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

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  2. Vacation Rentals with Private Pool
  3.  Italy

  4.  Tuscany
  5.  Cortona

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378 Best Vacation Rentals with Private Pool in Cortona (Starting from $127)

Villa Del Sole
Villa Del Sole
House
Cortona, Italy
1.4k from Cortona center

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

6 Bedrooms13 Guests
New to Booking
$319
Average price / night
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Villa La Perla. Splendid panoramic location. Private Pool
Villa La Perla. Splendid panoramic location. Private Pool
Villa
Cortona, 52044, Italy
0.0k from Cortona center

Barbecue, Fireplace, Free Parking, Internet, Laundry, Microwave, Pool, Washer

4 Bedrooms9 Guests
New to Booking
$261
Average price / night
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LA SORGENTE 8, Emma Villas
LA SORGENTE 8, Emma Villas
Villa
Cortona, Italy
2.4k from Cortona center

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

4 Bedrooms8 Guests
New to Booking
$852
Average price / night
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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
Villa
Cortona, 52044, Italy
0.2k from Cortona center

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

2 Bedrooms4 Guests
10.0

Exceptional

18 reviews

$188
Average price / night
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Nello's, Villa di pregio con SPA
Nello's, Villa di pregio con SPA
Villa
Cortona, Italy
2.8k from Cortona center

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

10 Bedrooms20 Guests
New to Booking
$2620
Average price / night
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Villa in Cortona with 6 bedrooms sleeps 12
Villa in Cortona with 6 bedrooms sleeps 12
Villa
Cortona, 52044, Italy
0.3k from Cortona center

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

6 Bedrooms12 Guests
9.8

Exceptional

13 reviews

$716
Average price / night
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Fattoria del Nonno Berto
Fattoria del Nonno Berto
House
Cortona, Tuscany, Italy
3.0k from Cortona center

Accommodations, Pools, Farm stays, Parking, Cottages, Pet-friendly, Lodgings, Vacation rentals, Hot tubs

6 Bedrooms15 Guests
9.7

Exceptional

19 reviews

$651
Average price / night
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Romantic Lux Country House
Romantic Lux Country House
Villa
Cortona, 52044, Italy
0.3k from Cortona center

AC, Barbecue, Crib, Dryer, Extra Bed, Free Parking, Heater, Hot Tub, Internet

3 Bedrooms8 Guests
9.8

Exceptional

10 reviews

$855
Average price / night
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Agriturismo Parco Fiorito
Agriturismo Parco Fiorito
House
Cortona, Tuscany, Italy
5.2k from Cortona center

Cheap, Accommodations, Pools, Farm stays, Parking, Cottages, Pet-friendly, Lodgings, Vacation rentals

21 Bedrooms34 Guests
8.2

Very Good

64 reviews

$127
Average price / night
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Casa del Sole 4, Emma Villas
Casa del Sole 4, Emma Villas
Villa
Cortona, 52044, Italy
0.4k from Cortona center

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

2 Bedrooms4 Guests
10.0

Exceptional

7 reviews

$703
Average price / night
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Stunning private villa for 12 guests with WIFI, private pool, TV, patio and panoramic view
Stunning private villa for 12 guests with WIFI, private pool, TV, patio and panoramic view
Villa
Cortona, 52044, Italy
0.4k from Cortona center

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

6 Bedrooms12 Guests
10.0

Exceptional

10 reviews

$924
Average price / night
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Stone house villa with Spa in Cortona
Stone house villa with Spa in Cortona
Villa
Cortona, 52044, Italy
0.4k from Cortona center

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

1 Bedroom6 Guests
8.6

Fabulous

29 reviews

$465
Average price / night
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Villa in Cortona with  pool
Villa in Cortona with pool
Villa
Cortona, 52044, Italy
0.4k from Cortona center

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

3 Bedrooms6 Guests
9.2

Superb

23 reviews

$413
Average price / night
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Villa Vento, elegant villa walking distance from CORTONA. Private Pool
Villa Vento, elegant villa walking distance from CORTONA. Private Pool
Villa
cORTONA, 52044, Italy
0.5k from Cortona center

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

4 Bedrooms8 Guests
New to Booking
$1546
Average price / night
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Antico Casale - Holiday Country Villa with swimming pool in Cortona
Antico Casale - Holiday Country Villa with swimming pool in Cortona
Villa
Cortona, 52044, Italy
0.5k from Cortona center

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

3 Bedrooms6 Guests
9.2

Superb

47 reviews

$278
Average price / night
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Casale Girifalco - Country house with private pool
Casale Girifalco - Country house with private pool
Villa
Cortona, 52044, Italy
0.5k from Cortona center

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

6 Bedrooms12 Guests
10.0

Exceptional

1 reviews

$829
Average price / night
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Stunning private villa for 8 people with WIFI, private pool, A/C, TV, terrace and panoramic view
Stunning private villa for 8 people with WIFI, private pool, A/C, TV, terrace and panoramic view
Villa
Cortona, 52044, Italy
0.5k from Cortona center

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

4 Bedrooms8 Guests
10.0

Exceptional

3 reviews

$572
Average price / night
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Villa in Cortona with 4 bedrooms sleeps 8
Villa in Cortona with 4 bedrooms sleeps 8
Villa
Cortona, 52044, Italy
0.5k from Cortona center

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

4 Bedrooms8 Guests
10.0

Exceptional

9 reviews

$443
Average price / night
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Antico Casale - Cortona ,Tuscany
Antico Casale - Cortona ,Tuscany
Villa
Cortona, 52044, Italy
0.5k from Cortona center

AC, Barbecue, Fireplace, Free Parking, Internet, Kitchen, Laundry, Outdoor Space, Pool

3 Bedrooms6 Guests
New to Booking
$269
Average price / night
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Villa:Wonderful Panoramic Position,Walking Distance From Cortona,Family-Friendly
Villa:Wonderful Panoramic Position,Walking Distance From Cortona,Family-Friendly
House
Cortona, 52044, Italy
0.7k from Cortona center

AC, Barbecue, Breakfast Available, Dryer, Fireplace, Free Parking, Heater, Internet, Kitchen

2 Bedrooms5 Guests
New to Booking
$219
Average price / night
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Villa in Cortona, family-friendly, close to the village, 2 pools, Wi-Fi,sleep 15
Villa in Cortona, family-friendly, close to the village, 2 pools, Wi-Fi,sleep 15
House
Cortona, 52044, Italy
0.7k from Cortona center

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

6 Bedrooms15 Guests
New to Booking
$925
Average price / night
Check Availability
Villa in Cortona, family-friendly, close to the village, pool, Wi-Fi, sleep 10
Villa in Cortona, family-friendly, close to the village, pool, Wi-Fi, sleep 10
House
Cortona, 52044, Italy
0.7k from Cortona center

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

4 Bedrooms10 Guests
8.8

Fabulous

3 reviews

$709
Average price / night
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Villa with swimming pool in Cortona, up to 5 people
Villa with swimming pool in Cortona, up to 5 people
House
Cortona, 52044, Italy
0.7k from Cortona center

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

2 Bedrooms5 Guests
New to Booking
$214
Average price / night
Check Availability
Villa Mulinoavento with magnificent view 5 minutes walking downtown
Villa Mulinoavento with magnificent view 5 minutes walking downtown
Villa
Cortona, 52044, Italy
0.8k from Cortona center

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

3 Bedrooms6 Guests
10.0

Exceptional

36 reviews

$719
Average price / night
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Spacious Cortona Villa
Spacious Cortona Villa
Villa
Cortona, 52044, Italy
0.9k from Cortona center

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

8 Bedrooms17 Guests
10.0

Exceptional

3 reviews

$1047
Average price / night
Check Availability
Large stone manor with 8BR and 7BA, extended grounds, large fully-equipped pool.
Large stone manor with 8BR and 7BA, extended grounds, large fully-equipped pool.
Villa
CORTONA, 52044, Italy
0.9k from Cortona center

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

8 Bedrooms17 Guests
9.4

Superb

12 reviews

$542
Average price / night
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Beautiful private villa with WIFI, private pool, A/C, TV, patio and panoramic view, close to Cor...
Beautiful private villa with WIFI, private pool, A/C, TV, patio and panoramic view, close to Cor...
Villa
Sodo, 52044, Italy
0.9k from Cortona center

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

11 Bedrooms21 Guests
10.0

Exceptional

3 reviews

$1307
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 Cortona.

Stay Near Cortona's Top Attractions

VacationByOwnerRentals can help you find hotels, resorts, and rentals near many of 's top attractions, neighborhoods, and points of interest.

Cortona Vacation Rentals with Private Pool on the Map

Frequently Asked Questions

You can explore 378 verified vacation rentals with a private pool in Cortona. These include standalone villas and private homes where the pool is reserved exclusively for your group.

Prices for rentals with a private pool in Cortona vary depending on the property size, location, and travel season. Rates typically start from around $127 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 Cortona also welcome pets. Currently, 33 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 Cortona often include additional features such as Fireplace/Heating, Pool, and Private Pool. These amenities enhance comfort and create a more relaxing, self-contained stay.

Some family-friendly vacation rentals in Cortona 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.