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Vacation rentals in Cortona

Italy

Tuscany/Elba

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Cortona

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72

Villa in Tuscany with Pool and Olive Garden
Villa in Tuscany with Pool and Olive Garden
Tucked into the rolling hills of Valdichiana, just a short drive from the enchanting medieval town of Cortona, Villa Maria Elena is a serene haven for those seeking to relax in the timeless beauty of the Tuscan countryside. Ideal for families and small groups, the villa effortlessly combines rustic charm with modern comforts. Surrounded by a lush, flower-filled garden and centuries-old olive trees, the property offers the perfect blend of privacy, natural beauty, and accessibility to Tuscany and Umbria's cultural treasures such as Montepulciano, Assisi, Siena, and Lake Trasimeno. Recently renovated and elegantly furnished, the villa accommodates up to six guests across two floors. The interiors feature warm parquet floors, stylish living areas, and three comfortable double bedrooms plus a single room. The well-equipped kitchen connects to a covered veranda where guests can dine alfresco or unwind with a glass of wine. A beautiful stone fireplace and cozy seating in the living room make evenings at home just as inviting. Outside, the sun-drenched swimming pool area is a highlight, complete with sun loungers, umbrellas, and a poolside bathroom — perfect for long, lazy days under the Tuscan sun. Villa Maria Elena also offers free Wi-Fi, Smart TV, mosquito nets, air conditioning (upon request), and a laundry room with washer and dryer. The fully fenced property provides peace of mind, with a private entrance gate and on-site parking. Nearby services, such as supermarkets, train stations, and tennis courts, are all within easy reach. Whether you’re exploring historic villages or simply enjoying the countryside from your veranda, this is a place where unforgettable memories are made.
Ground floor: (open kitchen(stove, electric kettle, toaster, coffee machine(espresso), oven, microwave, dishwasher, fridge-freezer, dishes and cutlery, Cooking basics), Living/diningroom(TV(satellite, smart TV), dining table, fireplace, air conditioning), bedroom(double bed, fireplace, air conditioning))\n\nOn the 1st floor: (bedroom(double bed, air conditioning), bedroom(double bed, air conditioning), bedroom(single bed, air conditioning), bathroom(shower, washbasin, toilet, bidet, hairdryer), bathroom(shower, washbasin, toilet, bidet, hairdryer))\n\nwashing machine, balcony, patio, garden, garden furniture, sun loungers, BBQ, parasol, swimming pool(private)

Guests

7

Bathrooms

2

Bedrooms

4

Villa

Price from €

per night

Price not yet available

Villa Farneta Comfortable holiday residence
Villa Farneta Comfortable holiday residence
Elegant villa with private garden and pool, located in the splendid countryside of Valdichiana, near Cortona.

Guests

17

Bathrooms

7

Bedrooms

8

Villa

Price from €

1958

per night

Price not yet available

Villa Montecchio Comfortable holiday residence
Villa Montecchio Comfortable holiday residence
Fantastic villa with pool and air conditioning, located in a panoramic position in the countryside of Castiglion Fiorentino, near Cortona.

Guests

11

Bathrooms

3

Bedrooms

4

Villa

Price from €

0

per night

Price not yet available

Farmhouse in Cortona with pool
Farmhouse in Cortona with pool
A charming holiday home nestled in the Tuscan countryside, this cozy farmhouse apartment accommodates up to four guests with two comfortable bedrooms and one bathroom. Ideal for families or couples, it is pet-friendly and welcomes up to two pets for an additional fee. Guests can enjoy complimentary activities such as table tennis in the garden area and unwind by the indoor fireplace. The property features a dedicated workspace and a TV with satellite channels, making it a relaxing yet practical retreat. While there's no balcony or sofa specifically mentioned, the property does have inviting outdoor seating areas perfect for leisure._x000D_ _x000D_ Located just 2 km from the historic center of Cortona, guests will find themselves surrounded by traditional restaurants, local markets, and charming cafés. A nearby forest (500 m) is perfect for scenic walks, while the tranquil Lake Trasimeno lies 20 km away for day trips. Public transport is easily accessible within 1 km, and the nearest motorway is 28 km from the property, offering good regional connectivity. Guests can explore cultural landmarks, wine estates, and artisan shops typical of this region in Tuscany._x000D_ _x000D_ The holiday home includes a fully equipped kitchen with an oven, toaster, freezer, kettle, and coffee maker-ideal for preparing home-cooked meals. The bathroom features a bidet and all essential toiletries, though shampoo and hairdryer are not provided. Additional conveniences include a washing machine, ironing facilities, garden with barbecue grill, and private entrance._x000D_
On the 1st floor: (Kitchen(hob, electric kettle, toaster, cooker, hood, espresso machine, oven, fridge-freezer), Living/diningroom(TV, dining table, fireplace, seating area), bedroom(double bed), bedroom(double bed or 2 single beds), bathroom(shower, washbasin, toilet, bidet))\n\nwashing room(washing machine, ironing board, iron), garden(shared with other guests), garden furniture, BBQ, swimming pool(shared with other guests, 8 x 4 m., opened from 1/2 May upto and including Sep), table tennis table

Guests

4

Bathrooms

1

Bedrooms

2

Farmhouse

Price from €

69

per night

Price not yet available

Villa in Cortona with Pool and Valley Views
Villa in Cortona with Pool and Valley Views
In the hills just outside the Etruscan gem of Cortona, this beautiful home offers a perfect blend of rustic charm and contemporary comfort. With sweeping views over the valley and the city, it provides a tranquil setting for a relaxing escape. The property features two tastefully furnished independent apartments and a delightful studio set right by the poolside, each with its own private outdoor space. A large, flower-filled garden, a sparkling pool with Jacuzzi, and thoughtfully designed shared spaces like the barbecue area and traditional wood-fired oven ensure guests enjoy a memorable and comfortable stay. Families are especially welcome with play equipment, a high chair, and a camping cot available. The historic centre of Cortona, just 3 km away, charms visitors with its cobbled streets, ancient walls, and stunning panoramic vistas. Nature lovers can head to Lake Trasimeno (18 km) for waterside relaxation, while culture enthusiasts can plan day trips to Perugia, Arezzo, Montepulciano, and even the medieval wonders of Siena and Assisi. For a unique shopping experience, Valdichiana Village offers designer outlets just 22 km away. Whether arriving by train or car, the property's proximity to transport hubs makes it a perfect base for exploration. Food lovers will find themselves in culinary heaven. Just minutes away in Camucia and Cortona, you'll find delightful bakeries and trattorias serving handmade pasta and locally sourced dishes. For an unforgettable dining experience, try La Bucaccia in Cortona, known for its rich Tuscan flavors in an intimate setting, or Osteria del Teatro with its refined menu and elegant ambience.
Ground floor: (Living room(double bed, TV(flatscreen, satellite), seating area, stereo unit), open kitchen(hob, electric kettle, boiling water tap, toaster, hood, coffee machine, microwave, fridge-freezer, Food processor), bathroom(shower, washbasin, toilet, bidet, hairdryer), Study(seating area))\n\nwashing room(washing machine(shared with other guests)), camping cot, heating(central), terrace(private), terrace(shared with other guests, roofed), garden(shared with other guests, fenced), garden furniture, BBQ(shared with other guests), parking, swimming pool(shared with other guests, outside, opened from May upto and including Sep), high chair, insect screens

Guests

2

Bathrooms

1

Bedrooms

0

Holiday home

Price from €

per night

Price not yet available

Villa near Cortona with Pool & Countryside Views
Villa near Cortona with Pool & Countryside Views
This property is 9 km from the charming Cortona immersed in the countryside with a splendid view of the surrounding hills. The Villa is located inside a ""Boboli Garden"" style park of about 5000 square meters, next to it is the main villa. This property can be rented individually or together with the main villa and is ideal for vacations with family and friends. The villa is near the Manzano Golf & Spa Resort designed by Gary Player Design. Spend the day at nearby Cortona or visit nice places such as Camucia (7 km) or Montepulciano (27 km). While enjoying a good glass of local wine, admire the surrounding landscape covered with sunflowers, age-old cypresses and pines. Take a cooling dip in the pool. If willing, prepare a meal of your choice in the well-equipped kitchen or on the barbecue. Parking is also available here. The property has been carefully restored using the highest quality materials from various parts of Italy to create a majestic experience. About Belvilla When you stay in a Belvilla home, you can rest assured of a unique holiday home in ideal surroundings at an attractive price. The portfolio of accommodations consists of more than 40,000-holiday homes in 20 European countries. Interested in a weekend getaway, a summer or winter sports holiday or simply a short break? Do you prefer the coast, the countryside or the mountains? Whatever your preference, there is a Belvilla home to meet your needs, from a cosy gîte for two to a castle big enough for the entire family, from an apartment in the heart of Rome to a cabin in the middle of nowhere, from a simple tree house to a luxury dream villa and from close to home to the other side of Europe. A Belvilla home gives you the freedom to enjoy breakfast in your pyjamas or continue a good conversation into the morning hours without having to worry about the bar's closing time. Prepare gourmet meals with fresh local ingredients in your own kitchen and take advantage of having your own swimming pool to do as many cannonballs as you want! In other words, you can enjoy complete privacy in your home away from home.
Ground floor: (Living room(seating area, DVD player), dining room(dining table), Kitchen(hob, electric kettle, boiling water tap, toaster, toaster, coffee machine, oven, microwave, dishwasher, fridge-freezer), bathroom(shower, washbasin, toilet, bidet, hairdryer))\n\nOn the 1st floor: (Living room(TV(flatscreen, satellite), seating area), bedroom(double bed), bedroom(double bed), bedroom(double bed), bedroom(double bed), bedroom(double bed), bathroom(shower, washbasin, toilet, bidet), bathroom(shower, washbasin, toilet, bidet), bathroom(shower, washbasin, toilet, bidet), bathroom(shower, washbasin, toilet, bidet), bathroom(bath tub, washbasin, toilet, bidet))\n\nwashing room(tumble dryer, washing machine, ironing board, iron), veranda, camping cot, heating, air conditioning, garden(private, fenced, 5000 m2), garden furniture, sun loungers, BBQ, parking, parasol, swimming pool(private, outside, 12 x 6 m., opened from May upto and including Sep), high chair

Guests

10

Bathrooms

6

Bedrooms

5

Villa

Price from €

per night

Price not yet available

Villa in Cortona with  pool
Villa in Cortona with pool
Nestled in the heart of Cortona’s historic landscape, this elegant villa blends Tuscan charm with modern comfort, creating a serene escape for families and friends. Step into a world where sun-drenched days unfold by your private pool, framed by olive trees and sweeping countryside views. The villa’s warm stone walls, tranquil garden, and inviting terraces make it a perfect place to unwind, share meals, and soak in the rhythm of Italian living. Set amid the rolling hills of Valdichiana, the villa is a gateway to some of Tuscany’s most beautiful cities. Spend your days exploring the art-filled streets of Florence, Siena, or Arezzo, each within easy reach. Wander through the cobbled alleys of Cortona — just a short walk away — where you’ll find charming cafés, local markets, and that timeless Tuscan atmosphere that makes this region so unforgettable. When evening falls, gather on the terrace for a glass of Chianti as the sun paints the hills in golden hues. Fire up the barbecue for an alfresco feast or simply relax under the stars, letting the quiet countryside wrap around you. With its panoramic views, private pool, and thoughtful touches — plus a kind caretaker nearby — this villa offers everything you need for a soulful, sun-soaked retreat in the heart of Tuscany.
On the 2nd floor: (Living room(TV, fireplace, seating area, air conditioning), Large kitchen(dining table, hob, hood, oven, fridge, washbasin), bedroom(double bed), Bedroom with bathroom(double bed, shower, washbasin, toilet, bidet), bathroom(shower, washbasin, toilet, bidet), mezzanine(via fairly steep stairs)(small double bed), heating, terrace(private, roofed, 15 m2))\n\nAnnex: (Bedroom with bathroom(double bed, shower, washbasin, toilet), veranda(seating area), heating, air conditioning, terrace)\n\nGuest house on the 1st floor: (relaxation area(bath tub), Turkish steambath(paid, 1 m2)(washbasin, toilet, fitness equipment))\n\nsanitary facility(shower, toilet, bidet), garden(private), garden furniture, sun loungers, BBQ, parking, swimming pool(private, outside, 6 x 3 m., opened from Jun upto and including Oct)

Guests

6

Bathrooms

3

Bedrooms

3

Villa

Price from €

per night

Price not yet available

Stone house villa with Spa in Cortona
Stone house villa with Spa in Cortona
Perched above Lake Trasimeno, Villa Serena is a peaceful, pet-friendly stone house designed for comfort, charm, and unforgettable views. Accommodating up to 6 guests, it’s the perfect retreat for families or friends seeking a true Tuscan experience. Just a short drive from Cortona, the home combines rustic beauty with modern wellness features, including WiFi and private parking. Inside, the villa showcases a welcoming living room with air conditioning and a large, well-equipped kitchen. Three bedrooms and two bathrooms provide comfort and functionality, while the antique furnishings add warmth and character. Step into the annex to enjoy the private hot tub, Turkish steam bath (paid), and fitness area. A log cabin with a private sauna (paid) completes the wellness offering. Outdoors, unwind in the lush private garden (200 m²) with a pool, bubble bath, barbecue, hammock, and patio for al fresco dining. Enjoy sunlit mornings, and calm evenings under the Tuscan sky. With wineries, historical landmarks, and the shores of Lake Trasimeno nearby, Villa Serena offers a perfect blend of relaxation and discovery.
On the 1st floor: (Living room(dining table, decorative fireplace, seating area, air conditioning), Large kitchen(dining table, hob, cooker, fridge-freezer, washbasin), bedroom(double bed), bedroom(8 m2)(small double bed), bedroom(10 m2)(small double bed), bathroom(shower(unit), washbasin, washbasin, toilet, bidet), toilet(washbasin, toilet), washing machine, heating)\n\nAnnex: (relaxation area(bath tub), Turkish steambath(paid, 1 m2), washbasin, toilet, fitness equipment)\n\nLog cabin: (sauna(private, paid, 3 persons))\n\nsanitary facility(shower, toilet, bidet), Bubble bath(private, outside, 5 persons), patio, garden(private, 200 m2), garden furniture, BBQ, parking, swimming pool(private, outside, 6 x 3 m.), hammock

Guests

6

Bathrooms

1

Bedrooms

3

Villa

Price from €

per night

Price not yet available

Holiday home in Cortona
Holiday home in Cortona
Casa Lamate,is a holiday home located in a panoramic position over the Valdichiana, holding features of Tuscan style. Surrounded by a large terrace and fenced garden represents the ideal place to spend relaxing moments underneath the olive and oak trees. A small corner is dedicated to the barbecue and wood-burning oven. Only a few km far from the well-known Etruscan town of Cortona rich in traditions, culture, art and culinary history. Its strategic position makes it the ideal base to visit the major cultural and city centres in Central Italy. The house is developed on 3 floors, each with direct access from the outside. The main entrance leads to the large kitchen, outer veranda, ideal to taste great dinners while enjoying the landscape. An arch door separates the kitchen from the cosy living room with sofas where the stone fireplace stands out. First floor is composed of 3 bedrooms, one of the doubles has an ensuite bathroom; the other two bedrooms share a bathroom with a shower.
Ground floor: (Living room(TV, fireplace, seating area), dining room(dining table), Kitchen(dining table, hob(6 ring stoves), coffee machine(filter), oven, microwave, dishwasher, fridge))\n\nOn the 1st floor: (bedroom(single bed, double loft bed(140 x 190 cm)), bedroom(double bed), Bedroom with bathroom(double bed, shower, washbasin, toilet, bidet), bathroom(shower, washbasin, toilet, bidet))\n\nBasement: (bedroom(single bed, double bed), bathroom(shower, washbasin, urinal), washing room(washing machine), fitness room)\n\ncot, heating, air conditioning, garden(private, 1500 m2), garden furniture, sun loungers, BBQ, parking, parasol, swimming pool(private, outside, 8 x 4 m., opened from May upto and including Sep), hairdryer, insect screens

Guests

10

Bathrooms

3

Bedrooms

4

Holiday home

Price from €

per night

Price not yet available

Chic Tuscan Stay with Steam
Chic Tuscan Stay with Steam
A few steps away from the Umbrian borders and the beautiful Etruscan city, Home Severina is immersed in the rolling hills and gentle vineyards of Tuscany where the well-known Sirah Cortona DOC is produced. The private garden is where the pool lies, equipped with the latest automation system and a private bathroom with a shower. 3 out of 4 upstairs bedrooms open onto a terrace to descend directly to the yard; the fifth bedroom is located on the ground floor and is linked to the outer areas too. The ground floor consists of the welcoming living room with sofas, a fireplace, and a TV to spend convivial moments reunited. On the same floor, guests can find bubble baths and a steam bath. You can reach the best wineries in the area after a walk or bike ride. Within a short distance, it is possible to reach by car some of the cellars of the famous Strada dei Vini to stop for interesting wine tastings, the nearby Trasimeno Lake, all the major highlights in Tuscany and Umbria.
Ground floor: (Sitting room(seating area), Sitting room(TV(satellite), fireplace), dining room(dining table), Kitchen(hob(6 ring stoves), coffee machine(espresso), oven, dishwasher, fridge), Bedroom with bathroom(double bed, shower, washbasin, toilet), bathroom(bath tub, washbasin, toilet), toilet, Bubble bath(private, paid))\n\nOn the 1st floor: (Bedroom with bathroom(double bed, shower, washbasin, toilet), Bedroom with bathroom(double bed, shower, washbasin, toilet), Bedroom with bathroom(double bed, shower, washbasin, toilet), Bedroom with bathroom(double bed, shower, washbasin, toilet))\n\ntumble dryer, washing machine, heating, air conditioning, garden(private, illuminated), BBQ, swimming pool(private, outside, 8 x 4 m., opened from May upto and including Sep), ironing board, iron, hairdryer, insect screens

Guests

10

Bathrooms

6

Bedrooms

5

Holiday home

Price from €

470

per night

Price not yet available

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