Rent The Cottages - Vacation Rentals in Montalcino

Secluded Farmhouse in Montalcino with Swimming Pool From US $45
         

Luxury Places to Stay in Montalcino

Over 805+ Luxury Places to Stay in or Near Montalcino
Antico Brunello From US $8,431
         

New
Villa
  • Air Conditioner
  • Pool
  • TV
Villa Salvia- Accommodation in Tuscany From US $5,845
         

8.0 (1 Review)
Resort
  • Air Conditioner
  • Parking
  • Pool
Villino Rosmarino - Cignella Resort Toscana From US $5,830
         

Villa Falco- Cignella Resort Tuscany From US $5,830
         

9.0 (2 Reviews)
House
  • Air Conditioner
  • Parking
  • Pet Friendly

Top-Rated Vacation Rentals with a Pool in Montalcino

Over 494+ Top-Rated Vacation Rentals with a Pool in or Near Montalcino
Castello Banfi - Il Borgo - Relais et Chateaux From US $1,394
         

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10.0 (130 Reviews)
Hotel
  • Air Conditioner
  • Parking
  • Pool
Villa Le Prata - Residenza del Vescovo From US $534
         

10.0 (85 Reviews)
Hotel
  • Air Conditioner
  • Parking
  • Pool
Il Burellino Wine & Resort From US $262
         

10.0 (80 Reviews)
Other
  • Air Conditioner
  • Parking
  • Pool
Castiglion del Bosco, A Rosewood Hotel From US $2,552
         

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10.0 (77 Reviews)
Hotel
  • Air Conditioner
  • Parking
  • Pool
Mastrojanni Relais - Small Luxury Hotels of the World From US $681
         

Classic, Private Villa with Breathtaking Views - Private Pool From US $683
         

10.0 (25 Reviews)
Villa
  • Air Conditioner
  • Parking
  • Pet Friendly

Pet-Friendly Vacation Rentals in Montalcino

Over 464+ Pet-Friendly Vacation Rentals in or Near Montalcino
Cerretalta - Country villa with private pool From US $694
         

10.0 (9 Reviews)
Villa
  • Air Conditioner
  • Parking
  • Pet Friendly
Villetta Caprili From US $58
         

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10.0 (9 Reviews)
Apartment
  • Parking
  • Pet Friendly
  • Designated Smoking Area
Apartment Pino - 2 bedroom apartment in Tuscany From US $282
         

Brunello 1 - Apartment with swimming pool From US $395
         

10.0 (8 Reviews)
Apartment
  • Air Conditioner
  • Parking
  • Pet Friendly
Brunello 2 - Apartment with swimming pool From US $424
         

10.0 (7 Reviews)
Apartment
  • Air Conditioner
  • Parking
  • Pet Friendly

Large Vacation Homes & Villas in Montalcino

Over 211+ Large Vacation Homes & Villas in or Near Montalcino
Villa Piazza della Fortezza - Villa with Jacuzzi From US $1,463
         

10.0 (12 Reviews)
Villa
  • Air Conditioner
  • Parking
  • Balcony/Terrace
Palazzo Tamanti - 4BR 6 Bath Estate Home in Montalcino Center From US $684
         

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10.0 (13 Reviews)
Villa
  • Air Conditioner
  • Parking
  • Designated Smoking Area
Antico Convento I Cappuccini - Villa & Wedding Venue From US $3,274
         

10.0 (3 Reviews)
Villa
  • Pet Friendly
  • Pool
  • Designated Smoking Area
Villa in Montalcino with 6 bedrooms sleeps 12 From US $1,348
         

10.0 (10 Reviews)
Villa
  • Air Conditioner
  • Parking
  • Pool

Wheelchair Accessible Vacation Homes in Montalcino

Over 17+ Wheelchair Accessible Vacation Homes in or Near Montalcino
Agriturismo Sole From US $345
         

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9.9 (282 Reviews)
House
  • Air Conditioner
  • Parking
  • Pet Friendly
Palazzo Saloni From US $431
         

10.0 (1 Review)
Resort
  • Parking
  • TV
  • Wheelchair Accessible
Podere Brizio From US $311
         

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9.4 (668 Reviews)
House
  • Air Conditioner
  • Parking
  • Pool
Podere Brizio From US $256
         

9.8 (159 Reviews)
House
  • Air Conditioner
  • Parking
  • Pool
Capanna Suites From US $570
         

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9.3 (482 Reviews)
House
  • Air Conditioner
  • Parking
  • Pool
Antica Grancia di Quercecchio From US $96
         

9.2 (5 Reviews)
Other
  • Air Conditioner
  • Parking
  • Pool
Antica Grancia Di Quercecchio From US $91
         

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9.2 (210 Reviews)
Apartment
  • Air Conditioner
  • Parking
  • Pool
SI Montalcino Hotel From US $186
         

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9.2 (389 Reviews)
Hotel
  • Air Conditioner
  • Parking
  • Pool

Montalcino Vacation Rentals and Airbnb Places to Stay Under $200

Over 235+ Montalcino Vacation Rentals and Airbnb Places to Stay Under $200
A Casa di Enrichetta From US $128
         

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10.0 (18 Reviews)
House
  • Parking
  • View
  • Balcony/Terrace
Idolina Guest House From US $145
         

9.4 (114 Reviews)
House
  • Parking
  • TV
  • Security/Safety
Podere Belsogno-camera Lavanda From US $138
         

10.0 (4 Reviews)
House
  • Air Conditioner
  • Parking
  • TV
Sibilla Guest House, home in the heart of Val d'Orcia From US $95
         

Instantly Bookable Vacation Homes in Montalcino

Over 366+ Instantly Bookable Vacation Homes in or Near Montalcino
Apartment 'Casa Francesca' with Hills View & Courtyard From US $174
         

10.0 (2 Reviews)
Apartment
  • Designated Smoking Area
  • TV
  • Balcony/Terrace
Historic home in Montalcino From US $503
         

10.0 (7 Reviews)
House
  • Air Conditioner
  • TV
  • Balcony/Terrace
Palazzo Tamanti - 4 King BR 6 Bath Estate Home in Montalcino Center From US $1,291
         

10.0 (3 Reviews)
House
  • Air Conditioner
  • Parking
  • Designated Smoking Area
Wine & History in Montalcino- Stay in an ancient mill From US $756
         

Casa Cerralta 14, Montalcino, Siena and Chianti From US $717
         

10.0 (2 Reviews)
Villa
  • Air Conditioner
  • Pet Friendly
  • Pool
Apartment 'Casa Francesca' with Hills View & Courtyard From US $390
         

10.0 (2 Reviews)
Apartment
  • Designated Smoking Area
  • TV
  • Balcony/Terrace

About Montalcino Vacation Rentals

With more than 814 Montalcino vacation rentals, we can help you find a place to stay. These rentals, including vacation rentals, Rentthecottages and other short-term private accommodations, have top-notch amenities with the best value, providing you with comfort and luxury at the same time. Get more value and more room when you stay at a rental property in Montalcino.

Looking for last-minute deals, or finding the best deals available for cottages, condos, private villas, and large vacation homes? With Rentthecottages Montalcino, you have the flexibility of comparing different options of various deals with a single click. Looking for a rental by owner with the best swimming pools, hot tubs, allows pets, or even those with huge master suite bedrooms and have large screen televisions? You can find vacation rentals by owner, and other popular Airbnb-style properties in Montalcino. Places to stay near Montalcino are 1102.96 ft² on average, with prices averaging US $529 a night.

Rentthecottages makes it easy and safe to find and compare vacation rentals in Montalcino with prices often at a 30-40% discount versus the price of a hotel. Just search for your destination and secure your reservation today.

Top Rental Accommodation Types in Montalcino

Type Count
Holiday Apartments 291
Vacation Homes 244
Villas 147
Others 62
B&B 27
Hotels 22
Ski Chalet Rentals 11
Resorts 8
Cottages 2

Use these Quick Filters to Find a Vacation Rental in Montalcino

Pro Tip: Rentthecottages makes it easy to compare the best listings on Rentthecottages homes from online vacation rental OTAs, including Booking.com and more. Use the Advanced Filter feature at the top to easily flip between Rentthecottages homes, vacation rentals, bed and breakfasts, private Airbnb-style rentals availability, eco-friendly properties, property type, cancellation policies, prices, and several different options. All these make it easier to find the perfect accommodation for your next vacation in Montalcino.

Weather in Montalcino

View the weather forecast for Montalcino before booking your Montalcino Vacation Rentals to confirm your best time to go.

December - February
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Montalcino Vacation Rental Frequently Asked Questions

What are the top vacation rentals in Montalcino?
How many vacation rentals are available in Montalcino?

Currently, the total number of properties listed in 2026 is over 814 in the Montalcino area, and still counting. By aggregating listings from multiple websites, offers an immense amount of choice of the best properties in Montalcino.