Vacation Rentals with Private Pool in Castle of Oliveto, Castelfiorentino: Compare 10+ Sites & Save

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

  4.  Tuscany
  5.  Castelfiorentino
  6.  Castle of Oliveto

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168 Best Vacation Rentals with Private Pool in Castle of Oliveto (Starting from $70)

Casale del Vacanziere
Casale del Vacanziere
Apartment
Castle of Oliveto, Castelfiorentino, Tuscany, Italy
5.2k from Castle of Oliveto center

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

4 Bedrooms13 Guests
8.8

Fabulous

89 reviews

$70
Average price / night
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Villa Luce in Tuscany by Fantasia Villas
Villa Luce in Tuscany by Fantasia Villas
Villa
Toscana, 50052, Italy
1.3k from Castle of Oliveto center

AC, Balcony, Barbecue, Free Parking, Heater, Hot Tub, Internet, Kitchen, Laundry

9 Bedrooms18 Guests
New to Booking
$1428
Average price / night
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Casa Vacanze Calandrino
Casa Vacanze Calandrino
House
Castle of Oliveto, Castelfiorentino, Tuscany, Italy
5.6k from Castle of Oliveto center

Air Conditioner, Parking, Internet, Kitchen, Hot Tub, Balcony/Terrace, Private Pool

2 Bedrooms5 Guests
10.0

Exceptional

9 reviews

$105
Average price / night
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PANORAMIC PRIVATE VILLA GELLO with landscaped pool
PANORAMIC PRIVATE VILLA GELLO with landscaped pool
Villa
Castelfiorentino, 50051, Italy
1.7k from Castle of Oliveto center

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

2 Bedrooms4 Guests
10.0

Exceptional

1 reviews

$245
Average price / night
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Exclusive, luxurious Villa. Unique location near Certaldo
Exclusive, luxurious Villa. Unique location near Certaldo
Villa
Certaldo, 50052, Italy
1.8k from Castle of Oliveto center

AC, Barbecue, Dryer, Free Parking, Internet, Laundry, Microwave, Pool, Washer

9 Bedrooms18 Guests
New to Booking
$1389
Average price / night
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Villa Certaldo Summar
Villa Certaldo Summar
Villa
S. Martino a Maiano, Certaldo, 50052, Italy
1.8k from Castle of Oliveto center

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

9 Bedrooms18 Guests
New to Booking
$2105
Average price / night
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VILLA BELSOLE -in Chianti in Tuscany, with heated pool and car charging.
VILLA BELSOLE -in Chianti in Tuscany, with heated pool and car charging.
Villa
CERTALDO, 50052, Italy
1.8k from Castle of Oliveto center

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

9 Bedrooms18 Guests
10.0

Exceptional

40 reviews

$1266
Average price / night
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Spectacular villa Sole with view
Spectacular villa Sole with view
Villa
Certaldo, 50052, Italy
1.9k from Castle of Oliveto center

Balcony, Barbecue, Internet, Kitchen, Laundry, Microwave, No Smoking, Outdoor Space, Patio

9 Bedrooms18 Guests
New to Booking
$1630
Average price / night
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Dimora Della Nobildonna
Dimora Della Nobildonna
Villa
Castelfiorentino, 50051, Italy
1.9k from Castle of Oliveto center

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

6 Bedrooms12 Guests
New to Booking
$1846
Average price / night
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Castle of Cabbiavoli - A Unique Refuge in the Heart of Tuscany
Castle of Cabbiavoli - A Unique Refuge in the Heart of Tuscany
Apartment
Castelfiorentino, 50051, Italy
1.9k from Castle of Oliveto center

AC, Balcony, Barbecue, Fireplace, Heater, Internet, Living Area, Microwave, Pool

6 Bedrooms12 Guests
New to Booking
$1554
Average price / night
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Villa il Vigneto By MMega
Villa il Vigneto By MMega
Villa
Montespertoli, 50025, Italy
2.3k from Castle of Oliveto center

AC, Fireplace, Free Parking, Heater, Hot Tub, Housekeeping, Internet, Kitchen, Laundry

5 Bedrooms10 Guests
New to Booking
$3027
Average price / night
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Cozy home in Castelfiorentino
Cozy home in Castelfiorentino
House
Castelfiorentino, 50051, Italy
2.5k from Castle of Oliveto center

Barbecue, Crib, Fireplace, Free Parking, Heater, Internet, Kitchen, Laundry, Living Area

5 Bedrooms10 Guests
New to Booking
$471
Average price / night
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Lovely Barn with Private Poolnear San Gimignano, between Florence and Siena.
Lovely Barn with Private Poolnear San Gimignano, between Florence and Siena.
House
Castelfiorentino, 50051, Italy
2.5k from Castle of Oliveto center

Barbecue, Extra Bed, Fireplace, Free Parking, Heater, Internet, Kitchen, Laundry, Living Area

2 Bedrooms6 Guests
9.8

Exceptional

71 reviews

$190
Average price / night
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Tognazzi Holiday Home - Villa San Martino - private panoramic pool
Tognazzi Holiday Home - Villa San Martino - private panoramic pool
Villa
Certaldo, 50052, Italy
2.5k from Castle of Oliveto center

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

4 Bedrooms9 Guests
8.8

Fabulous

5 reviews

$290
Average price / night
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Apartment With Private Pool framed with stunning view
Apartment With Private Pool framed with stunning view
Apartment
Castelfiorentino (FI), 50051, Italy
2.5k from Castle of Oliveto center

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

3 Bedrooms5 Guests
New to Booking
$259
Average price / night
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Villa Tessa: A splendid two-story villa with the strong charachter which derives from it actually being a converted barn house, with Free WI-FI.
Villa Tessa: A splendid two-story villa with the strong charachter which derives from it actually being a converted barn house, with Free WI-FI.
Villa
Castelfiorentino, 50051, Italy
2.5k from Castle of Oliveto center

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

5 Bedrooms10 Guests
9.6

Exceptional

5 reviews

$634
Average price / night
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Authentic Tuscan country house, dating back to around the year 1000
Authentic Tuscan country house, dating back to around the year 1000
Villa
Castelfiorentino, 50051, Italy
2.5k from Castle of Oliveto center

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

4 Bedrooms9 Guests
9.6

Exceptional

58 reviews

$412
Average price / night
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Apartment with pool and stunning landscape
Apartment with pool and stunning landscape
Apartment
Castelfiorentino, 50051, Italy
2.6k from Castle of Oliveto center

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

3 Bedrooms5 Guests
10.0

Exceptional

18 reviews

$291
Average price / night
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Casa Farsetti - Exclusive villa with private pool between Siena and Florence
Casa Farsetti - Exclusive villa with private pool between Siena and Florence
Villa
castelfiorentino, 50051, Italy
2.6k from Castle of Oliveto center

Barbecue, Breakfast Available, Crib, Fireplace, Free Parking, Internet, Kitchen, Laundry, Living Area

4 Bedrooms9 Guests
9.2

Superb

22 reviews

$385
Average price / night
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Villa 'Antica Sosta Renai' with Private Pool, Private Terrace and Wi-Fi
Villa 'Antica Sosta Renai' with Private Pool, Private Terrace and Wi-Fi
Villa
Castelfiorentino, 50051, Italy
2.7k from Castle of Oliveto center

Balcony, Barbecue, Fireplace, Free Parking, Heater, Internet, Kitchen, Laundry, Living Area

5 Bedrooms10 Guests
New to Booking
$646
Average price / night
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\"Villa Bellavista\" with Private Pool, Private Whirlpool & Wi-Fi
\"Villa Bellavista\" with Private Pool, Private Whirlpool & Wi-Fi
Villa
Certaldo, 50052, Italy
3.0k from Castle of Oliveto center

Balcony, Barbecue, Dryer, Extra Bed, Free Parking, Hot Tub, Internet, Kitchen, Laundry

5 Bedrooms10 Guests
New to Booking
$5196
Average price / night
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San Martino, Certaldo, Florence and Chianti
San Martino, Certaldo, Florence and Chianti
Villa
Certaldo, 50052, Italy
3.2k from Castle of Oliveto center

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

4 Bedrooms6 Guests
10.0

Exceptional

2 reviews

$537
Average price / night
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Comfortable house immersed in the Florentine Chianti vineyards pets welcome
Comfortable house immersed in the Florentine Chianti vineyards pets welcome
Apartment
Toscana, 50052, Italy
3.3k from Castle of Oliveto center

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

2 Bedrooms4 Guests
New to Booking
$145
Average price / night
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Villa in Chianti with private pool, walking to a restaurant Electric car charger
Villa in Chianti with private pool, walking to a restaurant Electric car charger
Villa
Ortimino, 50025, Italy
3.5k from Castle of Oliveto center

AC, Balcony, Barbecue, Crib, Fireplace, Free Parking, Heater, Hot Tub, Internet

7 Bedrooms14 Guests
10.0

Exceptional

18 reviews

$737
Average price / night
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Holiday Home 'Sandra House Certaldo' with Private Garden and Wi-Fi
Holiday Home 'Sandra House Certaldo' with Private Garden and Wi-Fi
House
Certaldo, 50052, Italy
3.7k from Castle of Oliveto center

Extra Bed, Heater, Internet, Kitchen, Laundry, Living Area, No Smoking, Outdoor Space, Pool

1 Bedroom4 Guests
10.0

Exceptional

1 reviews

$154
Average price / night
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VILLA BELLAVISTA-TUSCANY-POOL -JACUZZI- breath-taking view-great for family
VILLA BELLAVISTA-TUSCANY-POOL -JACUZZI- breath-taking view-great for family
Villa
Toscana, 50052, Italy
3.7k from Castle of Oliveto center

AC, Balcony, Barbecue, Dryer, Extra Bed, Fireplace, Free Parking, Heater, Hot Tub

5 Bedrooms10 Guests
9.6

Exceptional

5 reviews

$1227
Average price / night
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Villa Lola In Montespertoli, Tuscany
Villa Lola In Montespertoli, Tuscany
Villa
Montespertoli, 50025, Italy
4.2k from Castle of Oliveto center

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

6 Bedrooms12 Guests
9.0

Fabulous

2 reviews

$696
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 Castle of Oliveto.

Where to stay in Castle of Oliveto? Best neighborhoods & areas

Castle of Oliveto Vacation Rentals with Private Pool on the Map

Frequently Asked Questions

You can explore 168 verified vacation rentals with a private pool in Castle of Oliveto. These include standalone villas and private homes where the pool is reserved exclusively for your group.

Prices for rentals with a private pool in Castle of Oliveto vary depending on the property size, location, and travel season. Rates typically start from around $70 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 Castle of Oliveto also welcome pets. Currently, 31 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 Castle of Oliveto often include additional features such as Pool, Kitchen, and Private Pool. These amenities enhance comfort and create a more relaxing, self-contained stay.

Some family-friendly vacation rentals in Castle of Oliveto 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.