Vacation Rentals & Villas in Montepulciano

Updating...

age 0-16
2353 Results

Relevance

Price: low to high

Price: high to low

Reviews

2,353 Houses

Casa Baccianella, wonderful holiday home close to hilltop town

Montone house

  • 5 bedrooms
  • 5 bathrooms
  • sleeps 12

Match: Heated pool Staffed property Trampoline Walking trips

All filters match

Price per night from

$740

Relais La Costa-Dimora Storica

Monteriggioni hotel apartment

  • 10 bedrooms
  • 12 bathrooms
  • sleeps 20

Match: Heated pool Staffed property Trampoline Walking trips

All filters match

Price per night from

Inquire for Rates

These homes match some but not all of your filters. Clear all filters

Apartment I Pini

Asciano apartment

  • 2 bedrooms
  • 1 bathroom
  • sleeps 3

3 of 4 match: Heated pool, Walking trips, Staffed property, Trampoline

3 of 4 filters match

Price per night from

$136

Brigolante Guest Apartments

Assisi farmhouse

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

3 of 4 match: Heated pool, Walking trips, Staffed property, Trampoline

3 of 4 filters match

Price per night from

Inquire for Rates

Spacious 2-bedroom, 2-bath apartment patio & pool

Castellina In Chianti apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

3 of 4 match: Heated pool, Walking trips, Staffed property, Trampoline

3 of 4 filters match

Price per night from

$265

Assisi da Ginetto

Petrignano d'Assisi apartment

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

3 of 4 match: Heated pool, Walking trips, Staffed property, Trampoline

3 of 4 filters match

Price per night from

$87

Borgo di Vagli

Mercatale di Cortona house

  • 2 bedrooms
  • 3 bathrooms
  • sleeps 6

Responds fast! avg. 3 hours 1 minutes

3 of 4 match: Trampoline, Walking trips, Heated pool, Staffed property

3 of 4 filters match

Price per night from

$168

il Paluffo Forno House Luxury apartment

Certaldo apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 5

3 of 4 match: Heated pool, Walking trips, Staffed property, Trampoline

3 of 4 filters match

Price per night from

$379

the Mill house Photos

Certaldo apartment

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

3 of 4 match: Heated pool, Walking trips, Staffed property, Trampoline

3 of 4 filters match

Price per night from

$514

the Tower House Photos

Certaldo apartment

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 8

3 of 4 match: Heated pool, Walking trips, Staffed property, Trampoline

3 of 4 filters match

Price per night from

$576

La Francigena B&B

Staggia Senese apartment

  • 2 bedrooms
  • 1 bathroom
  • sleeps 7

3 of 4 match: Heated pool, Walking trips, Staffed property, Trampoline

3 of 4 filters match

Price per night from

Inquire for Rates

RELAIS CAMPIGLIONI

Montevarchi apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

3 of 4 match: Staffed property, Walking trips, Heated pool, Trampoline

3 of 4 filters match

Price per night from

$111

Holiday Villa in Cortona

Cortona villa

  • 6 bedrooms
  • 8 bathrooms
  • sleeps 14

3 of 4 match: Staffed property, Walking trips, Heated pool, Trampoline

3 of 4 filters match

Price per night from

$691

The Granary, villa with pool and heated spa

San Venanzo villa

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Responds fast! avg. 1 hour 24 minutes

3 of 4 match: Trampoline, Walking trips, Heated pool, Staffed property

3 of 4 filters match

Price per night from

$235

Amazing Assisi

Assisi villa

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

3 of 4 match: Staffed property, Walking trips, Heated pool, Trampoline

3 of 4 filters match

Price per night from

$438

La Tinaia, Podere Patrignone - a Tuscan cottage with garden, views and pool

Castellina In Chianti cottage

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

“A Slice of Paradise” We stayed at Podere Patrignone for 5 days in September. It was wonderful to stay in a self contained apartment after 4 weeks of hotels in France. The farmhouse is charming, the apartments are unique and quaint, the countryside was picture perfect and the weather was unseasonably warm. Simon and Verity were such hospitable hosts, yet give the guests their own space. We thoroughly enjoyed the weekly meal Verity and Pam created for all the guests. You must have a car to truely experience all the hidden charms of Tuscany, and everything is so close and the quality of food and wine was impressive. Our favourite memory of staying at Podere Patrignone was sharing sunsets on the terrace with other guests and partaking of good wine, great conversation and so many laughs. We will be back for another slice of paradise.

3 of 4 match: Heated pool, Walking trips, Staffed property, Trampoline

3 of 4 filters match

Price per night from

$185

Tenuta I Terzi d Ombrone

Poggi del Sasso villa

  • 7 bedrooms
  • 8 bathrooms
  • sleeps 14

3 of 4 match: Trampoline, Walking trips, Heated pool, Staffed property

3 of 4 filters match

Price per night from

$3,239

Casa Titty Residence Terme Siena

Serre di Rapolano apartment

  • 1 bedroom
  • 2 bathrooms
  • sleeps 4

3 of 4 match: Trampoline, Walking trips, Heated pool, Staffed property

3 of 4 filters match

Price per night from

$99

il Paluffo Stillo House

Certaldo apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

3 of 4 match: Heated pool, Walking trips, Staffed property, Trampoline

3 of 4 filters match

Price per night from

$465

Villa Patrignone - a beautiful large Tuscany Villa

Castellina In Chianti villa

  • 7 bedrooms
  • 7 bathrooms
  • sleeps 14

“My favorite vacation experience” My first trip to Podere Patrignone was in 1999, and I've been back four times since my initial visit. The setting is incredible, and the views extend to miles and miles of Tuscany. It's amazing to sit on the terrace and see the towers of San Gimignano far in the distance. The villa is located just 3 kilometers from Castellina in Chianti, a charming village with unbelievable shopping for leather goods (Cappelletti), artwork, and other wonderful Tuscan items. Patrignone is a perfect location for day trips to Florence, Siena, Montalcino, and many other wonderful towns filled with incredible history. Back to the villa...Simon and Verity are carrying on the tradition of Simon's mom Carla, who renovated this beautiful villa that was originally a 14th century farmhouse. The main house has 7 rooms (each with its own bathroom...no sharing!), a great kitchen, and lots of space for lounging and relaxing. I've stayed in the main house as well as each of the 2-bedroom apartments...each with its own kitchen and living area. They all are wonderful, clean, charming, and have beautiful views. This year I participated in a cooking class conducted by Verity. Even after multiple cooking classes that I've taken throughout Italy, I can say that this was one of the best learning experiences: Verity is a fantastic teacher, cooking all the courses was great fun, and we got to dine and wine on our results. She cooked dinner for all of us on our first night, and everything was delicious! There were 18 of us on this trip, although I've been here with as few as one other person. I have lots of other friends who are encouraging a return trip. This year was in the last week of May, but I think we'll return for a visit in September next year. Carla and Simon and Verity have created a paradise that continues to call to me even after all these years and visits. Podere Patrignone is absolutely amazing and I can't wait to return!

3 of 4 match: Heated pool, Walking trips, Staffed property, Trampoline

3 of 4 filters match

Price per night from

$610

Podere Patrignone - large private Chianti estate

Castellina In Chianti villa

  • 15 bedrooms
  • 15 bathrooms
  • sleeps 33

3 of 4 match: Heated pool, Walking trips, Staffed property, Trampoline

3 of 4 filters match

Price per night from

$1,701

Villa Nobile

Cortona villa

  • 9 bedrooms
  • 6 bathrooms
  • sleeps 18

3 of 4 match: Heated pool, Walking trips, Staffed property, Trampoline

3 of 4 filters match

Price per night from

$1,356

18th Century Century Park Villa with private pool

Arezzo villa

  • 14 bedrooms
  • 10 bathrooms
  • sleeps 30

3 of 4 match: Heated pool, Walking trips, Staffed property, Trampoline

3 of 4 filters match

Price per night from

$1,620

Po' del Vento:è tutto intorno a te:16, piscina riscaldata, parco giochi, camino

Citta della Pieve guest house

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 16

3 of 4 match: Trampoline, Walking trips, Heated pool, Staffed property

3 of 4 filters match

Price per night from

$1,110

"Olivo Junior". Charming apartment in Podere Pietreta, old farmhouse with pool

Radicofani apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 5

3 of 4 match: Trampoline, Walking trips, Heated pool, Staffed property

3 of 4 filters match

Price per night from

$173

2 of 4 match: Heated pool, Trampoline, Walking trips, Staffed property

2 of 4 filters match

Price per night from

$160

Hotel Rosati

Chiusi b&b

  • 5 bedrooms
  • 5 bathrooms
  • sleeps 3

Responds fast! avg. 3 hours 59 minutes

2 of 4 match: Heated pool, Trampoline, Walking trips, Staffed property

2 of 4 filters match

Price per night from

$111

Soarzio apartment with pool near San Gimignano 4

San Gimignano apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

2 of 4 match: Heated pool, Trampoline, Walking trips, Staffed property

2 of 4 filters match

Price per night from

$124

Papaveri family holiday apartment in the heart of Italy

San Giovanni del Pantano apartment

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

3 of 4 match: Trampoline, Walking trips, Heated pool, Staffed property

3 of 4 filters match

Price per night from

$331

3 of 4 match: Trampoline, Walking trips, Heated pool, Staffed property

3 of 4 filters match

Price per night from

$1,837

Ancient house for two in Maremma

Sovana townhouse

  • 1 bedroom
  • 1 bathroom
  • sleeps 3

2 of 4 match: Staffed property, Heated pool, Walking trips, Trampoline

2 of 4 filters match

Price per night from

$74

Villa Castellare de Sernigi stunning sunsets for 13/14 people

Tavarnelle Val di Pesa villa

  • 6 bedrooms
  • 8 bathrooms
  • sleeps 14

3 of 4 match: Trampoline, Walking trips, Heated pool, Staffed property

3 of 4 filters match

Price per night from

$2,113

Exclusive luxury villa in the Tuscan countryside. 14 rooms, pool, A/C and Wi-Fi!

Monticiano villa

  • 14 bedrooms
  • 14 bathrooms
  • sleeps 28

3 of 4 match: Trampoline, Walking trips, Heated pool, Staffed property

3 of 4 filters match

Price per night from

$3,599

casale herd

Fabro farmhouse

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 8

2 of 4 match: Heated pool, Trampoline, Walking trips, Staffed property

2 of 4 filters match

Price per night from

Inquire for Rates

Ancient Casolare Antico Cottage

Ficulle apartment

  • 6 bedrooms
  • 8 bathrooms
  • sleeps 16

2 of 4 match: Heated pool, Trampoline, Walking trips, Staffed property

2 of 4 filters match

Price per night from

$1,076

Villa Miralaghi 8-9 WI-FI, Biliardo, Camino, Piscina riscaldata, Jacuzzi, Bocce

Citta della Pieve house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 9

3 of 4 match: Trampoline, Walking trips, Heated pool, Staffed property

3 of 4 filters match

Price per night from

$1,110

Exclusive Villa in countryside 8pers., heatable pool, Umbria/Tuscany, historic

Citta della Pieve villa

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 8

3 of 4 match: Trampoline, Walking trips, Heated pool, Staffed property

3 of 4 filters match

Price per night from

$617

Casale dei Pianetti

Sovana farmhouse

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

2 of 4 match: Staffed property, Heated pool, Walking trips, Trampoline

2 of 4 filters match

Price per night from

$185

Viewing 38 of 2,353
rentals in Montepulciano

×

Also consider