Castiglione D'Orcia Villas with Pool
Results 321 - 340 of 387
Galleria di Brolio
Wonderful independent holiday home with private pool, A/C, WIFI, TV and veranda, near Cortona
- 10
- 4
- 3
Description
Galleria di Brolio is an old stone farmhouse whose origins date back to 1800, located between two of the most important towns of the Valdichiana, Castiglion Fiorentino and Foiano, and which is now part of the owners' farm. You will find the farmhouse just a few kilometres from the two towns and in both, as well as various monuments and sites of artistic interest that are definitely worth a visit, you will have shops, restaurants and all kinds of services. The small historic centres of the villages will be a pleasant destination for your aperitifs or dinners at the restaurant.
The farmhouse takes its name from the Galleria di Brolio, a conduit that is still in operation today and is located on the edge of the olive grove. The conduit is part of the canal built between 1932 and 1940 to improve the flow of water towards the Arno, planned by the engineer Vittorio Fossombroni for the reclamation of the valley at the end of the 18th century.
Galleria di Brolio is situated on the edge of a wood of about 20 hectares of oaks and pines used as a hunting reserve for the repopulation of animals; they live here in the utmost freedom and if you love wildlife you will frequently see hares and pheasants running in the olive grove, the vineyard and even in the house lawn.
On the ground floor there is the apartment where the owners live, as well as a cellar and a shed for the farm's agricultural tools, while the first floor is reserved for you. The furnishings are very nice and comfortable, enriched with local antiques, and blend in perfectly with the old features of the house. Not far away, on the other side of the wood, passes the railway line that connects central Italy with the main cities of the peninsula (Florence, Bologna, Rome, Milan), so it will be easy to move around even without a car.
A few metres from the house, surrounded by silver olive trees, you will find a beautiful swimming pool completely fenced and for your exclusive use (size 11x5 m, depth 1.10-1.40 m - open from 01st May to 30th September), together with a gazebo equipped with garden furniture, which will allow you to shelter from the hot summer sun.
There is also a large pergola supplied with wrought iron furniture for eating outside, equipped with a barbecue and a wood-burning oven, for those evenings when you want to enjoy a pizza or a grill “al fresco”.
The owner, on request, will prepare excellent typical Tuscan dinners and pizzas in the wood-fired oven which, we are told by customers who have stayed at the house, are truly delicious.
Galleria di Brolio
La Casa di Pino
Superb independent vacation rental with A/C, private pool, WIFI and TV, close to Cortona
- 4
- 1
- 1
Description
La Casa di Pino, a small jewel of rural architecture dating back to the year 1200, is located in the heart of the Val di Chio, on the border between Tuscany and Umbria and a few kilometers from the town of Castiglion Fiorentino. All around green woods that are part of the farm, where you can also admire the beautiful 'Majesty' in the grove, a few hundred meters from the house.
In our opinion the main feature of Casa di Pino, which makes it perfect for couples and romantic holidays, is the atmosphere that the owners have managed to create in this small space. In addition to the fact that it resembles a nest, the warm colors chosen for the rooms and the furniture itself, give the feeling of being at home, in an intimate and welcoming place.
In the wide garden the beautiful swimming pool (size 4x8 m., depth 1,20-1,50 m. - open from 01st May to 30th September) with Jacuzzi corner, barbecue and wood burning oven next to the gazebo and an equipped porch. A few meters from the house passes a panoramic side road that crosses the hills and connects Castiglion Fiorentino to the town of Cortona and the nearby region of Umbria. The property accepts small size pets. La Casa di Pino
Villa Mimosa
Independent Property with private pool, A/C, WIFI, TV, patio, pets allowed, close to Cortona
- 10
- 5
- 2
Description
Conveniently located 550 m (1795 ft) from Il Passaggio, Italy and only 6 km (4 mi) from Cortona. Villa Mimosa is a nice holiday home (175 sq m) with private pool, WiFi internet and air conditioning. The property can accommodate up to ten guests comfortably in five bedrooms with two bathrooms.
Your Experience
When you arrive you’ll find a lovely clean well-maintained property with views of the hills ideal for a peaceful vacation in Tuscany. For your pleasure you will find a private pool where you can relax while enjoying a nice cold beverage after a hectic day of visiting museums. Outside you will also find a patio and barbecue grill. Dining with friends and family is a huge part of the Tuscan culture. Take advantage of the well-equipped kitchen to prepare meals using local produce while on your vacation. The kitchen includes microwave, toaster, stove and refrigerator, as well as, plenty of tableware and cutlery for up to ten people.
What's Nearby?
Most people enjoy visiting close-by cities and towns while on vacation, so for your reference this is a list of popular places with distances (as the crow flies) from the property: Cortona 6 km (4 mi), Arezzo 34 km (21 mi), Montepulciano 35 km (22 mi), Perugia 53 km (33 mi) and Gubbio 63 km (39 mi).
Some other major tourist destinations you should consider visiting are: Florence 129 km (80 mi), Viareggio 222 km (138 mi), Forte Dei Marmi 229 km (142 mi), Rome 217 km (135 mi), Venice 378 km (235 mi) and Milan 421 km (262 mi).
Additional Information
Pets Welcome - If your pet is travelling with you on vacation that is not a problem at Villa Mimosa. If you have a large dog or multiple pets, please inquire for permission prior to booking.
Check-In Time: 16:00 - 20:00
Check-Out Time: 08:00 - 10:00
Pool Open: 1 June - 30 September (If you'd like the pool open outside these dates, please make that request prior to booking)
Nearest Airports (distances as the crow flies): Firenze Peretola (flr) 142 km (88 mi), Pisa (psa) 203 km (126 mi), Bologna (blq) 223 km (139 mi), Roma Ciampino (cia) 226 km (141 mi) and Roma Fiumicino (fco) 239 km (148 mi).
Additional Services
Cooking Lessons - Discover from a local chef the techniques needed to master Tuscan cuisine. The owner can schedule to have a chef come to the property for a cooking lesson for any number of people in your group. It's a pleasant way to spend time with friends and family while learning the secrets vital to prepare sumptuous Tuscan meals when you return home. For more details and the supplemental cost, please contact us.
Professional Chef - Are you looking for a real treat during your vacation? Why not book a professional chef to prepare and serve you a sumptuous meal using local produce? The chef will arrange the meal based on your preferences and dietary needs. The chef will offer suggestions for the various courses and the wine. Inquire for more details and the extra costs.
Tours - Custom tours can be organized by the owner for your group. For more details about the tours available, speak to the owner when you arrive or inquire prior to booking. The cost will vary depending in the specific tour and number of people.
Baby Sitting - If you're traveling with children and would like an evening alone, a babysitter can be organized. Speak to the owner directly about this service when you arrive.
Villa Mimosa
Collina dei Fiori
Stunning private property with WIFI, A/C, private pool, TV and pets allowed, near Arezzo
- 9
- 4
- 3
Description
Collina dei Fiori is the result of a painstaking restructuring of an old country house situated in an extremely panoramic position, waiting for you to spend unforgettable holidays with your family or friends. This beautiful villa is at the top of a hillside covered in age-old olive trees and green woods, where many small roads climb up the steep hills revealing enchanting views at every turn.
In a few minutes’ drive from the house you can easily reach Castiglion Fiorentino, Cortona, Arezzo and Lake Trasimeno, ideal destinations for day trips, to alternate with relaxing days at the swimming pool (size 5x10 m, depth 1,20-2,20 m - open from 01st May to 30th September) and funny tennis and table tennis tournaments. The tennis court is located a few hundred meters from the house and is shared only with the guests of the other two houses VILLA DEGLI OLIVI and VILLA GIOTTO.
Adjacent to the kitchen there is a pergola furnished with table and benches and a barbecue where you can spend your evenings together with family and friends, enjoying grilled meats and sipping a glass of wine. The large enclosed garden offers privacy and security for your family and your four-legged friends (a supplement may be charged for pets). If you want to stretch your legs in the hills around the house there are countless hiking trails, also suitable for children. Collina dei Fiori
- 4
- 2
- 1
Description
From the village of Castiglion Fiorentino, with its shops and services, following the suggestive road that crosses the entire Val di Chio and climbs the wooded hills and represent the natural border between Tuscany and Umbria, you will arrive at a small cluster of houses set on the slopes of the hill and overlooking a beautiful wooded landscape. The last stretch of road, about 200 m, is unpaved and sloping. La Casa del Nonno is a small, old stone house that is part of this original rural settlement once inhabited by farming families. Here you will find guaranteed peace; lazy summer days by the pool and in the solarium enjoying the sun, without hearing any noise except those of nature.
A careful renovation has brought La Casa del Nonno back to life. Rustic style furniture, old beams on the ceilings, the old fireplace in the living room, give it a warm atmosphere reminiscent of times gone by, when the house and the open fire were the shelter of the farmers after a hard day's work.
The house will be your own little nest, well-finished, comfortable and cosy and will immediately give you the feeling of being welcome.
In front of the house there is an outdoor area arranged on natural terraces connected by steps, completely fenced and equipped with garden furniture, barbecue and a small house with laundry. For your exclusive use there is also a beautiful swimming pool (size 6x4 m, depth 1.20 m - open from 1 May to 30th September), with a panoramic view and equipped with sunbeds, deckchairs and sunshade.
For your open-air dinners in the summer evenings, the owners have organised a special corner on a terrace in the garden, equipped with a wrought iron table and chairs and covered by a large parasol. La Casa del Nonno
Villa Portole Due
Independent Holiday home with WIFI, A/C, private pool, TV, patio, panoramic view, near Cortona
- 4
- 2
- 2
Description
Nice indipendent stone villa which have been recently restored. This property is situated in panoramic location on the hills surrounding the beautiful medieval town of Cortona which is only 10 km away. The villa offers comfortable interiors furnished in a rustic style and provide a private furnished outdoor area.
A secondary road connecting the small villages on the hills surrounding Cortona passes nearby.
The property, thanks to its spacious interiors and its large exteriors, guarantees a pleasure and safe stay. All the areas, including the swimming pool, are carefully sanitized and sterilized for the health and tranquility of guests.
Distances: Portole with a food shops and a restaurant 500 m away, Cortona with all kinds of shops 9 km, Lake Trasimeno approx. 20 km away, Città di Castello 30 km away. Arezzo 35 km away.
At guests’ disposal: private furnished outdoor area, private and fenced swimming-pool (8 x 4 m - maximum depth 1,40 m – open from 29/04 to 28/10), barbecue, playground for children. Parking within the grounds. The villa is provided with a laundry room and with air-conditioning.
Extra Services: baby bed available on request (free of charge). Maid service available by arrangement at € 18,- / per hour to be paid on the spot.
Please carefully check if there are any extra costs to be paid on site! Villa Portole Due
Book your vacation for the period from 25 April 2026 to 30 May 2026 and save 5% (minimum 7 nights).
- 8
- 4
- 2
Description
Nice farmhouse dating back to the beginning of the 20th century quietly situated on a large 6-hectare estate producing olive oil and wine. This villa, located in walking distance to the village of Ambra, was completely and tastefully restored in the 70’s and was turned into a welcoming country house offering nice interiors furnished in a rustic style.
Outside, guests can enjoy use of a large, entirely fenced-in park with century-old trees and a private and fenced pool.
The location is half-way between Siena and Arezzo in easy access to Florence, the Etruscan town of Cortona and the Chianti region.
Distances: Ambra with general stores 900 m away, Arezzo 33 km, Gaiole in Chianti 34 km away, Siena 36 km, Cortona and Radda in Chianti 63 km away, Florence 66 km, Lake Trasimeno 68 km away, San Gimignano 78 km, Marina di Grosseto (beaches) 120 km away, Pisa (airport) 170 km away, Rome 235 km away.
At guests’ disposal: fenced-in 5000-square-meter garden, private and fenced swimming-pool (6 x 12 m – depth from 1,2 to 2 m) with open-air shower (cold water), large solarium area, barbecue. Telephone available (payment on site), Wi Fi internet connection available in the house (free of charge).
Parking within the grounds.
Extra Services: Baby bed on request (free of charge). Maid service (€ 15,- / per hour to be paid on site). The olive oil and the wine produced on the estate are available for guests to be purchased.
Please carefully check if there are any extra costs to be paid on site! Casale Ambra
- 8
- 3
- 3
Description
An old farmhouse completely renovated, located near Castiglion Fiorentino. Casa Angela will be the ideal place where you can rediscover the flavours of the past, of a simple and quiet life. You will have at your disposal a large vegetable garden where you can pick up genuine fresh seasonal vegetables every morning. In the vicinity of the farmhouse there are farmyard animals, fruit trees and vineyards, making your stay a true country life experience.
Of this holiday you will surely remember the slow and warm days that village life, still regulated with rhythms of other times, gives us.
For your lazy summer days the beautiful swimming pool completely fenced and for your exclusive use (size mt. 6x12, depth mt. 1,20-1,50 - open from 16 May to 30th September) will be the ideal place also for your evening aperitifs, relaxed in the gazebo, with a good red wine in your glass and with the lights of Castiglion Fiorentino, which climbs up the hill, as a backdrop.
For children there is a large green outdoor space to explore with a five-a-side football goal for fun times with friends. The house is definitely perfect, in our opinion, for family holiday with children or for a small group of friends who want to discover the beauty of Tuscany and the nearby Umbria, renting a villa with private pool.
Pets are welcome (extra charge could be required).
We guarantee that you will leave your heart in Castiglion Fiorentino. A small town of steep, paved alleyways, ancient buildings, stone stairways and arches and mighty walls dominated by the imposing Cassero tower, guarding the valley. Many trattorias and restaurants invite you to go out in the evening and enjoy a dish of fresh, handmade pasta or a famous Florentine steak.
In Castiglion Fiorentino you will also find supermarkets for your daily shopping, other shops and all necessary services. From the house you can easily walk to a restaurant which is just 1 km far.
A few km away is the border with the region of Umbria, in 15 minutes by car you will be able to reach the golden beaches of Lake Trasimeno, with its characteristic villages and islets to discover. Casa Angela
Villa Il Borgo
Pretty private accommodation with A/C, private pool, WIFI, TV, patio, panoramic view, near Cortona
- 8
- 4
- 4
Description
Villa Il Borgo is located 3 km (2 mi) from Pergo, Italy and only 8 km (5 mi) from Cortona. Villa Il Borgo is a beautiful stone building (240 sq m) with WiFi internet, air conditioning and private pool. The property can sleep up to eight guests comfortably in four bedrooms with four bathrooms.
The Property is composed of the main Villa and an annex.
Your Experience
After arriving you’ll find a lovely clean well-maintained property with views of the hills perfect for a splendid holiday in Tuscany. For your enjoyment you will find a private pool where you can relax while enjoying a nice cold beverage after a hectic day of shopping. Outside you will also find a patio and barbecue grill. If you enjoy cooking for family and friends there is a well-equipped kitchen including coffee machine, microwave, toaster, stove and refrigerator, as well as, plenty of tableware and cutlery for up to eight people. If you prefer to dine 'al fresco', there is a fully furnished patio where you can enjoy the weather while dining outdoors.
Visit the Area
Most people enjoy visiting nearby cities and towns while on holiday, so for your reference this is a list of popular places with distances (as the crow flies) from the property: Cortona 8 km (5 mi), Arezzo 35 km (22 mi), Montepulciano 37 km (23 mi), Perugia 54 km (34 mi) and Gubbio 64 km (40 mi).
Some other major tourist destinations you should consider visiting are: Florence 137 km (85 mi), Viareggio 224 km (139 mi), Forte Dei Marmi 231 km (143 mi), Rome 219 km (136 mi), Venice 380 km (236 mi) and Milan 422 km (262 mi).
Additional Information
Pets Welcome - If your pet is travelling with you on vacation that is not a problem at Villa Il Borgo. If you have a large dog or multiple pets, please ask for permission prior to booking.
Check-In Time: 16:00 - 20:00
Check-Out Time: 08:00 - 10:00
Pool Open: 1 May - 30 September (If you'd like the pool open outside these dates, please make that request prior to booking)
Nearest Airports (distances as the crow flies): Firenze Peretola (flr) 142 km (88 mi), Pisa (psa) 205 km (127 mi), Roma Ciampino (cia) 228 km (142 mi), Bologna (blq) 229 km (142 mi) and Roma Fiumicino (fco) 240 km (149 mi).
More Services
Cooking Lessons - Learn from a local chef the techniques needed to master Tuscan cuisine. The owner can arrange to have a chef come to the property for a cooking lesson for any number of people in your group. It's a enjoyable way to spend time with friends and family while learning the secrets vital to prepare sumptuous Tuscan meals when you return home. For more details and the supplemental cost, please contact us.
Professional Chef - Are you looking for a real treat during your vacation? Why not book a professional chef to prepare and serve you a mouth-watering meal using local produce? The chef will arrange the meal based on your preferences and dietary requirements. The chef will offer advice for the various courses and the wine. Ask for more details and the additional costs.
Tours - The owner can schedule custom tours for your group. To learn about the tours available, speak to the owner when you arrive or ask prior to booking. The cost will vary depending in the specific tour and number of people.
Baby Sitting - If you're traveling with children and would like an evening alone, a babysitter can be arranged. Speak to the owner directly about this service when you arrive.
Villa Il Borgo
Villa Gelsomino
Unique independent house with WIFI, A/C, private pool, TV, patio, panoramic view, near Cortona
- 8
- 4
- 3
Description
Vacation rental Villa Gelsomino is a nice stone building (260 sq m) that includes private pool, WiFi internet and air conditioning. The property can sleep up to eight guests comfortably in four bedrooms with three bathrooms. Conveniently located 2 km (1 mi) from Pergo, Italy and only 7 km (4 mi) from Cortona.
What to Expect
After arriving you will be greeted by the owner or manager where you’ll find a beautiful clean well-maintained property with views of the hills ideal for a relaxing holiday in Tuscany. Regardless of how you spend your days - sightseeing, shopping, visiting museums or just driving in the countryside, when you arrive home you can relax with your family and friends at the pool for a perfect ending to another day in Tuscany. Also available outside are a barbecue grill and patio. Dining with friends and family is a huge part of the Tuscan culture. Take advantage of the well-equipped kitchen to prepare meals using local produce while on your vacation. The kitchen includes coffee machine, microwave, toaster, stove and refrigerator, as well as, plenty of tableware and cutlery for up to eight people. Dine 'al fresco' like a real Tuscan, the fully furnished veranda is the ideal setting to enjoy food, family and the lovely Tuscan weather.
What's Nearby?
Most people enjoy visiting nearby cities and towns while on vacation, so for your reference this is a list of popular places with distances (as the crow flies) from the property: Cortona 7 km (4 mi), Arezzo 34 km (21 mi), Montepulciano 35 km (22 mi), Perugia 53 km (33 mi) and Gubbio 64 km (40 mi).
Some other major tourist destinations you should consider visiting are: Florence 129 km (80 mi), Viareggio 222 km (138 mi), Forte Dei Marmi 229 km (142 mi), Rome 217 km (135 mi), Venice 378 km (235 mi) and Milan 422 km (262 mi).
Additional Information
Pets Welcome - If your pet is travelling with you on holiday that is not a problem at Villa Gelsomino. If you have a large dog or multiple pets, please ask for permission prior to booking.
Check-In Time: 16:00 - 20:00
Check-Out Time: 08:00 - 10:00
Pool Open: 1 May - 30 September (If you'd like the pool open outside these dates, please make that request prior to booking)
Nearest Airports (distances as the crow flies): Firenze Peretola (flr) 142 km (88 mi), Pisa (psa) 203 km (126 mi), Bologna (blq) 223 km (139 mi), Roma Ciampino (cia) 226 km (141 mi) and Roma Fiumicino (fco) 239 km (148 mi).
Special Services
Cooking Lessons - If you're interested in discovering more about Tuscan cooking, inquire about the cooking lessons that can be arranged at the property. It's a fun way to spend time with friends and family while learning the techniques required to master Tuscan cuisine. For more details and the supplemental cost, please contact us.
Professional Chef - Are you looking for a real treat during your vacation? Why not book a professional chef to prepare and serve you a delicious meal using local produce? The chef will organize the meal based on your preferences and dietary requirements. The chef will offer advice for the various courses and the wine. Ask for more details and the extra costs.
Tours - Custom tours can be scheduled by the owner for your group. For more details about the tours available, speak to the owner upon arrival or ask prior to booking. The cost will vary depending in the individual tour and number of people.
Baby Sitting - If you're traveling with children and would like an evening alone, a babysitter can be scheduled. Speak to the owner directly about this service after arriving.
Villa Gelsomino
Villa Torreone
Superb villa rental with private pool, WIFI, A/C, TV and panoramic view, close to Cortona
- 8
- 4
- 4
Description
Conveniently located 2 km (1 mi) from Torreone, Italy in the tourist area "Cortona And Surroundings" and only 4 km (3 mi) from Cortona. Holiday rental Villa Torreone is a nice stone building (300 sq m) that includes WiFi internet, private pool and air conditioning. The property can accommodate up to eight people comfortably in four bedrooms with four bathrooms.
Your Experience
Upon arrival you will be welcomed by the owner or manager where you’ll find a beautiful clean well-maintained property with views of the lake and the mountains ideal for a splendid vacation in Tuscany. Regardless of how you spend your days - shopping, sightseeing, visiting museums or just driving in the countryside, when you arrive home you can unwind with your family and friends at the pool for a perfect ending to another day in Tuscany. Dining with friends and family is a huge part of the Tuscan culture. Take advantage of the well-equipped kitchen to prepare meals using local produce while on your holiday. The kitchen includes coffee machine, microwave, toaster, stove and refrigerator, as well as, plenty of tableware and cutlery for up to eight people. Dine 'al fresco' like a real Tuscan, the fully furnished garden is the perfect setting to enjoy food, family and the beautiful Tuscan weather.
What's Nearby?
Most people enjoy visiting nearby cities and towns while on holiday, so for your reference this is a list of popular places with distances (as the crow flies) from the property: Cortona 4 km (3 mi), Arezzo 32 km (20 mi), Montepulciano 34 km (21 mi), Perugia 55 km (34 mi) and Montalcino 68 km (42 mi).
Some other major tourist destinations you should consider visiting are: Florence 122 km (76 mi), Viareggio 209 km (130 mi), Forte Dei Marmi 216 km (134 mi), Rome 214 km (133 mi), Venice 361 km (224 mi) and Milan 406 km (252 mi).
Additional Information
Check-In Time: 16:00 - 20:00
Check-Out Time: 08:00 - 10:00
Pool Open: 1 May - 1 October (If you'd like the pool open outside these dates, please make that request prior to booking)
Nearest Airports (distances as the crow flies): Firenze Peretola (flr) 127 km (79 mi), Pisa (psa) 190 km (118 mi), Bologna (blq) 214 km (133 mi), Roma Ciampino (cia) 223 km (138 mi) and Roma Fiumicino (fco) 235 km (146 mi).
Additional Services
Cooking Lessons - Learn from a local chef the techniques vital to master Tuscan cuisine. The owner can organize to have a chef come to the property for a cooking lesson for any number of people in your group. It's a enjoyable way to spend time with friends and family while discovering the secrets vital to prepare sumptuous Tuscan meals when you return home. For more details and the additional cost, please contact us.
Professional Chef - Are you looking for a real treat during your vacation? Why not book a professional chef to prepare and serve you a mouth-watering meal using local produce? The chef will arrange the meal based on your preferences and dietary requirements. The chef will offer advice for the various courses and the wine. Inquire for more details and the additional costs.
Tours - The owner can arrange custom tours for your group. To learn about the tours offered, speak to the owner upon arrival or ask prior to booking. The cost will vary depending in the specific tour and number of people.
Maid Service - If you'd like maid service during your visit that can be scheduled by the owner. Inquire for more details about the supplemental cost.
Pre-Stocked Fridge - Take advantage of the pre-stocking service to save time and start your vacation hassle-free after a long trip. Inquire for more details, including the additional cost and how to schedule this service.
Baby Sitting - If you're traveling with children and would like an evening alone, a babysitter can be organized. Speak to the owner directly about this service upon arrival.
Owner Assistance - Since the owner lives nearby, he is always available to offer advice and suggestions during your visit. In case you need assistance, it's nice to have someone available to help. In any case, the owner will always respect your privacy.
The owner lives in the property on the third floor of the villa and has an independent access to the property. Villa Torreone
Villa del Sole
Private Property with sauna, WIFI, pool, hot tub, A/C, TV, terrace, panoramic view, close to Cortona
- 10
- 4
- 5
Description
Villa Del Sole is a beautiful stone building (280 sq m) with WiFi internet and air conditioning. The property can sleep up to ten guests comfortably in four bedrooms with five bathrooms. Conveniently located 1 km (4276 ft) from Torreone, Italy in the tourist area "Cortona And Surroundings" and only 4 km (2 mi) from Cortona.
On site there is a further apartment occasionally used by the owner, which has a separate entrance and garden.
What to Expect
When you arrive you’ll find a nice clean well-maintained property with views of the mountains and the hills ideal for a relaxing holiday in Tuscany. After a busy day of sightseeing, spend some time with friends and family poolside enjoying a glass of wine - a perfect way to unwind at the end the day. Sharing a meal with friends and family is a huge part of the Tuscan culture. Take advantage of the well-equipped kitchen to prepare meals using local produce while on your vacation. The kitchen includes coffee machine, microwave, toaster, stove and refrigerator, as well as, plenty of tableware and cutlery for up to ten people. Dine 'al fresco' like a real Tuscan, the fully furnished terrace is the perfect setting to enjoy food, family and the lovely Tuscan weather.
What's Nearby?
Most people enjoy visiting close-by cities and towns while on holiday, so for your reference this is a list of popular places with distances (as the crow flies) from the property: Cortona 4 km (2 mi), Arezzo 31 km (19 mi), Montepulciano 33 km (21 mi), Perugia 55 km (34 mi) and Montalcino 67 km (42 mi).
Some other major tourist destinations you should consider visiting are: Florence 125 km (77 mi), Viareggio 218 km (135 mi), Forte Dei Marmi 225 km (140 mi), Rome 213 km (132 mi), Venice 374 km (233 mi) and Milan 418 km (259 mi).
Additional Information
Pets Welcome - If your pet is travelling with you on holiday that is not a problem at Villa Del Sole. If you have a large dog or multiple pets, please inquire for permission prior to booking.
Check-In Time: 17:00 - 19:00
Check-Out Time: 08:00 - 10:00
Pool Open: 1 May - 30 September (If you'd like the pool open outside these dates, please make that request prior to booking)
Nearest Airports (distances as the crow flies): Firenze Peretola (flr) 138 km (86 mi), Pisa (psa) 199 km (124 mi), Bologna (blq) 219 km (136 mi), Roma Ciampino (cia) 222 km (138 mi) and Roma Fiumicino (fco) 235 km (146 mi).
Special Services
Professional Chef - Are you looking for a real treat during your holiday? Why not book a professional chef to prepare and serve you a sumptuous meal using local produce? The chef will organize the meal based on your preferences and dietary needs. The chef will offer suggestions for the various courses and the wine. Ask for more details and the additional costs.
Tours - Custom tours can be organized by the owner for your group. For more details about the tours offered, speak to the owner upon arrival or ask prior to booking. The cost will vary depending in the individual tour and number of people.
Baby Sitting - If you're traveling with children and would like an evening alone, a babysitter can be arranged. Speak to the owner directly about this service after arriving.
Villa Del Sole
Podere i Gigli
Fabulous independent holiday home with private pool, A/C, WIFI, TV and terrace, near Cortona
- 6
- 3
- 3
Description
Podere I Gigli is a farmhouse just a few steps away from the centre of Castiglion Fiorentino, which you can easily reach on foot in less than 10 minutes when you want to stretch your legs. The railway station, which is 500 metres from the property, is also within easy reach and makes the house particularly suitable for all types of travel should you wish to visit Tuscany and Central Italy without taking a car.
The farm mainly produces cereals, but around the house you can also enjoy the view of vineyards, olive groves and fruit trees. The owners will be happy to let you taste and buy their pure Sangiovese wine, extra virgin olive oil and other products of the farm, proudly handed down from father to daughter.
The house is surrounded by a large, well-kept garden, shaded and filled with flowers and plants. In the relaxation area, furnished with table and chairs, you can comfortably enjoy your meals in the open air. At the back of the house, in a sunny position, there is a swimming pool measuring 4.5x9m, 1.50m deep and completely fenced ( open from 16 May to 30 September) for the safety of your children.
Another corner that we think you will appreciate is the sun terrace on the first floor, where you will find a small lounge with a sun umbrella, table and chairs, ideal for aperitifs in the cool of summer evenings.
There is also a vegetable garden with fresh seasonal vegetables that you can pick daily.
Podere I Gigli is an old stone farmhouse, dating back to the early 1900s, which has recently been renovated and brought back to life while maintaining the structure, which still exudes ancient history and farming traditions. The grit floors and exposed beams have been preserved and together with the rustic furnishings and antiques and local crafts, personally and carefully chosen by the owner, make the house a truly ideal place for your holidays.
The owners who live next door, although discreet, will be a sure reference point for any need you may have. Podere i Gigli
Villa degli Olivi
Unique private property with WIFI, A/C, private pool, TV, terrace and pets allowed, near Arezzo
- 14
- 7
- 7
Description
Villa degli Olivi is a beautiful holiday villa with attractive architectural features situated just outside Castiglion Fiorentino, a typical Tuscan town on the hills of the Valdichiana, surrounded by age-old olive groves and ancient cypress trees. The origins of the town date back in history. Today it's a quiet town which offers its visitors numerous cultural and eno-gastronomic events planned throughout the whole year.
The villa is situated on the slopes of a hill looking onto the Valdichiana below and is certainly the ideal spot for anyone wanting to spend their holiday in a charming country villa, without sacrificing any of the comforts of modern life. The internal fittings, equipment and furnishings of the house are of an high standard and ensure the maximum comfort.
Around the villa a large park of centuries-old olive trees, completely fenced in with a fence and equipped with gazebo, garden furniture, barbecue and wood-burning oven will be the ideal place to spend relaxing evenings in good company. For the amusement of adults and children there are: the beautiful fenced-in infinity pool (size m. 6 x 12, depth m. 1,20-3,00 - open from 01st May to 30th September), the table tennis and approx. 2 km far the private tennis court (size 18x36 m.) to be shared only with the guests of other 3 villas COLLINA DEI FIORI, CASALE IL TRECENTO and VILLA GIOTTO. Villa degli Olivi
Belvedere - Falceto, Ambra, Toscana
Stunning private holiday rental with WIFI, A/C, private pool, patio, pets allowed and panoramic view
- 18
- 6
- 7
Description
Belvedere - Falceto, Ambra, Toscana is located 2 km (1 mi) from Ambra, Italy and only 30 km (18 mi) from Arezzo in the tourist area "Arno Valley". Holiday rental Belvedere - Falceto, Ambra, Toscana is a beautiful stone building (450 sq m) that includes WiFi internet, private pool and air conditioning. The property can accommodate up to 18 people comfortably in six bedrooms with seven bathrooms.
The Experience
Upon arrival you will be welcomed by the owner or manager where you’ll find a beautiful clean well-maintained property with views of the hills perfect for a splendid vacation in Tuscany. Regardless of how you spend your days - visiting museums, sightseeing, shopping or just driving in the countryside, when you arrive home you can relax with your family and friends at the pool for a perfect ending to another day in Tuscany. Outside you will also find a patio, playground and barbecue grill. Dining with friends and family is a big part of the Tuscan culture. Take advantage of the well-equipped kitchen to prepare meals using local produce while on your vacation. The kitchen includes coffee machine, toaster, stove and refrigerator, as well as, plenty of tableware and cutlery for up to 18 people.
Visit the Area
Most people enjoy visiting close-by cities and towns while on vacation, so for your reference this is a list of popular places with distances (as the crow flies) from the property: Arezzo 30 km (18 mi), Siena 39 km (24 mi), Greve In Chianti 49 km (30 mi), Montepulciano 54 km (34 mi) and Cortona 65 km (40 mi).
Some other major tourist destinations you should consider visiting are: Florence 76 km (47 mi), Viareggio 162 km (101 mi), Forte Dei Marmi 169 km (105 mi), Rome 231 km (144 mi), Venice 315 km (196 mi) and Milan 360 km (224 mi).
Additional Information
Pets Welcome - If your pet is travelling with you on vacation that is not a problem at Belvedere - Falceto, Ambra, Toscana. If you have a large dog or multiple pets, please inquire for permission prior to booking.
Check-In Time: 15:00 - 19:00
Check-Out Time: 07:00 - 09:00
Pool Open: 1 May - 24 October (If you'd like the pool open outside these dates, please make that request prior to booking)
Nearest Airports (distances as the crow flies): Firenze Peretola (flr) 81 km (50 mi), Pisa (psa) 143 km (89 mi), Bologna (blq) 167 km (104 mi), Roma Ciampino (cia) 240 km (149 mi) and Roma Fiumicino (fco) 253 km (157 mi).
Please note: The last 200 m of the access road are unpaved. Belvedere - Falceto, Ambra, Toscana
Medieval Castle Living: Vineyards, Swimming Pool &
Lovely apartment with A/C, WIFI, private pool, balcony and panoramic view, near Siena
- 12
- 6
- 6
Description
Secluded Wine Rustic Estate: 1300S Castle Suite & is a nice stone building (800 sq m) with WiFi internet and private pool. The property can sleep up to 12 guests comfortably in six bedrooms with six bathrooms. Conveniently located 4 km (2 mi) from Sovicille, Italy in the tourist area "Siena And Surroundings" and only 14 km (8 mi) from Siena.
Nestled in the lush greenery of the Montagnola Senese, this magnificent property is a masterfully preserved 13th-century castle located just a 15-minute drive from the historic heart of Siena. The estate has been meticulously restored by its owners, who reside in the main tower in a secluded area that remains entirely private and separate from guest accommodations.
The estate is thoughtfully designed to offer both community and privacy. The first floor of the main castle features two charming apartments. Adjacent to the castle is a separate cottage housing two additional apartments, providing an ideal retreat for couples or guests seeking extra seclusion. With fully equipped kitchens in every unit and expansive common areas, the property perfectly balances independent living with shared moments.
Surrounded by rolling vineyards producing a refined selection of "Super Tuscan" wines, the estate invites you to embrace the slow pace of Italy. The grounds are a masterpiece of landscape design, featuring manicured lawns, traditional terracotta planters, and vibrant blooms. At the heart of the garden lies a generous swimming pool, fully outfitted with elegant sun loungers and umbrellas.
This elegant and spacious holiday home is perfectly suited for a luxurious escape with family or friends. The property comfortably accommodates up to twelve guests (with capacity for an additional two guests upon request).
The Experience
When you arrive at Secluded Wine Rustic Estate: 1300S Castle Suite & you’ll find a beautiful clean well-maintained property with views of the hills ideal for a peaceful holiday in Tuscany. For your pleasure you will find a private pool where you can relax while enjoying a nice cold beverage after a hectic day of shopping. For your pleasure, on the grounds there is a playground and barbecue grill. If you enjoy cooking for family and friends there is a well-equipped kitchen including coffee machine, microwave, toaster, stove and refrigerator, as well as, plenty of tableware and cutlery for up to 12 people. If you prefer to dine 'al fresco', there is a fully furnished balcony where you can enjoy the weather while dining outdoors.
What's Nearby?
Most people enjoy visiting nearby cities and towns while on vacation, so for your reference this is a list of popular places with distances (as the crow flies) from the property: Siena 14 km (8 mi), San Gimignano 46 km (28 mi), Montalcino 49 km (31 mi), Greve In Chianti 53 km (33 mi) and Montepulciano 72 km (45 mi).
Some other major tourist destinations you should consider visiting are: Florence 76 km (47 mi), Viareggio 170 km (105 mi), Forte Dei Marmi 177 km (110 mi), Rome 248 km (154 mi), Venice 322 km (200 mi) and Milan 372 km (231 mi).
Additional Information
Check-In Time: 16:00 - 20:00
Check-Out Time: 06:00 - 10:00
Pool Open: 15 May - 30 September (If you'd like the pool open outside these dates, please make that request prior to booking)
Nearest Airports (distances as the crow flies): Firenze Peretola (flr) 88 km (55 mi), Pisa (psa) 124 km (77 mi), Bologna (blq) 175 km (109 mi), Roma Ciampino (cia) 257 km (160 mi) and Roma Fiumicino (fco) 270 km (168 mi).
Additional Services
Cooking Lessons - Learn from a local chef the techniques required to master Tuscan cuisine. The owner can schedule to have a chef come to the property for a cooking lesson for any number of people in your group. It's a fun way to spend time with friends and family while discovering the secrets vital to prepare mouth-watering Tuscan meals when you return home. For more details and the extra cost, please contact us.
Professional Chef - Are you looking for a real treat during your holiday? Why not book a professional chef to prepare and serve you a delicious meal using local produce? The chef will arrange the meal based on your preferences and dietary requirements. The chef will offer advice for the various courses and the wine. Inquire for more details and the supplemental costs.
Meals - If you'd like to have meals provided during your stay, either half-board or full-board is available. If you prefer only breakfast be provided, that can be organized as well. Ask about the extra costs.
Tours - Custom tours can be scheduled by the owner for your group. For more details about the tours available, speak to the owner upon arrival or inquire prior to booking. The cost will vary depending in the specific tour and number of people.
Owner Assistance - Since the owner lives nearby, he is always available to offer advice and suggestions during your visit. In case you need assistance, it's nice to have someone available to help. In any case, the owner will always respect your privacy.
Exclusive Estate Inclusions : elevate your stay, we offer these bespoke services upon reservation:
When you choose the Castle Experience, your stay includes a curated selection of authentic local luxuries:
- Gourmet Farm-to-Table Breakfast: Start your morning in the castle’s elegant common wing with a signature breakfast prepared by the Castellana (the Lady of the Castle). Every ingredient is organic and locally sourced ("Km 0"), with each dish prepared à la minute to your preference upon your arrival at the table.
- Estate Wine Tasting: Enjoy an exclusive guided tour of the castle with a private tasting in the castle’s historic cellar. This experience can be scheduled at your convenience with a simple advance reservation.
Bespoke Guest Experiences (Optional)
To further enhance your Tuscan retreat, we are pleased to arrange the following premium services:
- Dining with the Castellana: Enjoy an elegant, candlelit dinner hosted in the castle's private courtyard—an intimate glimpse into authentic noble life.
- Culinary Arts: Participate in private cooking classes or enjoy professionally catered buffet dinners.
- Outdoor Adventures: Explore the region with curated wine tours, guided bike excursions, or scenic hiking trips through the Montagnola Senese.
- Tuscan Traditions: Experience the thrill of a professional truffle hunting.
Medieval Castle Living: Vineyards, Swimming Pool &
Book your vacation for the period from 15 May 2026 to 31 May 2026 and save 20% (minimum 2 nights).
Book now and save 15%. Offer valid until 31 March 2026 and for a minimum stay of 2 nights.
Book your vacation for the period from 01 July 2026 to 31 August 2026 and save 15% (minimum 2 nights).
Nido del Sorbino
Wonderful independent vacation home with WIFI, private pool, TV, terrace and pets allowed
- 3
- 1
- 1
Description
Property Summary
The "Nido del Sorbino" cottage offers a tranquil vacation rental nestled in the heart of Tuscany, situated on a private 2,000 square meter fenced plot with a terraced and natural garden. The property boasts a small seasonal swimming pool, a yard, internet WiFi access, and parking facilities, providing you with a comfortable and convenient stay.
Outdoors
The cottage embraces the beauty of the outdoors with its terraced and natural garden, creating a serene setting for outdoor activities. Indulge in the refreshing experience of the small swimming pool, measuring 3 x 2 meters with a depth of 140 centimeters, available seasonally from May 1 to September 30.
Other Information
Castiglion Fiorentino, Italy, serves as the idyllic location for this holiday rental, offering easy access to nearby amenities and attractions. Situated at an elevation of 460 meters above sea level, the cottage is a mere 4 kilometers from the town center and 15 kilometers from Arezzo. A narrow motor access of 200 meters via an unmade road leads to the property.
Distances and Attractions
The surrounding area offers a wealth of attractions and conveniences. The nearest shop is just 1.5 kilometers away, while a supermarket is conveniently located 2 kilometers from the property. The "Castiglion Fiorentino" railway station is situated 4 kilometers away, providing easy access to transportation. Outdoor enthusiasts can enjoy the sandy beach of "Castiglione della Pescaia" located 160 kilometers away or the "Trasimeno" bathing lake, which is 35 kilometers from the cottage. Additionally, a golf course with 18 holes is a short 15-kilometer drive away. Nearby towns and cities worth exploring include Cortona (15 km), Firenze (100 km), and Valdichiana Outlet Village (25 km). A car is highly recommended to fully experience the surrounding attractions. Nido del Sorbino
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- 2
- 2
Description
Property Summary
"Il Sorbino" is a charming rustic cottage located in Castiglion Fiorentino, Italy. Offering a tranquil holiday rental experience, the property boasts a private fenced area of 2,000 square meters with a terraced garden lawn. The highlight is the 10 x 5-meter swimming pool with depths ranging from 12 to 220 centimeters, available for use from May 1 to September 30. Guests can enjoy an outdoor shower, terrace, garden furniture, and the pool is maintained by the owner or gardener. Additionally, the property provides Internet WiFi and parking on the premises.
Outdoors
The property features a private area of 2,000 square meters, which is fenced and includes a terraced garden lawn. Guests can enjoy the highlight of the property, the swimming pool, measuring 10 x 5 meters with a depth ranging from 12 to 220 centimeters. The swimming pool is available for use from May 1 to September 30. An outdoor shower, terrace, and garden furniture are also provided, and the pool is maintained by the owner or gardener.
Other Information
Access to the property can be a bit challenging as the motor access is 200 meters long, bumpy, and narrow, making it recommended for guests to arrive by car. Parking is available on the premises. Bicycles are also available for an additional fee. The nearest shop is 1.5 kilometers away, while the supermarket is 2 kilometers away.
Distances and Attractions
The property is situated 4 kilometers away from the center of Castiglion Fiorentino, 15 kilometers from the center of Arezzo, and 35 kilometers from the lake. The railway station "Castiglion Fiorentino" is 4 kilometers away, and the sandy beach "Castiglione della Pescaia" is 160 kilometers away. For swimming, the bathing lake "Lago Trasimeno" is 35 kilometers away. Additionally, there is a 9-hole golf course located 15 kilometers away. Nearby attractions include the town of Cortona at 15 kilometers, Florence at 100 kilometers, and the Valdichiana Outlet Village at 25 kilometers. Il Sorbino
- 7
- 2
- 2
Description
Property Summary
Cottage "Santa Lucia" is a beautiful semi-detached holiday rental located near the center of Castiglion Fiorentino, a picturesque village in Tuscany. This charming cottage boasts a 3-hectare orchard, a private garden lawn with trees, and a highlight 12 x 6 meter swimming pool with a depth of 140-200 cm, available seasonally. You can enjoy the outdoor spaces, including an outdoor shower and parking on the premises, while staying connected with wifi internet.
Outdoors
The property is surrounded by a vast 3-hectare orchard, perfect for nature lovers and outdoor walks. You'll have access to a private garden lawn and trees, ideal for relaxing and soaking up the Tuscan sun. The swimming pool, measuring 12 x 6 meters with a depth of 140-200 cm, is a true highlight, available seasonally from May 1st to September 30th, providing a refreshing escape on hot summer days.
Other Information
Cottage "Santa Lucia" offers wifi internet access, allowing you to stay connected during your holiday rental. The property also features an outdoor shower and parking on the premises for your convenience.
Distances and Attractions
Castiglion Fiorentino, a charming village with shops and supermarkets for your daily needs, is just 2.5 km away. The railway station "Castiglion Fiorentino" is conveniently located 2.5 km from the cottage, making it easy to explore nearby areas. The Trasimeno lake, perfect for water sports enthusiasts, is 35 km away. Fashion lovers will appreciate the Valdichiana Outlet Village, located 25 km from the property. Additionally, the cities of Arezzo and Cortona, popular destinations in the region, are 20 km and 12 km away, respectively. Santa Lucia
- 6
- 3
- 2
Description
Property Summary
House "La Felcaia" is a vacation rental located in the beautiful countryside of Tuscany, Castiglion Fiorentino, Italy. It offers a peaceful retreat away from the city's hustle and bustle while still being conveniently located near the village. The property boasts a terraced garden filled with trees spanning 3 hectares, providing ample outdoor space. You can enjoy exclusive access to a swimming pool measuring 11 x 5 meters, with a depth of 90 - 190 cm, available from May 1 to October 6. The private property spans across 500 m2 and is surrounded by a fenced terraced garden. Amenities include internet WiFi, roofed parking for two cars, and a burglar alarm system.
Outdoors
The property offers a range of outdoor amenities for your enjoyment. For shared use, there is a 50 m2 pergola, garden furniture, and a table tennis table. Within the private fenced terraced garden, you can find a swimming pool with a WC and an outdoor shower in the pool area. Additional recreational facilities include a table tennis table and table football available inside the house. The terraced garden is filled with trees, creating a serene and natural environment for your vacation rental experience.
Other Information
House "La Felcaia" is situated on the owner's property, who resides on the same premises. To explore the surrounding areas, it is recommended that you have a car during your stay. The property is located at an elevation of 600 meters above sea level, providing a beautiful and scenic environment. The owner's presence on the property ensures assistance and support if needed.
Distances and Attractions
House "La Felcaia" enjoys a strategic location with easy access to various nearby attractions. The village center of Castiglion Fiorentino is just 2.5 km away, while the center of Cortona is 10 km away. Shops and supermarkets are conveniently located 2.5 km and 3.5 km away, respectively. The Castiglion Fiorentino railway station is 3.5 km away, making it easy to explore the region. For beach enthusiasts, Castiglione della Pescaia sandy beach is 160 km away, and Lago Trasimeno, a bathing lake, is 35 km from the property. Golf enthusiasts can enjoy the 9-hole golf course located 13 km away, and hiking enthusiasts can explore the walking paths directly from the house. Popular tourist destinations like Arezzo (25 km), Florence (100 km), and Valdichiana Outlet Village (20 km) are within easy reach. La Felcaia
