Montepulciano Vacation Rentals

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Mar 27 - Mar 29

Vacation Rentals in Montepulciano

Deluxe Apartment, 2 Bedrooms, Balcony | Free WiFi, bed sheets
Bellarmino Boutique Apartments

Apartment in Montepulciano

$84 nightly
The price is $97
Dec 8 - Dec 9
Total with taxes and fees
Bellarmino Boutique Apartments
Lobby
Residenza Fabroni

Residence in Montepulciano

8.8 out of 10, Excellent, (93)
"We had a great stay! Beautiful on the roof top terrace!"
United States
Jennifer
$83 nightly
The price is $96
Dec 2 - Dec 3
Total with taxes and fees
Residenza Fabroni
Property entrance
Il Tosco

Residence in Montepulciano

10.0 out of 10, Exceptional, (113)
"Stunning views. Excellent hostess! Fabulous breakfast!! Would definitely stay again if ever back"
Canada
stephen
$295 nightly
The price is $330
Dec 8 - Dec 9
Total with taxes and fees
Il Tosco
Standard Room | Exterior
Osteria del Borgo

Residence in Montepulciano

9.0 out of 10, Wonderful, (156)
"Staff and location were both excellent."
United States
Nicholas
Osteria del Borgo
Pool
Panoramic villa surrounded by vineyards and olive groves, 6 km from Montepulciano. Ideal for familie

Villa in Montepulciano

9.6 out of 10, Exceptional, (4)
"This was one of the highlights of our 3 week trip. The surroundings were beautiful and the hosts who only spoke Italian were absolutely lovely. We were about 15 minutes from Montepuciano in a quiet farm area. One night we had the hosts cook us an anniversary dinner for our friends which was so much fun. Highly recommended. "
United States
Debbie C.
Panoramic villa surrounded by vineyards and olive groves, 6 km from Montepulciano. Ideal for familie
Fridge, microwave, oven, stovetop
Charming House in the heart of Montepulciano

Apartment in 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
Typical villa with private pool in a panoramic position in southern Tuscany, a few kilometres from t

Villa in Montepulciano

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

Vacation Home in Montepulciano

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 crib
Entire Historic Residence in Tuscany (Val d'Orcia),in the Heart of Montepulciano

Vacation Home in 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)

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

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
$145 nightly
The price is $166
Dec 8 - Dec 9
Total with taxes and fees
Hotel San Gregorio
View from room
Abbadia Sicille Relais

Residence in Trequanda

4.0 star property
8.8 out of 10, Excellent, (163)
"We stayed there for 1 night our our way to Rome. BEAUTIFUL. Bed was very comfortable as well. 10/10 will recommend to everyone "
United States
Brittnay
$69 nightly
The price is $80
Dec 4 - Dec 5
Total with taxes and fees
Abbadia Sicille Relais
Pool
Farmhouse in the hills with panoramic view and swimming pool

Vacation Home in Ristonchia

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

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

3.0 star property
9.0 out of 10, Wonderful, (78)
"Fantastic place"
United States
Clifford
Casanova - Panoramic Rooms and Suites
Exterior
Il Poggio dell'Eremita

Villa in Sinalunga

10.0 out of 10, Exceptional, (59)
"Amazing property! Could not recommend more."
United States
Annika P.
$158 nightly
The price is $160
Dec 2 - Dec 3
Total with taxes and fees
Il Poggio dell'Eremita
Outdoor dining
PRIVATE TUSCAN VILLA WITH HEATED SWIMMING POOL - JACUZZI SPA - SAUNA - EVENTS

Villa in chiusi

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

Vacation Home in Montalcino (SI)

9.8 out of 10, Exceptional, (66)
"Really enjoyed our stay. Loved the town and the accommodation was superb. "
Australia
Michelle C.
$241 nightly
The price is $246
Dec 5 - Dec 6
Total with taxes and fees
The House of Alice, charm and relaxation
Outdoor dining
Hilltop house in the heart of Tuscany with private pool

Villa in Montisi

9.8 out of 10, Exceptional, (94)
"Wonderful, quiet, beautiful. Everything you could want in country stay near a small village."
United States
Timothy C.
Hilltop house in the heart of Tuscany with private pool
Pool
Country House With Private Pool

Villa in Toscane

10.0 out of 10, Exceptional, (13)
"Beautiful property with the most amazing pool, our hosts were so lovely and helpful, always at hand if we needed anything. I would recommend for a very relaxing holiday."
United States
Maxine B.
Country House With Private Pool
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.
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Top Montepulciano Hotel Reviews

Podere La Rocca

Podere La Rocca

10/10 Excellent
"Awesome.place to be and Antonio is a star at the restaurant."
Marco 1-night trip
Posted 2 days ago
Podere La Rocca

Find out more about Montepulciano

Everything you need to know about Montepulciano vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Montepulciano vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. The list goes on, and on …and on.

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Montepulciano vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Montepulciano vacation rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Montepulciano. If you’re looking for a little peace, consider booking during the quieter low season months. For more hustle and bustle, you may prefer to visit Montepulciano in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $80 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Montepulciano rentals

At Expedia, we put the best Montepulciano vacation rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia.

To find some top Montepulciano rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Montepulciano vacation.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Montepulciano. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.

Explore a world of travel with Expedia

Frequently asked questions

Are there vacation rentals in Montepulciano?

Yes, we offer vacation rentals close to top sights in Montepulciano, or you can go with a more remote option if you're looking for relaxation. 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 vacation home rentals that Montepulciano has to offer?

INDEPENDENT HOUSE LARGE TERRACES & SPECTACULAR VIEWS in CENTER W. PARKING: This highly rated vacation home rental in Montepulciano is located in the city center and has a fireplace, a balcony, and a barbecue grill 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 you can cook with friends or family. It offers a terrace, a garden, and a selection of books so you can immerse yourself in your vacation. Another good choice for your trip to Montepulciano is Entire Historic Residence in Tuscany (Val d'Orcia),in the Heart of Montepulciano.

How many vacation rentals are there in Montepulciano?

Expedia has 37 vacation 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 vacation rental in Montepulciano like?

A vacation rental is a private property you can book for a few weeks or just a few days in Montepulciano. Vacation rentals feature amenities such as laundry facilities and kitchens so you'll be comfy for your stay. If you're concerned about a clean environment, a vacation rental can offer a sense of security away from public hotel elevators and lobbies packed with people while still allowing you the excitement and enjoyment of travel. You'll also get more space in a vacation rental than in a standard hotel, which is another reason why a vacation rental is a great choice for a small group gathering.