Luxury Long Stay Rentals in Montepulciano

We selected the 2346 homes worth renting in this location!

Who's coming along?

Adults

Age 13+

0

Children

Age 1 to 12

0

Infants

Under 1

0

Pets

An extra fee may apply

0

Home spotlights in Montepulciano

Rustic Idyll

Rustic Idyll

  • 6 guests

  • 3 bedrooms

Torrita di Siena, Siena

It's homes like this that give Tuscany its reputation as a blissful place which to retreat for a week or three. The surrounding landscape of vineyards and rolling hillsides is as picturesque as you could possibly imagine, while the home itself is bursting with character.

Architectural Narrative

Architectural Narrative

  • 4 guests

  • 2 bedrooms

Montalcino, Siena

Bookended by the olive groves, cypress trees and rolling green hills of Southern Tuscany is this 1960s-style architectural feat designed and curated by a sculptor and architect duo. Perfect for two couples or a small group of friends looking to explore the region, this cleverly converted warehouse is airy and open-plan with large crittall-style windows looking out over the vineyard and rambling countryside beyond.

A Tuscan Rhapsody

A Tuscan Rhapsody

  • 10 guests

  • 5 bedrooms

Torrita di Siena, Siena

Peaceful Tuscan retreats don’t get much better than this. This stunning home – spread between the main villa and an annex – is a special base in Italy, tucked amid the Tuscan Hills yet within easy reach of the art and culture of nearby Montepulciano and Pienza.

The Tuscan Vineyard

The Tuscan Vineyard

  • 6 guests

  • 3 bedrooms

Torrita di Siena, Siena

Set on a farm, parts of which are more than 200 years old, you’ll find this apartment, which is light and bright thanks to the large arched windows. Outside, as you’d hope for – there are gorgeous vistas over the Tuscan countryside and instead of a farm pond, there’s now a beautiful shared pool, which is a short walk through the communal gardens.


We selected the top 3% holiday homes in Montepulciano Long Stay Rentals

Explore the 2346 most perfect homes in our collection

View on map

Most popular homes in Montepulciano

Little Hills

Little Hills

  • 14 guests

  • 7 bedrooms

Sarteano, Siena

Little Borghis

Little Borghis

  • 10 guests

  • 5 bedrooms

Cortona, Arezzo

The Old Watermill

The Old Watermill

  • 14 guests

  • 7 bedrooms

Montepulciano, Siena

Rural Idyll

Rural Idyll

  • 12 guests

  • 6 bedrooms

Montepulciano, Siena

The Olive Trees

The Olive Trees

  • 10 guests

  • 5 bedrooms

Chianciano Terme, Tuscany

Rosemary & Quill

Rosemary & Quill

  • 10 guests

  • 4 bedrooms

Montepulciano, Siena

Tuscan Sweet

Tuscan Sweet

  • 4 guests

  • 2 bedrooms

Torrita di Siena, Siena

The Olive & the Vine

The Olive & the Vine

  • 17 guests

  • 7 bedrooms

Sant'Albino, Montepulciano

View all

Check upcoming rates & availability for Montepulciano Long Stay Rentals


Frequently asked questions

Explore our collection of luxury Extended Stay Rentals available for you to rent in Montepulciano. Each and every home you'll find has been through a meticulous, multi-stage vetting process to ensure quality our guests can always count on. The Long Stay Rentals in our Montepulciano collection come fully furnished with well-equipped kitchens, all linens, and essential bathroom toiletries included. And if you need any assistance, our friendly team of experts is always on hand to help plan your perfect stay.

Search our collection