Cortona Holiday Rentals
10.0
Exceptional
(67 Reviews)
53820 ft²
12 Guests
5 Bedrooms
3 Bathrooms
Family Friendly
Villa
- Private Pool
- Fireplace/Heating
- Pool
د.إ.2,231/Night
For 7 Nights د.إ.15,615
New
4306 ft²
14 Guests
9 Bedrooms
7 Bathrooms
Family Friendly
Villa
- Private Pool
- Fireplace/Heating
- Pool
د.إ.2,678/Night
For 7 Nights د.إ.18,744
9.8
Exceptional
(29 Reviews)
- Cortona
- Cortona Old Town
- 0.08 mi to center
1184 ft²
6 Guests
2 Bedrooms
2 Bathrooms
Family Friendly
House
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
د.إ.629/Night
For 7 Nights د.إ.4,407
9.0
Exceptional
(6 Reviews)
- Cortona
- Monsigliolo
- 0.09 mi to center
1022.57 ft²
28 Guests
9 Bedrooms
4 Bathrooms
Family Friendly
Apartment
- Pool
- Balcony/Terrace
- Pet Friendly
د.إ.195/Night
For 7 Nights د.إ.1,366
10.0
Exceptional
(27 Reviews)
1615 ft²
4 Guests
2 Bedrooms
2 Bathrooms
Ocean View
Villa
- Private Pool
- Fireplace/Heating
- Pool
د.إ.2,085/Night
For 7 Nights د.إ.14,595
10.0
Exceptional
(60 Reviews)
807 ft²
4 Guests
2 Bedrooms
2 Bathrooms
Family Friendly
Villa
- Private Pool
- Fireplace/Heating
- Pool
د.إ.1,085/Night
For 7 Nights د.إ.7,595
10.0
Exceptional
(44 Reviews)
1722 ft²
6 Guests
3 Bedrooms
3 Bathrooms
Family Friendly
Villa
- Private Pool
- Fireplace/Heating
- Pool
د.إ.1,199/Night
For 7 Nights د.إ.8,392
10.0
Exceptional
(43 Reviews)
1561 ft²
6 Guests
3 Bedrooms
3 Bathrooms
Family Friendly
Villa
- Private Pool
- Fireplace/Heating
- Pool
د.إ.1,569/Night
For 7 Nights د.إ.10,984
Luxury Holiday Rentals in Cortona
Over 1746+ Luxury Holiday Rentals in or Near Cortona
New
5381.95 ft²
24 Guests
10 Bedrooms
13 Bathrooms
Family Friendly
Villa
- Pool
- Balcony/Terrace
- Breakfast
د.إ.23,387/Night
For 7 Nights د.إ.163,713
New
5920 ft²
34 Guests
16 Bedrooms
1 Bathroom
Family Friendly
Villa
- Pool
- Balcony/Terrace
- Kitchen
د.إ.22,657/Night
For 7 Nights د.إ.158,601
New
6458 ft²
17 Guests
8 Bedrooms
3 Bathrooms
Family Friendly
Villa
- Pool
- Kitchen
- Parking
د.إ.16,109/Night
For 7 Nights د.إ.112,764
New
- Cortona
- San Pietro a Cegliolo
- 0.40 mi to center
7782 ft²
30 Guests
1 Bedroom
1 Bathroom
Apartment
- Child Friendly
- Security/Safety
د.إ.10,191/Night
For 7 Nights د.إ.71,335
New
22 Guests
11 Bedrooms
11 Bathrooms
Ocean View
Villa
- Fireplace/Heating
- Pool
- Ocean View
د.إ.10,176/Night
For 7 Nights د.إ.71,235
New
3767 ft²
20 Guests
10 Bedrooms
11 Bathrooms
Family Friendly
Villa
- Private Pool
- Fireplace/Heating
- Pool
د.إ.9,680/Night
For 7 Nights د.إ.67,758
New
4305.56 ft²
20 Guests
10 Bedrooms
10 Bathrooms
Ocean View
Villa
- Private Pool
- Oceanfront
- Hot Tub
د.إ.9,622/Night
For 7 Nights د.إ.67,354
10.0
Exceptional
(16 Reviews)
- Cortona
- Cortona Old Town
- 0.13 mi to center
1506.95 ft²
6 Guests
3 Bedrooms
3 Bathrooms
Apartment
- Fireplace/Heating
- Parking
- Air Conditioner
د.إ.9,178/Night
For 7 Nights د.إ.64,243
New
2690.98 ft²
8 Guests
4 Bedrooms
1 Bathroom
Family Friendly
Villa
- Pool
- Parking
- Air Conditioner
د.إ.8,652/Night
For 7 Nights د.إ.60,567
Top-Rated Holiday Rentals with a Pool in Cortona
Over 1041+ The Best Private Villas and Holiday Rentals in Cortona with a Pool
10.0
Exceptional
(260 Reviews)
- Cortona
- Cortona Old Town
- 0.17 mi to center
1 Bathroom
Couples Retreat
Hotel
- Hot Tub
- Spa
- Fireplace/Heating
د.إ.1,228/Night
For 7 Nights د.إ.8,594
10.0
Exceptional
(62 Reviews)
4306 ft²
8 Guests
4 Bedrooms
5 Bathrooms
Ocean View
Villa
- Private Pool
- Fireplace/Heating
- Pool
د.إ.1,890/Night
For 7 Nights د.إ.13,232
10.0
Exceptional
(50 Reviews)
5382 ft²
12 Guests
6 Bedrooms
7 Bathrooms
Ocean View
Villa
- Private Pool
- Fireplace/Heating
- Pool
د.إ.2,762/Night
For 7 Nights د.إ.19,336
10.0
Exceptional
(48 Reviews)
1830 ft²
7 Guests
4 Bedrooms
3 Bathrooms
Ocean View
Villa
- Private Pool
- Fireplace/Heating
- Pool
د.إ.1,713/Night
For 7 Nights د.إ.11,991
10.0
Exceptional
(47 Reviews)
8 Guests
3 Bedrooms
3 Bathrooms
Ocean View
Other
- Private Pool
- Fireplace/Heating
- Pool
د.إ.2,258/Night
For 7 Nights د.إ.15,806
10.0
Exceptional
(41 Reviews)
969 ft²
6 Guests
2 Bedrooms
2 Bathrooms
Family Friendly
Villa
- Fireplace/Heating
- Pool
- Balcony/Terrace
د.إ.1,003/Night
For 7 Nights د.إ.7,022
10.0
Exceptional
(40 Reviews)
1722 ft²
6 Guests
3 Bedrooms
1 Bathroom
Ocean View
House
- Private Pool
- Fireplace/Heating
- Pool
د.إ.1,119/Night
For 7 Nights د.إ.7,837
10.0
Exceptional
(38 Reviews)
646 ft²
4 Guests
1 Bedroom
1 Bathroom
Ocean View
Apartment
- Fireplace/Heating
- Pool
- Ocean View
د.إ.478/Night
For 7 Nights د.إ.3,346
10.0
Exceptional
(36 Reviews)
2260 ft²
6 Guests
3 Bedrooms
3 Bathrooms
Family Friendly
Villa
- Private Pool
- Fireplace/Heating
- Pool
د.إ.2,644/Night
For 7 Nights د.إ.18,506
Pet-Friendly Holiday Rentals in Cortona
Over 804+ Pet-Friendly Holiday Rentals in or Near Cortona
9.6
Exceptional
(46 Reviews)
2153 ft²
9 Guests
5 Bedrooms
2 Bathrooms
Family Friendly
Villa
- Private Pool
- Fireplace/Heating
- Pool
د.إ.1,020/Night
For 7 Nights د.إ.7,139
8.6
Fabulous
(5 Reviews)
766.39 ft²
19 Guests
7 Bedrooms
6 Bathrooms
Family Friendly
House
- Pool
- Balcony/Terrace
- Pet Friendly
د.إ.408/Night
For 7 Nights د.إ.2,854
10.0
Exceptional
(1 Review)
1 Bedroom
1 Bathroom
Family Friendly
Villa
- Fireplace/Heating
- Pool
- Balcony/Terrace
د.إ.1,351/Night
For 7 Nights د.إ.9,460
9.2
Exceptional
(47 Reviews)
2153 ft²
6 Guests
3 Bedrooms
2 Bathrooms
Family Friendly
Villa
- Private Pool
- Hot Tub
- Fireplace/Heating
د.إ.1,105/Night
For 7 Nights د.إ.7,734
9.0
Exceptional
(26 Reviews)
215.28 ft²
6 Guests
2 Bedrooms
2 Bathrooms
Pet Friendly
Bed & Breakfast
- Hot Tub
- Balcony/Terrace
- Breakfast
د.إ.419/Night
For 7 Nights د.إ.2,931
9.8
Exceptional
(29 Reviews)
3875 ft²
8 Guests
4 Bedrooms
4 Bathrooms
Ocean View
Villa
- Private Pool
- Fireplace/Heating
- Pool
د.إ.1,520/Night
For 7 Nights د.إ.10,639
9.0
Exceptional
(19 Reviews)
1830 ft²
8 Guests
4 Bedrooms
3 Bathrooms
Family Friendly
Villa
- Private Pool
- Fireplace/Heating
- Pool
د.إ.1,242/Night
For 7 Nights د.إ.8,693
10.0
Exceptional
(30 Reviews)
1830 ft²
12 Guests
5 Bedrooms
2 Bathrooms
Ocean View
House
- Private Pool
- Fireplace/Heating
- Pool
د.إ.1,507/Night
For 7 Nights د.إ.10,547
9.8
Exceptional
(15 Reviews)
2260 ft²
12 Guests
4 Bedrooms
5 Bathrooms
Family Friendly
Villa
- Private Pool
- Fireplace/Heating
- Pool
د.إ.1,211/Night
For 7 Nights د.إ.8,472
Large Holiday Rentals and Private Villas in Cortona
Over 672+ Large Holiday Rentals and Private Villas in or Near Cortona
9.8
Exceptional
(35 Reviews)
2691 ft²
9 Guests
4 Bedrooms
4 Bathrooms
Ocean View
Villa
- Private Pool
- Fireplace/Heating
- Pool
د.إ.1,195/Night
For 7 Nights د.إ.8,362
8.0
Excellent
(1 Review)
1679.17 ft²
8 Guests
4 Bedrooms
4 Bathrooms
Family Friendly
Villa
- Pool
- Balcony/Terrace
- Breakfast
د.إ.2,167/Night
For 7 Nights د.إ.15,171
New
1 Bedroom
1 Bathroom
Couples Retreat
Villa
- Fireplace/Heating
- Pool
- Balcony/Terrace
د.إ.940/Night
For 7 Nights د.إ.6,581
10.0
Exceptional
(22 Reviews)
- Cortona
- San Pietro a Cegliolo
- 0.43 mi to center
3229 ft²
15 Guests
8 Bedrooms
7 Bathrooms
Family Friendly
Villa
- Private Pool
- Fireplace/Heating
- Pool
د.إ.2,533/Night
For 7 Nights د.إ.17,731
New
1614.59 ft²
10 Guests
4 Bedrooms
4 Bathrooms
Pet Friendly
Villa
- Pool
- Balcony/Terrace
- Breakfast
د.إ.1,840/Night
For 7 Nights د.إ.12,876
10.0
Exceptional
(1 Review)
4306 ft²
22 Guests
10 Bedrooms
9 Bathrooms
Family Friendly
Villa
- Private Pool
- Fireplace/Heating
- Pool
د.إ.2,743/Night
For 7 Nights د.إ.19,200
9.4
Exceptional
(13 Reviews)
3660 ft²
10 Guests
4 Bedrooms
4 Bathrooms
Family Friendly
Villa
- Private Pool
- Fireplace/Heating
- Pool
د.إ.1,502/Night
For 7 Nights د.إ.10,514
10.0
Exceptional
(8 Reviews)
592 ft²
4 Guests
1 Bedroom
1 Bathroom
Family Friendly
Villa
- Private Pool
- Fireplace/Heating
- Pool
د.إ.913/Night
For 7 Nights د.إ.6,390
10.0
Exceptional
(5 Reviews)
- Cortona
- Fratticciola
- 0.01 mi to center
8181 ft²
24 Guests
12 Bedrooms
13 Bathrooms
Family Friendly
Villa
- Private Pool
- Hot Tub
- Fireplace/Heating
د.إ.6,053/Night
For 7 Nights د.إ.42,373
Wheelchair Accessible Holiday Homes in Cortona
Over 52+ Wheelchair Accessible Holiday Homes in or Near Cortona
10.0
Exceptional
(4 Reviews)
- Cortona
- Cortona Old Town
- 0.26 mi to center
1399 ft²
6 Guests
3 Bedrooms
3 Bathrooms
Family Friendly
Apartment
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
د.إ.929/Night
For 7 Nights د.إ.6,500
10.0
Exceptional
1722.23 ft²
8 Guests
4 Bedrooms
3 Bathrooms
Family Friendly
Villa
- Pool
- Pet Friendly
- Kitchen
د.إ.712/Night
For 7 Nights د.إ.4,987
New
- Cortona
- Cortona Old Town
- 0.18 mi to center
1 Bedroom
1 Bathroom
Couples Retreat
Bed & Breakfast
- Breakfast
- Internet
- Child Friendly
د.إ.869/Night
For 7 Nights د.إ.6,082
10.0
Exceptional
(3 Reviews)
- Cortona
- Metelliano
- 0.03 mi to center
2852 ft²
10 Guests
5 Bedrooms
6 Bathrooms
Family Friendly
Villa
- Private Pool
- Fireplace/Heating
- Pool
د.إ.6,461/Night
For 7 Nights د.إ.45,227
New
3229.17 ft²
12 Guests
6 Bedrooms
4 Bathrooms
Family Friendly
Villa
- Pool
- Balcony/Terrace
- Kitchen
د.إ.1,224/Night
For 7 Nights د.إ.8,568
New
1399 ft²
6 Guests
3 Bedrooms
3 Bathrooms
Family Friendly
Apartment
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
د.إ.1,299/Night
For 7 Nights د.إ.9,089
10.0
Exceptional
(2 Reviews)
753 ft²
4 Guests
2 Bedrooms
1 Bathroom
Family Friendly
House
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
د.إ.603/Night
For 7 Nights د.إ.4,220
New
- Cortona
- Fratticciola
- 0.06 mi to center
8073 ft²
18 Guests
10 Bedrooms
10 Bathrooms
Family Friendly
Villa
- Private Pool
- Pool
- Balcony/Terrace
د.إ.5,683/Night
For 7 Nights د.إ.39,781
New
8 Guests
4 Bedrooms
5 Bathrooms
Family Friendly
Villa
- Fireplace/Heating
- Pool
- Balcony/Terrace
د.إ.4,719/Night
For 7 Nights د.إ.33,034
Cortona Private Villas and Holiday Homes Under $200
Over 721+ Cortona Private Villas and Holiday Homes Under $200
10.0
Exceptional
(67 Reviews)
969 ft²
4 Guests
2 Bedrooms
2 Bathrooms
Family Friendly
Apartment
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
د.إ.627/Night
For 7 Nights د.إ.4,392
10.0
Exceptional
(4 Reviews)
645.84 ft²
8 Guests
4 Bedrooms
2 Bathrooms
Free Cancellation
Villa
- Hot Tub
- Balcony/Terrace
- Breakfast
د.إ.599/Night
For 7 Nights د.إ.4,190
10.0
Exceptional
(1 Review)
- Cortona
- Casorbica-Salcotto
- 0.11 mi to center
1 Bedroom
1 Bathroom
Family Friendly
House
- Private Pool
- Fireplace/Heating
- Pool
د.إ.708/Night
For 7 Nights د.إ.4,954
10.0
Exceptional
(17 Reviews)
- Cortona
- Cortona Old Town
- 0.24 mi to center
538 ft²
2 Guests
1 Bedroom
1 Bathroom
Family Friendly
Apartment
- Fireplace/Heating
- Kitchen
- Parking
د.إ.406/Night
For 7 Nights د.إ.2,839
9.0
Exceptional
(1 Review)
- Cortona
- Cortona Old Town
- 0.18 mi to center
1076.39 ft²
6 Guests
2 Bedrooms
2 Bathrooms
Pet Friendly
Apartment
- Pet Friendly
- Air Conditioner
- Internet
د.إ.343/Night
For 7 Nights د.إ.2,402
10.0
Exceptional
(12 Reviews)
700 ft²
4 Guests
1 Bedroom
1 Bathroom
Family Friendly
Apartment
- Fireplace/Heating
- Pool
- Balcony/Terrace
د.إ.663/Night
For 7 Nights د.إ.4,642
9.8
Exceptional
(36 Reviews)
- Cortona
- Cortona Old Town
- 0.04 mi to center
936 ft²
4 Guests
2 Bedrooms
1 Bathroom
Family Friendly
Apartment
- Fireplace/Heating
- Kitchen
- Parking
د.إ.664/Night
For 7 Nights د.إ.4,646
7.4
Very Good
(3 Reviews)
1399 ft²
9 Guests
4 Bedrooms
2 Bathrooms
Family Friendly
House
- Fireplace/Heating
- Pet Friendly
- Kitchen
د.إ.639/Night
For 7 Nights د.إ.4,477
10.0
Exceptional
(2 Reviews)
- Cortona
- Cortona Old Town
- 0.41 mi to center
377 ft²
2 Guests
1 Bedroom
1 Bathroom
Family Friendly
Apartment
- Fireplace/Heating
- Breakfast
- Kitchen
د.إ.551/Night
For 7 Nights د.إ.3,856
Instantly Bookable Holiday Homes in Cortona
Over 1000+ Instantly Bookable Holiday Homes in or Near Cortona
10.0
Exceptional
(21 Reviews)
1292 ft²
6 Guests
2 Bedrooms
2 Bathrooms
Family Friendly
House
- Fireplace/Heating
- Pool
- Balcony/Terrace
د.إ.1,366/Night
For 7 Nights د.إ.9,563
10.0
Exceptional
(2 Reviews)
969 ft²
4 Guests
2 Bedrooms
1 Bathroom
Family Friendly
Other
- Fireplace/Heating
- Pool
- Balcony/Terrace
د.إ.1,214/Night
For 7 Nights د.إ.8,502
New
3229 ft²
14 Guests
6 Bedrooms
6 Bathrooms
Family Friendly
House
- Private Pool
- Fireplace/Heating
- Pool
د.إ.1,369/Night
For 7 Nights د.إ.9,582
10.0
Exceptional
(10 Reviews)
1938 ft²
12 Guests
5 Bedrooms
3 Bathrooms
Family Friendly
Villa
- Private Pool
- Fireplace/Heating
- Pool
د.إ.1,236/Night
For 7 Nights د.إ.8,649
10.0
Exceptional
(4 Reviews)
2691 ft²
6 Guests
3 Bedrooms
3 Bathrooms
Family Friendly
Apartment
- Fireplace/Heating
- Pool
- Balcony/Terrace
د.إ.2,138/Night
For 7 Nights د.إ.14,965
10.0
Exceptional
(4 Reviews)
538 ft²
2 Guests
1 Bedroom
1 Bathroom
Family Friendly
Apartment
- Fireplace/Heating
- Pool
- Balcony/Terrace
د.إ.976/Night
For 7 Nights د.إ.6,831
9.8
Exceptional
(6 Reviews)
- Cortona
- Fratticciola
- 0.09 mi to center
8181 ft²
24 Guests
12 Bedrooms
13 Bathrooms
Family Friendly
Villa
- Private Pool
- Hot Tub
- Fireplace/Heating
د.إ.6,247/Night
For 7 Nights د.إ.43,728
10.0
Exceptional
(1 Review)
4628 ft²
15 Guests
7 Bedrooms
7 Bathrooms
Family Friendly
House
- Private Pool
- Fireplace/Heating
- Pool
د.إ.1,478/Night
For 7 Nights د.إ.10,342
9.4
Exceptional
(3 Reviews)
- Cortona
- San Pietro a Cegliolo
- 0.39 mi to center
3229 ft²
14 Guests
7 Bedrooms
5 Bathrooms
Family Friendly
Villa
- Private Pool
- Fireplace/Heating
- Pool
د.إ.2,140/Night
For 7 Nights د.إ.14,980
Book a Last Minute Place to Stay in Cortona
About Casai's Private Villas and Holiday Rentals in Cortona
Discover more than 1755 vacation rentals available in Cortona. These rentals, ranging from vacation rentals to Casai Homes and other short-term private accommodations, offer top-notch amenities with unbeatable value, ensuring both comfort and luxury. Enjoy more space and value when you stay at a Casai property in Cortona.
Seeking last-minute deals or the best available offers for cottages, condos, private villas, and spacious vacation homes? With Casai in Cortona, you can effortlessly compare various deals with just a click. Whether you're looking for a Casai with exceptional swimming pools, hot tubs, pet-friendly options, or large master suite bedrooms equipped with large screen televisions, you'll find a variety of options near Cortona. On average, places to stay near Cortona offer 1413.93 ft², with nightly prices averaging د.إ.1,505.
With Casai, finding and comparing holiday rentals in Cortona is easy and secure, often at a 30-40% discount compared to hotel prices. Simply search for your destination and secure your reservation today.
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Top Accommodation Types in Cortona
| Type | Count |
|---|---|
| Holiday Apartments | 599 |
| Villas | 514 |
| Vacation Homes | 447 |
| Cottages | 17 |
Use these Quick Filters to Find a Holiday Rental in Cortona
★ Pro Tip: Casai simplifies the process of comparing the finest listings across various online vacation rental platforms, including Booking.com and more. Utilize the Advanced Filter feature located at the top to effortlessly switch between Casai homes, vacation rentals, bed and breakfasts, private Airbnb-style rentals, eco-friendly properties, and different property types. Explore various cancellation policies, prices, and numerous options to find the ideal accommodation for your next vacation in Cortona.
Top Attractions Around Cortona, IT
Casai offers a large selection of top attractions around Cortona . Research things to do on your vacation before you visit Cortona.
Other Places to Stay in Cortona, IT
Frequently Asked Questions About Cortona?
What are the top holiday rentals in Cortona?
With numerous options available in Cortona, planning to stay in the area? Consider booking a few nights at one of these properties, rated as the Top Holiday Rentals in Cortona:
- Hotel Villa Marsili
- Monastero di Cortona Hotel & Spa
- Your Holiday Under the Tuscan Sun
- "Villa Stefania" Old Tuscan Farmhouse - Great View on Cortona
- City/Village Apartment in Cortona with 2 bedrooms sleeps 4
- Tuscan Villa private infinity pool, exclusive location, AC, extra services
- Villa Portole Due - Holiday Country Villa with swimming pool in Cortona, Tuscany
- Luxury Cortona view hilltop Villa
- Heritage Tuscan Farmhouse with private swimming pool
- Cortona Farmhouse in Tuscany - Casa Sant'Angelo
How many holiday rentals have private pools in Cortona?
Discover a selection of holiday rentals with private pools near Cortona with Casai. Experience the epitome of luxury and relaxation in our top-rated villas and holiday homes, where you can enjoy exclusive access to refreshing swimming pools.
- Casale Miro - Country villa with private pool
- Fattoria del Nonno Berto
- Villa Eugenio
- Villa in Cortona with Pool & Garden
Which holiday homes in Cortona are best for families?
If you're searching for a family-friendly holiday home in Cortona, consider one of the following properties. Each comes highly recommended, with excellent reviews for families or groups staying in Cortona:
How many Casai.ae holiday rentals are available in Cortona?
As of 2026, Casai boasts over 1755 properties listed in the Cortona area, with more being added continually. By consolidating listings from various websites, Casai provides an extensive selection of the finest Casai properties in Cortona.
Nearby Neighborhood (1)
| Neighborhood | Property Count |
|---|---|
| Cortona Old Town Vacation Rentals in Cortona, Tuscany | 814 |
People Also Ask
Finding the best prices in Cortona
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