Agriturismo Casa Paradiso, near Cortona, offers a peaceful countryside retreat approximately 30km from Piazza Grande and 37km from Montepulciano Terme. This pet-friendly house boasts a fully equipped kitchen, private parking, a garden, and barbecue facilities, providing bicycle use and easy access to local walking tours.
9.5 55 reviews
Cortona
14/09 – 24/09
SG$453/nighttotal: SG$4530 (10 )
Villa Primula By Posarellivillas
5 4
house , Cortona
Villa Primula is located in the village of Camucia, just 3.5 kilometres from the medieval town of Cortona and a 15-minute drive from Lake Trasimeno, offering a peaceful escape from the hustle and bustle. This property has received excellent user ratings for its location and cleanliness, as well as a very good rating overall. This five-bedroom villa, spread across 200 square metres, offers ample space for families or groups of friends. The property is equipped with modern amenities such as Wi-Fi, a washing machine, and a swimming pool, as well as a charming garden and terrace, perfect for enjoying the Tuscan sunshine.
8.7 298 reviews
Cortona
21/06 – 24/06
SG$210/nighttotal: SG$630 (3 )
Beautiful Holiday Home With View Over Cortona In Beautiful Surroundings
2 4
chalet , Cortona
This charming chalet is located in the tranquil countryside just outside Cortona, a short drive from the historic Piazza Grande and the thermal baths of Montepulciano Terme. It has received excellent ratings for its cleanliness, location, and overall experience, making it a popular choice for travellers seeking a peaceful retreat. The property features spacious terraces, a private swimming pool, and a well-equipped kitchen. Guests can enjoy stunning views of the surrounding countryside, relax in the spa, or dine at the on-site restaurant.
10 33 reviews
Cortona
21/06 – 24/06
SG$489/nighttotal: SG$1467 (3 )
Romantic Cottage On A Farm With A View Of Cortona
2 4
farm , Cortona
This family-friendly farmhouse is located just outside Cortona, within 5 kilometres of the Casali Palace, Museo Diocesano, Cortona Cathedral, Palazzo Comunale, and Signorelli Theatre. The gîte offers a private garden, barbecue grills, a swimming pool, a fitness centre, and a peaceful lakeside setting.
9.3 84 reviews
Cortona
12/09 – 03/10
SG$171/nighttotal: SG$3591 (21 )
Villa Il Giuggiolo Villa In Tuscany
1 4
house , Cortona
Villa il Giuggiolo is a luxurious villa located in Cortona, Tuscany, 34km from Piazza Grande and 48km from Perugia Cathedral. This family-friendly property offers a private infinity pool, an open-air bath, a well-equipped kitchen, a fireplace, a restaurant, a tennis court, and a fitness centre.
10 1 review
Cortona
27/06 – 01/07
SG$581/nighttotal: SG$2324 (4 )
Casa Bel Tramonto Con Giardino Privato A Cortona
3 4
house , Cortona
Casa Bel Tramonto is a charming house situated in Cortona, just 30 kilometres from Piazza Grande and 37 kilometres from Montepulciano Terme, offering a peaceful escape in the Tuscan countryside. The property is a spacious 300 square metre home with 3 bedrooms and 3 bathrooms, comfortably accommodating up to 11 guests. Enjoy a well-equipped kitchen, air conditioning, a private garden with terrace, and access to a washing machine, satellite TV and Wi-Fi.
8.8 292 reviews
Cortona
21/06 – 24/06
SG$438/nighttotal: SG$1314 (3 )
Agriturismo Frantoio Valiani
3 4
farm , Cortona
Agriturismo Frantoio Valiani is a charming farm stay situated in the peaceful countryside, just 17 miles from the historic Piazza Grande in Cortona and 23 miles from Montepulciano Terme. The property has consistently received excellent ratings for its location, cleanliness, and overall experience. This one-bedroom farmhouse offers a peaceful retreat with a garden and a dedicated picnic area. Guests can enjoy free Wi-Fi, parking, and a continental or Italian breakfast, as well as cycling opportunities in the surrounding countryside.
9.1 117 reviews
Cortona
27/06 – 01/07
SG$241/nighttotal: SG$964 (4 )
Borgo In San Angelo
2 4
house , Cortona
This detached house is situated in the countryside near Cortona, approximately 34 kilometres from Piazza Grande and 50 kilometres from Perugia Cathedral. The property offers a private entrance, stunning garden views, a swimming pool, yoga classes, a fully equipped kitchen, air-conditioned rooms, free Wi-Fi, parking and a sun terrace.
9.9 28 reviews
Cortona
27/06 – 01/07
SG$851/nighttotal: SG$3404 (4 )
Agriturismo Le Celle
4 4
house , Cortona
Agriturismo Le Celle is a charming villa located just 31 km from Cortona's historic Piazza Grande, offering a peaceful setting outside the bustling town centre. This property enjoys excellent user, location and cleanliness ratings. The villa spans 130 square metres and features four bedrooms. Guests can enjoy a private pool, a shared outdoor pool, a garden with barbecue facilities, free Wi-Fi, and private parking.
9.6 4 reviews
Cortona
15/11 – 17/11
SG$230/nighttotal: SG$460 (2 )
Agriturismo Villa Augusto
1 1
gîte , Cortona
Villa Augusto, in Cortona's tourist district, offers easy access to the town's attractions, its precise location within the historic centre unspecified. This family-friendly hotel boasts an outdoor pool, tennis courts, billiards, a tranquil garden, BBQ facilities, and room service, ensuring a comfortable stay.
Cortona
14/09 – 24/09
SG$242/nighttotal: SG$2420 (10 )
La Limonaia Cortona
2 4
house , Cortona
La Limonaia Cortona, a recently renovated holiday home, is located 27 kilometres from Piazza Grande, offering a peaceful retreat with easy access to local sights. This property features 2 bedrooms accommodating up to 7 guests, a fully equipped kitchen with a dishwasher, air conditioning, a seasonal outdoor swimming pool, a garden, and a terrace with mountain views, all set within 50 square metres of floor area and with complimentary private parking and Wi-Fi.
9.7 8 reviews
Cortona
12/09 – 03/10
SG$287/nighttotal: SG$6027 (21 )
Borgo La Fonte - Together In Tuscany
2 4
house , Cortona
This Cortona holiday home, located in the Borgo La Fonte district, is 30.6km from Piazza Grande and offers easy access by car to Montepulciano Terme (35.4km) and the Magione Motorspeedway (32.2km). The 105 square metre property features two bedrooms, two bathrooms, and can accommodate seven guests, boasting a fully equipped kitchen, air conditioning, free Wi-Fi, private parking, and a terrace.
Best Cortona villas and holiday homes with a pool
Among the 74 accommodations in Cortona, here are the 4 best villas and holiday homes with a pool
8.7 3 reviews
Cortona
12/09 – 03/10
SG$689/nighttotal: SG$14469 (21 )
Villa Mimosa
5 4
house , Cortona
Villa Mimosa, near Cortona, is situated approximately 34 kilometres from Piazza Grande and 39 kilometres from Montepulciano Terme, offering easy access to these Tuscan landmarks. This five-bedroom property boasts 175 square metres of living space, sleeping up to 19 guests, and features a private swimming pool, garden, and free Wi-Fi; it also includes a fully equipped kitchen, air conditioning and ample parking.
10 1 review
Cortona
21/06 – 24/06
SG$235/nighttotal: SG$705 (3 )
Rina
3 4
farm , Cortona
This farmhouse, situated in Camucia, 5km from Cortona and 20km from Lake Trasimeno, offers easy access to other Tuscan towns such as Castiglion Fiorentino and Arezzo. The 'Rina' apartment boasts 120 square metres of space, comprising three bedrooms, two bathrooms, a terrace, and a private patio, sleeping up to six guests and featuring a kitchen with a microwave and dishwasher, plus a shared swimming pool and barbecue area.
8.9 154 reviews
Cortona
27/06 – 01/07
SG$422/nighttotal: SG$1688 (4 )
Villa In Cortona With Pool
1 4
house , Cortona
Villa Nigra is situated in Cortona, just 30km from Piazza Grande and 37km from Montepulciano Terme, making it an ideal base for exploring the charming Tuscan countryside. The property has received very good ratings for cleanliness and user experience, with an excellent location rating. This holiday home offers a private swimming pool, a fitness centre, and air conditioning for a comfortable stay. Guests can enjoy a fully equipped kitchen, an outdoor terrace with barbecue facilities, free Wi-Fi, a peaceful garden, a sauna, a spa, and parking.
Cortona
17/09 – 15/10
SG$812/nighttotal: SG$22736 (28 )
Casa Pippin 8, Emma Villas
4 2
house , Cortona
Casa Pippin, a 200 square metre farmhouse, is situated in the Tuscan countryside a few kilometres from Cortona, offering easy access to explore both Tuscany and Umbria. This five-bedroom, three-bathroom property sleeps eight guests and boasts a private infinity pool, 2400 square metre garden with barbecue, and stunning panoramic views; utilities, linen and cleaning are included in the rental price, along with Zer0Dep accidental damage cover.
Best Cortona villas and holiday homes with a kitchen
10 7 reviews
Cortona
10/08 – 16/08
SG$258/nighttotal: SG$1548 (6 )
La Vecchia Casa Di Moda
3 2
house , Cortona
This charming house is situated in Cortona, just 19km from the historic Piazza Grande and 23km from the spa town of Montepulciano Terme, offering a peaceful retreat in a quiet neighbourhood. The property has received excellent ratings for its location, cleanliness and overall experience. The house spans 70 square metres and features two bedrooms and two bathrooms. Guests can enjoy a fully equipped kitchen, a terrace with city views, a garden, a tennis court, and free Wi-Fi, ensuring a comfortable and enjoyable stay.
Cortona
14/09 – 24/09
SG$248/nighttotal: SG$2480 (10 )
Villa Le Dodici Querce Cortona
3 4
house , Cortona
This villa in Cortona offers proximity to Piazza Grande, 34 kilometres away, and Magione Motorspeedway, 37 kilometres distant. This 100 square metre property accommodates up to five guests in three bedrooms and two bathrooms, featuring air conditioning, WiFi, a kitchen with a microwave and dishwasher, a terrace, garden, tennis court, and private parking, with bicycle hire available for exploring the area.
9.1 666 reviews
Cortona
21/06 – 24/06
SG$318/nighttotal: SG$954 (3 )
Monastero San Silvestro
2 4
farm , Cortona
Monastero San Silvestro is a farm located near Cortona in the Valdichiana Valley, just 15 kilometres from Lake Trasimeno and a short drive from Mount Amiata. This property has received excellent ratings for location, cleanliness, and overall user experience. The farm offers spacious apartments decorated in a traditional Tuscan style. Guests can enjoy the outdoor swimming pool with views of Cortona and the Valdichiana Valley, as well as BBQ facilities, a garden, and free parking.
9.8 10 reviews
Cortona
17/09 – 15/10
SG$857/nighttotal: SG$23996 (28 )
Romantic Lux Country House
3 2
house , Cortona
This charming villa is located in a peaceful hamlet in the Tuscan hills, just 35km from Cortona and 45km from Siena. It has received excellent reviews from previous guests, who have praised its stunning views and luxurious amenities. The property offers 105 square meters of living space, comfortably accommodating up to 8 guests. It features a private infinity pool with a jacuzzi, a spacious garden, and a covered patio, perfect for enjoying the Tuscan sunshine and al fresco dining.
Frequently asked questions about villa rentals in Cortona
What are the must-see attractions in and around Cortone?
Cortona is a treasure trove of historical and cultural attractions. You absolutely must visit the Etruscan Academy Museum, which houses a vast collection of Etruscan artefacts. And don't miss the stunning views from the Fortezza Medicea, a 16th-century fortress overlooking the valley.
What types of wildlife can travelers expect to see in the area of Cortone?
The countryside around Cortona is a haven for wildlife. You're likely to spot red squirrels scampering through the trees, as well as numerous species of birds, including owls, hawks, and woodpeckers. If you're lucky, you might even catch a glimpse of a wild boar or a fox.
What are the best villa rentals with a pool in Cortona?
Spring and autumn are the most pleasant times to visit Cortona, as the weather is mild and the crowds are smaller. You'll enjoy beautiful blooms in the spring and vibrant colours in the fall.
What are the best villa rentals with a jacuzzi in Cortona?
When is it easiest to book a villa rental in Cortone?
Booking a villa rental in Cortona is easiest outside of the peak season, which is from June to August. You'll find better availability and often lower prices if you travel in the shoulder seasons, April to May or September to October.
What are the best villa rentals for families and kids in Cortona?
The area around Cortona is a hiker's paradise. Two popular trails are the Sentiero del Perugino, which leads to a stunning viewpoint overlooking Lake Trasimeno, and the Sentiero della Val di Chiana, offering beautiful views of the valley.
What are the best pet friendly villa rentals in Cortona?
What are the advantages of renting a house or a villa in Cortone
Renting a villa in Cortona offers a more authentic and private experience. You'll have your own space to relax and enjoy the beautiful surroundings, and you'll be able to cook your own meals and enjoy the local produce.
What are the best villa rentals with parking in Cortona?
Cortona is perfectly situated for exploring Tuscany. Within easy reach are the charming towns of Montepulciano, Pienza, and Arezzo. And of course, the beautiful city of Florence is just a short drive away.
Destinations nearby
Best Cortona villas and holiday homes with a fireplace
9.7 9 reviews
Cortona
27/06 – 01/07
SG$536/nighttotal: SG$2144 (4 )
550 M² House ∙ 3 Bedrooms ∙ 8 Guests
3 4
house , Cortona
This spacious villa is located in the Cortona countryside, approximately 20km from Lake Trasimeno and 30km from Arezzo, offering easy access to both. The 550 square metre property boasts three bedrooms, three bathrooms, and sleeps eight, featuring a swimming pool, fitness centre, and large garden with stunning views; bike trails and water sports are also nearby.
9.3 6 reviews
Cortona
14/09 – 24/09
SG$478/nighttotal: SG$4780 (10 )
170 M² Villa ∙ 4 Bedrooms ∙ 8 Guests
4 4
house , Cortona
This spacious 170 square metre villa, located in Cortona's historic district, offers convenient access to the town's Renaissance architecture and cultural sites, with its precise location placing it within easy reach of local landmarks. This property accommodates up to 8 guests across 4 bedrooms, featuring air conditioning, a fully equipped kitchen with a dishwasher and freezer, a swimming pool, garden, parking, and multiple living areas including one with a fireplace.
Cortona
12/09 – 03/10
SG$895/nighttotal: SG$18795 (21 )
Villa In Cortona With 8 Bedrooms Sleeps 16
8 4
house , Cortona
Villa Il Gelso is a historic 16th-century stone and brick villa located at the foot of Cortona, with the Etruscan Archaeological Park just meters away, offering convenient access to Tuscan and Umbrian cities. This substantial property, spanning 400 square meters, features 8 bedrooms and 8 bathrooms to accommodate up to 16 guests, a 5x12 meter fenced swimming pool open from May to October, a fully equipped communal kitchen, and is equipped with Wi-Fi and air conditioning.
9.0 3 reviews
Cortona
12/09 – 03/10
SG$795/nighttotal: SG$16695 (21 )
Casale Il Gelso By Vacavilla
8 4
house , Cortona
Il Gelso is a renovated farmhouse located just outside Cortona, less than 3km from the town centre and a 15-minute drive from Lake Trasimeno. The property has received very good ratings for its location, cleanliness and overall experience. The apartments feature traditional Tuscan furnishings, tiled floors, and some have wood-beamed ceilings. Guests can enjoy amenities such as a swimming pool, BBQ facilities, free bike rental, and a spacious garden.
Best Cortona villas and holiday homes with jacuzzi
8.6 104 reviews
Cortona
27/06 – 01/07
SG$387/nighttotal: SG$1548 (4 )
Spacious Villa In Cortona With Private Pool
1 4
house , Cortona
This charming house is located in Cortona Old Town, just a short walk from the Santa Margherita Basilica, Signorelli Theatre, and Piazza della Repubblica, offering easy access to the area's historical attractions and vibrant atmosphere. It has received very good ratings for user experience, location, and cleanliness. The house spans 120 square metres and comfortably accommodates up to 6 guests across 3 bedrooms and 1 bathroom. It features a private pool, a sauna, a spa, a fitness centre, a garden, a terrace, and a fully equipped kitchen, allowing guests to enjoy a relaxing and luxurious stay.
9.8 17 reviews
Cortona
17/09 – 15/10
SG$447/nighttotal: SG$12516 (28 )
Fattoria Del Nonno Berto
2 2
farm , Cortona
Fattoria del Nonno Berto is a farm stay situated near Cortona, approximately 30 kilometres from Piazza Grande and 39 kilometres from Montepulciano Terme. This family-friendly farm offers guests a range of amenities including a swimming pool, jacuzzi, spa, restaurant, tennis court, and fitness centre, as well as packed lunches for exploring the Tuscan countryside.
9.6 57 reviews
Cortona
15/11 – 17/11
SG$308/nighttotal: SG$616 (2 )
Fonte Comelia
2 1
house , Cortona
The Fonte Comelia house is situated on the hills outside Cortona, 1.9 kilometres from the town centre, with Lake Trasimeno 12 kilometres away and Arezzo and Montepulciano both 30 kilometres distant. It has received excellent ratings for location, cleanliness and overall user experience. The property is a 96 square metre, two-bedroom villa that can accommodate up to four guests. It offers a range of amenities, including a terrace with a hot tub, a rustic-style patio with free BBQ facilities, a fireplace, air conditioning, a fully equipped kitchen, two bathrooms, and access to a nearby hotel’s restaurant and swimming pool.
10 1 review
Cortona
14/09 – 24/09
SG$1309/nighttotal: SG$13090 (10 )
Villa Casupoli
3 4
house , Castiglion Fiorentino
Villa Casupoli, a secluded property 24 kilometres from Castiglion Fiorentino's Piazza Grande, offers tranquil accommodation with easy access to the town. This 160 square metre villa boasts three bedrooms, five bathrooms, and can comfortably sleep eleven guests, featuring a private pool, hot tub, and terrace with barbecue facilities.