Bagni San Filippo (27 kilometres). The apartment has consistently received excellent ratings for its location, cleanliness, and overall experience.
The 400 square metre property comfortably accommodates up to 19 guests and offers a fully equipped kitchen, a dining area, a seating area, a flat-screen TV, a terrace, a garden, and a shared kitchen. Guests can enjoy a welcome basket with wine, champagne, chocolates, and cookies, as well as concierge service, airport transfers, bicycle rentals, and free Wi-Fi.
60 M² Apartment ∙ 1 Bedroom ∙ 4 Guests - Montepulciano
10 1 review

60 M² Apartment ∙ 1 Bedroom ∙ 4 Guests

apartment, Chianciano Terme
This one-bedroom apartment in Chianciano Terme offers panoramic views and is conveniently located for exploring nearby towns like Montepulciano and Pienza.
The 60-square-metre property features a fully equipped kitchen with fridge and dishwasher, a private terrace, and can comfortably accommodate four guests, boasting air conditioning and free parking.
80 M² Farmhouse ∙ 2 Bedrooms ∙ 4 Guests - Montepulciano
9.6 29 reviews

80 M² Farmhouse ∙ 2 Bedrooms ∙ 4 Guests

farm, Montepulciano
Farm rental for up to 4 guests with an excellent rating of 96% based on 29 reviews. Your accommodation will be located in Montepulciano.
Facilities and services include an iron, a swimming pool and a washing machine. Take advantage of the gym in this accommodation.
Residenza Villa Tosca - Montepulciano
9.5 127 reviews

Residenza Villa Tosca

apartment, Sinalunga
Residenza Villa Tosca is located in Bettolle, a town 39 kilometres from Piazza Grande and 21 kilometres from Montepulciano Terme.
This family-friendly apartment complex offers a range of amenities including a swimming pool, tennis court, and a garden with stunning views, perfect for relaxing after a day exploring the local area.

Frequently Asked Questions about vacation rentals in Montepulciano

  • What are some interesting places to visit in or near Montepulciano?

    Montepulciano is a real gem! You have to visit the historic centre, with its stunning Piazza Grande and the Duomo. For a day trip, head to the nearby Pienza, a charming hilltop town known for its Renaissance architecture. And if you love wine, a visit to the vineyards in the surrounding countryside is a must.
  • What are the best Airbnb and vacation rentals in Montepulciano?

    Podere Fontecastello, Case Vacanza - Villa Paola and Villa Cicolina are the most popular Airbnb and vacation rentals in Montepulciano among travelers.

  • Which walking or cycling routes are the best in Montepulciano?

    The walk along the walls of the historic centre offers incredible views of the Tuscan countryside. For cyclists, the route from Montepulciano to the nearby town of Chiusi is a favourite, with rolling hills and vineyards along the way.
  • What are the most popular Airbnbs in Montepulciano?

  • What sports or outdoor activites can visitors enjoy in and around Montepulciano?

    You can find some great hiking trails in the surrounding countryside, perfect for exploring the rolling hills and vineyards. If you're feeling adventurous, try a hot air balloon ride over the Tuscan landscape. And of course, the region is famous for its wine, so a visit to a local winery for a tasting is a must.
  • What are the best vacation rentals with a pool in Montepulciano?

    Podere Fontecastello, Villa Cicolina and Residenza Fabroni are the best vacation rentals with a pool in Montepulciano.

  • What other towns or cities can be easily accessed from Montepulciano?

    You can easily reach Siena, Florence, and Perugia by car, all within a 1-2 hour drive. For a day trip, consider visiting the charming towns of Cortona, Pienza, or Chiusi, all within a short distance from Montepulciano.
  • What are the best rentals for families and kids in Montepulciano?

    The best rentals for families and kids in Montepulciano are Podere Fontecastello, Case Vacanza - Villa Paola and Villa Cicolina.

  • What amenities are commonly available in vacation rentals in Montepulciano?

    Most vacation rentals in Montepulciano offer basic amenities like Wi-Fi, a kitchen, and a washing machine. Many also have outdoor spaces like a patio or garden, perfect for enjoying the beautiful Tuscan weather. Some rentals even have private pools, ideal for a relaxing escape.
  • What are the best rentals or Airbnbs with a jacuzzi in Montepulciano?

    The best vacation rentals or Airbnb with a jacuzzi in Montepulciano are Villa Cicolina, Residenza Fabroni and Agriturismo Sanguineto.

  • What time of year is best to rent a vacation rental Montepulciano?

    Spring and autumn are ideal for visiting Montepulciano, with pleasant temperatures and less crowds. Summer can be very hot, but the town is still beautiful and lively. If you're looking for a quieter experience, winter can be a good option, though some attractions may have limited hours.
  • What are the local dishes in Montepulciano region?

    The local cuisine in Montepulciano is truly delicious. You must try the famous Pici, a thick hand-rolled pasta, often served with a rich meat sauce or a simple tomato sauce. And of course, no visit to Montepulciano is complete without sampling the local Vino Nobile di Montepulciano, a full-bodied red wine.

Popular destinations

Best Montepulciano vacation rentals with a sauna

Terra Antica - Resort, Winery & Spa - Montepulciano
9.6 914 reviews

Terra Antica - Resort, Winery & Spa

farm, Montepulciano
Terra Antica - Resort, Winery & SPA is located just 10.6 kilometres from Montepulciano Terme, close to other attractions like Bagno Vignoni and Bagni San Filippo, offering a peaceful escape in the Tuscan countryside. The property has received excellent ratings for its location, cleanliness, and overall experience.
The resort offers a range of accommodation options, from spacious suites to comfortable rooms, all featuring modern amenities like free Wi-Fi and private bathrooms. Guests can enjoy a host of on-site facilities, including a swimming pool, spa, fitness centre, restaurant, and bar, as well as a range of activities like cycling and wine tasting.
Le Ginestre Arte Vacanze - Montepulciano
9.5 20 reviews

Le Ginestre Arte Vacanze

apartment, Chianciano Terme
Le Ginestre Arte Vacanze is located just 0.9 kilometres outside Chianciano Terme, a short distance from the spa town's centre and offering a peaceful setting. The apartment has received very good user ratings, with excellent ratings for location and cleanliness.
The apartment is a one-bedroom, one-bathroom property with a floor area of 30 square metres. Guests can enjoy a range of amenities including a private outdoor pool, BBQ area, a spacious living room with an LCD TV, free Wi-Fi and on-site parking, as well as access to a hydromassage pool, gym and spa at a nearby sister hotel.
Gli Ulivi Apartment & Spa - Montepulciano
10 83 reviews

Gli Ulivi Apartment & Spa

apartment, Montepulciano
Gli Ulivi Apartment & Spa, a self-catering property in S. Albino di Montepulciano, boasts panoramic views and is just a short drive from both Montepulciano and Pienza.
This 110 sq m apartment features two double bedrooms, two bathrooms, sleeps five, and includes a private spa with a jacuzzi, sauna, and a fully equipped kitchen, plus a garden with BBQ and private parking.
Nobilis Charme Relais - Montepulciano
9.0 12 reviews

Nobilis Charme Relais

gîte, Montepulciano
This farm stay in Montepulciano is situated within 3.2 kilometres of Val di Chiana, the Church of St. Agnes and Tenuta Valdipiatta, offering easy access to the Tuscan countryside and historical sites.
Guests at this gîte can enjoy amenities such as air conditioning, a swimming pool, jacuzzi, sauna, spa services, a rooftop terrace, and a poolside bar, with complimentary buffet breakfast and free WiFi in public areas enhancing the stay.

Best Montepulciano vacation rentals with a fireplace

Elegant Ground Floor Apartment Of 92 M2, Composed Of A Large Living Room With Fireplace, Kitchen Complete With Dishwasher, Microwave Oven, Electric Oven, Coffee Machine, Kettle, Fridge And Freezer, Internal And External Dining Area, A Double Bedroom With - Montepulciano
No reviews

Elegant Ground Floor Apartment Of 92 M2, Composed Of A Large Living Room With Fireplace, Kitchen Complete With Dishwasher, Microwave Oven, Electric Oven, Coffee Machine, Kettle, Fridge And Freezer, Internal And External Dining Area, A Double Bedroom With

apartment, Trequanda
This three-bedroom apartment, 'Three-room Apartment Pine In Resort With Pool', is situated in Trequanda, Tuscany, within 15km of the Saints Peter and Andrew Church and the Sant'Anna in Camprena Monastery, offering easy access to the Val di Chiana.
The 92 square metre property features two bathrooms, a fully equipped kitchen, a fireplace, and accommodates up to four guests, boasting a swimming pool, terrace, garden, and parking, plus convenient amenities like a washing machine and TV/DVD player.
Terre Di Nano - Montepulciano
10 20 reviews

Terre Di Nano

farm, Pienza
Terre di Nano farm, in Val d'Orcia, is situated approximately 1.6km from Monticchiello, offering stunning views of Montepulciano and Pienza.
This one-bedroom, one-bathroom self-catering apartment in a 19th-century building features terracotta floors, exposed beams, a fully equipped kitchen, fireplace, swimming pool, and on-site olive oil and Chianti Terre di Nano wine tasting and tours.
15 Min Da Montepulciano - Villa Chiara - Montepulciano
8.4 39 reviews

15 Min Da Montepulciano - Villa Chiara

apartment, Torrita di Siena
This three-bedroom, two-bathroom apartment in Montefollonico, a peaceful district 15 minutes' drive (approx. 24km) from Montepulciano, offers easy access to Tuscan hill towns and thermal baths.
The 120 square metre property sleeps 11, features a well-equipped kitchen, terrace, garden, parking, and Wi-Fi, plus a baby safety gate.
Villa In Montepulciano With 7 Bedrooms Sleeps 14 - Montepulciano
No reviews

Villa In Montepulciano With 7 Bedrooms Sleeps 14

house, Montepulciano
Villa San Biagio, situated in the Orcia Valley, is a 3km walk from Montepulciano and within easy driving distance of other Tuscan towns such as Cortona (34km) and Montalcino (37km).
This seven-bedroom, seven-bathroom property sleeps fourteen guests, offering a private pool, garden, Jacuzzi, and well-equipped kitchens in the main house and a separate building; on-site services include winery tours and e-bike rentals.
©2026 cozycozy.com