We noticed that you're using an unsupported browser. The TripAdvisor website may not display properly.
We support the following browsers:
Windows: Internet Explorer, Mozilla Firefox, Google Chrome. Mac: Safari.

Smoking Allowed Vacation Rentals in Montepulciano

Professionally managed typically means…
  • Dedicated on-site help
  • Experienced local staff
  • Professional hospitality services
  • Secure credit card payment
Verified property owner typically means…
  • Enhanced property ownership verification in addition to verification of owner name and address via valid credit card
  • Established history of renting online
  • Direct & personal contact
  • Detailed rental knowledge
  • Flexible dates & rates
  • More options in smaller towns
Property owner typically means…
  • Verification of owner name and address via valid credit card
  • Direct & personal contact
  • Detailed rental knowledge
  • Flexible dates & rates
  • More options in smaller towns
Use a credit card to book with our Peace of Mind Protection.
Learn more
Find a rental
Price per night
Min
to
Max
Bedrooms
Any
Amenities
Select
More filters
Find more rentals you can book on TripAdvisor!   We're showing you properties you can book on TripAdvisor first.
loading...
Sort by
From
$772
Per Night
7 Bedrooms, 8 Bathrooms, Sleeps 16
24 photos Details
Reviews (13) Make Enquiry
From
$583
Per Night
3 Bedrooms, 3 Bathrooms, Sleeps 6
56 photos Details
Reviews (5) Make Enquiry
From
$94
Per Night
2 Bedrooms, 2 Bathrooms, Sleeps 6
22 photos Details
Reviews (6) Make Enquiry
From
$133
Per Night
3 Bedrooms, 2 Bathrooms, Sleeps 5
20 photos Details
Reviews (4) Make Enquiry
From
$154
Per Night
3 Bedrooms, 1 Bathroom, Sleeps 7
16 photos Details
Make Enquiry
From
$2,841
Per Week
3 Bedrooms, 3 Bathrooms, Sleeps 6
19 photos Details
Make Enquiry
From
$201
Per Night
1 Bedroom, 1 Bathroom, Sleeps 3
20 photos Details
Make Enquiry
From
$100
Per Night
1 Bedroom, 2 Bathrooms, Sleeps 2
9 photos Details
Make Enquiry
Get the List
From
$102
Per Night
1 Bedroom, 1 Bathroom, Sleeps 2
6 photos Details
Make Enquiry
From
$132
Per Night
1 Bedroom, 1 Bathroom, Sleeps 2
22 photos Details
Make Enquiry
From
$138
Per Night
Valiano
7 Bedrooms, 5 Bathrooms, Sleeps 23
53 photos Details
Make Enquiry
From
$2,873
Per Week
5 Bedrooms, 5 Bathrooms, Sleeps 10
24 photos Details
Make Enquiry
From
$151
Per Night
1 Bedroom, 1 Bathroom, Sleeps 2
4 photos Details
Make Enquiry
From
$175
Per Night
2 Bedrooms, 1 Bathroom, Sleeps 5
6 photos Details
Make Enquiry
From
$947
Per Night
6 Bedrooms, 5 Bathrooms, Sleeps 16
21 photos Details
Make Enquiry
From
$341
Per Night
4 Bedrooms, 3 Bathrooms, Sleeps 8
17 photos Details
Make Enquiry
From
$94
Per Night
2 Bedrooms, 1 Bathroom, Sleeps 4
6 photos Details
Make Enquiry
From
$154
Per Night
2 Bedrooms, 1 Bathroom, Sleeps 6
11 photos Details
Make Enquiry
From
$109
Per Night
1 Bedroom, 1 Bathroom, Sleeps 4
13 photos Details
Make Enquiry
From
$100
Per Night
13 Bedrooms, 28 Bathrooms, Sleeps 25
12 photos Details
Make Enquiry
From
$87
Per Night
1 Bedroom, 1 Bathroom, Sleeps 2
5 photos Details
Make Enquiry
From
$116
Per Night
3 Bedrooms, 2 Bathrooms, Sleeps 6
11 photos Details
Reviews (6) Make Enquiry
From
$116
Per Night
3 Bedrooms, 3 Bathrooms, Sleeps 13
12 photos Details
Reviews (15) Make Enquiry
From
$116
Per Night
1 Bedroom, 1 Bathroom, Sleeps 2
25 photos Details
Reviews (1) Make Enquiry
From
$167
Per Night
2 Bedrooms, 2 Bathrooms, Sleeps 6
27 photos Details
Reviews (2) Make Enquiry
From
$167
Per Night
3 Bedrooms, 2 Bathrooms, Sleeps 6
28 photos Details
Reviews (8) Make Enquiry
From
$430
Per Night
3 Bedrooms, 3 Bathrooms, Sleeps 6
12 photos Details
Make Enquiry
From
$158
Per Night
1 Bedroom, 1 Bathroom, Sleeps 4
11 photos Details
Make Enquiry
From
$158
Per Night
1 Bedroom, 1 Bathroom, Sleeps 4
13 photos Details
Make Enquiry
From
$158
Per Night
1 Bedroom, 1 Bathroom, Sleeps 4
13 photos Details
Make Enquiry
From
$190
Per Night
2 Bedrooms, 1 Bathroom, Sleeps 5
11 photos Details
Make Enquiry
From
$190
Per Night
2 Bedrooms, 1 Bathroom, Sleeps 5
13 photos Details
Make Enquiry
From
$158
Per Night
1 Bedroom, 1 Bathroom, Sleeps 4
13 photos Details
Make Enquiry
From
$197
Per Night
16 Bedrooms, 16 Bathrooms, Sleeps 36
20 photos Details
Make Enquiry
From
$1,856
Per Week
5 Bedrooms, 4 Bathrooms, Sleeps 10
11 photos Details
Make Enquiry
From
$8,523
Per Week
7 Bedrooms, 7 Bathrooms, Sleeps 14
58 photos Details
Make Enquiry
From
$142
Per Night
1 Bedroom, 1 Bathroom, Sleeps 3
15 photos Details
Make Enquiry
From
$700
Per Night
2 Bedrooms, 2 Bathrooms, Sleeps 4
27 photos Details
Make Enquiry
From
$430
Per Night
3 Bedrooms, 3 Bathrooms, Sleeps 6
31 photos Details
Make Enquiry
From
$7,226
Per Week
8 Bedrooms, 6 Bathrooms, Sleeps 16
12 photos Details
Make Enquiry
From
$1,669
Per Week
5 Bedrooms, 4 Bathrooms, Sleeps 13
10 photos Details
Make Enquiry
From
$300
Per Night
1 Bedroom, Sleeps 2
47 photos Details
Make Enquiry
From
$469
Per Night
1 Bedroom, 1 Bathroom, Sleeps 2
19 photos Details
Make Enquiry
From
$2,550
Per Week
4 Bedrooms, 3 Bathrooms, Sleeps 10
20 photos Details
Make Enquiry
From
$1,041
Per Night
8 Bedrooms, 7 Bathrooms, Sleeps 16
24 photos Details
Make Enquiry
From
$7,284
Per Week
8 Bedrooms, 6 Bathrooms, Sleeps 16
12 photos Details
Make Enquiry
Go to map view
Book Online(30)
Use filters to find the best results!

Suitability

  • Wheelchair access (7)
  • Elder access (30)
  • Suitable for children (40)
  • Pet friendly (24)
  • Smoking allowed (54)

Amenities

  • Parking (37)
  • All pools (32)
  • Garden (32)
  • Internet (24)
  • Other outdoor space (24)
  • View all amenities