Villa Rentals in Isole e Olena Winery, Barberino Tavarnelle: Compare 10+ Sites & Save

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  3.  Italy
  4.  Tuscany
  5.  Barberino Tavarnelle
  6.  Isole e Olena Winery

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409 Best Villa Rentals in Isole e Olena Winery (Starting from $284)

Pieve di Campoli by VacaVilla
Pieve di Campoli by VacaVilla
Villa
San Donato in Poggio, Italy
2.0k from Isole e Olena Winery center

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

3 Bedrooms6 Guests
7.0

Good

1 reviews

$361
Average price / night
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Beautiful historic Villa on organic olive farm, with pool & sunset views
Beautiful historic Villa on organic olive farm, with pool & sunset views
Villa
Siena, 53011, Italy
0.8k from Isole e Olena Winery center

Arcade, Balcony, Barbecue, Dryer, Fireplace, Free Parking, Heater, Internet, Kitchen

7 Bedrooms14 Guests
9.0

Fabulous

4 reviews

$664
Average price / night
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Casa Fioraie by PosarelliVillas
Casa Fioraie by PosarelliVillas
Villa
Isole e Olena Winery, Barberino Tavarnelle, Tuscany, Italy
2.2k from Isole e Olena Winery center

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

2 Bedrooms6 Guests
10.0

Exceptional

1 reviews

$445
Average price / night
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Beautiful historic 7-bedroom Villa on organic olive farm, pool & sunset views
Beautiful historic 7-bedroom Villa on organic olive farm, pool & sunset views
Villa
Castellina in Chianti, 50021, Italy
0.8k from Isole e Olena Winery center

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

7 Bedrooms14 Guests
9.4

Superb

20 reviews

$609
Average price / night
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COUNTRY HOUSE LO SPIGO 4, Emma Villas
COUNTRY HOUSE LO SPIGO 4, Emma Villas
Villa
San Donato in Poggio, Italy
2.5k from Isole e Olena Winery center

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

2 Bedrooms4 Guests
New to Booking
$800
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
1.5k from Isole e Olena Winery 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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Podere Beccalorzo con piscina
Podere Beccalorzo con piscina
Villa
San Donato in Poggio, Italy
2.7k from Isole e Olena Winery center

Cheap, Accommodations, Parking, Villas, Vacation homes, Cottages, Lodgings, Places to stay

6 Bedrooms13 Guests
9.8

Exceptional

6 reviews

$683
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
1.6k from Isole e Olena Winery 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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Villa Sonia by PosarelliVillas
Villa Sonia by PosarelliVillas
Villa
San Donato in Poggio, Italy
2.9k from Isole e Olena Winery center

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

5 Bedrooms12 Guests
New to Booking
$916
Average price / night
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Private Villa with WIFI, private pool, A/C, TV, patio, panoramic view, close to Greve In Chianti
Private Villa with WIFI, private pool, A/C, TV, patio, panoramic view, close to Greve In Chianti
Villa
Castellina In Chianti, 53011, Italy
1.8k from Isole e Olena Winery center

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

2 Bedrooms6 Guests
New to Booking
$501
Average price / night
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Villa 9P, 3BdR Chianti, near Florence and Siena
Villa 9P, 3BdR Chianti, near Florence and Siena
Villa
Barberino di Val dʼElsa, Italy
3.3k from Isole e Olena Winery center

Accommodations, Parking, Villas, Vacation homes, Cottages, Pet-friendly, Lodgings, Places to stay

3 Bedrooms9 Guests
New to Booking
$302
Average price / night
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Casa Fioraie - House with private pool
Casa Fioraie - House with private pool
Villa
Castellina In Chianti, 53011, Italy
2.2k from Isole e Olena Winery center

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

2 Bedrooms6 Guests
9.8

Exceptional

7 reviews

$522
Average price / night
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Ginestra
Ginestra
Villa
Castellina in Chianti, Italy
3.4k from Isole e Olena Winery center

Security/Safety, Pet Friendly, Guest Services, Parking, Internet, Child Friendly

1 Bedroom2 Guests
New to Booking
$284
Average price / night
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Fioraie villa with pool and breathtaking views for 6 people
Fioraie villa with pool and breathtaking views for 6 people
Villa
Castellina in Chianti, 53011, Italy
2.2k from Isole e Olena Winery center

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

2 Bedrooms6 Guests
8.0

Good

4 reviews

$370
Average price / night
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Casale Cipressi
Casale Cipressi
Villa
Castellina in Chianti, Italy
3.7k from Isole e Olena Winery center

Wellness Facilities, Parking, Internet, Pet Friendly, Child Friendly

5 Bedrooms9 Guests
New to Booking
$543
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
2.3k from Isole e Olena Winery 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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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
2.3k from Isole e Olena Winery 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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TENUTA DI MACERICCA 10, Emma Villas
TENUTA DI MACERICCA 10, Emma Villas
Villa
Poggibonsi, Italy
4.3k from Isole e Olena Winery center

Accommodations, Pools, Parking, Villas, Vacation homes, Cottages, Pet-friendly, Lodgings, Vacation rentals

5 Bedrooms10 Guests
9.0

Fabulous

3 reviews

$1015
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
2.6k from Isole e Olena Winery 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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Luxury Villa Basilio Chianti
Luxury Villa Basilio Chianti
Villa
Castellina in Chianti, Italy
4.7k from Isole e Olena Winery center

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

7 Bedrooms14 Guests
New to Booking
$1333
Average price / night
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Casale Sandonatino by VacaVilla
Casale Sandonatino by VacaVilla
Villa
Castellina in Chianti, Italy
4.8k from Isole e Olena Winery center

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

6 Bedrooms12 Guests
New to Booking
$616
Average price / night
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Villa Belchianti by MMega
Villa Belchianti by MMega
Villa
Madonna di Pietracupa, 50028, Italy
2.7k from Isole e Olena Winery 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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Villa Raggiola - Six Bedroom Villa, Sleeps 12
Villa Raggiola - Six Bedroom Villa, Sleeps 12
Villa
Barberino Tavarnelle, 50028, Italy
2.7k from Isole e Olena Winery 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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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
2.9k from Isole e Olena Winery 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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Stunning private villa with private pool, WIFI, A/C, patio, panoramic view, close to San Gimignano
Stunning private villa with private pool, WIFI, A/C, patio, panoramic view, close to San Gimignano
Villa
Monsanto Ii, 50021, Italy
3.0k from Isole e Olena Winery center

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

5 Bedrooms11 Guests
New to Booking
$1124
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
3.1k from Isole e Olena Winery 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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Private villa for families or friends
Private villa for families or friends
Villa
Monsanto II, 50021, Italy
3.2k from Isole e Olena Winery center

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

5 Bedrooms10 Guests
10.0

Exceptional

2 reviews

$921
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 Villa Rentals in Isole e Olena Winery.

Where to stay in Isole e Olena Winery? Best neighborhoods & areas

Isole e Olena Winery Villa Rentals on the Map

Frequently Asked Questions

You can currently explore 409 verified villa rentals in Isole e Olena Winery. Our listings are sourced from multiple leading booking platforms, giving you a broad and up-to-date selection of luxury and private villas in one place.

Villa prices in Isole e Olena Winery vary depending on the season, location, and amenities. Rates typically start from around $284 per night, with premium properties costing more during peak travel periods. Comparing options across different platforms can help you find the best value for your dates.

Many villas in Isole e Olena Winery are designed for privacy and comfort, and a large number of them feature private pools. You can easily filter your search to find villas with pools, helping you choose the perfect stay for relaxation or group travel in Isole e Olena Winery.

Yes, Isole e Olena Winery offers a wide range of villas ideal for group stays. Many properties include 9 or more bedrooms, making them well-suited for family gatherings, events, or trips with friends. You can filter by bedroom count to quickly find options that match your group size.

For popular travel periods, it’s generally recommended to book your Isole e Olena Winery villa around 60 to 90 days in advance to secure the best selection. However, since we compare 10+ sites, it’s still possible to find great last-minute options even 2 to 4 weeks before your trip.

Villas in Isole e Olena Winery often include highly sought-after amenities such as Internet, Balcony/Terrace, and Pool. These features enhance comfort and convenience, making them especially popular among travelers visiting Isole e Olena Winery.

To discover top-rated villas in Isole e Olena Winery, you can sort listings by guest ratings and reviews. Our platform aggregates feedback from multiple trusted sources, helping you identify highly rated properties based on real guest experiences. Use the "Rating" filter above to start your search.