Holiday Rental Villas - Vacation Rentals in Calzaiolo

Villa Il Conventino From US $1,341
         

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10.0 (2 Reviews)
Villa
  • Air Conditioner
  • Parking
  • Pet Friendly
Historic Villa-Farm with Vineyards & Olives Trees From US $2,370
         

Villa D'Agnola by MMega From US $1,744
         

10.0 (2 Reviews)
Villa
  • Air Conditioner
  • Pool
  • TV

Luxury Places to Stay in Calzaiolo

Over 352+ Luxury Places to Stay in or Near Calzaiolo

Top-Rated Vacation Rentals with a Pool in Calzaiolo

Over 217+ Top-Rated Vacation Rentals with a Pool in or Near Calzaiolo
Pozzo dei Desideri 1 - Apartment with swimming pool From US $164
         

10.0 (20 Reviews)
Apartment
  • Air Conditioner
  • Parking
  • Pet Friendly
Cottage in Tuscany with Pool & BBQ From US $269
         

10.0 (6 Reviews)
House
  • Pet Friendly
  • Pool
  • Balcony/Terrace
Macinello Farmhouse - App.to Blue From US $233
         

Au Coeur du Chianti From US $309
         

10.0 (3 Reviews)
House
  • Air Conditioner
  • Parking
  • Pet Friendly

Pet-Friendly Vacation Rentals in Calzaiolo

Over 155+ Pet-Friendly Vacation Rentals in or Near Calzaiolo
Archipettoli From US $400
         

|
10.0 (2 Reviews)
Villa
  • Air Conditioner
  • Parking
  • Pet Friendly
The colors of Chianti From US $195
         

10.0 (1 Review)
House
  • Air Conditioner
  • Parking
  • Pet Friendly
Casa delle Fiabe by Interhome From US $319
         

Pozzo dei Desideri 2 - Apartment with swimming pool From US $358
         

Large Vacation Homes & Villas in Calzaiolo

Over 91+ Large Vacation Homes & Villas in or Near Calzaiolo
Agriturismo Macinello From US $133
         

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9.9 (27 Reviews)
House
  • Air Conditioner
  • Parking
  • Pet Friendly
Bulleri by Interhome From US $724
         

8.4 (16 Reviews)
House
  • Parking
  • Pet Friendly
  • Pool

Wheelchair Accessible Vacation Homes in Calzaiolo

Over 18+ Wheelchair Accessible Vacation Homes in or Near Calzaiolo
Salvadonica From US $568
         

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9.4 (1120 Reviews)
House
  • Air Conditioner
  • Parking
  • Pet Friendly
Villa I Barronci Resort & Spa From US $252
         

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9.2 (425 Reviews)
Hotel
  • Air Conditioner
  • Parking
  • Pool
I Greppi di Silli From US $222
         

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9.4 (33 Reviews)
House
  • Parking
  • Pet Friendly
  • Pool
Park Hotel Chianti From US $151
         

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9.0 (262 Reviews)
Hotel
  • Air Conditioner
  • Parking
  • Pool

Calzaiolo Vacation Rentals and Airbnb Places to Stay Under $200

Over 167+ Calzaiolo Vacation Rentals and Airbnb Places to Stay Under $200
B&b San Jacopo a Mucciana From US $75
         

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8.8 (203 Reviews)
Bed & Breakfast
  • Air Conditioner
  • Parking
  • Balcony/Terrace
Awesome apartment in Montespertoli (FI) From US $85
         

8.0 (3 Reviews)
Apartment
  • Air Conditioner
  • Parking
  • Pool
Cozy home in Montespertoli FI From US $197
         

Il Convento by Interhome From US $158
         

10.0 (5 Reviews)
Apartment
  • Parking
  • Pet Friendly
  • Security/Safety
Characteristic apartment in historic 1300s tower From US $108
         

Instantly Bookable Vacation Homes in Calzaiolo

Over 137+ Instantly Bookable Vacation Homes in or Near Calzaiolo
House with garden in the hills of Chianti From US $273
         

Torretta Villa Borri Chianti Classico From US $226
         

About Calzaiolo Vacation Rentals

With more than 69 Calzaiolo vacation rentals, we can help you find a place to stay. These rentals, including vacation rentals, Holidayrentalvillas 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 Calzaiolo.

Looking for last-minute deals, or finding the best deals available for cottages, condos, private villas, and large vacation homes? With Holidayrentalvillas Calzaiolo, 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 Calzaiolo. Places to stay near Calzaiolo are 2205.82 ft² on average, with prices averaging US $1,093 a night.

Holidayrentalvillas makes it easy and safe to find and compare vacation rentals in Calzaiolo 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 Calzaiolo

Type Count
Villas 59
Vacation Homes 6
Hotels 3
Holiday Apartments 1

Use these Quick Filters to Find a Vacation Rental in Calzaiolo

Pro Tip: Holidayrentalvillas makes it easy to compare the best listings on Holidayrentalvillas homes from online vacation rental OTAs, including Booking.com and more. Use the Advanced Filter feature at the top to easily flip between Holidayrentalvillas 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 Calzaiolo.

Weather in Calzaiolo

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

December - February
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March - May
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June - August
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Calzaiolo Vacation Rental Frequently Asked Questions

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

Currently, the total number of properties listed in 2026 is over 69 in the Calzaiolo area, and still counting. By aggregating listings from multiple websites, offers an immense amount of choice of the best properties in Calzaiolo.