Autumn Vacation Rentals in Castelfranco di Sopra

Excellent 1929 Guest Reviews 4.56 /5

Results 401 - 420 of 495

Total Results: 495


Il Sogno di Pietro: Cloud, Sky, Water, Dusk, Swimming Pool, Afterglow, Sunset, Horizon, Tree, Landscape   Special Offer 0% Interest Installments € 773 - € 1099/night

Pretty private villa rental with private pool, WIFI, A/C, TV, patio, pets allowed and panoramic view

  •   11
  •   5
  •   4
: EAS207898
€ 773 - € 1099per Night

Description

Property Summary
Il Sogno Di Pietro is a beautiful and comfortable villa surrounded by trees and fields in Castiglion Fiorentino, Italy. The property features a main house and an outbuilding, offering a spacious and private setting. It boasts a fenced 6,500 square meter grounds with a lush lawn, a seasonal swimming pool (12 x 4 meters, depth 140 cm, available from April 15 to October 30), an outdoor shower, a pergola, garden furniture, a barbecue area, and parking on the premises. With amenities like Internet Wi-Fi, it provides a perfect setting for a relaxing vacation rental.

Outdoors
The property offers an idyllic outdoor experience with its expansive 6,500 square meter fenced grounds. Guests can enjoy the well-manicured lawn, perfect for lounging or outdoor activities. The highlight is the seasonal swimming pool, measuring 12 x 4 meters with a depth of 140 cm, available from April 15 to October 30. Enhance your alfresco experience with the outdoor shower, pergola, garden furniture, and barbecue area. Just an example, you can savor delightful meals prepared on the grill while enjoying the beautiful surroundings.

Other Information
The property is conveniently located near essential amenities. A grocery store and a supermarket are just 3 km away, ensuring easy access to supplies. For dining options, a restaurant is only 1 km from the villa. The "Firenze-Roma" railway station is 3 km away, providing convenient transportation links. Those seeking relaxation can visit the thermal baths at "Rapolano Terme," situated 37 km from the property, or the bathing lake "Trasimeno." The owner does not accept youth groups, ensuring a peaceful atmosphere for families and couples.

Distances and Attractions
Il Sogno Di Pietro offers a prime location to explore the region's rich cultural and historical attractions. Nearby destinations include Cortona (13 km), Arezzo (16 km), Lucignano (20 km), Passignao Sul Trasimeno (31 km), Castiglione Del Lago (33 km), and Pienza (47 km). These charming towns and cities offer a glimpse into the region's rich heritage, with stunning architecture, museums, and picturesque landscapes to explore. Whether you're seeking cultural immersion or natural beauty, this holiday rental provides a convenient base to experience the best of the area. Il Sogno di Pietro

Casa Laura: Interior Design, Furniture, Flooring, Wood, Cabinetry, Ceiling, Floor, Countertop, Room, Kitchen   Special Offer 0% Interest Installments € 79 - € 267/night

Unique private vacation rental with WIFI, TV and pets allowed

  •   6
  •   3
  •   3
: EAS221861
€ 79 - € 267per Night

Description

Property Summary

Casa Laura is a cosy, rustic single-family house situated at 580 metres above sea level, surrounded by trees in the peaceful countryside, just 9.4 kilometres from the centre of Anghiari, Italy. This charming holiday rental features a private small garden that is not fenced, providing you with a tranquil outdoor space to enjoy the natural surroundings. The property offers convenient parking at the house, ensuring easy access for your vehicle throughout your stay. You will have access to Internet Wifi, keeping you connected during your time at this retreat. The accommodation's location combines rural serenity with practical accessibility to nearby amenities and attractions.

Outdoors

The property boasts a private small garden surrounded by trees, creating a peaceful natural setting at 580 metres above sea level. Please note that the garden is not fenced. You will find parking available directly at the house for your convenience. The rustic countryside location provides a serene environment whilst remaining accessible to local services and attractions.

Other Information

A grocery store is located 6.4 kilometres from the property, whilst a restaurant can be found just 5 metres away. A bus stop is conveniently situated 50 metres from the house. Please note that a car is recommended for your stay to fully explore the surrounding area and access amenities with ease.

Distances and Attractions

Casa Laura is positioned 9.4 kilometres from the centre of Anghiari, Italy, offering easy access to this historic town. Nearby attractions include Arezzo at 16 kilometres, Sansepolcro at 17 kilometres, Città Di Castello at 32 kilometres, Cortona at 55 kilometres, and Firenze at 95 kilometres. The well-known Lago Trasimeno can be easily reached at a distance of 80 kilometres from the property, providing opportunities for day trips and exploration of the beautiful Italian landscape. Casa Laura

Volpe: Sky, Property, Building, Snow, Window, Wood, Slope, House, Tree   Special Offer 0% Interest Installments € 88 - € 154/night

Wonderful holiday villa with A/C, WIFI, TV, balcony and pets allowed

  •   4
  •   2
  •   2
: EAS200973
€ 88 - € 154per Night

Description

Property Summary
You are considering Casa Volpe, a beautiful, comfortable 2-family detached house in Castiglion Fiorentino, Italy. It is a renovated property located 1 km from the town center in a residential area. The property boasts a private garden of 250 m2, on-site parking, and an EV charging station. It offers amenities such as a yard, internet WiFi, parking, and an EV charging station. The property is ideal for a vacation rental.

Outdoors
The property features a shared garden of 2,000 m2 that is fenced, providing ample outdoor space for you to enjoy. Additionally, you have access to a private garden of 250 m2, perfect for relaxing or dining al fresco.

Other Information
Please note that the owner does not accept youth groups and resides on the same property in a separate semi-detached house. A car is recommended during your stay.

Distances and Attractions
The property is conveniently located near various amenities, including a grocery store 400 m away, a supermarket 500 m away, a restaurant and bar within 1 km, and the "Firenze-Roma" railway station just 3 km away. For those seeking relaxation, the "Rapolano" thermal baths are 45 km away, and the "Trasimeno" bathing lake is only 20 km from the property. Nearby attractions include the charming towns of Cortona (11 km), Arezzo (16 km), Passignano sul Trasimeno (29 km), Castiglion Del Lago (29 km), Pienza (45 km), and the beautiful city of Siena (60 km). Volpe

Il Fienile di Leo: Tree, House, Cottage, Home, Rural Area, Landscape, Hill, Land Lot, Hill Station   Special Offer 0% Interest Installments € 77 - € 178/night

Stunning private vacation rental with WIFI, A/C, TV, patio and panoramic view

  •   4
  •   1
  •   1
: EAS214626
€ 77 - € 178per Night

Description

Property Summary
Il Fienile di Leo is a beautiful, rustic house with two stories, recently renovated in 2025. Surrounded by meadows and vineyards, this vacation rental offers a private, natural state property with a terraced garden. Located in a hamlet just 1 km from the center of Castel San Gimignano and 12 km from San Gimignano itself, the property boasts a secluded, sunny position on a slope in the countryside. Enjoy the convenience of parking at the house, as well as amenities like a yard, internet Wi-Fi, and parking.

Outdoors
The property features a private, natural state property with a terraced garden, offering a serene outdoor space to relax and enjoy the surroundings. It is situated in a hamlet with three houses, providing a peaceful and tranquil setting.

Other Information
The property is suitable for two adults and two children, making it an ideal choice for a family vacation rental. Local farm products are available for purchase, allowing you to experience the region's fresh and authentic flavors. Please note that the owner resides on the same property. Baby equipment is included, ensuring a convenient and comfortable stay for families with young children.

Distances and Attractions
The property is conveniently located just 1 km from the center of Castel San Gimignano and 12 km from the center of San Gimignano, a charming town in the province of Siena, Italy. Nearby attractions include Volterra (20 km), Siena (50 km), and Florence (70 km), offering ample opportunities to explore the rich cultural heritage and scenic beauty of the region. Additionally, the sandy beach of Cecina Mare is approximately 60 km away, and an outdoor swimming pool is located within 10 km of the property. Il Fienile di Leo

Borgo Santinovo: Swimming Pool, Property, Leisure, Resort Town, Real Estate, Building, Leisure Centre, Backyard, Estate, Resort € 91 - € 264/night

Amazing multi-unit vacation home with pool, TV, patio and pets allowed

  •   12
  •   42
  •   22
  •   14
€ 91 - € 264per Night
  Accommodation
Caminetto 2 1 1
Loggiatino 1 2 1 1
Loggiatino 2 2 1 1
Soppalco 4 2 1
Torrino 2 2 1
Archi 4 2 1
Olivi 4 2 1
Pergola 4 2 1
Granaio 6 3 2
Belvedere 4 2 1
Casa Fienile 6 3 2
Stalla 2 1 1
42 22 14

Description

Borgo Santinovo is a nice property with pool. Borgo Santinovo is a vacation home that has a total of 12 private apartments. The property can accommodate up to 42 guests comfortably in 22 bedrooms with 14 bathrooms. Conveniently located 6 km (4 mi) from Colle Di Val D'elsa, Italy in the tourist area "San Gimignano And Surroundings" and only 26 km (16 mi) from San Gimignano.


The farmhouse dining room can seat about 45 people comfortably (a maximum of 50 can be accommodated, but obviously space will be tighter). It is equipped with a kitchen and a small bathroom. It is used for dinners and breakfasts and is generally for the exclusive use of the property.
However, in the case of groups renting all 12 flats, it is possible for them to rent it at an extra cost to be paid on the spot ( on request) + € 1000.00 cash deposit to be paid on arrival. In the event of damage to the lounge, furniture, kitchen equipment or bathroom, the full amount will be retained.

The Experience
Upon arrival you will be greeted by the owner or manager where you’ll find a nice clean well-maintained property perfect 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. A lot of people traveling with friends prefer a multi-unit holiday rental where they can spend time together in the common areas, like the pool or garden, but still have their own private living quarters with bedroom and bathroom. In addition, each unit has its own kitchen with plenty of utensils, tableware and cutlery.

Places 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: San Gimignano 26 km (16 mi), Siena 32 km (20 mi), Greve In Chianti 50 km (31 mi), Florence 56 km (35 mi) and Montalcino 68 km (42 mi).

Some other major tourist destinations you should consider visiting are: Florence 56 km (35 mi), Viareggio 152 km (94 mi), Forte Dei Marmi 159 km (99 mi), Rome 267 km (166 mi), Venice 308 km (191 mi) and Milan 351 km (218 mi).

Additional Information
Pets Welcome - If your pet is travelling with you on vacation that is not a problem at Borgo Santinovo. If you have a large dog or multiple pets, please inquire for permission prior to booking.
Check-In Time: 16:00 - 19:00
Check-Out Time: 08:00 - 10:00
Pool Open: 20 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) 72 km (45 mi), Pisa (psa) 93 km (58 mi), Bologna (blq) 153 km (95 mi), Roma Ciampino (cia) 276 km (171 mi) and Roma Fiumicino (fco) 288 km (179 mi).

More Services
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.

Borgo Santinovo

Colle Val D'Elsa 615: Water, Swimming Pool, Reflection, Resort, Water Feature, Reflecting Pool, Shade, Garden, Landscaping, Pond   Special Offer 0% Interest Installments € 134 - € 223/night

Pretty multi-unit holiday villa with pool, WIFI, TV, patio, pets allowed and panoramic view

  •   2
  •   6
  •   2
  •   2
: EAS176590
€ 134 - € 223per Night
  Accommodation
Podere Fontemaggio - Monolocale 615.1 2 1 1
Podere Fontemaggio - Fienile 615.2 4 1 1
All 2 Accommodations 6 2 2

Description

Property Summary

Podere Fontemaggio is a cosy country house situated in the charming district of Campiglia, just 4 km from the centre of Colle Di Val D'elsa, Italy. This holiday rental is surrounded by trees and fields, offering a peaceful retreat in the Tuscan countryside. The property consists of 2 houses within the residence, containing 4 apartments total. The residence features a refreshing swimming pool measuring 16 x 6 m with a depth of 140 cm, available seasonally from 25.Apr.-17.Oct., equipped with a modern salt-electrolysis pool-cleaning system. The expansive yard encompasses 3 ha of property, including a garden with plants and trees as well as an orchard. You will have access to Internet Wifi throughout your stay. Parking is conveniently available on the premises, accessible via a 400 m long motor access road (via unmade road). The property offers an installment plan for your convenience. The residence is equipped with electric gates, and the owner lives on the same property.

Outdoors

The outdoor amenities at Podere Fontemaggio provide an idyllic setting for relaxation and enjoyment. The property spans 3 ha and is for shared use among guests, featuring a beautifully maintained garden with plants and trees as well as a productive orchard. The swimming pool area is well-appointed with shower/WC facilities, an outdoor shower, and a terrace perfect for lounging. A barbecue is available for guests who wish to enjoy al fresco dining while taking in the scenic views of the surrounding countryside.

Other Information

The residence includes shared facilities such as a washing machine and tumble dryer for guest convenience. The property is located in the district of Campiglia (700 m), positioned 13 km from the centre of San Gimignano and 33 km from the centre of Siena, outside the main resort area. Local sale of farm products is available on site, allowing you to experience authentic Tuscan produce.

Distances and Attractions

The property is ideally situated for exploring the treasures of Tuscany. You will find a grocery store just 700 m away, while a supermarket and restaurant are both 4 km from the residence. The bus stop is conveniently located 700 m from the property, and the railway station "Colle di Val d'Elsa" is 4 km away. The historic centre of San Gimignano is 13 km from Podere Fontemaggio, and the beautiful city of Siena is 33 km away. For beach enthusiasts, the park "Cecina Mare" is 60 km from the property. Both outdoor and indoor swimming pools are available 4 km from the residence. Colle Val D'Elsa 615

Pieve di Sant Ippolito: Water, Sky, Plant, Property, Swimming Pool, Nature, Azure, Tree, Body Of Water, Shade € 126 - € 210/night

Wonderful private vacation rental with WIFI, pool, A/C, TV and terrace

  •   4
  •   2
  •   1
€ 126 - € 210per Night

Description

The Pieve di Sant'Ippolito is a small outbuilding in the heart of the Crete Senesi. You will find it on the outskirts of the village of Asciano, in a panoramic and sunny position. The property is composed of the manor house where the owners' family lives, an annexe and the very ancient Church of "Sant'Ippolito e Cassiano", whose origins date back to the 3rd-4th century AD. Inside the church you can admire a beautiful fresco painted by several renowned artists of the Umbrian school, such as Pinturicchio and Raphael, but erroneously attributed to the Sienese painter Giacomo Pacchiarotti a minor artist of the Sienese school. On 13 August, for the feast of Saints Ippolito and Cassiano, the church will be open to the public and a Holy Mass will be celebrated there. During the rest of the year, being part of private property, the owners allow it to be opened only on rare occasions, while guests of the house will be able to visit it freely.
You will reach the village of Asciano, with shops and services of all kinds, by a pleasant walk of just a few minutes.
All around the house you will find a large, fully fenced garden equipped with children's games, a table tennis table, barbecue and tables and chairs for your outdoor meals. The beautiful round swimming pool (dimensions 13 x 8 m, depth 1.20 - 2.10 m) with water geyser, infinity edge with waterfall and 3-seater whirlpool bath will be at your disposal during the whole year. Near the pool there are two gazebos furnished with relaxing armchairs, table, deckchairs and sun loungers for your days of rest in the company of your favourite book. Some outdoor spaces and the swimming pool are in common use with the owners.
At Sant'Ippolito you will find well-kept furnishings and the many facilities inside the house (air conditioning, satellite TV, barbecue, microwave, washing machine, dishwasher, iron, mosquito nets, alarm system and Wi-Fi connection) will guarantee a comfortable and relaxing holiday.
The owners are very helpful for any needs during your stay and particularly sensitive to energy saving, in fact the house is equipped with solar panels for the production of hot water. Pieve di Sant Ippolito

La Casa di Pino: Swimming Pool, Resort, Garden, Eco Hotel, Outdoor Furniture, Thermae, Water Feature, Shade, Estate, Landscaping € 141 - € 212/night

Pretty private villa rental with A/C, WIFI, private pool and TV, near Cortona

  •   4
  •   1
  •   1
€ 141 - € 212per Night

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

Galleria di Brolio: Water, Sky, Plant, Property, Swimming Pool, Building, Azure, Tree, Leisure, Grass € 197 - € 303/night

Pretty private villa with A/C, WIFI, private pool, TV and veranda, near Cortona

  •   10
  •   4
  •   3
€ 197 - € 303per Night

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

Colle Val D'Elsa 620: Swimming Pool, Outdoor Furniture, Resort, Sunlounger, Eco Hotel, Chair, Umbrella, Outdoor Table, Hotel, Landscaping   Special Offer 0% Interest Installments € 544 - € 1166/night

Wonderful multi-unit villa rental with WIFI, A/C, private pool, TV, patio and panoramic view

  •   2
  •   28
  •   14
  •   16
: EAS214869
€ 544 - € 1166per Night
  Accommodation
Podere San Giuseppe 620.1 16 8 9
Podere San Giuseppe 620.2 12 6 7
All 2 Accommodations 28 14 16

Description

Property Summary

Podere San Giuseppe is a spacious and comfortable cottage situated in a tranquil location near Colle Di Val D'elsa, Italy. This vacation rental consists of a main house and an outbuilding, offering guests a private retreat surrounded by natural beauty. The property features a fenced swimming pool (6 x 12 m), available from May 15 to October 15, well-maintained grounds, convenient parking on the premises, and complimentary internet WiFi access.

Outdoors

The natural state property encompasses a serene garden setting positioned 100 meters from the forest edge. The outdoor amenities include a pool house with shower facilities, a dedicated area for table tennis, and a welcoming patio with terrace. Guests can enjoy the provided garden furniture and make use of the barbecue facilities. The pool and grounds are regularly maintained by the owner/gardener, ensuring a pristine environment throughout your stay.

Other Information

The property is particularly suitable for hosting events and comes equipped with baby equipment at no additional cost. Groups of teenagers are welcome but must make special arrangements prior to booking. Access to the property is via a 1-kilometer unpaved road, making a car essential for your stay.

Distances and Attractions

The property is situated 7 kilometers from the center of Colle di Val d'Elsa, where you'll also find the nearest bus stop. The secluded location offers both privacy and convenience, with easy access to the historic town center and local attractions. The positioning provides an ideal base for exploring the broader Tuscan region while maintaining a peaceful countryside retreat. Colle Val D'Elsa 620

La Casa del Nonno: Water, Sky, Cloud, Plant, Green, Swimming Pool, Azure, Natural Landscape, Tree, Building € 95 - € 142/night

Great home with WIFI, private pool, TV and pets allowed

  •   4
  •   2
  •   1
€ 95 - € 142per Night

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

Casa Angela: Swimming Pool, Residential Area, Resort, Leisure, Thermae, Estate, Outdoor Furniture, Human Settlement, Villa, Hacienda € 205 - € 338/night

Private Villa rental with A/C, private pool, WIFI, TV, balcony, pets allowed, near Cortona

  •   8
  •   3
  •   3
€ 205 - € 338per Night

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

Collina dei Fiori: Water, Plant, Sky, Cloud, Umbrella, Azure, Swimming Pool, Shade, Outdoor Furniture, Tree € 350 - € 574/night

Stunning independent holiday villa with WIFI, A/C, private pool, TV and pets allowed, near Arezzo

  •   9
  •   4
  •   3
€ 350 - € 574per Night

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

Podere i Gigli: Water, Plant, Sky, Property, Swimming Pool, Azure, Tree, Shade, Rectangle, Outdoor Furniture € 140 - € 240/night

Unique private holiday rental with private pool, A/C, WIFI, TV and terrace, near Cortona

  •   6
  •   3
  •   3
€ 140 - € 240per Night

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: Water, Building, Sky, Property, Furniture, Plant, Swimming Pool, Table, Azure, Umbrella € 515 - € 865/night

Private Property with A/C, WIFI, private pool, TV, terrace, pets allowed, near Arezzo

  •   14
  •   7
  •   7
€ 515 - € 865per Night

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

Colle Val D'Elsa 616: Property, Swimming Pool, Building, House, Vacation, Real Estate, Villa, Home, Architecture, Hacienda 0% Interest Installments € 106 - € 238/night

Fabulous multi-unit vacation home with pool, WIFI, TV, patio and panoramic view

  •   8
  •   24
  •   12
  •   10
: EAS176591
€ 106 - € 238per Night
  Accommodation
Bardeggiano - Caterina 7 616.1 2 1 1
Bardeggiano - Caterina 5 616.2 2 1 1
Bardeggiano - Caterina 6 616.3 2 1 1
Bardeggiano - Caterina 8 (Col243) 616.4 2 1 1
Bardeggiano - Caterina 1 616.5 4 2 1
Bardeggiano - Caterina 2 (Col245) 616.6 4 2 1
Bardeggiano - Caterina 3 (Col246) 616.7 4 2 2
Bardeggiano - Caterina 4 (Col247) 616.8 4 2 2
24 12 10

Description

Property Summary
Agriturismo "Bardeggiano" offers a unique vacation rental experience in Tuscany. This two-story property comprises five houses and nine apartments, ideal for families or groups. It boasts a well-kept 12-hectare fenced garden, a large swimming pool (15 x 6 meters, 150 cm depth) available seasonally from May 13 to November 4, an outdoor shower, terrace, and barbecue area. Additionally, it provides WiFi, a washing machine (shared use, extra fee), parking on premises with electric gates, and the owner resides on-site, ensuring assistance when needed. The individually designed and furnished houses and apartments offer amenities like linen and towel changes (extra fee) and baby equipment included in the rental.

Outdoors
Agriturismo "Bardeggiano" is surrounded by trees and fields, offering a tranquil and secluded environment. The property features a meticulously maintained 12-hectare garden, fenced for privacy and security. Guests can enjoy a refreshing swim in the large 15 x 6-meter swimming pool with a depth of 150 cm, available seasonally from May 13 to November 4, maintained by the owner/gardener. Additionally, there is an outdoor shower, terrace, and barbecue area for al fresco dining and relaxation.

Other Information
Agriturismo "Bardeggiano" provides additional services for guests, such as linen and towel changes (for an extra fee) and baby equipment included in the rental. The property has WiFi and a washing machine available for shared use (extra fee). Parking is available on the premises, accessible through electric gates, adding convenience and security. The owner resides on the same property, ensuring assistance and peace of mind for guests.

Distances and Attractions
Agriturismo "Bardeggiano" is conveniently located just 4 km from the center of Colle di Val d'Elsa and 8.5 km from Monteriggioni, Italy. It is 26 km from Siena and 70 km from the sea, providing easy access to the region's top attractions. Nearby local attractions include San Gimignano (20 km), Florence, and Volterra, all within driving distance, making it an ideal base for exploring Tuscany's rich cultural and historical sites. Colle Val D'Elsa 616

Pozzonovo: Water, Plant, Sky, Property, Cloud, Swimming Pool, Tree, Nature, Azure, Grass € 72 - € 164/night

Cosy flat with WIFI, pool, TV and pets allowed, near Cortona

  •   3
  •   10
  •   3
  •   3
€ 72 - € 164per Night
  Accommodation
Il Susino 2 1 1
Il Ciliegio 4 1 1
Il Pesco 4 1 1
All 3 Accommodations 10 3 3

Description

Pozzonovo is an old farmhouse divided into 3 comfortable apartments and is the result of the skilful and careful renovation of a stone building. The three units have independent entrances and in the garden their own area equipped with a table, chairs, sun umbrella and barbecue, perfect for enjoying your meals in the open air.
You will find the farmhouse immersed in the Valdichiana countryside and, at the same time, close to the village of Castiglion Fiorentino, which can be easily reached on foot with a walk of about 1.5 km. From the railway station in Castiglion Fiorentino it will be easy to travel by train for day trips to Florence, Rome and other interesting cities in central Italy.
We advise you to immerse yourself in the life of the small village, its shops, bars and restaurants; you will get a glimpse of country life that still harks back to ancient traditions and customs.
The stone walls, wooden and brick ceilings and simple but comfortable furnishings give the apartments a special charm. You will immediately feel at home, welcomed by a warm atmosphere and by Mrs Rita, the owner, who is always ready to assist her guests in times of need.
Together with the owner, you will be able to make use of the large outdoor area, a cool, large 6 x 12 m swimming pool (depth 0.90-1.40 m - open from 01 May to 30 September) located in front of the house, the badminton court, table tennis and bowling green.
Internet access available only in the garden. Pozzonovo

San Martino: Swimming Pool, Property, Grass, Leisure, House, Real Estate, Estate, Building, Home, Lawn € 179 - € 265/night

Great flat with A/C, pool, TV, patio and panoramic view

  •   4
  •   10
  •   5
  •   4
€ 179 - € 265per Night
  Accommodation
Gelsomino 2601 2 1 1
Girasole 2602 2 1 1
Fiordaliso 2603 2 1 1
Melograno 2604 4 2 1
10 5 4

Description

San Martino is located 9 km (6 mi) from Colle Di Val D'elsa, Italy and only 25 km (16 mi) from San Gimignano in the tourist area "San Gimignano And Surroundings". Vacation rental San Martino is a lovely stone building that includes shared pool and air conditioning. The apartment has been designed with a total of four private units. The property can accommodate up to ten guests comfortably in five bedrooms with four bathrooms. If you enjoy a round of golf while on holiday, then you will be happy to know there is a golf course nearby.

What to Expect
Upon arrival you’ll find a lovely clean well-maintained property with views of the hills ideal for a splendid holiday in Tuscany. For your pleasure you will find a pool where you can unwind while enjoying a nice cold beverage after a hectic day of shopping. Outside you will also find a patio and barbecue grill. Many people traveling with friends prefer a multi-unit vacation rental where they can spend time together in the common areas, such as the pool or garden, but still have their own private living quarters with bedroom and bathroom. In addition, each unit has its own kitchen with plenty of utensils, tableware and cutlery.

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: San Gimignano 25 km (16 mi), Siena 35 km (22 mi), Greve In Chianti 52 km (33 mi), Florence 59 km (37 mi) and Montalcino 71 km (44 mi).

Some other major tourist destinations you should consider visiting are: Florence 59 km (37 mi), Viareggio 154 km (96 mi), Forte Dei Marmi 161 km (100 mi), Rome 269 km (167 mi), Venice 310 km (193 mi) and Milan 354 km (220 mi).

Additional Information
Check-In Time: 16:00 - 19:00
Check-Out Time: 09:00 - 09:30
Pool Open: 1 May - 15 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) 76 km (47 mi), Pisa (psa) 92 km (57 mi), Bologna (blq) 155 km (97 mi), Roma Ciampino (cia) 278 km (173 mi) and Roma Fiumicino (fco) 291 km (181 mi).


San Martino

Agriturismo Il Molinello: Aerial Photography, Bird'S-Eye View, Residential Area, Urban Design, Property, Suburb, Landscape, Land Lot, Estate, Photography 0% Interest Installments € 87 - € 265/night

Fabulous multi-unit villa rental with WIFI, pool, A/C, TV, patio, pets allowed and panoramic view

  •   5
  •   18
  •   9
  •   9
€ 87 - € 265per Night
  Accommodation
Cipresso 6 3 3
Gelso 2 1 1
Pini 2 1 1
Pomo 4 2 2
Albicocco 4 2 2
18 9 9

Description

In 1996 we moved to the Crete Senesi and we fell in love with this farmhouse Etruscan origins, medieval mill, peace and tranquillity. That’s why we decided to share it with our guests and their four-legged friends.
The farm keeps the whole family busy: Alessandro (biologist, nature guide and Sommelier), Elisa who looks after the administration, Mauro and Paola, retired but full time busy on the farm. And we hope that in the future even Emma and Guido will give us a helping hand.
We produce vegetables and fruit, olive oil and truffles from organic agriculture.
For our guests we organize a rich programme of initiatives discovering the colours and flavours of the Crete, wine tasting in our cosy winery and excursions by bike guided by Alessandro who is fond of cycling.
Distances:
Serre di Rapolano at 2 km, Rapolano Terme with all kind of shops at 5 km, Siena at 25 km.
Only 4 km from our farm there are the thermal baths of Rapolano which grant special discounts to our guests.
At guests disposal:
Wi-Fi internet connection in common room available free of charge
Baby bed available free of charge
weekly change of linen and towels Agriturismo Il Molinello

Villa Dei Michelangioli a Brolio: Swimming Pool, Property, Building, House, Real Estate, Resort, Villa, Home, Leisure, Apartment 0% Interest Installments € 787 - € 1300/night

Private Vacation home with hot tub, A/C, private pool, sauna, WIFI, TV, patio, near Cortona

  •   18
  •   9
  •   9
€ 787 - € 1300per Night

Description

Villa Dei Michelangioli a Brolio is located 630 m (2059 ft) from Fattoria, Italy and only 17 km (11 mi) from Cortona in the tourist area "Cortona And Surroundings". Villa Dei Michelangioli a Brolio is a beautiful property (800 sq m) with air conditioning, WiFi internet and private pool. The property can sleep up to 18 people comfortably in nine bedrooms with nine bathrooms. If you enjoy a round of golf while on holiday, then you will be happy to know there is a golf course nearby.

Your Experience
When you arrive at Villa Dei Michelangioli a Brolio you’ll find a nice clean well-maintained property ideal for a peaceful vacation in Tuscany. After a busy day of shopping, spend some time with friends and family poolside enjoying a glass of wine - a perfect way to relax at the end the day. For your pleasure, on the grounds there is a barbecue grill and patio. There is a kitchen including microwave and stove, as well as, plenty of tableware and cutlery for up to 18 people.

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 17 km (11 mi), Arezzo 27 km (17 mi), Montepulciano 27 km (17 mi), Montalcino 52 km (32 mi) and Perugia 64 km (40 mi).

Some other major tourist destinations you should consider visiting are: Florence 105 km (65 mi), Viareggio 192 km (119 mi), Forte Dei Marmi 199 km (124 mi), Rome 201 km (125 mi), Venice 348 km (216 mi) and Milan 391 km (243 mi).

Additional Information
Check-In Time: 17:00 - 19:00
Check-Out Time: 09:00 - 10:00
Pool Open: 6 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) 114 km (71 mi), Pisa (psa) 173 km (107 mi), Bologna (blq) 193 km (120 mi), Roma Ciampino (cia) 210 km (130 mi) and Roma Fiumicino (fco) 222 km (138 mi).

Villa Dei Michelangioli a Brolio is equipped with a SPA and 2 swimming pools: one indoor with whirlpool and sauna (which can be used against supplement payment) and one outdoor in the garden. The indoor pool is heated (it can reach 30°/32° C) and open throughout the whole year on request and against payment).


Special Services
Cooking Lessons - If you're interested in learning more about Tuscan cooking, inquire about the cooking lessons that can be arranged at the property. It's a enjoyable way to spend time with friends and family while learning the techniques vital to master Tuscan cuisine. 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 sumptuous 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 extra costs.
Maid Service - If you'd like maid service during your trip that can be scheduled by the owner. Inquire for more details about the supplemental cost.

Villa De' Michelangioli