Cortona Holiday Rentals
Villa
10.0Exceptional
(67 Reviews)
5 Bedrooms
3 Baths
12 Guests
53820 ft²
Private Pool
Fireplace/Heating
Pool
Balcony/Terrace
د.إ.2,153/Night
7 Nights - د.إ.15,071
Bed & Breakfast
10.0Exceptional
(21 Reviews)
1 Bedroom
1 Bath
Hot Tub
Spa- Fireplace/Heating
- Pool
د.إ.965/Night
7 Nights - د.إ.6,759
House
- Cortona
- ·
- Cortona Old Town
- 0.08 mi to center
9.8Exceptional
(29 Reviews)
2 Bedrooms
2 Baths
6 Guests
1184 ft²
- Fireplace/Heating
- Balcony/Terrace
Pet Friendly
Kitchen
د.إ.630/Night
7 Nights - د.إ.4,408
Apartment
- Cortona
- ·
- Monsigliolo
- 0.09 mi to center
9.0Exceptional
(6 Reviews)
9 Bedrooms
4 Baths
28 Guests
1022.57 ft²
- Pool
- Balcony/Terrace
- Pet Friendly
Parking
د.إ.195/Night
7 Nights - د.إ.1,366
Villa
10.0Exceptional
(27 Reviews)
2 Bedrooms
2 Baths
4 Guests
1615 ft²
- Private Pool
- Fireplace/Heating
- Pool
Ocean View
د.إ.2,122/Night
7 Nights - د.إ.14,854
Villa
10.0Exceptional
(60 Reviews)
2 Bedrooms
2 Baths
4 Guests
807 ft²
- Private Pool
- Fireplace/Heating
- Pool
- Balcony/Terrace
د.إ.1,246/Night
7 Nights - د.إ.8,720
Villa
10.0Exceptional
(46 Reviews)
3 Bedrooms
3 Baths
6 Guests
1722 ft²
- Private Pool
- Fireplace/Heating
- Pool
- Balcony/Terrace
د.إ.2,685/Night
7 Nights - د.إ.18,796
Villa
10.0Exceptional
(43 Reviews)
3 Bedrooms
3 Baths
6 Guests
1561 ft²
- Private Pool
- Fireplace/Heating
- Pool
- Balcony/Terrace
د.إ.1,848/Night
7 Nights - د.إ.12,937
Luxury Holiday Rentals in Cortona
Over 1764+ Luxury Holiday Rentals in or Near Cortona
Villa
10 Bedrooms
13 Baths
24 Guests
5381.95 ft²
- Pool
- Balcony/Terrace
Breakfast- Kitchen
د.إ.23,392/Night
7 Nights - د.إ.163,742
Villa
16 Bedrooms
1 Bath
34 Guests
5920 ft²
- Pool
- Balcony/Terrace
- Kitchen
- Parking
د.إ.22,661/Night
7 Nights - د.إ.158,629
Apartment
- Cortona
- ·
- San Pietro a Cegliolo
- 0.40 mi to center
1 Bedroom
1 Bath
30 Guests
7782 ft²
Child Friendly
Security/Safety
د.إ.11,238/Night
7 Nights - د.إ.78,664
Villa
11 Bedrooms
11 Baths
22 Guests
- Fireplace/Heating
- Pool
- Ocean View
- Balcony/Terrace
د.إ.10,241/Night
7 Nights - د.إ.71,689
Villa
10 Bedrooms
11 Baths
20 Guests
3767 ft²
- Private Pool
- Fireplace/Heating
- Pool
- Balcony/Terrace
د.إ.9,681/Night
7 Nights - د.إ.67,770
Villa
10 Bedrooms
10 Baths
20 Guests
4305.56 ft²
- Private Pool
Oceanfront- Hot Tub
- Spa
د.إ.9,624/Night
7 Nights - د.إ.67,366
Apartment
- Cortona
- ·
- Cortona Old Town
- 0.13 mi to center
10.0Exceptional
(13 Reviews)
3 Bedrooms
3 Baths
6 Guests
1506.95 ft²
- Fireplace/Heating
- Parking
Air Conditioner
Internet
د.إ.9,179/Night
7 Nights - د.إ.64,254
Villa
10.0Exceptional
(3 Reviews)
9 Bedrooms
10 Baths
18 Guests
11324 ft²
- Private Pool
- Hot Tub
- Fireplace/Heating
- Pool
د.إ.8,955/Night
7 Nights - د.إ.62,682
Villa
4 Bedrooms
1 Bath
8 Guests
2690.98 ft²
- Pool
- Parking
- Air Conditioner
- Internet
د.إ.8,654/Night
7 Nights - د.إ.60,578
Top-Rated Holiday Rentals with a Pool in Cortona
Over 1047+ The Best Private Villas and Holiday Rentals in Cortona with a Pool
Hotel
- Cortona
- ·
- Cortona Old Town
- 0.17 mi to center
10.0Exceptional
(272 Reviews)
1 Bath
- Hot Tub
- Spa
- Fireplace/Heating
- Pool
د.إ.1,408/Night
7 Nights - د.إ.9,859
Villa
10.0Exceptional
(62 Reviews)
4 Bedrooms
5 Baths
8 Guests
4306 ft²
- Private Pool
- Fireplace/Heating
- Pool
- Ocean View
د.إ.1,932/Night
7 Nights - د.إ.13,525
Villa
10.0Exceptional
(50 Reviews)
6 Bedrooms
7 Baths
12 Guests
5382 ft²
- Private Pool
- Fireplace/Heating
- Pool
- Ocean View
د.إ.3,873/Night
7 Nights - د.إ.27,112
Villa
10.0Exceptional
(49 Reviews)
4 Bedrooms
3 Baths
7 Guests
1830 ft²
- Private Pool
- Fireplace/Heating
- Pool
- Ocean View
د.إ.1,730/Night
7 Nights - د.إ.12,114
Other
10.0Exceptional
(47 Reviews)
3 Bedrooms
3 Baths
8 Guests
- Private Pool
- Fireplace/Heating
- Pool
- Ocean View
د.إ.2,258/Night
7 Nights - د.إ.15,809
Villa
10.0Exceptional
(41 Reviews)
2 Bedrooms
2 Baths
6 Guests
969 ft²
- Fireplace/Heating
- Pool
- Balcony/Terrace
- Kitchen
د.إ.1,104/Night
7 Nights - د.إ.7,728
House
10.0Exceptional
(40 Reviews)
3 Bedrooms
1 Bath
6 Guests
1722 ft²
- Private Pool
- Fireplace/Heating
- Pool
- Ocean View
د.إ.1,116/Night
7 Nights - د.إ.7,816
Apartment
10.0Exceptional
(38 Reviews)
1 Bedroom
1 Bath
4 Guests
646 ft²
- Fireplace/Heating
- Pool
- Ocean View
- Balcony/Terrace
د.إ.499/Night
7 Nights - د.إ.3,489
Villa
10.0Exceptional
(37 Reviews)
3 Bedrooms
3 Baths
6 Guests
2260 ft²
- Private Pool
- Fireplace/Heating
- Pool
- Balcony/Terrace
د.إ.2,684/Night
7 Nights - د.إ.18,788
Pet-Friendly Holiday Rentals in Cortona
Over 812+ Pet-Friendly Holiday Rentals in or Near Cortona
Villa
9.6Exceptional
(46 Reviews)
5 Bedrooms
2 Baths
9 Guests
2153 ft²
- Private Pool
- Fireplace/Heating
- Pool
- Balcony/Terrace
د.إ.2,207/Night
7 Nights - د.إ.15,449
House
8.6Fabulous
(5 Reviews)
7 Bedrooms
6 Baths
19 Guests
766.39 ft²
- Pool
- Balcony/Terrace
- Pet Friendly
- Kitchen
د.إ.408/Night
7 Nights - د.إ.2,854
Villa
10.0Exceptional
(1 Review)
1 Bedroom
1 Bath
- Fireplace/Heating
- Pool
- Balcony/Terrace
- Pet Friendly
د.إ.1,352/Night
7 Nights - د.إ.9,462
Villa
9.2Exceptional
(47 Reviews)
3 Bedrooms
2 Baths
6 Guests
2153 ft²
- Private Pool
- Hot Tub
- Fireplace/Heating
- Pool
د.إ.1,962/Night
7 Nights - د.إ.13,738
Bed & Breakfast
9.0Exceptional
(26 Reviews)
2 Bedrooms
2 Baths
6 Guests
215.28 ft²
- Hot Tub
- Balcony/Terrace
- Breakfast
- Pet Friendly
د.إ.419/Night
7 Nights - د.إ.2,931
Villa
9.8Exceptional
(29 Reviews)
4 Bedrooms
4 Baths
8 Guests
3875 ft²
- Private Pool
- Fireplace/Heating
- Pool
- Ocean View
د.إ.1,678/Night
7 Nights - د.إ.11,747
Villa
9.0Exceptional
(19 Reviews)
4 Bedrooms
3 Baths
8 Guests
1830 ft²
- Private Pool
- Fireplace/Heating
- Pool
- Balcony/Terrace
د.إ.1,327/Night
7 Nights - د.إ.9,289
House
10.0Exceptional
(30 Reviews)
5 Bedrooms
2 Baths
12 Guests
1830 ft²
- Private Pool
- Fireplace/Heating
- Pool
- Ocean View
د.إ.1,492/Night
7 Nights - د.إ.10,443
Villa
9.8Exceptional
(15 Reviews)
4 Bedrooms
5 Baths
12 Guests
2260 ft²
- Private Pool
- Fireplace/Heating
- Pool
- Balcony/Terrace
د.إ.1,211/Night
7 Nights - د.إ.8,474
Large Holiday Rentals and Private Villas in Cortona
Over 679+ Large Holiday Rentals and Private Villas in or Near Cortona
Villa
9.8Exceptional
(35 Reviews)
4 Bedrooms
4 Baths
9 Guests
2691 ft²
- Private Pool
- Fireplace/Heating
- Pool
- Ocean View
د.إ.1,202/Night
7 Nights - د.إ.8,415
Villa
8.0Excellent
(1 Review)
4 Bedrooms
4 Baths
8 Guests
1679.17 ft²
- Pool
- Balcony/Terrace
- Breakfast
- Kitchen
د.إ.2,167/Night
7 Nights - د.إ.15,174
Villa
1 Bedroom
1 Bath
- Fireplace/Heating
- Pool
- Balcony/Terrace
- Pet Friendly
د.إ.940/Night
7 Nights - د.إ.6,582
Villa
- Cortona
- ·
- San Pietro a Cegliolo
- 0.43 mi to center
10.0Exceptional
(22 Reviews)
8 Bedrooms
7 Baths
15 Guests
3229 ft²
- Private Pool
- Fireplace/Heating
- Pool
- Balcony/Terrace
د.إ.2,674/Night
7 Nights - د.إ.18,718
Villa
4 Bedrooms
4 Baths
10 Guests
1614.59 ft²
- Pool
- Balcony/Terrace
- Breakfast
- Pet Friendly
د.إ.1,840/Night
7 Nights - د.إ.12,878
Villa
10.0Exceptional
(1 Review)
10 Bedrooms
9 Baths
22 Guests
4306 ft²
- Private Pool
- Fireplace/Heating
- Pool
- Balcony/Terrace
د.إ.2,761/Night
7 Nights - د.إ.19,324
Villa
9.4Exceptional
(13 Reviews)
4 Bedrooms
4 Baths
10 Guests
3660 ft²
- Private Pool
- Fireplace/Heating
- Pool
- Balcony/Terrace
د.إ.1,520/Night
7 Nights - د.إ.10,641
Villa
10.0Exceptional
(8 Reviews)
1 Bedroom
1 Bath
4 Guests
592 ft²
- Private Pool
- Fireplace/Heating
- Pool
- Balcony/Terrace
د.إ.893/Night
7 Nights - د.إ.6,252
Villa
- Cortona
- ·
- Fratticciola
- 0.01 mi to center
10.0Exceptional
(5 Reviews)
12 Bedrooms
13 Baths
24 Guests
8181 ft²
- Private Pool
- Hot Tub
- Fireplace/Heating
- Pool
د.إ.7,386/Night
7 Nights - د.إ.51,700
Wheelchair Accessible Holiday Homes in Cortona
Over 51+ Wheelchair Accessible Holiday Homes in or Near Cortona
Apartment
- Cortona
- ·
- Cortona Old Town
- 0.26 mi to center
10.0Exceptional
(4 Reviews)
3 Bedrooms
3 Baths
6 Guests
1399 ft²
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
- Air Conditioner
د.إ.929/Night
7 Nights - د.إ.6,501
Villa
10.0Exceptional
4 Bedrooms
3 Baths
8 Guests
1722.23 ft²
- Pool
- Pet Friendly
- Kitchen
- Parking
د.إ.713/Night
7 Nights - د.إ.4,988
Bed & Breakfast
- Cortona
- ·
- Cortona Old Town
- 0.18 mi to center
1 Bedroom
1 Bath
- Breakfast
- Internet
- Child Friendly
Wheelchair Accessible
د.إ.955/Night
7 Nights - د.إ.6,681
Villa
- Cortona
- ·
- Metelliano
- 0.03 mi to center
10.0Exceptional
(3 Reviews)
5 Bedrooms
6 Baths
10 Guests
2852 ft²
- Private Pool
- Fireplace/Heating
- Pool
- Balcony/Terrace
د.إ.6,462/Night
7 Nights - د.إ.45,235
Villa
6 Bedrooms
4 Baths
12 Guests
3229.17 ft²
- Pool
- Balcony/Terrace
- Kitchen
- Parking
د.إ.1,224/Night
7 Nights - د.إ.8,569
Apartment
3 Bedrooms
3 Baths
6 Guests
1399 ft²
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
- Air Conditioner
د.إ.1,377/Night
7 Nights - د.إ.9,638
House
10.0Exceptional
(2 Reviews)
2 Bedrooms
1 Bath
4 Guests
753 ft²
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
- Kitchen
د.إ.601/Night
7 Nights - د.إ.4,209
Villa
- Cortona
- ·
- Fratticciola
- 0.06 mi to center
10 Bedrooms
10 Baths
18 Guests
8073 ft²
- Private Pool
- Pool
- Balcony/Terrace
- Kitchen
د.إ.5,684/Night
7 Nights - د.إ.39,788
Villa
4 Bedrooms
5 Baths
8 Guests
- Fireplace/Heating
- Pool
- Balcony/Terrace
- Kitchen
د.إ.4,720/Night
7 Nights - د.إ.33,040
Cortona Private Villas and Holiday Homes Under $200
Over 701+ Cortona Private Villas and Holiday Homes Under $200
Apartment
10.0Exceptional
(67 Reviews)
2 Bedrooms
2 Baths
4 Guests
969 ft²
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
- Parking
د.إ.627/Night
7 Nights - د.إ.4,393
Villa
10.0Exceptional
(4 Reviews)
4 Bedrooms
2 Baths
8 Guests
645.84 ft²
- Hot Tub
- Balcony/Terrace
- Breakfast
- Kitchen
د.إ.599/Night
7 Nights - د.إ.4,191
House
- Cortona
- ·
- Casorbica-Salcotto
- 0.11 mi to center
10.0Exceptional
(1 Review)
1 Bedroom
1 Bath
- Private Pool
- Fireplace/Heating
- Pool
- Balcony/Terrace
د.إ.322/Night
7 Nights - د.إ.2,252
Apartment
- Cortona
- ·
- Cortona Old Town
- 0.24 mi to center
10.0Exceptional
(17 Reviews)
1 Bedroom
1 Bath
2 Guests
538 ft²
- Fireplace/Heating
- Kitchen
- Parking
- Air Conditioner
د.إ.406/Night
7 Nights - د.إ.2,839
Apartment
- Cortona
- ·
- Cortona Old Town
- 0.18 mi to center
9.0Exceptional
(1 Review)
2 Bedrooms
2 Baths
6 Guests
1076.39 ft²
- Pet Friendly
- Air Conditioner
- Internet
Laundry
د.إ.343/Night
7 Nights - د.إ.2,402
Apartment
10.0Exceptional
(12 Reviews)
1 Bedroom
1 Bath
4 Guests
700 ft²
- Fireplace/Heating
- Pool
- Balcony/Terrace
- Kitchen
د.إ.713/Night
7 Nights - د.إ.4,992
Apartment
- Cortona
- ·
- Cortona Old Town
- 0.04 mi to center
9.8Exceptional
(36 Reviews)
2 Bedrooms
1 Bath
4 Guests
936 ft²
- Fireplace/Heating
- Kitchen
- Parking
- Air Conditioner
د.إ.709/Night
7 Nights - د.إ.4,959
Apartment
- Cortona
- ·
- Cortona Old Town
- 0.41 mi to center
10.0Exceptional
(2 Reviews)
1 Bedroom
1 Bath
2 Guests
377 ft²
- Fireplace/Heating
- Breakfast
- Kitchen
- Air Conditioner
د.إ.546/Night
7 Nights - د.إ.3,820
Apartment
10.0Exceptional
(2 Reviews)
1 Bedroom
1 Bath
2 Guests
538 ft²
- Fireplace/Heating
- Kitchen
- Parking
- Internet
د.إ.520/Night
7 Nights - د.إ.3,640
Instantly Bookable Holiday Homes in Cortona
Over 1012+ Instantly Bookable Holiday Homes in or Near Cortona
House
10.0Exceptional
(21 Reviews)
2 Bedrooms
2 Baths
6 Guests
1292 ft²
- Fireplace/Heating
- Pool
- Balcony/Terrace
- Kitchen
د.إ.1,507/Night
7 Nights - د.إ.10,549
Villa
9 Bedrooms
7 Baths
14 Guests
4306 ft²
- Private Pool
- Fireplace/Heating
- Pool
- Balcony/Terrace
د.إ.2,678/Night
7 Nights - د.إ.18,748
House
6 Bedrooms
6 Baths
14 Guests
3229 ft²
- Private Pool
- Fireplace/Heating
- Pool
- Kitchen
د.إ.3,057/Night
7 Nights - د.إ.21,403
Villa
10.0Exceptional
(10 Reviews)
5 Bedrooms
3 Baths
12 Guests
1938 ft²
- Private Pool
- Fireplace/Heating
- Pool
- Balcony/Terrace
د.إ.1,428/Night
7 Nights - د.إ.9,995
Apartment
10.0Exceptional
(4 Reviews)
3 Bedrooms
3 Baths
6 Guests
2691 ft²
- Fireplace/Heating
- Pool
- Balcony/Terrace
- Kitchen
د.إ.2,392/Night
7 Nights - د.إ.16,742
Apartment
10.0Exceptional
(4 Reviews)
1 Bedroom
1 Bath
2 Guests
538 ft²
- Fireplace/Heating
- Pool
- Balcony/Terrace
- Kitchen
د.إ.1,065/Night
7 Nights - د.إ.7,453
Villa
- Cortona
- ·
- Fratticciola
- 0.09 mi to center
9.8Exceptional
(6 Reviews)
12 Bedrooms
13 Baths
24 Guests
8181 ft²
- Private Pool
- Hot Tub
- Fireplace/Heating
- Pool
د.إ.7,962/Night
7 Nights - د.إ.55,733
House
7.4Very Good
(3 Reviews)
4 Bedrooms
2 Baths
9 Guests
1399 ft²
- Fireplace/Heating
- Pet Friendly
- Kitchen
- Parking
د.إ.918/Night
7 Nights - د.إ.6,424
House
10.0Exceptional
(1 Review)
7 Bedrooms
7 Baths
15 Guests
4628 ft²
- Private Pool
- Fireplace/Heating
- Pool
- Balcony/Terrace
د.إ.1,606/Night
7 Nights - د.إ.11,244
Book a Last Minute Place to Stay in Cortona
About Casai's Private Villas and Holiday Rentals in Cortona
Discover more than 1773 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 1411.38 ft², with nightly prices averaging د.إ.1,555.
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.
Show more
Show less
Top Accommodation Types in Cortona
| Type | Count |
|---|---|
| Holiday Apartments | 602 |
| Villas | 519 |
| Vacation Homes | 455 |
| 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.
- Stunning private villa with private pool, A/C, WIFI, TV, patio, panoramic view, close to Cortona
- Fattoria del Nonno Berto
- Villa Eugenio
- Casale Miro - Country villa with private pool
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:
- Stunning private villa with private pool, A/C, WIFI, TV, patio, panoramic view, close to Cortona
- Casale Pietrenta
- Casa Kita
How many Casai.ae holiday rentals are available in Cortona?
As of 2026, Casai boasts over 1773 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 | 697 |
People Also Ask
Finding the best prices in Cortona
Map
