Vacation Rentals with Private Pool in Montecalvario, Castellina in Chianti: Compare 10+ Sites & Save

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  1. VBOR
  2. Vacation Rentals with Private Pool
  3.  Italy

  4.  Tuscany
  5.  Castellina in Chianti
  6.  Montecalvario

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276 Best Vacation Rentals with Private Pool in Montecalvario (Starting from $143)

Villa Terra di Siena - Homelike Villas
Villa Terra di Siena - Homelike Villas
Villa
Greve in Chianti, Italy
9.0k from Montecalvario center

Accommodations, Pools, Villas, Vacation homes, Cottages, Lodgings, Jacuzzis, Places to stay

18 Bedrooms36 Guests
New to Booking
$8235
Average price / night
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ISOLA SERENA Newly Expanded Private Luxury Villa, Tuscany, Infinity Pool & Views
ISOLA SERENA Newly Expanded Private Luxury Villa, Tuscany, Infinity Pool & Views
Villa
Castellina in Chianti, 53011, Italy
0.0k from Montecalvario center

AC, Balcony, Barbecue, Breakfast Available, Crib, Dryer, Fireplace, Fitness Equipment, Free Parking

11 Bedrooms23 Guests
10.0

Exceptional

64 reviews

$3564
Average price / night
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Amore Rentals - Villa Bellaflore
Amore Rentals - Villa Bellaflore
Villa
Panzano, Italy
9.1k from Montecalvario center

Accommodations, Pools, Villas, Vacation homes, Cottages, Lodgings, Vacation rentals, Places to stay

7 Bedrooms14 Guests
New to Booking
$2400
Average price / night
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detached villa with private pool and garden
detached villa with private pool and garden
House
Castellina in Chianti, 53011, Italy
0.6k from Montecalvario center

AC, Balcony, Barbecue, Crib, Dryer, Fireplace, Free Parking, Heater, Internet

3 Bedrooms4 Guests
8.8

Fabulous

26 reviews

$190
Average price / night
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Amore Rentals - Ville Il Paradiso
Amore Rentals - Ville Il Paradiso
House
Panzano, Italy
9.1k from Montecalvario center

Accommodations, Pools, Parking, Villas, Vacation homes, Cottages, Lodgings, Vacation rentals, Jacuzzis

18 Bedrooms37 Guests
New to Booking
$4098
Average price / night
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Wonderful private villa for 14 guests with A/C, WIFI, private pool, TV, patio and panoramic view
Wonderful private villa for 14 guests with A/C, WIFI, private pool, TV, patio and panoramic view
Villa
Castellina In Chianti, 53011, Italy
0.7k from Montecalvario center

AC, Barbecue, Crib, Free Parking, Heater, Internet, Kitchen, Laundry, Microwave

7 Bedrooms14 Guests
New to Booking
$804
Average price / night
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AMORE RENTALS - Villa Bacci
AMORE RENTALS - Villa Bacci
Villa
Panzano, Italy
9.2k from Montecalvario center

Accommodations, Pools, Parking, Villas, Vacation homes, Cottages, Lodgings, Vacation rentals, Places to stay

4 Bedrooms9 Guests
New to Booking
$1373
Average price / night
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Agriturismo La Ferrozzola
Agriturismo La Ferrozzola
House
Loc. Ferrozzola, 1, Castellina in Chianti, 53011, Italy
0.7k from Montecalvario center

Barbecue, Crib, Free Parking, Heater, Internet, Kitchen, Living Area, No Smoking, Outdoor Space

1 Bedroom2 Guests
9.4

Superb

9 reviews

$143
Average price / night
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Vacation home Olivo by Interhome
Vacation home Olivo by Interhome
House
Castellina in Chianti, 53011, Italy
0.7k from Montecalvario center

AC, Barbecue, Free Parking, Heater, Internet, Kitchen, Laundry, No Smoking, Outdoor Space

2 Bedrooms4 Guests
9.6

Exceptional

4 reviews

$249
Average price / night
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Cerretino group house 14 sleeps by Interhome
Cerretino group house 14 sleeps by Interhome
House
Castellina in Chianti, 53100, Italy
0.8k from Montecalvario center

AC, Barbecue, Dryer, Free Parking, Heater, Kitchen, Laundry, Microwave, No Smoking

7 Bedrooms14 Guests
New to Booking
$693
Average price / night
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Agriturismo apartment with pool and AC near the center of Castellina in Chianti
Agriturismo apartment with pool and AC near the center of Castellina in Chianti
Apartment
Castellina in Chianti, 53011, Italy
1.2k from Montecalvario center

AC, Free Parking, Heater, Hot Tub, Internet, Living Area, Outdoor Space, Pool

1 Bedroom4 Guests
New to Booking
$195
Average price / night
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Lovely apartment for 4 guests with A/C, hot tub, WIFI, private pool, TV, patio and panoramic view
Lovely apartment for 4 guests with A/C, hot tub, WIFI, private pool, TV, patio and panoramic view
Apartment
Castellina In Chianti, 53011, Italy
1.2k from Montecalvario center

AC, Barbecue, Free Parking, Heater, Hot Tub, Internet, Kitchen, Microwave, No Smoking

2 Bedrooms4 Guests
New to Booking
$273
Average price / night
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Casa Belmonte In Castellina in Chianti, Tuscany
Casa Belmonte In Castellina in Chianti, Tuscany
Villa
Castellina in Chianti, 53011, Italy
1.2k from Montecalvario center

Fireplace, Heater, Internet, Kitchen, Laundry, Living Area, Microwave, Outdoor Space, Pool

4 Bedrooms8 Guests
9.4

Superb

13 reviews

$536
Average price / night
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Casanovina, Castellina in Chianti, Siena and Chianti
Casanovina, Castellina in Chianti, Siena and Chianti
Villa
Castellina in Chianti, 53011, Italy
1.2k from Montecalvario center

Barbecue, Fireplace, Heater, Kitchen, Laundry, Living Area, Microwave, No Smoking, Outdoor Space

4 Bedrooms8 Guests
10.0

Exceptional

3 reviews

$431
Average price / night
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Agriturismo with pool and view close to the center of Castellina in Chianti
Agriturismo with pool and view close to the center of Castellina in Chianti
House
Castellina in Chianti, 53011, Italy
1.4k from Montecalvario center

AC, Barbecue, Extra Bed, Free Parking, Heater, Hot Tub, Internet, Kitchen, Microwave

1 Bedroom4 Guests
9.8

Exceptional

95 reviews

$195
Average price / night
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FABULOUS 6BD - 6BA VILLA WITH STUNNING POOL & VIEWS IN TOP CHIANTI LOCATION!
FABULOUS 6BD - 6BA VILLA WITH STUNNING POOL & VIEWS IN TOP CHIANTI LOCATION!
Villa
Castellina in Chianti, 53011, Italy
1.4k from Montecalvario center

AC, Balcony, Barbecue, Crib, Dryer, Fireplace, Free Parking, Heater, Internet

6 Bedrooms13 Guests
9.8

Exceptional

32 reviews

$1322
Average price / night
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Agriturismo with swimming pool and view near the center of Castellina in Chianti
Agriturismo with swimming pool and view near the center of Castellina in Chianti
Apartment
Castellina in Chianti, 53011, Italy
1.5k from Montecalvario center

AC, Barbecue, Free Parking, Heater, Hot Tub, Internet, Kitchen, Living Area, Microwave

2 Bedrooms6 Guests
9.8

Exceptional

16 reviews

$316
Average price / night
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Castellare in Poggio 10, Emma Villas
Castellare in Poggio 10, Emma Villas
Villa
Castellina in Chianti, 53100, Italy
1.6k from Montecalvario center

AC, Free Parking, Heater, Internet, Kitchen, Laundry, Living Area, Microwave, No Smoking

5 Bedrooms10 Guests
8.0

Good

1 reviews

$1696
Average price / night
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Villa Arnica B: A graceful cottage surrounded by vineyards and olive groves, with Free WI-FI.
Villa Arnica B: A graceful cottage surrounded by vineyards and olive groves, with Free WI-FI.
House
Castellina in Chianti, 53011, Italy
1.7k from Montecalvario center

Balcony, Extra Bed, Fireplace, Free Parking, Heater, Hot Tub, Internet, Kitchen, Laundry

2 Bedrooms4 Guests
10.0

Exceptional

2 reviews

$836
Average price / night
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Villa Delle Upupe 8, Emma Villas
Villa Delle Upupe 8, Emma Villas
Villa
Castellina in Chianti, 53011, Italy
1.8k from Montecalvario center

Free Parking, Heater, Internet, Kitchen, Laundry, Living Area, Microwave, No Smoking, Outdoor Space

4 Bedrooms8 Guests
New to Booking
$1792
Average price / night
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Macia Viva, Castellina in Chianti, Siena and Chianti
Macia Viva, Castellina in Chianti, Siena and Chianti
Villa
Castellina in Chianti, 53011, Italy
1.9k from Montecalvario center

AC, Kitchen, Laundry, Living Area, Microwave, No Smoking, Outdoor Space, Pool, TV

2 Bedrooms4 Guests
8.0

Good

3 reviews

$483
Average price / night
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Muricciaglia 14, Emma Villas
Muricciaglia 14, Emma Villas
Villa
Castellina in Chianti, 53017, Italy
2.1k from Montecalvario center

AC, Barbecue, Dryer, Free Parking, Heater, Internet, Kitchen, Living Area, Microwave

7 Bedrooms14 Guests
New to Booking
$2091
Average price / night
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Casale Sandonatino In Castellina in Chianti, Tuscany
Casale Sandonatino In Castellina in Chianti, Tuscany
Villa
Castellina in Chianti, 53011, Italy
2.5k from Montecalvario center

Fireplace, Internet, Kitchen, Laundry, Living Area, Outdoor Space, Pool, Toys, TV

6 Bedrooms12 Guests
8.8

Fabulous

9 reviews

$721
Average price / night
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Villa Tregole by MMega
Villa Tregole by MMega
Villa
Castellina in Chianti, 53017, Italy
2.6k from Montecalvario center

AC, Balcony, Barbecue, Dryer, Fireplace, Heater, Internet, Kitchen, Laundry

7 Bedrooms16 Guests
10.0

Exceptional

1 reviews

$785
Average price / night
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Tuscan Villa with private swimming pool
Tuscan Villa with private swimming pool
Villa
Castellina in Chianti (SIENA), 53011, Italy
2.6k from Montecalvario center

AC, Arcade, Balcony, Barbecue, Crib, Dryer, Fireplace, Fitness Equipment, Free Parking

5 Bedrooms8 Guests
9.6

Exceptional

5 reviews

$504
Average price / night
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Il Cipresso, Radda in Chianti, Siena and Chianti
Il Cipresso, Radda in Chianti, Siena and Chianti
Villa
Radda in Chianti, 53017, Italy
2.8k from Montecalvario center

Barbecue, Fireplace, Kitchen, Laundry, Living Area, Microwave, No Smoking, Outdoor Space, Pool

2 Bedrooms4 Guests
10.0

Exceptional

2 reviews

$211
Average price / night
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Villa Castagnoli In Castellina in Chianti, Tuscany
Villa Castagnoli In Castellina in Chianti, Tuscany
Villa
Castellina in Chianti, 53011, Italy
2.9k from Montecalvario center

AC, Dryer, Fireplace, Fitness Equipment, Heater, Living Area, Microwave, No Smoking, Pool

5 Bedrooms10 Guests
10.0

Exceptional

1 reviews

$1786
Average price / night
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Pro Tip:
VacationByOwnerRentals aggregates the best inventory from leading travel sites, including Booking.com, Agoda.com, Expedia.com, Vrbo.com, and Airbnb.com. Use our Advanced Filters to compare verified homes, villas, cabins, condos, cottages, vacation rentals, hotels, and eco-friendly stays. Our goal is to help you find the absolute best Vacation Rentals with Private Pool in Montecalvario.

Where to stay in Montecalvario? Best neighborhoods & areas

Montecalvario Vacation Rentals with Private Pool on the Map

Frequently Asked Questions

You can explore 276 verified vacation rentals with a private pool in Montecalvario. These include standalone villas and private homes where the pool is reserved exclusively for your group.

Prices for rentals with a private pool in Montecalvario vary depending on the property size, location, and travel season. Rates typically start from around $143 per night, with higher prices for larger homes, prime locations, or peak travel periods.

Yes, properties listed with private pools are intended for the exclusive use of guests staying at that home. You can review listing photos and descriptions to better understand the layout and level of privacy offered.

Yes, some vacation rentals with private pools in Montecalvario also welcome pets. Currently, 33 listings allow pets, although policies may vary. It’s a good idea to review any rules related to pets and outdoor areas before booking.

Private pool properties are often in high demand, especially during holidays and warmer months, so booking 90 to 120 days in advance is recommended. During quieter periods, you may still find availability closer to your travel dates.

Vacation rentals with private pools in Montecalvario often include additional features such as Private Pool, Pool, and Fireplace/Heating. These amenities enhance comfort and create a more relaxing, self-contained stay.

Some family-friendly vacation rentals in Montecalvario include safety features such as pool fences, covers, or screened enclosures. It’s recommended to check the property details to confirm whether a specific rental meets your safety preferences.