Vacation Rentals with Private Pool in Castello di Radda Winery, Radda in Chianti: Compare 10+ Sites & Save

AirbnbBooking.comVrboExpediaKayakTripadvisorHotels.comAgoda.com
  1. VBOR
  2. Vacation Rentals with Private Pool
  3.  Italy

  4.  Tuscany
  5.  Radda in Chianti
  6.  Castello di Radda Winery

Refine your search

Price per night

Amenity Filter

Rating

309 Best Vacation Rentals with Private Pool in Castello di Radda Winery (Starting from $193)

Villa Terra di Siena - Homelike Villas
Villa Terra di Siena - Homelike Villas
Villa
Greve in Chianti, Italy
7.7k from Castello di Radda Winery center

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

18 Bedrooms36 Guests
New to Booking
$8235
Average price / night
Check Availability
Villa Piandolce - Radda In Chianti
Villa Piandolce - Radda In Chianti
Villa
SI, 53017, Italy
0.4k from Castello di Radda Winery center

AC, Barbecue, Breakfast Included, Dryer, Elevator, Fireplace, Heater, Internet, Kitchen

6 Bedrooms12 Guests
New to Booking
$5195
Average price / night
Check Availability
Amore Rentals - Ville Il Paradiso
Amore Rentals - Ville Il Paradiso
House
Panzano, Italy
7.7k from Castello di Radda Winery center

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

18 Bedrooms37 Guests
New to Booking
$4098
Average price / night
Check Availability
Amore Rentals - Villa Bellaflore
Amore Rentals - Villa Bellaflore
Villa
Panzano, Italy
7.8k from Castello di Radda Winery center

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

7 Bedrooms14 Guests
New to Booking
$2400
Average price / night
Check Availability
Villa Poggio la Croce by MMega
Villa Poggio la Croce by MMega
Villa
Radda in Chianti, 53017, Italy
0.8k from Castello di Radda Winery center

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

6 Bedrooms12 Guests
8.0

Good

1 reviews

$951
Average price / night
Check Availability
AMORE RENTALS - Villa Bacci
AMORE RENTALS - Villa Bacci
Villa
Panzano, Italy
7.8k from Castello di Radda Winery center

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

4 Bedrooms9 Guests
New to Booking
$1373
Average price / night
Check Availability
Casa Ceperano, Radda in Chianti, Siena and Chianti
Casa Ceperano, Radda in Chianti, Siena and Chianti
Villa
Radda in Chianti, 53017, Italy
0.9k from Castello di Radda Winery center

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

7 Bedrooms12 Guests
New to Booking
$627
Average price / night
Check Availability
Il Corno, Radda in Chianti, Siena and Chianti
Il Corno, Radda in Chianti, Siena and Chianti
Villa
Radda in Chianti, 53017, Italy
0.9k from Castello di Radda Winery center

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

5 Bedrooms8 Guests
10.0

Exceptional

2 reviews

$673
Average price / night
Check Availability
Fico del Corno, Radda in Chianti, Siena and Chianti
Fico del Corno, Radda in Chianti, Siena and Chianti
Villa
Radda in Chianti, 53017, Italy
0.9k from Castello di Radda Winery center

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

2 Bedrooms2 Guests
New to Booking
$284
Average price / night
Check Availability
Fienile al Corno, Radda in Chianti, Siena and Chianti
Fienile al Corno, Radda in Chianti, Siena and Chianti
Villa
Radda in Chianti, 53017, Italy
0.9k from Castello di Radda Winery center

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

3 Bedrooms4 Guests
10.0

Exceptional

1 reviews

$357
Average price / night
Check Availability
Le Bonatte by Interhome
Le Bonatte by Interhome
House
Radda in Chianti, 53017, Italy
1.0k from Castello di Radda Winery center

Balcony, Barbecue, Fireplace, Free Parking, Heater, Internet, Kitchen, Laundry, Microwave

7 Bedrooms14 Guests
New to Booking
$429
Average price / night
Check Availability
Timeless stillness, steps from the piazza
Timeless stillness, steps from the piazza
Villa
Radda in Chianti, 53017, Italy
1.2k from Castello di Radda Winery center

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

5 Bedrooms10 Guests
New to Booking
$2695
Average price / night
Check Availability
Wonderful private villa for 14 guests with WIFI, private pool, TV, terrace and pets allowed
Wonderful private villa for 14 guests with WIFI, private pool, TV, terrace and pets allowed
Villa
Radda In Chianti, 53017, Italy
1.2k from Castello di Radda Winery center

Balcony, Barbecue, Crib, Fireplace, Free Parking, Heater, Internet, Kitchen, Laundry

7 Bedrooms14 Guests
New to Booking
$498
Average price / night
Check Availability
A paradise of cypress and olive trees
A paradise of cypress and olive trees
House
Radda in Chianti, 53107, Italy
1.2k from Castello di Radda Winery center

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

2 Bedrooms4 Guests
10.0

Exceptional

39 reviews

$270
Average price / night
Check Availability
Villa Eterna, Tuscan Haven in the Heart of Chianti
Villa Eterna, Tuscan Haven in the Heart of Chianti
Villa
Radda in Chianti, 53017, Italy
1.3k from Castello di Radda Winery center

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

5 Bedrooms10 Guests
New to Booking
$2940
Average price / night
Check Availability
Villa in Radda In Chianti with 6 bedrooms sleeps 12
Villa in Radda In Chianti with 6 bedrooms sleeps 12
Villa
Radda In Chianti, 53017, Italy
1.4k from Castello di Radda Winery center

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

6 Bedrooms12 Guests
New to Booking
$3955
Average price / night
Check Availability
Campo Agli Olivi, Radda in Chianti, Siena and Chianti
Campo Agli Olivi, Radda in Chianti, Siena and Chianti
Villa
Radda in Chianti, 53017, Italy
1.4k from Castello di Radda Winery center

Heater, Kitchen, Living Area, Microwave, No Smoking, Outdoor Space, Pool, Tennis Court, TV

4 Bedrooms4 Guests
New to Booking
$314
Average price / night
Check Availability
La Casa di Radda, Radda in Chianti, Siena and Chianti
La Casa di Radda, Radda in Chianti, Siena and Chianti
Villa
Radda in Chianti, 53017, Italy
1.4k from Castello di Radda Winery center

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

3 Bedrooms5 Guests
10.0

Exceptional

1 reviews

$419
Average price / night
Check Availability
La Casanova, Radda in Chianti, Siena and Chianti
La Casanova, Radda in Chianti, Siena and Chianti
Villa
Radda in Chianti, 53017, Italy
1.5k from Castello di Radda Winery center

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

2 Bedrooms2 Guests
10.0

Exceptional

3 reviews

$193
Average price / night
Check Availability
Beautiful private villa with WIFI, private pool, A/C, TV, patio, pets allowed and panoramic view
Beautiful private villa with WIFI, private pool, A/C, TV, patio, pets allowed and panoramic view
House
Villa, 53017, Italy
1.5k from Castello di Radda Winery center

AC, Barbecue, Crib, Extra Bed, Fireplace, Free Parking, Heater, Internet, Kitchen

3 Bedrooms8 Guests
New to Booking
$320
Average price / night
Check Availability
Cielo di Radda, Radda in Chianti, Siena and Chianti
Cielo di Radda, Radda in Chianti, Siena and Chianti
Villa
Radda in Chianti, 53017, Italy
1.5k from Castello di Radda Winery center

AC, Barbecue, Dryer, Fireplace, Kitchen, Laundry, Living Area, Microwave, No Smoking

3 Bedrooms6 Guests
10.0

Exceptional

1 reviews

$452
Average price / night
Check Availability
Il Torrino In Radda in Chianti, Tuscany
Il Torrino In Radda in Chianti, Tuscany
Villa
Radda in Chianti, 53017, Italy
1.6k from Castello di Radda Winery center

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

6 Bedrooms12 Guests
10.0

Exceptional

1 reviews

$927
Average price / night
Check Availability
Il Casetto, Radda in Chianti, Siena and Chianti
Il Casetto, Radda in Chianti, Siena and Chianti
Villa
Radda in Chianti, 53017, Italy
1.6k from Castello di Radda Winery center

AC, Barbecue, Fireplace, Free Parking, Kitchen, Laundry, Living Area, Microwave, No Smoking

4 Bedrooms8 Guests
New to Booking
$803
Average price / night
Check Availability
Villa Al Bosco: An elegant and welcoming three-story villa situated in a secluded location surrounded by meadows and by green hills, with Free WI-FI.
Villa Al Bosco: An elegant and welcoming three-story villa situated in a secluded location surrounded by meadows and by green hills, with Free WI-FI.
Villa
Radda in Chianti, 53017, Italy
1.6k from Castello di Radda Winery center

Balcony, Fireplace, Free Parking, Heater, Internet, Kitchen, Laundry, Microwave, Outdoor Space

6 Bedrooms12 Guests
New to Booking
$1152
Average price / night
Check Availability
Villa del Poggio by Interhome
Villa del Poggio by Interhome
House
Radda in Chianti, 53017, Italy
1.8k from Castello di Radda Winery center

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

3 Bedrooms8 Guests
10.0

Exceptional

14 reviews

$276
Average price / night
Check Availability
L'Angolino In Radda in Chianti, Tuscany
L'Angolino In Radda in Chianti, Tuscany
Villa
Radda in Chianti, 53017, Italy
1.8k from Castello di Radda Winery center

AC, Fireplace, Heater, Internet, Kitchen, Living Area, Microwave, No Smoking, Outdoor Space

3 Bedrooms6 Guests
9.6

Exceptional

11 reviews

$317
Average price / night
Check Availability
Poggio della Villa, Radda in Chianti, Siena and Chianti
Poggio della Villa, Radda in Chianti, Siena and Chianti
Villa
Radda in Chianti, 53017, Italy
1.8k from Castello di Radda Winery center

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

3 Bedrooms6 Guests
New to Booking
$405
Average price / night
Check Availability

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 Castello di Radda Winery.

Where to stay in Castello di Radda Winery? Best neighborhoods & areas

Castello di Radda Winery Vacation Rentals with Private Pool on the Map

Frequently Asked Questions

You can explore 309 verified vacation rentals with a private pool in Castello di Radda Winery. These include standalone villas and private homes where the pool is reserved exclusively for your group.

Prices for rentals with a private pool in Castello di Radda Winery vary depending on the property size, location, and travel season. Rates typically start from around $193 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 Castello di Radda Winery also welcome pets. Currently, 19 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 Castello di Radda Winery 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 Castello di Radda Winery 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.