Montepulciano Holiday Rentals

Start date: Check-in selected.
To Date
End date: Check-out

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
26 Dec - 28 Dec
In two months
6 Feb - 8 Feb
In three months
6 Mar - 8 Mar
In four months
3 Apr - 5 Apr

Our top choices for Montepulciano holiday rentals

Free WiFi, bed sheets
Bellarmino Boutique Apartments

Apartment in Montepulciano

Bellarmino Boutique Apartments
6.0 out of 10, (1)
"Heat didnt work, it was FREEZING. Contact didnt seem to be local, seemed like they were managing remotely and couldnt or wouldnt send anyone to help. Nor did they really seem to care. Beautiful area though!"
United States
JON
The price is HK$828
HK$947 total
includes taxes & fees
11 Dec - 12 Dec
Bellarmino Boutique Apartments
Lobby
Residenza Fabroni

Residence in Montepulciano

Residenza Fabroni
8.8 out of 10, Excellent, (94)
"gorgeous historical property, very attentive host, great location"
United States
Sarah
The price is HK$697
HK$803 total
includes taxes & fees
11 Dec - 12 Dec
Residenza Fabroni
Property entrance
Il Tosco

Residence in Montepulciano

Il Tosco
10.0 out of 10, Exceptional, (114)
"The staff was courteous, the food was amazing, and the location was great. We were very impressed"
United States
Joshua
The price is HK$2,004
HK$2,240 total
includes taxes & fees
15 Dec - 16 Dec
Il Tosco
Exterior
Osteria del Borgo

Residence in Montepulciano

Osteria del Borgo
9.0 out of 10, Wonderful, (156)
"Staff and location were both excellent."
United States
Nicholas
Osteria del Borgo
Fridge, microwave, oven, stovetop
Charming House in the heart of Montepulciano

Apartment in Montepulciano

Charming House in the heart of Montepulciano
9.8 out of 10, Exceptional, (65)
"Location, location, location. The room was great. The host was easy to communicate with and was very helpful."
United States
peter m.
Charming House in the heart of Montepulciano
Pool
Panoramic villa surrounded by vineyards and olive groves, 6 km from Montepulciano. Ideal for familie

Villa in Montepulciano

Panoramic villa surrounded by vineyards and olive groves, 6 km from Montepulciano. Ideal for familie
9.6 out of 10, Exceptional, (4)
"My two friends and I enjoyed our stay at San Bono. The highlight was having the family make and serve us an authentic Tuscan meal! The view is amazing and the location was perfect!"
United States
Flourish Flowers
Panoramic villa surrounded by vineyards and olive groves, 6 km from Montepulciano. Ideal for familie
Pool
Typical villa with private pool in a panoramic position in southern Tuscany, a few kilometres from t

Villa in Montepulciano

Typical villa with private pool in a panoramic position in southern Tuscany, a few kilometres from t
10.0 out of 10, Exceptional, (2)
"The villa is spacious with big bedrooms and five good bathrooms. The kitchen is well equipped and our big family with 8 adults and 6 children had everything we needed for our 14-day stay. There is a big pool beautifully located in a separate part of the garden. The trees and bushes give shadow all through the day so there is no need for umbrellas. The whole property is well cared for by the very friendly owners who live nearby. This is a perfect location for a visit in Toscana, close to many...
Sweden
Kristina M.
Typical villa with private pool in a panoramic position in southern Tuscany, a few kilometres from t
Interior
INDEPENDENT HOUSE LARGE TERRACES & SPECTACULAR VIEWS in CENTER W. PARKING

Holiday Home in Montepulciano

INDEPENDENT HOUSE LARGE TERRACES & SPECTACULAR VIEWS in CENTER W. PARKING
9.6 out of 10, Exceptional, (81)
"This house and location was perfect. Beautiful views and a great kitchen. Montepulciano was our favorite town that we visited on our trip. Easy check in and the host had a document that she sent us that had a lot of great info."
United States
Tom K.
INDEPENDENT HOUSE LARGE TERRACES & SPECTACULAR VIEWS in CENTER W. PARKING
4 bedrooms, desk, iron/ironing board, travel cot
Entire Historic Residence in Tuscany (Val d'Orcia),in the Heart of Montepulciano

Holiday Home in Montepulciano

Entire Historic Residence in Tuscany (Val d'Orcia),in the Heart of Montepulciano
9.8 out of 10, Exceptional, (8)
"Absolutely loved this property. It’s in a great location and has so much character. "
United States
Randy C.
Entire Historic Residence in Tuscany (Val d'Orcia),in the Heart of Montepulciano
Interior
LA CASINA CANTINI - Panoramic apartment in Montepulciano in the historic center

Apartment in Montepulciano (SI)

LA CASINA CANTINI - Panoramic apartment in Montepulciano in the historic center
9.6 out of 10, Exceptional, (53)
"This was an ideal little find, centrally located across from the Fortezza and behind the historic town center. The space was perfect for a two-person stay."
United States
Lynne S.
LA CASINA CANTINI - Panoramic apartment in Montepulciano in the historic center
Breakfast, lunch, dinner served; local cuisine
Hotel San Gregorio

Residence in Pienza

Hotel San Gregorio
3.0 star property
9.4 out of 10, Exceptional, (134)
"Such friendly staff, loved Pienza and the property was such a good location! "
United Kingdom
Bethan
The price is HK$1,581
HK$1,794 total
includes taxes & fees
5 Jan - 6 Jan 2026
Hotel San Gregorio
View from room
Abbadia Sicille Relais

Residence in Trequanda

Abbadia Sicille Relais
4.0 star property
8.8 out of 10, Excellent, (166)
"Room was beyond expectations. Helpful staff and overall great experience. "
United States
Robert
The price is HK$554
HK$637 total
includes taxes & fees
18 Dec - 19 Dec
Abbadia Sicille Relais
Pool
Farmhouse in the hills with panoramic view and swimming pool

Holiday Home in Ristonchia

Farmhouse in the hills with panoramic view and swimming pool
9.6 out of 10, Exceptional, (75)
"Was wonderful and beautiful. "
United States
Alana A.
Farmhouse in the hills with panoramic view and swimming pool
Pool
Private and cozy retreat in Montalcino with private pool surrounded by vineyards

Villa in Siena

Private and cozy retreat in Montalcino with private pool surrounded by vineyards
9.4 out of 10, Exceptional, (67)
"What a lovely place, I will recommend this fabulous home to friends and family and will be returning sometime soon."
United Kingdom
peter H.
Private and cozy retreat in Montalcino with private pool surrounded by vineyards
Front of property – evening/night
Casanova - Panoramic Rooms and Suites

Residence in San Quirico d'Orcia

Casanova - Panoramic Rooms and Suites
3.0 star property
9.0 out of 10, Wonderful, (78)
"Fantastic place"
United States
Clifford
The price is HK$1,464
HK$1,647 total
includes taxes & fees
11 Dec - 12 Dec
Casanova - Panoramic Rooms and Suites
Exterior
Il Poggio dell'Eremita

Villa in Sinalunga

Il Poggio dell'Eremita
10.0 out of 10, Exceptional, (59)
"Amazing property! Could not recommend more."
United States
Annika P.
The price is HK$1,100
HK$1,281 total
includes taxes & fees
11 Dec - 12 Dec
Il Poggio dell'Eremita
Outdoor dining
PRIVATE TUSCAN VILLA WITH HEATED SWIMMING POOL - JACUZZI SPA - SAUNA - EVENTS

Villa in chiusi

PRIVATE TUSCAN VILLA WITH HEATED SWIMMING POOL - JACUZZI SPA - SAUNA - EVENTS
10.0 out of 10, Exceptional, (57)
"We had a very nice stay and a well organized pizza night in the villa. Glad to come again:) "
Germany
Florian Maria W.
PRIVATE TUSCAN VILLA WITH HEATED SWIMMING POOL - JACUZZI SPA - SAUNA - EVENTS
Exterior detail
The House of Alice, charm and relaxation

Holiday Home in Montalcino (SI)

The House of Alice, charm and relaxation
9.8 out of 10, Exceptional, (66)
"Really enjoyed our stay. Loved the town and the accommodation was superb. "
Australia
Michelle C.
The price is HK$1,448
HK$1,955 total
includes taxes & fees
15 Dec - 16 Dec
The House of Alice, charm and relaxation
Pool
Country House With Private Pool

Villa in Toscane

Country House With Private Pool
10.0 out of 10, Exceptional, (13)
"We had such a lovely week staying in this farmhouse just outside Citta della Pieve. The house itself and interiors are beautiful - the kitchen is well equipped, the beds are incredibly comfortable, the bathrooms modern, the pool is an excellent size, and the views are amazing. The hosts were incredibly friendly and generous, and really added to our overall experience. I would highly recommend a stay here - you will not be disappointed!"
United Kingdom
Clare C.
Country House With Private Pool
Outdoor pool
Villa in Montalcino, exclusive for you, stunning view!!!

Villa in Montalcino

Villa in Montalcino, exclusive for you, stunning view!!!
10.0 out of 10, Exceptional, (86)
"Lovely villa in a beautiful location. "
United Kingdom
helen S.
Villa in Montalcino, exclusive for you, stunning view!!!
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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Montepulciano Hotel Reviews

Residenza Fabroni

Residenza Fabroni

10/10 Excellent
"gorgeous historical property, very attentive host, great location"
Sarah 1-night trip
Posted 2 days ago
Residenza Fabroni

Find out more about Montepulciano

Search for holiday rentals in Montepulciano on Expedia! You can easily find your home rentals, villas, holiday apartments in Montepulciano using one of the methods below:

  • View our selection of featured holiday rentals in Montepulciano
  • Use the map to find apartments and other holiday homes in the Montepulciano neighbourhood you prefer
  • Enter your travel dates to view the best deals on holiday rentals in Montepulciano while they last

Look no further and take a look at our great range of rental properties in Montepulciano!

Frequently asked questions

Are there holiday rentals in Montepulciano?

Yes, there are holiday rentals close to the most popular sights in Montepulciano, or you can select a more secluded option if you're looking for a relaxing stay. Visitors to Montepulciano speak positively about the countryside and wineries in this destination. Make sure you have time to check out the sightseeing tours and festivals during your trip.

What are some of the best holiday rentals that Montepulciano has to offer?

INDEPENDENT HOUSE LARGE TERRACES & SPECTACULAR VIEWS in CENTER W. PARKING: This highly rated holiday home rental in Montepulciano is located in the city centre, and has a fireplace, a balcony and a BBQ to put you at ease in your new surroundings. It has 4 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. It offers a terrace, a garden and a selection of books so that you can immerse yourself in your holiday. Another good choice for your trip to Montepulciano is Entire Historic Residence in Tuscany (Val d'Orcia),in the Heart of Montepulciano.

How many holiday rentals are there in Montepulciano?

Expedia has 37 holiday rentals for your stay in Montepulciano.

What’s there to see and do in Montepulciano?

Terme di Montepulciano Spa and Val di Chiana are a couple of scenic spots to enjoy the outdoors, whereas Civic Museum is one of the cultural attractions. While here, Palazzo Avignonesi and Cantina del Redi are other places worth a visit.

What’s a holiday rental in Montepulciano like?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in Montepulciano. Holiday rentals feature extras such as hot tubs, fire pits and patios so you'll have all the comforts of home. If you're concerned about a sanitised environment, holiday rentals can offer a sense of security away from public hotel lifts and busy lobbies while still allowing you the experience of travel. You'll also get more space in a holiday rental than in a hotel, which is another reason why a holiday rental is a great choice for family gatherings.