Vacation Rentals & Villas in Montepulciano

Close

Enter dates for more accurate prices

Payment Protection
Your payment for this rental is protected when you pay through FlipKey. Learn more

4,378 Houses

(28) Excellent 

34

Villa Nobile, Luxury Tuscan Home, Walk to Town

Province of Siena / Montepulciano

Montepulciano villa

5 18 min stay varies

  • 5 bedrooms
  • sleeps 18
  • min stay varies
  • Nearest beach 152 mi
  • Swimming pool
  • Child Friendly

Price per night from

$751

Responds fast!
avg. 2 hours 17 minutes

Price per night from

$751

(2) Excellent 

17

Very nice home in the historical center

Montepulciano / Valiano

Valiano apartment

3 6 3 nights min

  • 3 bedrooms
  • sleeps 6
  • 3 nights min
  • Child Friendly
  • Pet Friendly

Price per night from

$94

Price per night from

$94

(1) Excellent 

29

Colombi Palace Montepulciano

Province of Siena / Montepulciano

Montepulciano apartment

2 4 2 nights min

  • 2 bedrooms
  • sleeps 4
  • 2 nights min
  • Beach / lakeside relaxation
  • Child Friendly
  • Air conditioning

Price per night from

$190

Price per night from

$190

(1) Excellent 

39

Apartment "The Hague" at The House of the Oaks - Montepulciano

Montepulciano / Acquaviva di Montepulciano

Acquaviva di Montepulciano apartment

2 5 min stay varies

  • 2 bedrooms
  • sleeps 5
  • min stay varies
  • Nearest beach 120 mi
  • Swimming pool
  • Child Friendly

Price per night from

$127

Responds fast!
avg. 1 hour 57 minutes

Price per night from

$127

(9) Excellent 

36

Charming Apartment in Historic Center of Montepulciano, Tuscany

Province of Siena / Montepulciano

Montepulciano apartment

2 6 min stay varies

  • 2 bedrooms
  • sleeps 6
  • min stay varies
  • Child Friendly
  • Car not necessary
  • Air conditioning

Price per night from

$92

Price per night from

$92

(17) Excellent 

38

Tigli #1, two bedrooms apartment close to Montepulciano with Wi-Fi and pool

Province of Siena / Montepulciano

Montepulciano apartment

2 6 min stay varies

  • 2 bedrooms
  • sleeps 6
  • min stay varies
  • Nearest beach 185 mi
  • Swimming pool
  • Child Friendly
“Outstanding accommodations!” Tucked away and hard to find. There was a small wooden sign which we missed, but well worth the extra miles we had to drive. The property is well kept and can't beat the views. The apartment we had was a 2br and 2bath and
…see more

Price per night from

$134

Price per night from

$134

32

Maramai

Province of Siena / Montepulciano

Montepulciano villa

4 7 7 nights min

  • 4 bedrooms
  • sleeps 7
  • 7 nights min
  • Ask about children
  • Ask about pets

Price per night from

$309

Responds fast!
avg. 1 hour 28 minutes

Price per night from

$309

(37) Excellent 

99

LA VALIANA Luxury Villa Rental (Montepulciano) - HEATED POOL Incl./ FREE WI-FI

Province of Siena / Montepulciano

Montepulciano villa

4 8 min stay varies

  • 4 bedrooms
  • sleeps 8
  • min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 15 mi
  • Swimming pool
“Paradise in Tuscany!” This lovely villa has it all and is the kind of place that makes you want to stay and 'while away' the afternoon among its many outdoor spaces: whether it's dining in the gazebo overlooking the vineyard, watching as the evening
…see more

Price per night from

$653

Price per night from

$653

(2) Very Good 

39

Tigli #6, ground floor flat with one bedroom in Montepulciano area. Wi-Fi & pool

Province of Siena / Montepulciano

Montepulciano apartment

1 2 min stay varies

  • 1 bedroom
  • sleeps 2
  • min stay varies
  • Nearest beach 185 mi
  • Swimming pool
  • Child Friendly
“Wow! A relaxing well appointed holiday home” This is central rural position 6ks from Torrita di Siena makes it easy to enjoy beautiful Tuscany. With easy day trips with a car to Seina, Arezzo, Cortona, Castiglione del Lago or Firenze to name a few.Qu
…see more

Price per night from

$95

Price per night from

$95

(1) Very Good 

32

Maramai

Montepulciano / Abbadia di Montepulciano

Abbadia di Montepulciano villa

5 10 7 nights min

  • 5 bedrooms
  • sleeps 10
  • 7 nights min
  • Ask about children
  • Ask about pets

Price per night from

$370

Responds fast!
avg. 1 hour 28 minutes

Price per night from

$370

8

villa in South Toscany

Province of Siena / Montepulciano

Montepulciano villa

3 8 14 nights min

  • 3 bedrooms
  • sleeps 8
  • 14 nights min
  • Swimming pool
  • Ask about children
  • Air conditioning

Price per night from

$590

Responds fast!
avg. 29 minutes

Price per night from

$590

(9) Very Good 

34

Tigli #2, apt Montepulciano area for 5 persons with A/C, Wi-Fi and swimming pool

Province of Siena / Montepulciano

Montepulciano apartment

3 6 min stay varies

  • 3 bedrooms
  • sleeps 6
  • min stay varies
  • Nearest beach 185 mi
  • Swimming pool
  • Child Friendly
“Stunning setting” The apartment complex ( once we found it with a little help!) was stunning and beautifully kept. Unfortunately we had an unseasonably cold week so couldn't make use of the pool and much of the outdoor areas although as our large balc
…see more

Price per night from

$135

Price per night from

$135

(1) Excellent 

20

4 bedrooms in a tower, home of a sculptor

Province of Siena / Montepulciano

Montepulciano b and b

4 8 2 nights min

  • 4 bedrooms
  • sleeps 8
  • 2 nights min
  • Swimming pool
  • Private garden

Price per night from

$431

Responds fast!
avg. 3 hours 30 minutes

Price per night from

$431

(11) Excellent 

33

Tigli #5, flat near Montepulciano with 2 bedrooms. A/C, Wi-Fi and swimming pool

Province of Siena / Montepulciano

Montepulciano apartment

2 5 min stay varies

  • 2 bedrooms
  • sleeps 5
  • min stay varies
  • Nearest beach 185 mi
  • Swimming pool
  • Child Friendly
“Stunning estate and perfect location” I went with by partner in June for a 5 night stay after a couple nights in Florence. It was the perfect holiday and this appartment was exactly what we wanted - somewhere quiet, with a pool and close to Tuscan vi
…see more

Price per night from

$118

Price per night from

$118

24

Villa Abbadia

Montepulciano / Abbadia di Montepulciano

Abbadia di Montepulciano villa

4 10 7 nights min

  • 4 bedrooms
  • sleeps 10
  • 7 nights min
  • Nearest beach 201 mi
  • Swimming pool
  • Child Friendly

Price per night from

$319

Price per night from

$319

(2) Very Good 

10

Villa Iris - Perfect for families or group of friends

Province of Siena / Montepulciano

Montepulciano apartment

3 5 3 nights min

  • 3 bedrooms
  • sleeps 5
  • 3 nights min
  • Swimming pool
  • Child Friendly
  • Air conditioning

Price per night from

$225

Price per night from

$225

28

Villa Croce

Montepulciano / Sant'Albino

Sant'Albino villa

5 11 7 nights min

  • 5 bedrooms
  • sleeps 11
  • 7 nights min
  • Swimming pool
  • Child Friendly
  • Air conditioning

Price per night from

$393

Price per night from

$393

(5) Excellent 

36

CasaMontepulciano Into the sunset

Province of Siena / Montepulciano

Montepulciano apartment

2 4 2 nights min

  • 2 bedrooms
  • sleeps 4
  • 2 nights min
  • Child Friendly
  • Car not necessary
  • Ask about pets

Price per night from

$176

Responds fast!
avg. 1 hour 12 minutes

Price per night from

$176

(2) Very Good 

14

Agriturismo I Fuochi

Montepulciano / Valiano

Valiano farmhouse

11 22 2 nights min

  • 11 bedrooms
  • sleeps 22
  • 2 nights min
  • Swimming pool
  • Child Friendly
  • Pet Friendly

Price per night from

$1,115

Responds fast!
avg. 3 hours 11 minutes

Price per night from

$1,115

(19) Excellent 

17

Tuscan Tower - A unique castle apartment

Province of Siena / Montepulciano

Montepulciano apartment

2 4 7 nights min

  • 2 bedrooms
  • sleeps 4
  • 7 nights min
  • Suitable for children age 5+
“Great Place. Quiet town. Beautiful Views” Excellent location. Beautiful apartment. John and Wendy were great to work with. They provided ideas of where to visit and outlined helpful tips for the week we were there. I would highly recommend staying wi
…see more

Price per night from

$261

Price per night from

$261

(1) Excellent 

32

Apartment "Belvedere" at The House of the Oaks - Montepulciano

Montepulciano / Acquaviva di Montepulciano

Acquaviva di Montepulciano apartment

1 4 min stay varies

  • 1 bedroom
  • sleeps 4
  • min stay varies
  • Nearest beach 130 mi
  • Swimming pool
  • Child Friendly

Price per night from

$105

Responds fast!
avg. 1 hour 57 minutes

Price per night from

$105

(1) Very Good 

42

"Policiano Suite" at The House of the Oaks - Montepulciano

Montepulciano / Acquaviva di Montepulciano

Acquaviva di Montepulciano apartment

2 6 min stay varies

  • 2 bedrooms
  • sleeps 6
  • min stay varies
  • Nearest beach 120 mi
  • Swimming pool
  • Child Friendly

Price per night from

$173

Responds fast!
avg. 1 hour 57 minutes

Price per night from

$173

(24) Excellent 

38

CasaMontepulciano, In the heart of Montepulciano

Province of Siena / Montepulciano

Montepulciano apartment

2 4 2 nights min

  • 2 bedrooms
  • sleeps 4
  • 2 nights min
  • Child Friendly
  • Air conditioning
  • Pet Friendly
“Beautiful Montepulciano, Fantastic Host (Luca), Great apartment” We honestly cannot say enough good things about wonderful Luca and his beautiful place in Montepulciano. If you are thinking of staying in this delightful hill town (and it makes a great
…see more

Price per night from

$137

Responds fast!
avg. 1 hour 12 minutes

Price per night from

$137

24

Country House at Antico Podere in Montepulciano, Tuscany

Province of Siena / Montepulciano

Montepulciano apartment

1 2 1 night min

  • 1 bedroom
  • sleeps 2
  • 1 night min
  • Swimming pool
  • Child Friendly
  • Pet Friendly

Price per night from

$138

Price per night from

$138

(2) Excellent 

39

Tigli #3, 2 bedrooms and 2 bathrooms apt close Montepulciano. Wi-Fi, A/C & pool

Province of Siena / Montepulciano

Montepulciano apartment

2 6 min stay varies

  • 2 bedrooms
  • sleeps 6
  • min stay varies
  • Nearest beach 185 mi
  • Swimming pool
  • Child Friendly
“Excellent apartments in a gorgeous location” I stayed with my family and another family for a week in apartments #1 and #3. The couple managing the compound are very nice and helpful, but also very strict and professional about the rules concerning pa
…see more

Price per night from

$134

Price per night from

$134

28

Luxury villa Vignola

Province of Siena / Montepulciano

Montepulciano villa

7 19 7 nights min

  • 7 bedrooms
  • sleeps 19
  • 7 nights min
  • Swimming pool
  • Child Friendly
  • Air conditioning

Price per night from

$832

Price per night from

$832

37

7 bedroom Villa in Castelluccio, Tuscany, Italy - 5247920

Montepulciano / Sant'Albino

Sant'Albino villa

7 14 7 nights min

  • 7 bedrooms
  • sleeps 14
  • 7 nights min
  • Swimming pool
  • Child Friendly
  • Ask about pets

Price per night from

$779

Price per night from

$779

39

Apartment "Poggino" - Montepulciano

Montepulciano / Acquaviva di Montepulciano

Acquaviva di Montepulciano apartment

2 4 min stay varies

  • 2 bedrooms
  • sleeps 4
  • min stay varies
  • Nearest beach 120 mi
  • Swimming pool
  • Child Friendly

Price per night from

$118

Responds fast!
avg. 1 hour 57 minutes

Price per night from

$118

30

Luxury villa Ivory

Montepulciano / Sant'Albino

Sant'Albino villa

8 16 7 nights min

  • 8 bedrooms
  • sleeps 16
  • 7 nights min
  • Swimming pool
  • Child Friendly
  • Air conditioning

Price per night from

$2,275

Price per night from

$2,275

(4) Excellent 

38

DOWNTOWN WITH A VIEW!Entire Home w. huge Terraces

Province of Siena / Montepulciano

Montepulciano house

4 10 2 nights min

  • 4 bedrooms
  • sleeps 10
  • 2 nights min
  • Nearest beach 41 mi
  • Child Friendly
  • Private garden

Price per night from

$201

Responds fast!
avg. 1 hour 32 minutes

Price per night from

$201

(1) Very Good 

37

Studio "Rustic" at The House of the Oaks - Montepulciano

Montepulciano / Acquaviva di Montepulciano

Acquaviva di Montepulciano apartment

1 2 min stay varies

  • 1 bedroom
  • sleeps 2
  • min stay varies
  • Nearest beach 120 mi
  • Swimming pool
  • Child Friendly

Price per night from

$85

Responds fast!
avg. 1 hour 57 minutes

Price per night from

$85

37

Villa Viole - Dream under the tuscan sun

Province of Siena / Montepulciano

Montepulciano apartment

2 4 3 nights min

  • 2 bedrooms
  • sleeps 4
  • 3 nights min
  • Swimming pool
  • Child Friendly
  • Air conditioning

Price per night from

$197

Price per night from

$197

(2) Very Good 

55

Rustic Tuscan Farmhouse at Podere Pisinano

Province of Siena / Montepulciano

Montepulciano villa

4 10 7 nights min

  • 4 bedrooms
  • sleeps 10
  • 7 nights min
  • Ask about children
  • Ask about pets

Price per night from

$456

Price per night from

$456

12

L'ANTICO GRANAIO

Province of Siena / Montepulciano

Montepulciano cottage

2 4 2 nights min

  • 2 bedrooms
  • sleeps 4
  • 2 nights min
  • Child Friendly
  • Air conditioning
  • Ask about pets

Price per night from

$144

Price per night from

$144

(3) Very Good 

22

Villa Montepulciano

Province of Siena / Montepulciano

Montepulciano villa

6 15 7 nights min

  • 6 bedrooms
  • sleeps 15
  • 7 nights min
  • Ask about children
  • Ask about pets
“Perfect...” Perfect Villa and setting to enjoy all the splendors that Tuscany and Montepulciano has to offer. - Rose L., ,
…see more

Price per night from

$911

Responds fast!
avg. 1 hour 28 minutes

Price per night from

$911

(1) Excellent 

51

The Molinaccio 10 + 2

Montepulciano / Acquaviva di Montepulciano

Acquaviva di Montepulciano villa

5 12 7 nights min

  • 5 bedrooms
  • sleeps 12
  • 7 nights min
  • Ask about children
  • Pet Friendly

Price per night from

$429

Price per night from

$429

(1) Excellent 

20

5 bedroom Tuscan villa with pool

Province of Siena / Montepulciano

Montepulciano house

5 10 min stay varies

  • 5 bedrooms
  • sleeps 10
  • min stay varies
  • Swimming pool
  • Child Friendly
  • Air conditioning
“fantastic, beautiful villa” 10 of us stayed here for my wedding and there was nothing we could find fault with. The bedrooms were all spacious. Lovely en suite to the master bedroom.kitchen had all the mod cons required whilst keeping a tuscan charm.
…see more

Price per night from

$600

Price per night from

$600

(1) Excellent 

22

Room in a tower between Cortona and Montepulciano

Province of Siena / Montepulciano

Montepulciano b and b

1 2 1 night min

  • 1 bedroom
  • sleeps 2
  • 1 night min
  • Swimming pool

Price per night from

$118

Responds fast!
avg. 3 hours 30 minutes

Price per night from

$118

About Montepulciano

Montepulciano is a beautiful village in a hilly area of Tuscany overlooking the Valdichiana countryside. The streets here leave a lasting impression on visitors because of their old world charm and also because of their steep inclines, which can make an adventure out of an ordinary day spent exploring markets and relaxing in cafes.

These sloping streets wind among some unforgettable restaurants and wine cellars. They can also take you to some of the most beautiful renaissance churches in Tuscany. Head beyond the center of town and take a hike through the rolling countryside of world famous vineyards and olive groves. At the end of the day, head back to experience the delicious cuisine that brings knowledgeable foodies to Montepulciano from all over the world and enjoy a glass of vino nobile as the sun sets.

Here are a few additional suggestions as you plan your trip:

  • Visit the Chiesa di San Biagio: This domed renaissance church with its fantastic marble alter piece lies in a valley just to the west of the Chiesa del Gesu, another impressive work of religious architecture.
  • Explore the Museo Civico: The town of Montepulciano has its own civic museum, which houses artifacts documenting its long history.
  • Explore the cantinas of Montepulciano: Tuscany is known for its wine, but Montepulciano in particular has a charming community of cantinas that offer tours through cellars packed with casks followed by a unique tasting experience.
  • Take a tour of the Azienda Agricola Canneto: This sprawling vineyard close to the Church of San Biagio produces regional vino nobile and extra virgin olive oil. Come to tour the grounds and learn more about how these precious items are produced.
  • Take an Italian cooking class: Sample the unforgettable flavors of Tuscany at the restaurants and trattorias of Montepulciano, then take a course from a skilled chef and learn how to bring these flavors home with you.
  • Visit the Formaggi Cugusi Silvana: The family that runs this artisanal pecorino cheese shop makes cheese with the milk from their own sheep that graze in the pastures of the Val d'Orcia.

You'll have no trouble finding world class dining opportunities, and you'll also have no trouble finding a vacation rental that offers luxurious views of the Tuscan countryside. Find an elegant condo downtown or a beautiful rustic villa overlooking the vineyards. While you're visiting Montepulciano, you may want to include a day trip to the beautiful town of Torrita di Siena in your plans.