Vacation Rentals with Private Pool in Chianti Observatory, Barberino Tavarnelle: Compare 10+ Sites & Save

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

  4.  Tuscany
  5.  Barberino Tavarnelle
  6.  Chianti Observatory

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322 Best Vacation Rentals with Private Pool in Chianti Observatory (Starting from $149)

Villa Terra di Siena - Homelike Villas
Villa Terra di Siena - Homelike Villas
Villa
Greve in Chianti, Italy
6.0k from Chianti Observatory 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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Villa Belchianti by MMega
Villa Belchianti by MMega
Villa
Madonna di Pietracupa, 50028, Italy
0.8k from Chianti Observatory center

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

6 Bedrooms12 Guests
New to Booking
$944
Average price / night
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Amore Rentals - Villa Bellaflore
Amore Rentals - Villa Bellaflore
Villa
Panzano, Italy
6.1k from Chianti Observatory 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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Villa Raggiola - Six Bedroom Villa, Sleeps 12
Villa Raggiola - Six Bedroom Villa, Sleeps 12
Villa
Barberino Tavarnelle, 50028, Italy
0.8k from Chianti Observatory center

AC, Barbecue, Fireplace, Free Parking, Heater, Kitchen, No Smoking, Outdoor Space, Pool

6 Bedrooms12 Guests
New to Booking
$1112
Average price / night
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AMORE RENTALS - Villa Bacci
AMORE RENTALS - Villa Bacci
Villa
Panzano, Italy
6.1k from Chianti Observatory 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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Villa Sonia - Luxury Villa Rental in Madonna di Pietracupa, Chianti
Villa Sonia - Luxury Villa Rental in Madonna di Pietracupa, Chianti
Villa
Madonna Di Pietracupa, 50028, Italy
0.8k from Chianti Observatory center

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

6 Bedrooms12 Guests
10.0

Exceptional

39 reviews

$1285
Average price / night
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Amore Rentals - Ville Il Paradiso
Amore Rentals - Ville Il Paradiso
House
Panzano, Italy
6.1k from Chianti Observatory 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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Country House Lo Spigo 4, Emma Villas
Country House Lo Spigo 4, Emma Villas
Villa
San Donato, 50028, Italy
0.8k from Chianti Observatory center

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

2 Bedrooms4 Guests
10.0

Exceptional

1 reviews

$885
Average price / night
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Private Villa with WIFI, A/C, private pool, TV, patio, panoramic view, close to Greve In Chianti
Private Villa with WIFI, A/C, private pool, TV, patio, panoramic view, close to Greve In Chianti
Villa
Madonna Di Pietracupa, 50028, Italy
0.9k from Chianti Observatory center

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

6 Bedrooms12 Guests
10.0

Exceptional

12 reviews

$974
Average price / night
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\"Casolare Belchianti\"
\"Casolare Belchianti\"
House
San Donato, 50028, Italy
0.9k from Chianti Observatory center

AC, Barbecue, Crib, Dryer, Fitness Equipment, Free Parking, Heater, Internet, Kitchen

6 Bedrooms12 Guests
10.0

Exceptional

2 reviews

$926
Average price / night
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Le Volpaie, Barberino Val d'Elsa, Florence and Chianti
Le Volpaie, Barberino Val d'Elsa, Florence and Chianti
Villa
Barberino Val d'Elsa, 50021, Italy
1.1k from Chianti Observatory center

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

5 Bedrooms7 Guests
New to Booking
$579
Average price / night
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5 bedrooms villa in the Chianti region with private swimming poo, A/C and Wi-Fi
5 bedrooms villa in the Chianti region with private swimming poo, A/C and Wi-Fi
Villa
Barberino Val D'elsa, 50021, Italy
1.1k from Chianti Observatory center

AC, Balcony, Barbecue, Breakfast Available, Crib, Dryer, Fireplace, Free Parking, Heater

5 Bedrooms12 Guests
9.8

Exceptional

6 reviews

$1647
Average price / night
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Vintage 70s Home - your place in Tuscany. Holiday Home, Events & Retreats.
Vintage 70s Home - your place in Tuscany. Holiday Home, Events & Retreats.
Villa
Barberino Tavarnelle, 50028, Italy
2.3k from Chianti Observatory center

Arcade, Balcony, Barbecue, Crib, Dryer, Fireplace, Free Parking, Heater, Housekeeping

4 Bedrooms10 Guests
10.0

Exceptional

4 reviews

$553
Average price / night
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Villa la Corte by MMega
Villa la Corte by MMega
Villa
Chianti, 50022, Italy
2.4k from Chianti Observatory center

AC, Balcony, Crib, Dryer, Fireplace, Heater, Housekeeping, Internet, Kitchen

6 Bedrooms12 Guests
10.0

Exceptional

4 reviews

$2430
Average price / night
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Villa 'Podere Beccalorzo with Private Pool, Wi-Fi and Air Conditioning'
Villa 'Podere Beccalorzo with Private Pool, Wi-Fi and Air Conditioning'
Villa
Barberino Tavarnelle, 50021, Italy
2.7k from Chianti Observatory center

AC, Barbecue, Fireplace, Free Parking, Heater, Internet, Kitchen, Laundry, No Smoking

6 Bedrooms12 Guests
10.0

Exceptional

2 reviews

$618
Average price / night
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Roccia 2BR apart PRM OK in restored Farm w Pool and Spa, ground floor terrace
Roccia 2BR apart PRM OK in restored Farm w Pool and Spa, ground floor terrace
Apartment
Castellina in Chianti, 53011, Italy
2.7k from Chianti Observatory center

Barbecue, Crib, Dryer, Fireplace, Free Parking, Heater, Hot Tub, Internet, Kitchen

2 Bedrooms7 Guests
10.0

Exceptional

35 reviews

$276
Average price / night
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Podere La Valle 9BR, 16-20 Guests Retreats & Family In Restored Farm  Spa & Pool
Podere La Valle 9BR, 16-20 Guests Retreats & Family In Restored Farm Spa & Pool
Villa
Castellina in Chianti, 53011, Italy
2.7k from Chianti Observatory center

Barbecue, Breakfast Available, Dryer, Fireplace, Free Parking, Heater, Hot Tub, Internet, Kitchen

9 Bedrooms27 Guests
10.0

Exceptional

38 reviews

$1483
Average price / night
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Forno 1BR Apartment In a Restored Farm, Pool & Spa, 1st floor, 140/190cm sofabed
Forno 1BR Apartment In a Restored Farm, Pool & Spa, 1st floor, 140/190cm sofabed
Apartment
Castellina in Chianti, 53011, Italy
2.7k from Chianti Observatory center

Barbecue, Dryer, Fireplace, Free Parking, Heater, Hot Tub, Internet, Kitchen, Laundry

1 Bedroom4 Guests
10.0

Exceptional

48 reviews

$149
Average price / night
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Belvedere 2+1 BR Luxe Apart In a Restored Tuscan Farm with Pool and Spa
Belvedere 2+1 BR Luxe Apart In a Restored Tuscan Farm with Pool and Spa
Apartment
Castellina in Chianti, 53011, Italy
2.7k from Chianti Observatory center

Barbecue, Dryer, Fireplace, Free Parking, Heater, Hot Tub, Internet, Kitchen, Laundry

3 Bedrooms8 Guests
10.0

Exceptional

68 reviews

$287
Average price / night
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Spacious Villa with Pool in the heart of Chianti, ideal for exploring Tuscany
Spacious Villa with Pool in the heart of Chianti, ideal for exploring Tuscany
Villa
San Donato in Poggio, 50028, Italy
2.7k from Chianti Observatory center

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

3 Bedrooms7 Guests
9.4

Superb

53 reviews

$335
Average price / night
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Lovely home in San Donato in P. FI
Lovely home in San Donato in P. FI
House
San Donato in P. FI, 50028, Italy
2.7k from Chianti Observatory center

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

4 Bedrooms9 Guests
10.0

Exceptional

3 reviews

$411
Average price / night
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Holiday Home 'Casa Colombaia, Dimora Nel Chianti' with Private Pool, Wi-Fi and Air Conditioning
Holiday Home 'Casa Colombaia, Dimora Nel Chianti' with Private Pool, Wi-Fi and Air Conditioning
House
Barberino Tavarnelle, 50028, Italy
2.8k from Chianti Observatory center

AC, Barbecue, Fireplace, Free Parking, Heater, Internet, Kitchen, Microwave, No Smoking

4 Bedrooms8 Guests
New to Booking
$691
Average price / night
Check Availability
Single-level Villa, panoramic position, AC, 6x16m private Pool, Whirlpool & Spa
Single-level Villa, panoramic position, AC, 6x16m private Pool, Whirlpool & Spa
Villa
Castellina in Chianti, 53011, Italy
2.8k from Chianti Observatory center

AC, Barbecue, Dryer, Fireplace, Free Parking, Heater, Hot Tub, Internet, Kitchen

4 Bedrooms10 Guests
10.0

Exceptional

155 reviews

$673
Average price / night
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La Torre Beautiful 1BR Love Nest In a Restored Farm. Pool, spa private terrace
La Torre Beautiful 1BR Love Nest In a Restored Farm. Pool, spa private terrace
House
Castellina in Chianti, 53011, Italy
2.8k from Chianti Observatory center

Barbecue, Dryer, Fireplace, Free Parking, Heater, Hot Tub, Internet, Kitchen, Laundry

1 Bedroom4 Guests
10.0

Exceptional

49 reviews

$207
Average price / night
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Beautiful villa for large groups, family reunions, and weddings and workshops
Beautiful villa for large groups, family reunions, and weddings and workshops
House
Castellina in Chianti, 50021, Italy
2.8k from Chianti Observatory center

Arcade, Babysitting, Barbecue, Breakfast Available, Crib, Dryer, Fireplace, Free Parking, Heater

15 Bedrooms33 Guests
New to Booking
$1830
Average price / night
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Arco : 2BR apart in a restored Farm w Pool and Spa, ground floor terrace
Arco : 2BR apart in a restored Farm w Pool and Spa, ground floor terrace
Apartment
Castellina in Chianti, 53011, Italy
3.1k from Chianti Observatory center

Barbecue, Crib, Dryer, Free Parking, Heater, Hot Tub, Internet, Kitchen, Laundry

2 Bedrooms6 Guests
10.0

Exceptional

35 reviews

$184
Average price / night
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Villa Noce by My Villa Collection
Villa Noce by My Villa Collection
Villa
Barberino Tavarnelle, 50028, Italy
3.2k from Chianti Observatory center

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

9 Bedrooms24 Guests
New to Booking
$2561
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 Chianti Observatory.

Where to stay in Chianti Observatory? Best neighborhoods & areas

Chianti Observatory Vacation Rentals with Private Pool on the Map

Frequently Asked Questions

You can explore 322 verified vacation rentals with a private pool in Chianti Observatory. These include standalone villas and private homes where the pool is reserved exclusively for your group.

Prices for rentals with a private pool in Chianti Observatory vary depending on the property size, location, and travel season. Rates typically start from around $149 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 Chianti Observatory also welcome pets. Currently, 9 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 Chianti Observatory 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 Chianti Observatory 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.