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

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  2. Vacation Rentals with Private Pool
  3.  Italy

  4.  Tuscany
  5.  Montespertoli

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141 Best Vacation Rentals with Private Pool in Montespertoli (Starting from $70)

Casale del Vacanziere
Casale del Vacanziere
Apartment
Montespertoli, Tuscany, Italy
9.4k from Montespertoli 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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Locanda del podestà: 17th century mansion in Chianti
Locanda del podestà: 17th century mansion in Chianti
Villa
Montespertoli, 50025, Italy
0.9k from Montespertoli center

Balcony, Barbecue, Free Parking, Heater, Internet, Kitchen, Laundry, Living Area, Outdoor Space

5 Bedrooms12 Guests
9.8

Exceptional

60 reviews

$262
Average price / night
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Villa Ginestruzze – Villa with Private Pool and Exclusive Suites in Tuscany
Villa Ginestruzze – Villa with Private Pool and Exclusive Suites in Tuscany
Villa
Montespertoli, 50025, Italy
1.6k from Montespertoli center

AC, Barbecue, Free Parking, Heater, Internet, Kitchen, Microwave, No Smoking, Outdoor Space

5 Bedrooms10 Guests
New to Booking
$548
Average price / night
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Villa Paola Private Pool Gym in Chianti, Montespertoli, Italy
Villa Paola Private Pool Gym in Chianti, Montespertoli, Italy
House
Montespertoli, 50025, Italy
2.5k from Montespertoli center

AC, Barbecue, Fireplace, Fitness Equipment, Free Parking, Heater, Internet, Kitchen, Laundry

5 Bedrooms11 Guests
10.0

Exceptional

1 reviews

$581
Average price / night
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ANCIENT AIR-CND PRIVATE VILLA POOL & JACUZZI ON  FLORENCE HILLS FAMILY FRIENDLY
ANCIENT AIR-CND PRIVATE VILLA POOL & JACUZZI ON FLORENCE HILLS FAMILY FRIENDLY
Villa
Montespertoli, 50025, Italy
2.5k from Montespertoli center

Barbecue, Fireplace, Fitness Equipment, Free Parking, Heater, Hot Tub, Internet, Kitchen, Laundry

5 Bedrooms12 Guests
9.6

Exceptional

13 reviews

$500
Average price / night
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Tuscan Apart for 4/5 persons, WIFI, AIR-CO, SW-POOL, all comforts in the country
Tuscan Apart for 4/5 persons, WIFI, AIR-CO, SW-POOL, all comforts in the country
Apartment
Montespertoli, 50025, Italy
2.7k from Montespertoli center

AC, Breakfast Available, Crib, Extra Bed, Fireplace, Free Parking, Heater, Internet, Kitchen

2 Bedrooms5 Guests
10.0

Exceptional

22 reviews

$452
Average price / night
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Villa Lola In Montespertoli, Tuscany
Villa Lola In Montespertoli, Tuscany
Villa
Montespertoli, 50025, Italy
2.8k from Montespertoli 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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Villa La Torre 16, Montespertoli, Florence and Chianti
Villa La Torre 16, Montespertoli, Florence and Chianti
Villa
Montespertoli, 50025, Italy
2.8k from Montespertoli center

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

8 Bedrooms16 Guests
New to Booking
$980
Average price / night
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Amazing Rustic One Bedroom Apartment
Amazing Rustic One Bedroom Apartment
Apartment
Toscana, 50025, Italy
2.8k from Montespertoli center

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

1 Bedroom4 Guests
New to Booking
$236
Average price / night
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Holidays in the heart of Toscany
Holidays in the heart of Toscany
Villa
Montespertoli, 50025, Italy
3.1k from Montespertoli center

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

3 Bedrooms6 Guests
10.0

Exceptional

3 reviews

$289
Average price / night
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Casa Rosita - Surrounded by nature
Casa Rosita - Surrounded by nature
House
Montespertoli, 50025, Italy
3.1k from Montespertoli center

Barbecue, Fireplace, Heater, Internet, Kitchen, Laundry, Microwave, No Smoking, Outdoor Space

3 Bedrooms6 Guests
8.0

Good

1 reviews

$369
Average price / night
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Villa between Florence  Siena and Pisa. 1 km to village.  A/C in all rooms-Wi Fi
Villa between Florence Siena and Pisa. 1 km to village. A/C in all rooms-Wi Fi
Villa
Montespertoli, 50025, Italy
3.3k from Montespertoli center

AC, Barbecue, Breakfast Available, Crib, Free Parking, Heater, Internet, Kitchen, Laundry

10 Bedrooms21 Guests
9.4

Superb

66 reviews

$829
Average price / night
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Bright villa between Florence (20 km), Siena (50) -1 km from the village Air conditioning
Bright villa between Florence (20 km), Siena (50) -1 km from the village Air conditioning
Villa
Montespertoli, 50025, Italy
3.3k from Montespertoli center

AC, Barbecue, Breakfast Available, Free Parking, Heater, Internet, Kitchen, Laundry, Living Area

10 Bedrooms21 Guests
10.0

Exceptional

1 reviews

$829
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
4.0k from Montespertoli 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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Luxury villa Bargino
Luxury villa Bargino
Villa
Montespertoli/ firenze, 50025, Italy
4.3k from Montespertoli center

AC, Balcony, Breakfast Available, Dryer, Fireplace, Fitness Equipment, Free Parking, Heater, Internet

5 Bedrooms10 Guests
10.0

Exceptional

3 reviews

$1468
Average price / night
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Beautiful  villa with private pool, A/C, WIFI, TV, patio and panoramic view, close to San Gimign...
Beautiful villa with private pool, A/C, WIFI, TV, patio and panoramic view, close to San Gimign...
Villa
Trecento, 50025, Italy
4.6k from Montespertoli center

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

5 Bedrooms14 Guests
New to Booking
$1667
Average price / night
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Charming ancient farm house in Chianti
Charming ancient farm house in Chianti
House
San Giusto a Montalbino, 50025, Italy
4.6k from Montespertoli center

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

4 Bedrooms8 Guests
9.8

Exceptional

47 reviews

$464
Average price / night
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Villa il Vigneto By MMega
Villa il Vigneto By MMega
Villa
Montespertoli, 50025, Italy
4.8k from Montespertoli 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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Villa Rinaldi
Villa Rinaldi
House
Montespertoli, 50025, Italy
4.9k from Montespertoli center

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

4 Bedrooms8 Guests
9.6

Exceptional

4 reviews

$1413
Average price / night
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San Carlo - Holiday Villa Rental with private swimming pool in Chianti, Tuscany
San Carlo - Holiday Villa Rental with private swimming pool in Chianti, Tuscany
Villa
Montagnana, 50025, Italy
4.9k from Montespertoli center

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

5 Bedrooms10 Guests
9.8

Exceptional

41 reviews

$552
Average price / night
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Historical private villa in Chianti for up to 10guests one step from Florence
Historical private villa in Chianti for up to 10guests one step from Florence
Villa
Montespertoli, 50025, Italy
5.0k from Montespertoli center

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

New to Booking
$1145
Average price / night
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Gorgeous home in Montespertoli FI
Gorgeous home in Montespertoli FI
House
Montespertoli FI, 50025, Italy
5.2k from Montespertoli center

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

1 Bedroom6 Guests
10.0

Exceptional

1 reviews

$127
Average price / night
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Lovely home in Montespertoli FI
Lovely home in Montespertoli FI
House
Montespertoli FI, 50025, Italy
5.3k from Montespertoli center

Barbecue, Crib, Free Parking, Heater, Kitchen, Laundry, Living Area, No Smoking, Outdoor Space

3 Bedrooms6 Guests
10.0

Exceptional

1 reviews

$381
Average price / night
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House with garden CASAVACANZE B&T CHIANTI VACANZE
House with garden CASAVACANZE B&T CHIANTI VACANZE
House
Montespertoli, 50025, Italy
5.7k from Montespertoli center

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

2 Bedrooms7 Guests
9.6

Exceptional

23 reviews

$110
Average price / night
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Houses in Val di Pesa
Houses in Val di Pesa
House
San Vincenzo a Torri, 50025, Italy
5.8k from Montespertoli center

Barbecue, Free Parking, Heater, Kitchen, Microwave, No Smoking, Pool, TV

1 Bedroom2 Guests
9.4

Superb

15 reviews

$90
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
5.8k from Montespertoli 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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Au Coeur du Chianti
Au Coeur du Chianti
House
montespertoli, 50025, Italy
5.8k from Montespertoli center

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

2 Bedrooms6 Guests
10.0

Exceptional

3 reviews

$192
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 Montespertoli.

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Montespertoli Vacation Rentals with Private Pool on the Map

Frequently Asked Questions

You can explore 141 verified vacation rentals with a private pool in Montespertoli. These include standalone villas and private homes where the pool is reserved exclusively for your group.

Prices for rentals with a private pool in Montespertoli 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 Montespertoli also welcome pets. Currently, 26 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 Montespertoli often include additional features such as Fireplace/Heating, Pool, and Kitchen. These amenities enhance comfort and create a more relaxing, self-contained stay.

Some family-friendly vacation rentals in Montespertoli 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.