Home Vacation Rentals By Owner In Cortona, TOS

Showing 240 Of 371 Vacation Rentals
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Exceptional(3)

$356.18

/ Nightly
Apartment

Holiday Home 'Magazzino 4 Superior' with Shared Pool, Wi-Fi and Air Conditioning

Cortona, Cortona, Italy

Located in Cortona, the holiday home Magazzino 4 Superior has everything you need for a comfortable holiday. The 2-storey property consists of a living room, a kitchen, 2 bedrooms and 2 bathrooms as well as an additional toilet and can therefore accommodate 4 people. Additional amenities include high-speed Wi-Fi (suitable for video calls) with a dedicated workspace for home office, a TV, air conditioning as well as beach/pool towels. On top of that, a shared gym and gym equipment are also provided for your enjoyment. This vacation rental features a private outdoor area with a garden, covered terrace, and outdoor shower. An additional single bed can be added upon previous request and for an extra fee.brbrEnjoy the shared outdoor area with a fenced pool and outdoor shower. The pool is open from May 15 to October 15, 8:30 a.m. to 8:00 p.m. The on-site restaurant operates from June to November 5. Guests have access to a shared gym. There are 22 parking spaces on the property. Only one pet is allowed. Smoking, parties, and events are not permitted. Cot and high chair available on request. There is a shared laundry room. For stays longer than one week, an extra set of bed linen and towels is included. For shorter stays, it is available for an extra fee. Wine tastings can be arranged on request. Waste sorting guidelines are provided; more info on site.brbr- Pet allowed payment 10,00 € per pet per night
Bed 2

Bed

Bath 2

Bath

Sleep 4

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Exceptional(1)

$359.93

/ Nightly
Apartment

Holiday Home 'Magazzino 1' with Shared Pool, Wi-Fi and Air Conditioning

Cortona, Cortona, Italy

Located in Cortona, the holiday home Magazzino 1 Superior has everything you need for a comfortable holiday. The 2-storey property consists of a living room, a kitchen, 2 bedrooms and 2 bathrooms as well as an additional toilet and can therefore accommodate 4 people. Additional amenities include high-speed Wi-Fi (suitable for video calls) with a dedicated workspace for home office, a TV, air conditioning as well as beach/pool towels. In addition, a shared gym and gym equipment are available for your use. This vacation rental features a private outdoor space with a garden and an outdoor shower. An additional single bed can be added upon request and for an extra fee.brbrEnjoy the shared outdoor area with a fenced pool and outdoor shower. The pool is open from May 15 to October 15, 8:30 a.m. to 8:00 p.m. The on-site restaurant operates from June to November 5. Guests have access to a shared gym. There are 22 parking spaces on the property. Only one pet is allowed. Smoking, parties, and events are not permitted. Cot and high chair available on request. There is a shared laundry room. For stays longer than one week, an extra set of bed linen and towels is included. For shorter stays, it is available for an extra fee. Wine tastings can be arranged on request. Waste sorting guidelines are provided; more info on site.brbr- Pet allowed payment 10,00 € per pet per night
Bed 2

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Bath 2

Bath

Sleep 4

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$579.02

/ Nightly
Villa

Villa 'Residenza 2' with Shared Pool, Wi-Fi and Air Conditioning

Cortona, Cortona, Italy

Villa Residenza 2 is located in Cortona and is the perfect spot for a relaxing getaway. The 200 m² property features a living room, kitchen, 2 bedrooms, 3 bathrooms, an extra toilet, and accommodates up to 6 guests. Additional amenities include high-speed Wi-Fi (suitable for video calls) with a dedicated workspace for remote work, TV, air conditioning, and beach/pool towels. Guests also have access to a shared gym and fitness equipment. The villa offers a private outdoor area with a garden, covered terrace, and outdoor shower. Private garage with direct access is available. An extra single bed can be provided on request for an additional fee.brbrEnjoy the shared outdoor area with a fenced pool and outdoor shower. The pool is open from May 15 to October 15, 8:30 a.m. to 8:00 p.m. The on-site restaurant operates from June to November 5. Guests have access to a shared gym. There are 22 parking spaces on the property. Only one pet is allowed. Smoking, parties, and events are not permitted. Cot and high chair available on request. There is a shared laundry room. For stays longer than one week, an extra set of bed linen and towels is included. For shorter stays, it is available for an extra fee. Wine tastings can be arranged on request. Waste sorting guidelines are provided; more info on site.brbr- Pet allowed payment 10,00 € per pet per night
Bed 2

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Bath 3

Bath

Sleep 6

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$930.88

/ Nightly
Villa

Pierle Cuiano Villa: Mountain Views, Private Pool & Wi-Fi in Agriturismo

Cortona, Cortona, Italy

Travel along the road between Tuscany and Umbria to reach Pierle, a medieval village nestled in the hills between Cortona and Lake Trasimeno, dominated by its castle overlooking the lush valley below. Here, surrounded by olive groves and chestnut and oak woods, you'll find the agriturismo.brbrbrbrThe property consists of four independent apartments, each with its own kitchen and dining area—ideal for groups of families or friends who want to spend time together while maintaining privacy. Heating is available for an extra charge.brbrbrbrThe large garden offers tables, chairs, a barbecue, and a wood-fired oven, perfect for picnics, barbecues, pizzas, tasting local products, and enjoying aperitifs outdoors. The garden opens onto a panoramic terrace with spectacular views of the valley and Umbrian mountains.brbrbrbrThe pool, open from May to September, is reserved exclusively for guests.brbrbrbrNature lovers will find many trails nearby for hiking or walking among the chestnut woods or ancient olive trees. In autumn, you can gather mushrooms and chestnuts. A stay here places you among the woods and beauty of Pierle, Cortona, Montepulciano, Pienza, Perugia, Assisi, Orvieto, and Lake Trasimeno, promising relaxation and unforgettable memories.brbrbrbrThe nearest airports are Perugia San Francesco (50 min), Florence Peretola (90 min), Pisa (2 hr 20 min), and Bologna (2 hr 20 min). The closest train stations are Terontola/Cortona and Camucia/Cortona, both about 20 km away. Nearby places to visit include Mercatale (4 km), Cortona (20 km), and Umbertide (22 km).brbr- Pet allowed payment 20,00 € per pet
Bed 9

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Bath 7

Bath

Sleep 14

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Exceptional(1)

$290.44

/ Nightly
Agritourism

Agriturismo 'Cuiano La Loggetta' with Shared Pool, Garden and Wi-Fi

Cortona, Cortona, Italy

Traveling along the road between Tuscany and Umbria, you’ll reach Pierle, a medieval village perched on the hills between Cortona and Lake Trasimeno, with its castle overlooking the green valley below. Here, surrounded by olive trees and chestnut and oak woods, lies our agriturismo.brbrbrbrThe La Loggetta apartment is on the upper floor, accessible via stone stairs leading to a small terrace. Inside, you’ll find a bright living room with a sofa, dining table, TV, stereo, and an antique stone fireplace. The sleeping area is separated by a door opening onto a landing, leading to a spacious bedroom with a private bathroom. This apartment is ideal for couples or families with a child, even a baby; we can provide an extra bed or a crib depending on age, at no extra charge.brbrbrbrHeating is available for an additional fee.brbrbrbrThe restoration preserved the Tuscan style of rural stone houses, with exposed chestnut beams and 19th-century stone fireplaces.brbrbrbrThe large garden surrounding the agriturismo offers tables, chairs, a barbecue, and a wood-fired oven for picnics, barbecues, pizzas, local product tastings, and outdoor aperitifs. The garden opens like a terrace with a spectacular view of the lush valley and the Umbrian mountains in the distance.brbrbrbrThe pool, reserved for guests (12x6 meters, 140 cm maximum depth), is perfect for relaxing; by the pool you’ll find loungers, tables, chairs, and umbrellas. Children can play safely in the spacious playground area.brbrbrbrIf you love trekking or simply walking outdoors, you’ll find fantastic trails surrounded by chestnut and oak trees around the agriturismo.brbr- Pet allowed payment 20,00 € per pet
Bed 1

Bed

Bath 1

Bath

Sleep 3

Sleeps

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Exceptional(2)

$364.48

/ Nightly
Apartment

Holiday Home 'Frantoio 5 Superior' with Shared Pool, Wi-Fi and Air Conditioning

Cortona, Cortona, Italy

The holiday home Frantoio 5 Superior is located in Cortona and is perfect for an unforgettable holiday with your loved ones. The 2-storey property consists of a living room, a kitchen, 2 bedrooms and 2 bathrooms as well as an additional toilet and can therefore accommodate 4 people. Additional amenities include high-speed Wi-Fi (suitable for video calls) with a dedicated workspace for home office, a TV, air conditioning as well as beach/pool towels. On top of that, a shared gym and gym equipment are also provided for your enjoyment. This vacation rental features a private outdoor area with a garden, covered terrace, and outdoor shower. An additional single bed can be added upon previous request and for an extra fee.brbrEnjoy the shared outdoor area with a fenced pool and outdoor shower. The pool is open from May 15 to October 15, 8:30 a.m. to 8:00 p.m. The on-site restaurant operates from June to November 5. Guests have access to a shared gym. There are 22 parking spaces on the property. Only one pet is allowed. Smoking, parties, and events are not permitted. Cot and high chair available on request. There is a shared laundry room. For stays longer than one week, an extra set of bed linen and towels is included. For shorter stays, it is available for an extra fee. Wine tastings can be arranged on request. Waste sorting guidelines are provided; more info on site.brbr- Pet allowed payment 10,00 € per pet per night
Bed 2

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Bath 2

Bath

Sleep 4

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Exceptional(2)

$300.58

/ Nightly
Apartment

Apartment 'Frantoio 2 Classic' with Shared Pool, Wi-Fi and Air Conditioning

Cortona, Cortona, Italy

Located in Cortona, the holiday apartment Frantoio 2 Classic has everything you need for a relaxing holiday. The 2-storey property consists of a living room, a kitchen, 2 bedrooms and 1 bathroom as well as an additional toilet and can therefore accommodate 3 people. Additional amenities include high-speed Wi-Fi (suitable for video calls) with a dedicated workspace for home office, a TV, air conditioning as well as beach/pool towels. On top of that, a shared gym and gym equipment are also provided for your enjoyment. This vacation rental offers a private outdoor space with a garden, covered terrace, and outdoor shower.brbrEnjoy the shared outdoor area with a fenced pool and outdoor shower. The pool is open from May 15 to October 15, 8:30 a.m. to 8:00 p.m. The on-site restaurant operates from June to November 5. Guests have access to a shared gym. There are 22 parking spaces on the property. Only one pet is allowed. Smoking, parties, and events are not permitted. Cot and high chair available on request. There is a shared laundry room. For stays longer than one week, an extra set of bed linen and towels is included. For shorter stays, it is available for an extra fee. Wine tastings can be arranged on request. Waste sorting guidelines are provided; more info on site.brbr- Pet allowed payment 10,00 € per pet per night
Bed 2

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Bath 1

Bath

Sleep 3

Sleeps

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$251.34

/ Nightly
Private Vacation Home

Beautiful home in Cortona with WiFi

Cortona, Cortona, Italy

Look forward to a wonderful break in beautiful surroundings in this cozy vacation home.brbrbrbrWelcome to the inviting house, where you can relax to the full in a beautiful location on the slopes of Cortona. The bright rooms and attractive furnishings create a homely atmosphere and the spacious house is the ideal setting for a wonderful time with the whole family. Settle down at home after your excursions, stream your favorite series and make plans for the days ahead.brbrStep out onto the terrace, the ideal place to soak up the sun while your children jump on the trampoline, dine al fresco or enjoy a cold drink on a balmy summer evening.brbrbrbrClose to the vacation home you will find numerous activity options, here you can go cycling or mountain biking and hiking and get to know the beautiful surroundings better. Cortona offers its visitors a particularly splendid and lively old town, picturesque squares, the venerable old town hall, the Etruscan Museum and the castle. Stores, bars and trattorias invite you to linger. You will spend your vacation just a few kilometers from Arezzo, Perugia, Lake Trasimeno, Siena and other sights in Tuscany and Umbria.brbrbrbr- Free parking nearbybrbr- Consumption costs incl.brbr- Bedlinen incl towels (included)brbr- Final cleaning (included)brbrbrbrbrbrbrbr- Air conditioning cold/hotbrbr- Split-level holiday rentalbrbr- Houseowner lives on the sitebrbr- One additional child free of charge (max 4 years old)brbr- Cot: 1brbr- Child's chair: 1
Bed 4

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Bath 5

Bath

Sleep 12

Sleeps

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$389.81

/ Nightly
Villa

Villa L'Antico Mulino

Cortona, arezzo, Italy

L'Antico Mulino di Sant'Angelo in Cortona is an ancient building dating from the year 1000, built by the monks of time to maximize the strength of the water stream flowing around to move the gears of the millstones used for grinding grain and produce flour, it was the work of the most advanced mechanical engineering for its time, and certainly was run by monks for centuries. We have not found as a documentary record of the mill and just doing the renovations we realized what was hidden below ground level. Currently the house so externally reflects that for which it was originally built, while inside the rooms trying to adapt to the needs of today's living space were created. The house is 180 square meters on the ground floor there are two living areas, one is located on the front and has a glass room where the dining table (heated with air conditioning and heating) and a sofa, here seems to live in the middle of nature and under the natural sky you can pass pleasant moments at the table. Entering further inland we are in the living area with the kitchen to the left and to right a living area with sofa and TV area. At the center of the house is the staircase leading to the upper floor and the passage leading to the back of the ground floor where there are two double bedrooms and two bathrooms with shower. Upstairs there are two double bedrooms one of which has a small terrace with a staircase or direct pool access and a single bedroom. Also on the upper floor there is a bathroom with no shower. Outside the house there is a garden of 500 square and used as a park of 5,000 square meters olive grove meters, on the side of the house is the old intake basin of the mill that has been transformed in the pool, it is built entirely with the original stone and maintains the appearance of the reservoir created many years ago '. In the garden there is a BBQ area with outdoor sink and an electric stove and a shower with hot water.brbrThe costs for air conditioning and heating are not included, they are according to consumption and paid in cash at the end of the stay € 0.60 / kwh. There is a tourist tax of 8 euros per person for the first week only and children under 12 do not pay. The costs of final cleaning are included, there is a supplement of 50 euros in the case of animals, all other costs are included, linen and towels for the bathroom and swimming pool, electricity (not for air conditioning)brBooking conditionsbrWeekly rental from Saturday to SaturdaybrArrival after 16:00brDeparture before 10:00brbrPool openingbrFrom mid-May to mid-SeptemberbrbrCostsbrSecurity deposit € 500.00brTourist tax € 8.00 for each person per week from 12 years upwardsbrheating and air conditioning according to consumption (€ 0.60 kw / h)
Bed 5

Bed

Bath 3

Bath

Sleep 8

Sleeps

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$356.85

/ Nightly
Villa

New listing: Casale Burcinella, Cortona. beautiful villa - pool, great location

Cortona, Ar, Italy

Immerse yourself in the heart of Tuscany at this carefully renovated 200-year-old traditional farmhouse, offering fantastic facilities, extensive private gardens, a private pool, and is ideally placed for exploring the region.brbrThe tranquil setting comprises one acre of private gardens adorned with olive trees, fruit trees, and thoughtfully planned recreational areas. An inviting private pool with a large gazebo, together with a spacious covered terrace featuring sofas, a dining table, barbecue and open fireplace, create an idyllic retreat for families and independent travellers alike.brbrPeacefully secluded yet conveniently connected, Casale Burcinella provides the perfect base for touring the magnificent surrounding countryside, hill towns and cultural highlights of Tuscany and Umbria. Alternatively, guests may choose to simply unwind by the pool, soaking up the calm and natural beauty that define this enchanting setting.brbrSet against a scenic backdrop and bordering an adjacent vineyard, Casale Burcinella also enjoys splendid views of Cortona, famously featured in the film Under the Tuscan Sun, inviting guests to savour the region’s rich history, celebrated cuisine, vineyards and renowned wines.brbrAccommodation is accessed by a traditional external stone staircase to the first-floor, leading to a charming dining terrace with panoramic views. Inside, discover high ceilings featuring original chestnut beams throughout, terracotta floors, modern kitchen facilities, antique hand-painted furniture, and quality furnishings and fixtures.brbrThe farmhouse is conveniently positioned, just minutes from Fratta Santa Caterina for day to day shopping needs, bakery and bar/cafe.brbrIt's an easy 10-minute drive from the bustling market town of Camucia, providing a full range of services, including banks, supermarkets, coffee shops, restaurants, and regular train services to Rome and Florence.brbrExplore the ancient charm of Cortona, just minutes from Camucia, revealing captivating views, exceptional restaurants, galleries, coffee, gelato and stylish shops. A host of other beautiful medieval towns are easily accessible from the house, as is lovely Lake Trasemino, at 30-minutes, with boating, beach, restaurants and cafes and other fantastic touring activities.brbrMedieval towns such as Pienza, Perugia, Assisi, Montepulciano, and cultural gems like Siena and Florence are within an hour. brbrThe region's rich history is evident, featuring an important 2000-year-old Etruscan tomb nearby. Historical highlights include Hannibal's advance in 217 BC with his formidable army and war elephant, as well as Leonardo da Vinci's ingenious drainage scheme for the area's ancient marshlands. You are in the centre of St Francis's legacy with numerous beautiful, iconic sites nearby.brbrAccommodation:br• Large, bright open plan living, dining, kitchen brimming with character. Beautiful large feature fireplace with wood burner. Generous dining table for 6 people.br• Three lovely, large bedrooms: Master bedroom with king-size bed, beautiful hand-painted furniture, views over pool and vineyard. Large ensuite bathroom with shower, toilet, bidet. Second bedroom with king-size bed, well furnished with views over vineyard and Cortona, large hand-painted wardrobe and dressing table. Third bedroom with 2 large single beds, well furnished with views to Cortona and farmland.br• Second bathroom with large shower, toilet, bidet.br• Good quality hair driers are provided.br• A large independent laundry room, equipped with a Bosch washing machine, adds practicality to the accommodation.br• Bed linen and all towels including pool towels are provided and are changed weekly for stays over one week.
Bed 3

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Bath 2

Bath

Sleep 6

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Exceptional(3)

$767.94

/ Nightly
Villa

Villa Pietrenta- beautiful rural farmhouse surrounded by lush vegetation

Cortona, Arezzo, Italy

This 250 sqm farmhouse comprises of two self-contained apartments. Both have a ground floor entrance. You can choose to rent the entire property or just one of the units.brbrbrbrApartment Chiara (Unit 1) | Apartment Chiara can accommodate up to 4 people.brbrThe entrance to this apartment opens onto the living room. Here one can find a stone fireplace, sofas and comfortable armchairs. An archway frames the fully-equipped kitchen which can easily accommodate 10 people. A bathroom with shower and a laundry room can also be found on this floor.brbrA wooden staircase in the living room leads to the first floor where there are two double bedrooms and a bathroom with shower.brbrbrbrApartment Laura (Unit 2) | Apartment Laura can accommodate up to 6 people.brbrAs you enter this apartment, you’ll be welcomed by a cozy living room with a fireplace, sofas and armchairs and an antique chest of drawers. A dining room, with a large table and straw chairs in different colors, is joined by a fully-equipped kitchen, an ideal space for the entire family to gather around the table and enjoy delicious homemade food.brbrA bathroom with shower is also on this floor. A wooden staircase in the living room leads to the first floor, where there are two double bedrooms, one twin bedroom (with two single beds) and another bathroom with shower.brbrBoth apartments feature a gorgeous patio with outdoor furniture.brbrBoth apartments are decorated with upcycled, traditional pieces, which the owners hand painted in bright colors. Many chandeliers are vintage and there’s an antique credenza in the dining room.brbrbrbrThe owners live about 500 meters from the farmhouse. Guests are guaranteed every privacy and complete independence. Nonetheless, the owner is always on hand and ready to help, should you have any requests.brbrbrbrThe terraced villa grounds offer many lovely spots where to relax, all with outdoor furniture. Elegant stone stairs lead you from one level to another. The pool deck and swimming pool, which guests have exclusive use of, are entirely fenced and just a few steps away from the farmhouse.brbrbrbrAmenities: LCD TV (with italian channels only), Wi-Fi, dishwasher, oven, cooker/stove, fridge and freezer, American-style coffee maker, Moka pot, toaster, kettle, washing machine, iron and ironing board, hairdryer, cot and highchair. Free parking on site for 3 cars
Bed 5

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Bath 4

Bath

Sleep 10

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