By using Plum Guide, you agree to our Cookie Policy.

Book Luxury Airbnb Alternatives in Montepulciano

We selected the 2224 homes worth renting in this location

Find your destination

Suggested destinations
Mon
Tue
Wed
Thu
Fri
Sat
Sun

February 2025

Mon
Tue
Wed
Thu
Fri
Sat
Sun
1
2
3
4
5
6
7
8
9
10
11
12
13
14
15
16
17
18
19
20
21
22
23
24
25
26
27
28

March 2025

Mon
Tue
Wed
Thu
Fri
Sat
Sun
1
2
3
4
5
6
7
8
9
10
11
12
13
14
15
16
17
18
19
20
21
22
23
24
25
26
27
28
29
30
31

April 2025

Mon
Tue
Wed
Thu
Fri
Sat
Sun
1
2
3
4
5
6
7
8
9
10
11
12
13
14
15
16
17
18
19
20
21
22
23
24
25
26
27
28
29
30

May 2025

Mon
Tue
Wed
Thu
Fri
Sat
Sun
1
2
3
4
5
6
7
8
9
10
11
12
13
14
15
16
17
18
19
20
21
22
23
24
25
26
27
28
29
30
31

June 2025

Mon
Tue
Wed
Thu
Fri
Sat
Sun
1
2
3
4
5
6
7
8
9
10
11
12
13
14
15
16
17
18
19
20
21
22
23
24
25
26
27
28
29
30

July 2025

Mon
Tue
Wed
Thu
Fri
Sat
Sun
1
2
3
4
5
6
7
8
9
10
11
12
13
14
15
16
17
18
19
20
21
22
23
24
25
26
27
28
29
30
31

August 2025

Mon
Tue
Wed
Thu
Fri
Sat
Sun
1
2
3
4
5
6
7
8
9
10
11
12
13
14
15
16
17
18
19
20
21
22
23
24
25
26
27
28
29
30
31

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

Rosemary & Quill

Rosemary & Quill

  • 10 guests

  • 4 bedrooms

Montepulciano, Siena

Just like the romantic notion of Tuscany we've all gleaned from books and films over the years, this beautiful, rustic farmhouse stands on an enormous estate, filled with centuries-old olive groves and famed for its high-quality olive oil. Peaceful and secluded, yet only five minutes from the town, it's the quintessential Tuscan retreat – complete with a new pool and a huge private garden dotted with cypress trees, shady oaks and olive trees.

Little Hills

Little Hills

  • 14 guests

  • 7 bedrooms

Sarteano, Siena

You can't beat the views of the beautiful Val D'Orcia, itself a UNESCO World Heritage Site, from this Tuscan farmhouse lying in the Siena Province on a private two-acre estate. Tear yourself away from the vistas, and you'll find a deft renovation, combining contemporary interiors and historic charm.

Marbled with Flowers

Marbled with Flowers

  • 26 guests

  • 13 bedrooms

Sarteano, Siena

Ten minutes from Sarteano town and an easy drive from Montepulciano, this charming Tuscan estate has its own outdoor pool and wellness facilities. The gym and spa are well-equipped, with a heated indoor pool, Finnish sauna and professional exercise equipment.

Yellow Harvest Moon

Yellow Harvest Moon

  • 12 guests

  • 6 bedrooms

Montepulciano, Siena

With a traditional farmhouse style and situated within some of the most beautiful landscapes that this part of the Tuscan countryside has to offer, this warm, welcoming, and characterful home is perfect for anyone looking to slow down and experience the simple pleasures of life in an idyllic location. Nestled in the shadow of Montepulciano, the home is ideally placed for those with a penchant for hiking and biking, not to mention those hoping for a taste of 'la dolce vita' by exploring sleepy local villages and typically Tuscan towns.


We selected the top 3% holiday homes in Montepulciano Airbnb Alternatives

Explore the 2224 most perfect homes in our collection

View on map

Most popular homes in Montepulciano

The Rose Blush

The Rose Blush

  • 4 guests

  • 2 bedrooms

Chianciano Terme, Tuscany

Golden Panorama

Golden Panorama

  • 8 guests

  • 4 bedrooms

Pienza, Siena

Tuscan White

Tuscan White

  • 6 guests

  • 3 bedrooms

Torrita di Siena, Siena

Tuscany's Charms

Tuscany's Charms

  • 10 guests

  • 6 bedrooms

Monticchiello, Pienza

Architectural Narrative

Architectural Narrative

  • 4 guests

  • 2 bedrooms

Montalcino, Siena

Sweet, Sweet Tuscany

Sweet, Sweet Tuscany

  • 16 guests

  • 8 bedrooms

Torrita di Siena, Siena

Aglio e Olio

Aglio e Olio

  • 9 guests

  • 5 bedrooms

Montepulciano, Siena

Casa di Siena

Casa di Siena

  • 4 guests

  • 2 bedrooms

Torrita di Siena, Siena

View all


Frequently asked questions

Airbnb is a shot in the dark. We meticulously vet all our homes in Montepulciano to ensure you won’t waste your precious holiday. Every home you'll find on Plum Guide comes fully furnished with the best-equipped kitchens, essential bathroom toiletries and all linen included. Before being accepted into our collection, each home much pass a meticulous vetting process, culminating in a personal home visit from an independent Home Critic. Rent one of Plum Guide's luxury Montepulciano Airbnb Alternatives, and enjoy a long or short stay to remember. Should you need any assistance with your booking, our friendly team of experts will be on hand to guide you through the process.

Search our collection