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

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  2. Vacation Rentals with Private Pool
  3.  Italy

  4.  Tuscany
  5.  Castellina in Chianti

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192 Best Vacation Rentals with Private Pool in Castellina in Chianti (Starting from $143)

Tuscan Villa with private swimming pool
Tuscan Villa with private swimming pool
Villa
Castellina in Chianti (SIENA), 53011, Italy
0.7k from Castellina in Chianti 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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Setriolo by Arceno Rentals Club, exclusive Villa and Annex, Pool A/C Concierge
Setriolo by Arceno Rentals Club, exclusive Villa and Annex, Pool A/C Concierge
Villa
Castellina in Chianti, 53011, Italy
1.0k from Castellina in Chianti center

AC, Crib, Dryer, Fireplace, Free Parking, Heater, Internet, Kitchen, Laundry

5 Bedrooms10 Guests
New to Booking
$958
Average price / night
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Luxury Villa in Chianti with Winery up to 10pax
Luxury Villa in Chianti with Winery up to 10pax
Villa
Castellina in Chianti, 53011, Italy
1.2k from Castellina in Chianti center

AC, Barbecue, Dryer, Fireplace, Heater, Internet, Kitchen, Microwave, Outdoor Space

5 Bedrooms10 Guests
New to Booking
$2327
Average price / night
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Luxury Villa in Chianti with Winery up to 6 Guests
Luxury Villa in Chianti with Winery up to 6 Guests
Villa
Castellina in Chianti, 53011, Italy
1.2k from Castellina in Chianti center

AC, Barbecue, Dryer, Fireplace, Heater, Internet, Kitchen, Microwave, Outdoor Space

4 Bedrooms6 Guests
New to Booking
$1336
Average price / night
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Luxury Villa in Chianti with Winery up to 4 Guests
Luxury Villa in Chianti with Winery up to 4 Guests
Villa
Castellina in Chianti, 53011, Italy
1.2k from Castellina in Chianti center

AC, Barbecue, Dryer, Fireplace, Heater, Internet, Kitchen, Microwave, Outdoor Space

4 Bedrooms4 Guests
New to Booking
$1139
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
1.2k from Castellina in Chianti 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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Villa Castagnoli 6 In Castellina in Chianti, Tuscany
Villa Castagnoli 6 In Castellina in Chianti, Tuscany
Villa
Castellina in Chianti, 53011, Italy
1.2k from Castellina in Chianti center

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

3 Bedrooms6 Guests
10.0

Exceptional

1 reviews

$995
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
1.2k from Castellina in Chianti 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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Casa Belmonte In Castellina in Chianti, Tuscany
Casa Belmonte In Castellina in Chianti, Tuscany
Villa
Castellina in Chianti, 53011, Italy
1.2k from Castellina in Chianti 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 Castellina in Chianti 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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Castellare in Poggio 10, Emma Villas
Castellare in Poggio 10, Emma Villas
Villa
Castellina in Chianti, 53100, Italy
1.3k from Castellina in Chianti 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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Casale Sandonatino In Castellina in Chianti, Tuscany
Casale Sandonatino In Castellina in Chianti, Tuscany
Villa
Castellina in Chianti, 53011, Italy
1.3k from Castellina in Chianti 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 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
1.4k from Castellina in Chianti 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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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
1.5k from Castellina in Chianti 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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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 Castellina in Chianti 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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Agriturismo La Ferrozzola
Agriturismo La Ferrozzola
House
Loc. Ferrozzola, 1, Castellina in Chianti, 53011, Italy
1.6k from Castellina in Chianti 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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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
1.7k from Castellina in Chianti 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
2.0k from Castellina in Chianti 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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Umiliati In Castellina in Chianti, Tuscany
Umiliati In Castellina in Chianti, Tuscany
Villa
Castellina in Chianti, 53011, Italy
2.1k from Castellina in Chianti center

Barbecue, Fireplace, Free Parking, Kitchen, Laundry, Pool, TV, Washer

5 Bedrooms9 Guests
9.4

Superb

8 reviews

$397
Average price / night
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Beautiful private villa for 9 guests with private pool, WIFI, pets allowed and panoramic view
Beautiful private villa for 9 guests with private pool, WIFI, pets allowed and panoramic view
Villa
Castellina In Chianti, 53011, Italy
2.2k from Castellina in Chianti center

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

5 Bedrooms9 Guests
New to Booking
$342
Average price / night
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Vacation home Olivo by Interhome
Vacation home Olivo by Interhome
House
Castellina in Chianti, 53011, Italy
2.2k from Castellina in Chianti 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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In The Heart Of Chianti, Pool, Wifi, View
In The Heart Of Chianti, Pool, Wifi, View
Villa
Lilliano, 53011, Italy
2.3k from Castellina in Chianti center

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

4 Bedrooms10 Guests
New to Booking
$818
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
2.3k from Castellina in Chianti 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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detached villa with private pool and garden
detached villa with private pool and garden
House
Castellina in Chianti, 53011, Italy
2.3k from Castellina in Chianti 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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Large beautiful villa in Tuscan Hills of Chianti, Stunning gardens w large pool
Large beautiful villa in Tuscan Hills of Chianti, Stunning gardens w large pool
Villa
Lilliano, 53011, Italy
2.4k from Castellina in Chianti center

AC, Balcony, Barbecue, Fireplace, Fitness Equipment, Heater, Internet, Kitchen, Laundry

9 Bedrooms18 Guests
New to Booking
$5661
Average price / night
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Casale Monte
Casale Monte
Cottage
Castellina in Chianti, 53011, Italy
2.4k from Castellina in Chianti center

Barbecue, Free Parking, Internet, Kitchen, Laundry, Outdoor Space, Pool, TV, Washer

6 Bedrooms12 Guests
New to Booking
$1043
Average price / night
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Bettini In Castellina in Chianti, Tuscany
Bettini In Castellina in Chianti, Tuscany
Villa
Castellina in Chianti, 53011, Italy
2.4k from Castellina in Chianti center

Barbecue, Fireplace, Free Parking, Kitchen, Laundry, Pool, TV, Washer

6 Bedrooms11 Guests
7.8

Good

6 reviews

$375
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 Castellina in Chianti.

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Castellina in Chianti Vacation Rentals with Private Pool on the Map

Frequently Asked Questions

You can explore 192 verified vacation rentals with a private pool in Castellina in Chianti. These include standalone villas and private homes where the pool is reserved exclusively for your group.

Prices for rentals with a private pool in Castellina in Chianti 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 Castellina in Chianti also welcome pets. Currently, 35 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 Castellina in Chianti often include additional features such as Pool, Private Pool, and Kitchen. These amenities enhance comfort and create a more relaxing, self-contained stay.

Some family-friendly vacation rentals in Castellina in Chianti 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.