Montepulciano holiday rentals

We found 2,703 holiday rentals — enter your dates for availability
Find the perfect place for you stay in Montepulciano by choosing from 47 houses, 129 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:25 Dec - 1 Jan

Interior
Pool
Exterior
Living area
Exceptional
(130 reviews)

Tuscan villa pool spa Siena Montepulciano Perugia Pienza Florence 2 hours from Rome

Cetona

9% off
S$5,725
for 7 nights, 1 home
S$818 per night
includes taxes & fees
Tuscan villa pool spa Siena Montepulciano Perugia Pienza Florence 2 hours from Rome
Exterior
Pool
Dining
Exterior detail
Exceptional
(17 reviews)

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

Montepulciano

5% off
S$6,178
for 7 nights, 1 villa
S$883 per night
includes taxes & fees
Charming ancient watching tower near Montepulciano and Val d'Orcia - Siena
Exterior
Outdoor dining
Pool
Interior
Exceptional
(57 reviews)

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

Citta della Pieve

9% off
S$9,553
for 7 nights, 1 home
S$1,365 per night
includes taxes & fees
Villa on the Umbria-Tuscany border—for families and friends—with a private pool
Dining
Pool
Outdoor dining
Private kitchen
Exceptional
(14 reviews)

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

Montalcino

9% off
S$24,339
for 7 nights, 1 villa
S$3,477 per night
includes taxes & fees
Recently restored Villa in Tuscany, sleeps 12, sw.pool, gym, big garden.
Property grounds
Exterior detail
Pool
Room
Wonderful
(8 reviews)

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

Paciano

8% off
S$8,553
for 7 nights, 1 cottage
S$1,222 per night
includes taxes & fees
Villa Antico Casale DCC - D. C. whole property 14 beds
Outdoor dining
Pool
Large kitchen
Exterior
Exceptional
(52 reviews)

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

Pienza

9% off
S$5,595
for 7 nights, 1 villa
S$799 per night
includes taxes & fees
Charming Ancient Watch Tower with Swimming Pool in Val d'Orcia
Exterior detail
Outdoor dining
Pool
Exterior
Exceptional
(6 reviews)

Apartment in Farmhouse

Cortona

6% off
S$1,409
for 7 nights, 1 room
S$201 per night
includes taxes & fees
Apartment in Farmhouse
Interior
Property grounds
Outdoor dining
Exterior
Exceptional
(37 reviews)

Villa Mulinoavento with magnificent view 5 minutes walking downtown

Cortona

9% off
S$6,510
for 7 nights, 1 villa
S$930 per night
includes taxes & fees
Villa Mulinoavento with magnificent view 5 minutes walking downtown
Living room + Sofa bed
View from the outside
entrance
Dining Room
Exceptional
(59 reviews)

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

Cortona

14% off
S$2,169
for 7 nights, 1 home
S$310 per night
includes taxes & fees
Il Roseto - Special prices for 2024-25! ! Get a quote ! ! "Plan your dream"
Exterior
Outdoor dining
Property grounds
Dining
Exceptional
(25 reviews)

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

Cortona

7% off
S$2,315
for 7 nights, 1 room
S$331 per night
includes taxes & fees
Farm on the hills of Cortona with a spectacular view of the Valdichiana Valley
Pool
Exterior detail
Living area
Exterior
Exceptional
(16 reviews)

Ray's House - GLICINE Apartment

Passignano sul Trasimeno

8% off
S$1,569
for 7 nights, 1 apartment
S$224 per night
includes taxes & fees
Ray's House - GLICINE Apartment
Room
Outdoor dining
Private kitchen
Bathroom
Exceptional
(5 reviews)

Magnificent and Bright 2 BR Apt. with Terrace

Montepulciano

9% off
S$3,852
for 7 nights, 1 apartment
S$550 per night
includes taxes & fees
Magnificent and Bright 2 BR Apt. with Terrace
Pool
Property grounds
Stalla Private Garden with BBQ
Living area
Exceptional
(19 reviews)

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

Cortona

7% off
S$4,339
for 7 nights, 1 apartment
S$620 per night
includes taxes & fees
Large country apartment in Cortona 3bed3bath with shared pool & gorgeous gardens
Exterior detail
Outdoor dining
Room
Interior
Exceptional
(12 reviews)

My house with steam room, theater view, chromtherapy, relaxing music, jacuzzi...

Cortona

7% off
S$1,809
for 7 nights, 1 apartment
S$258 per night
includes taxes & fees
My house with steam room, theater view, chromtherapy, relaxing music, jacuzzi...
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$3,656
for 7 nights, 1 apartment
S$522 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)
  • 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)
  • Valdorcia Terre Senesi (11.2 mi / 18.1 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)
  • Terme Sant'Elena (3.4 mi / 5.5 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)

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.

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