Montepulciano holiday rentals

We found 2,714 holiday rentals — enter your dates for availability
Find the perfect place for you stay in Montepulciano by choosing from 47 houses, 117 apartments and other holiday rentals. Holiday homes offer the amenities that you expect for your family, friends or furry companion, such as a garden and pool. Whatever you're looking for, you're sure to find a property to rent that has what everyone needs, including a place that's non-smoking or offers accessibility.

Holiday rentals with weekly discounts – Montepulciano

Showing deals for:4 Dec - 11 Dec

Outdoor dining
Pool
Living area
Dining
Exceptional
(14 reviews)

Recently restored Villa in Tuscany, sleeps 12, sw.pool, gym, big garden.

Montalcino

9% off
S$24,521
for 7 nights, 1 villa
S$3,503 per night
includes taxes & fees
Recently restored Villa in Tuscany, sleeps 12, sw.pool, gym, big garden.
Pool
Outdoor dining
Interior
Interior
Exceptional
(57 reviews)

Villa on the Umbria-Tuscany border—for families and friends—with a private pool

Citta della Pieve

9% off
S$6,305
for 7 nights, 1 home
S$901 per night
includes taxes & fees
Villa on the Umbria-Tuscany border—for families and friends—with a private pool
Exterior detail
Pool
Dining
Outdoor dining
Exceptional
(17 reviews)

Charming ancient watching tower near Montepulciano and Val d'Orcia - Siena

Montepulciano

9% off
S$5,496
for 7 nights, 1 villa
S$785 per night
includes taxes & fees
Charming ancient watching tower near Montepulciano and Val d'Orcia - Siena
Room
Exterior detail
Property grounds
Dining
Wonderful
(8 reviews)

Villa Antico Casale DCC - D. C. whole property 14 beds

Paciano

8% off
S$4,939
for 7 nights, 1 cottage
S$706 per night
includes taxes & fees
Villa Antico Casale DCC - D. C. whole property 14 beds
Outdoor dining
Pool
Pool
Exterior
Exceptional
(14 reviews)

Elegant farmhouse, with private pool, table tennis & ping pong in Val D'orcia,

Castiglione d'Orcia

43% off
S$4,831
for 7 nights, 1 villa
S$690 per night
includes taxes & fees
Elegant farmhouse, with private pool, table tennis & ping pong in Val D'orcia,
Outdoor dining
Pool
Exterior
Large kitchen
Exceptional
(52 reviews)

Charming Ancient Watch Tower with Swimming Pool in Val d'Orcia

Pienza

9% off
S$5,014
for 7 nights, 1 villa
S$716 per night
includes taxes & fees
Charming Ancient Watch Tower with Swimming Pool in Val d'Orcia
Private kitchen
Private kitchen
Exterior
Room
Exceptional
(11 reviews)

"Il Focolare" Superior Apartment in Monticchiello

Pienza

5% off
S$1,174
for 7 nights, 1 home
S$168 per night
includes taxes & fees
"Il Focolare" Superior Apartment in Monticchiello
Exterior
Exterior
Lunch on the rear patio.
The Casa Castagni  living room
Exceptional
(5 reviews)

Gorgeously restored tranquil farmhouse

Castiglione del Lago

18% off
S$1,887
for 7 nights, 1 home
S$270 per night
includes taxes & fees
Gorgeously restored tranquil farmhouse
Pool
Outdoor dining
Exterior detail
Dining
Exceptional
(6 reviews)

Apartment in Farmhouse

Cortona

6% off
S$1,423
for 7 nights, 1 room
S$203 per night
includes taxes & fees
Apartment in Farmhouse
Living area
Outdoor dining
Living area
Room
Exceptional
(5 reviews)

Suite Gioconda - Podere Casa Rossa in Pienza

Pienza

9% off
S$2,548
for 7 nights, 1 home
S$364 per night
includes taxes & fees
Suite Gioconda - Podere Casa Rossa in Pienza
Property grounds
Property grounds
Interior
Exterior
Exceptional
(12 reviews)

Splendid farmhouse in Val d'Orcia with private swimming pool and sauna

Radicofani

9% off
S$3,291
for 7 nights, 1 home
S$470 per night
includes taxes & fees
Splendid farmhouse in Val d'Orcia with private swimming pool and sauna
Private kitchen
Exterior
Outdoor dining
Property grounds
Exceptional
(26 reviews)

Villa Banditello, secluded, panoramic view over Montepulciano valley.

Torrita di Siena

9% off
S$2,306
for 7 nights, 1 home
S$329 per night
includes taxes & fees
Villa Banditello, secluded, panoramic view over Montepulciano valley.
Master Bedroom
View from the outside
Living room + Sofa bed
entrance
Exceptional
(58 reviews)

Il Roseto - Special prices for 2024-25! ! Get a quote ! ! "Plan your dream"

Cortona

13% off
S$2,239
for 7 nights, 1 home
S$320 per night
includes taxes & fees
Il Roseto - Special prices for 2024-25! ! Get a quote ! ! "Plan your dream"
Living area
Property grounds
Stalla Private Garden with BBQ
Exterior
Exceptional
(19 reviews)

Large country apartment in Cortona 3bed3bath with shared pool & gorgeous gardens

Cortona

7% off
S$4,423
for 7 nights, 1 apartment
S$632 per night
includes taxes & fees
Large country apartment in Cortona 3bed3bath with shared pool & gorgeous gardens
Living area
Outdoor dining
Room
Bathroom
Exceptional
(5 reviews)

Magnificent and Bright 2 BR Apt. with Terrace

Montepulciano

8% off
S$2,803
for 7 nights, 1 apartment
S$400 per night
includes taxes & fees
Magnificent and Bright 2 BR Apt. with Terrace
Pool
Outdoor dining
Property grounds
Exterior
Exceptional
(25 reviews)

Farm on the hills of Cortona with a spectacular view of the Valdichiana Valley

Cortona

7% off
S$2,339
for 7 nights, 1 room
S$334 per night
includes taxes & fees
Farm on the hills of Cortona with a spectacular view of the Valdichiana Valley
Living room with large sofa bed and dining/working table and smart tv.
Kitchen with View.
Kitchen
Bedroom2
Exceptional
(12 reviews)

Large shining148sqmt wififiber apartment, view and free parking in Montepulciano

Montepulciano

23% off
S$1,353
for 7 nights, 1 apartment
S$193 per night
includes taxes & fees
Large shining148sqmt wififiber apartment, view and free parking in Montepulciano
Interior
Gorgeous View to wake up to in the mornings!
Classic Apt. in a Palazzo with modern comforts and classic features
Room
Exceptional
(36 reviews)

Classic Stunning 3 Bedroom Apartment in Montepulciano with Air Conditioning,

Montepulciano

13% off
S$3,558
for 7 nights, 1 apartment
S$508 per night
includes taxes & fees
Classic Stunning 3 Bedroom Apartment in Montepulciano with Air Conditioning,
  • Peace of mind

    Our Book with Confidence guarantee gives you 24/7 support
  • More quality time

    From booking to staying, the whole process is simple and enjoyable
  • All the privacy of home

    Enjoy full kitchens, laundry, pools, gardens and more
  • More for less

    More space, more privacy, more amenities — more value

The culturally rich city of Montepulciano awaits you

Enjoy the area's wineries, culture and history with a rental holiday home in Montepulciano. This city's sightseeing, festivals and local tours draw many visitors. A holiday rental can help make your stay complete—many rentals come with a full kitchen and laundry facilities.

Sightseeing in and around Montepulciano

Do you want to find attractions to visit in the area? Although it can be tempting to stay in your comfortable holiday rental, you'll want to experience everything that makes Montepulciano a one-of-a-kind holiday spot. These are some of the most popular attractions to put on your list, all within 30 miles (48.2 km) of the city centre:

  • Cantina del Redi (0.5 mi / 0.8 km)
  • Cantina Contucci (0.5 mi / 0.8 km)
  • Consorzio del Vino Nobile di Montepulciano (0.5 mi / 0.8 km)
  • Piscine Termali Theia (4 mi / 6.5 km)
  • Terme di Chianciano (4.2 mi / 6.8 km)
  • Baths of San Filippo (12.5 mi / 20 km)

Exploring the natural landscape of Montepulciano

Whether you're looking for adventure or just want to take in the scenery, Montepulciano is a great place to get out in nature. Here are a few of the area's noteworthy natural features, all within 30 miles (48.2 km) of the city centre:

  • Terme di Montepulciano Spa (1.9 mi / 3.1 km)
  • Val di Chiana (1.9 mi / 3.1 km)
  • Piscine Termali Theia (4 mi / 6.5 km)
  • La Foce (5.1 mi / 8.3 km)
  • Historic Centre of Pienza (5.7 mi / 9.1 km)
  • Lake Trasimeno (15.7 mi / 25.2 km)

Transport to and around Montepulciano

The nearest airport is in Perugia San Francesco d'Assisi – Umbria Intl. Airport (PEG), located 36.1 mi (58.1 km) from the city centre.

If you prefer train travel, the main station serving the city is Montepulciano Station.

Frequently asked questions

What is the best area to stay in Montepulciano when booking a holiday rental?
If you're thinking about a getaway to Montepulciano, Acquaviva is one of the most popular locations to stay. Whether you prefer a cottage, condo or different property type, you'll always have the entire place to yourself.
What is the most popular type of holiday rental accommodation in Montepulciano?
The most desirable types of holiday rentals in Montepulciano are apartments. Looking for something different? Vrbo has a variety of options to match the unique needs of our guests, so you'll see properties in lots of sizes and shapes. The perfect home away from home is waiting for you — find yours today.
How much does it cost to rent a holiday rental in Montepulciano?
Several things can affect how much you'll pay for a holiday rental in Montepulciano, including the type of property, season and length of stay. However, all of our holiday homes have something in common — exceptional value. Simply add your travel dates to find your ideal escape.
How much does it cost to rent a beach house in Montepulciano?
The average price for a holiday rental close to the beach in Montepulciano depends on when you're going and the size and style of property you're searching for. You can find prices easily and quickly on Vrbo by entering your destination and travel dates. Then use the filter tool to choose the number of bedrooms and amenities important to you, such as air conditioning, WiFi and a pool.
Are there pet-friendly holiday rentals in Montepulciano?
Yes. There are. You'll have your pick of 89 stays that roll out the welcome mat in Montepulciano on Vrbo. Our cuddly best friends deserve a break too, so simply use our search function for pet-friendly holiday rentals to book a pad where your pup can share in the good times.
Can I rent a house with a pool in Montepulciano?
Pack your swimwear and inflatable flamingo, because there are 21 houses with a private pool in Montepulciano. Book a stay at one of these terrific holiday homes and let every day be a pool day. Simply enter your travel dates into Vrbo, then use the "pool" filter to find the ideal place for a splashing good time!
What are popular rental amenities in Montepulciano?
When it comes to rental amenities that people prefer in Montepulciano, a chef, a fireplace and an ocean view are at the top of the list. With Vrbo holiday homes, there are choices to suit your style and taste, whether you're planning to get away with your partner, your friends or even pets.
Are there large group holiday rentals in Montepulciano?
Take your pick of nine holiday rentals in Montepulciano that can host a group of 10 or more people. Whether you're planning time away with extended family or an event like a party, there's enough space to get your favourite people together under the same roof.
Are there holiday rentals in Montepulciano that welcome kids?
Montepulciano has 89 family-friendly holiday rentals to choose from. And securing a stay that welcomes kiddos is a cinch with Vrbo's "Properties good for families" filter. As well as having the entire place to yourselves, you'll have access to amenities and perks like bunk beds, private pools and yards.
What are the top attractions for families in Montepulciano?
Keep the kids happy at these fabulous family-friendly attractions in Montepulciano:
  • Piscine Termali Theia
  • Terme di Montepulciano Spa
  • Palazzo Piccolomini
Are there one-bedroom holiday rentals in Montepulciano?
Yes, Montepulciano has 34 one-bedroom rentals on offer. Often positioned in prime areas because of their compact size, a one-bedroom holiday rental is ideal if you're getting away with your partner or a pal. And with home comforts such as kitchens and more privacy than a standard hotel, you'll be able to kick back while exploring this fantastic destination.
Can I find two-bedroom holiday rentals in Montepulciano?
Montepulciano has 36 two-bedroom properties for you to select from. Find a holiday home with all the space and comfort you're looking for at a price that won't break the bank on Vrbo.
Are there holiday rentals with WiFi in Montepulciano?
Whether you want to keep up with world events, send some emails or surf social media, there are 32 holiday homes with WiFi in Montepulciano. Check the "WiFi" box when searching on Vrbo and stay connected on your holiday.
How can I find holiday rentals with air conditioning in Montepulciano?
Pick your dates and then make use of the filters to search for holiday rentals with ac in Montepulciano on Vrbo. With 47 air-conditioned properties available here, you can enjoy a cool and comfy break.
How old do you have to be to rent a holiday rental in Montepulciano?
We recommend you check with the Montepulciano holiday rental you're considering on Vrbo as age restrictions differ. However, typically it's 16, 18 or 21.
How long can I rent a holiday rental in Montepulciano for?
It's up to the Montepulciano property. To see a list of options offering extended stays, just enter your dates and guest number into Vrbo's search page. Look forward to having the property to yourself, along with amenities such as a fully-equipped kitchen, air conditioning and a yard to run around in. Keep your eyes peeled for any long-term stays that offer weekly or monthly discounts.