Vacation Rentals with Air Conditioning in Penna, Italy

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Casa Di Luca, Pool, Castelnuovo Berardenga: Swimming Pool, Landscape, Garden, Landscaping, Resort, Eco Hotel, Shade, Sunlounger, Outdoor Furniture, Estate € 420 - € 847/night

Pretty independent property with private pool, WIFI, A/C, TV, patio, pets allowed, panoramic view

  •   10
  •   4
  •   3
: EAS202998
€ 420 - € 847per Night

Description

Casa Di Luca, Pool, Castelnuovo Berardenga is located 14 km (9 mi) from Siena, Italy and only 39 km (24 mi) from Greve In Chianti in the tourist area "Siena And Surroundings". Casa Di Luca, Pool, Castelnuovo Berardenga is a lovely stone building (160 sq m) with private pool, air conditioning and WiFi internet. The property can sleep up to ten guests comfortably in four bedrooms with three bathrooms.

What to Expect
Upon arrival at Casa Di Luca, Pool, Castelnuovo Berardenga you’ll find a lovely clean well-maintained property with views of the hills ideal for a relaxing vacation 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. For your pleasure, on the grounds there is a playground, barbecue grill and patio. 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 ten people.

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: Greve In Chianti 39 km (24 mi), San Gimignano 51 km (31 mi), Montalcino 54 km (34 mi), Montepulciano 63 km (39 mi) and Arezzo 72 km (45 mi).

Some other major tourist destinations you should consider visiting are: Florence 80 km (50 mi), Viareggio 175 km (108 mi), Forte Dei Marmi 182 km (113 mi), Rome 240 km (149 mi), Milan 375 km (233 mi) and Naples 430 km (267 mi).

Additional Information
Pets Welcome - If your pet is travelling with you on holiday that is not a problem at Casa Di Luca, Pool, Castelnuovo Berardenga. 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: 15 May - 6 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) 93 km (58 mi), Pisa (psa) 128 km (79 mi), Bologna (blq) 180 km (112 mi), Roma Ciampino (cia) 249 km (154 mi) and Roma Fiumicino (fco) 261 km (162 mi).

Front outdoor space of about 100 square meters private and fenced.
Backyard space and pool (4x10 m) occasionally shared with the owner who has reserved a small portion of the house.

Casa Di Luca, Pool, Castelnuovo Berardenga

Il Tiglioré: Grass, Garden, Shade, Lawn, Landscaping, Leisure, Outdoor Furniture, Yard, Artificial Turf, Park   Special Offer 0% Interest Installments € 93 - € 264/night

Beautiful private villa with private pool, WIFI, A/C, TV, patio and pets allowed

  •   4
  •   2
  •   1
: EAS221918
€ 93 - € 264per Night

Description

Property Summary

Il Tiglioré presents a modern and cosy semi-detached house that has been thoughtfully renovated, positioned amidst tranquil fields just 5 km from the centre of Castiglion Fiorentino, Italy. This holiday rental features a well-maintained, fenced private garden adorned with a wildlife garden and mature trees, creating a serene outdoor environment. The property includes an above-ground swimming pool measuring 6 x 3 m with a depth of 132 cm, available seasonally from 01.Jun. through 31.Aug. You will benefit from convenient parking on the premises, ensuring ease of access throughout your stay. Internet WiFi connectivity is available to keep you connected during your visit. The spacious yard provides ample outdoor space for relaxation and recreation, complemented by an arbour, garden furniture, and barbecue facilities for outdoor dining and entertainment.

Outdoors

The outdoor spaces at Il Tiglioré offer you an inviting retreat surrounded by nature. The property's well-kept, fenced garden features a charming wildlife garden and established trees that provide natural shade and privacy. The above-ground swimming pool, measuring 6 x 3 m with a depth of 132 cm, is available for your enjoyment from 01.Jun. until 31.Aug., offering refreshing respite during the warmer months. An arbour provides a shaded spot for outdoor relaxation, while the garden furniture and barbecue facilities create perfect opportunities for al fresco dining and entertaining. The peaceful surroundings of fields enhance the tranquil atmosphere of this semi-detached residence.

Other Information

Please note that a car is recommended for convenient access to the property and surrounding areas. The owner resides in the same residence. A supermarket is located 3.3 km from the property, while restaurant options can be found 3 km away. A bus stop is situated 600 m from Il Tiglioré for those wishing to use public transportation.

Distances and Attractions

Il Tiglioré enjoys a favourable location for exploring the renowned attractions of Tuscany and Umbria. The historic town of Cortona is situated 16 km from the property, while Arezzo can be reached within 19 km. The celebrated hilltop town of Montepulciano lies 33 km away, and the cultural capital of Firenze is accessible at 99 km. Nature enthusiasts will appreciate the proximity to Lago Trasimeno, a well-known lake that can easily be reached at 40 km from the property. The property is positioned 5 km from the centre of Castiglion Fiorentino, Italy, providing convenient access to local amenities and attractions. Il Tiglioré

Il Cottage Roccaio: Swimming Pool, Blue, Water, Resort, Outdoor Furniture, Thermae, Eco Hotel, Hacienda, Water Feature, Villa 0% Interest Installments € 209 - € 426/night

Wonderful independent property with private pool, A/C, WIFI, TV, patio and pets allowed

  •   8
  •   3
  •   3
: EAS221882
€ 209 - € 426per Night

Description

Property Summary

Cottage Roccaio is a cosy, rustic, and comfortable semi-detached house featuring two storeys, nestled in a secluded and quiet position surrounded by fields and vineyards, located 3 km from the centre of Castiglion Fiorentino, Italy. This charming holiday rental offers a private, well-kept fenced garden and a seasonal swimming pool with salt water, available from 1st May to 30th October, with regular maintenance provided by the owner or gardener. The property includes convenient amenities such as a laundry room with a washing machine, ensuring a comfortable stay for guests. Internet WiFi connectivity keeps you connected throughout your visit, while a spacious yard provides ample outdoor space for relaxation. Private parking is available on the premises, with motor access to the house via a 600 m unmade road. Please note that the owner lives on the same property and has a dog, adding to the authentic countryside experience.

Outdoors

The outdoor spaces at Cottage Roccaio provide an idyllic setting for relaxation and enjoyment of the Tuscan countryside. You will have access to a private, well-kept garden that is fully fenced, offering both privacy and security. The seasonal swimming pool features salt water and is available for use from 1st May through 30th October, providing a refreshing retreat during the warmer months. The property is surrounded by picturesque fields and vineyards, creating a tranquil atmosphere perfect for unwinding. The pool maintenance is regularly handled by the owner or gardener, ensuring the facilities remain in excellent condition throughout your stay.

Other Information

Access to the property is via motor vehicle along a 600 m unmade road, and a car is recommended for your stay. The owner resides on the same property and has a dog. Essential amenities are conveniently located nearby, with a grocery store 2 km away, a supermarket 4 km from the property, and a restaurant situated 3 km from Cottage Roccaio. Public transportation is accessible via a bus stop located 3 km from the house.

Distances and Attractions

Cottage Roccaio is ideally positioned for exploring the renowned attractions of Tuscany and Umbria. The charming hilltop town of Cortona is just 11 km away, while the historic city of Arezzo can be reached within 22 km. The picturesque town of Montepulciano, famous for its wine, is located 38 km from the property, and the magnificent city of Firenze is 100 km away. Nature enthusiasts will appreciate the proximity to Lago Trasimeno, a well-known lake that is easily accessible at 29 km from the house. The property's location in Castiglion Fiorentino, Italy, serves as an excellent base for discovering the cultural and natural treasures of the region. Il Cottage Roccaio

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

Stunning private property with WIFI, A/C, private pool, 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

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

L'Oliviera: Water, Plant, Azure, Tree, Sky, Swimming Pool, Arecales, Shade, Leisure, Real Estate   Special Offer 0% Interest Installments € 105 - € 148/night

Superb private house with WIFI, A/C, TV, terrace and panoramic view

  •   4
  •   2
  •   1
: EAS73700
€ 105 - € 148per Night

Description

Property Summary

Nestled in the rolling Tuscan countryside of Siena, Italy, the charming detached house "L'Oliviera" offers a truly peaceful and sun-drenched retreat for those seeking an authentic holiday rental experience. Positioned in a quiet, elevated setting just 5 km from the historic centre of Siena, this beautiful property is surrounded by trees, open fields, and sits only 100 metres from the edge of a forest, creating a natural and serene atmosphere. The house benefits from complimentary Wi-Fi throughout, allowing guests to stay connected while enjoying the tranquillity of the Tuscan landscape. Private parking is conveniently available directly at the property, ensuring effortless arrivals and departures for those exploring the surrounding region by car.

Outdoors

The outdoor spaces of "L'Oliviera" are a true highlight of the property, offering guests a private and immersive connection with the natural Tuscan environment. The grounds feature a well-maintained lawn alongside a wildlife garden, thoughtfully designed to blend harmoniously with the surrounding countryside and its native flora and fauna. The property is enveloped by trees and open fields, providing a sense of seclusion and privacy that makes it an ideal setting for relaxing outdoors, breathing in the fresh country air, and enjoying the unspoiled beauty of the Sienese hills.

Other Information

Guests should be aware that heating at "L'Oliviera" is available and billed on-site, applicable during the period from 10 April to 31 October. Baby equipment is provided and included at no additional charge, making the property a practical and welcoming choice for families travelling with young children. The owner resides on the same property, ensuring a reassuring presence and the opportunity for personalised local assistance throughout the stay. Guests should also be aware that the owner keeps a dog on the premises. As the property is situated in a rural setting, the use of a car is strongly recommended in order to fully enjoy the surrounding area and access nearby services with ease.

Distances and Attractions

"L'Oliviera" enjoys a convenient location with easy access to a wide range of everyday amenities and cultural landmarks. A grocery store is located just 3 km away, while a shopping centre can be reached within 4 km, and a restaurant is a short 2 km drive from the property. Public transport is readily accessible, with a bus stop situated only 100 metres from the house, and the railway station "Siena" reachable within 6 km. For those wishing to explore the wider Tuscan region, the thermal baths of "Rapolano Terme" are approximately 35 km away, offering a wonderful opportunity for relaxation and wellness. The medieval village of Monteriggioni lies just 16 km from the property, while the iconic hilltop town of San Gimignano is 36 km away. The breathtaking landscape of the Crete Senesi can be explored within 30 km, and the celebrated wine town of Montalcino is situated 45 km from the house. The Renaissance gem of Pienza is approximately 50 km away, and Montepulciano, renowned for its Vino Nobile, can be reached within 65 km, making "L'Oliviera" an exceptional base from which to discover the very best of Tuscany. L'Oliviera

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

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

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

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

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

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

Villa del Mangia, 5Panoramic Pool and Chef Service: Swimming Pool, Tree, Resort, Outdoor Furniture, Garden, Shade, Eco Hotel, Landscaping, Hacienda, Estate 10% Off Discount  Special Offer € 2243 - € 2829/night

Wonderful independent holiday home with private pool, A/C, WIFI, terrace and panoramic view

  •   11
  •   6
  •   6
: EAS212162
€ 2243 - € 2829per Night

Description

Villa del Mangia is a villa located just a few kilometers from Siena.

The villa consists of a main building spread over two floors and an external annex, a former stone barn, which serves as the guesthouse. The total area of the property is 400 sqm. The entire complex was fully renovated in 2024, with incredible attention to detail and the use of high-quality materials, skillfully combining the charm of Tuscan tradition with modern comforts, furnishings, and top-tier materials, offering a luxurious and sophisticated environment. The villa, meticulously curated in every detail, reflects the refined taste of the owner and an emphasis on rare, high-quality materials.

The outdoor spaces have been designed with great care, creating a harmonious connection between the villa and the surrounding natural environment. The garden features lush terraced areas, olive trees, and spacious open areas, ideal for hosting large families or groups of friends seeking a relaxing and convivial vacation.

The interiors, enhanced by marbles that provide luminosity and contemporary design, are equipped with a floor heating and cooling system to ensure maximum comfort. At the same time, original elements such as the ceilings and exposed beams preserve the villa's historic charm, offering a perfect balance between the old and the new.

The annexed barn is equally welcoming, with a breathtaking view of Siena: every window in this building frames a picture-perfect scene.

The spacious indoor and outdoor areas provide the opportunity to enjoy moments together without sacrificing tranquility or the possibility of retreating to more intimate spaces. Ideal for large families or groups wanting to spend a pleasant vacation together while maintaining privacy, this villa allows you to fully enjoy the Sienese countryside, while being just a short drive from some of Tuscany's most famous destinations, such as Siena, San Gimignano, and Florence. Villa del Mangia, 5Panoramic Pool and Chef Service

Casa Lucia: Swimming Pool, Property, Real Estate, Azure, Building, Estate, Leisure, House, Vacation, Resort € 140 - € 417/night

Amazing independent property with WIFI, pool, A/C, balcony and panoramic view, near Greve In Chianti

  •   4
  •   2
  •   1
€ 140 - € 417per Night

Description

Nice independent house with pool situated in a fantastic position offering beautiful panoramic views over the Tuscan hills and the towers of San Gimignano in the distance.
This beautiful house sits on a large estate (10.000 square meters) with olive groves and vineyards. The pool is approx. 20 m from the house away and it is to be shared with the owners. The house provides a nice, well-kept private garden.
Casa Lucia is sets on 2 levels (both with access on to the outside) and offers welcoming, nicely furnished interiors.
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.
The location is ideal for those who want to enjoy the peace of the Tuscan countryside and at the same time wish to visit all the Chianti little towns such as Castellina in Chianti, Radda in Chianti, Greve in Chianti, Gaiole in Chianti.

Distances: Tavarnelle with general stores 2 km away, San Gimignano 20 km, Florence (airport) 33 km away, Siena 39 km, Pisa (airport) 95 km, Lucca 105 km away.
At guests’ disposal: large outside areas with furnished garden (ideal for al-fresco dining), panoramic swimming-pool (13 x 6 m – min. depth 1,3 m – max. depth 2,1 m – open from 01/06 to 30/09) to be shared with the owners, open-air shower (only cold water available) and barbecue. Parking within the grounds.

Pets are not allowed.

Please carefully check if there are any extra costs to be paid on site! Casa Lucia

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

Dimora Di Castroncello: Swimming Pool, Garden, Resort, Landscaping, Lawn, Park, Shade, Yard, Backyard, Eco Hotel 10% Off Discount  Special Offer € 616 - € 1176/night

Pretty private holiday villa with WIFI, A/C, private pool, veranda and panoramic view, near Cortona

  •   12
  •   6
  •   4
: EAS212154
€ 616 - € 1176per Night

Description

Dimora Di Castroncello is located 2 km (1 mi) from Castroncello, Italy and only 15 km (9 mi) from Cortona in the tourist area "Cortona And Surroundings". Dimora Di Castroncello is a beautiful vacation rental (300 sq m) with private pool, WiFi internet and air conditioning. The property can accommodate up to 12 guests comfortably in six bedrooms with four bathrooms.

What to Expect
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 relaxing holiday in Tuscany. After a hectic 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. 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 12 people. Dine 'al fresco' like a real Tuscan, the fully furnished veranda is the ideal setting to enjoy food, family and the nice Tuscan weather.

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: Cortona 15 km (9 mi), Arezzo 21 km (13 mi), Montepulciano 38 km (24 mi), Montalcino 58 km (36 mi) and Perugia 70 km (44 mi).

Some other major tourist destinations you should consider visiting are: Florence 108 km (67 mi), Viareggio 195 km (121 mi), Forte Dei Marmi 202 km (125 mi), Rome 206 km (128 mi), Venice 351 km (218 mi) and Milan 395 km (245 mi).

Additional Information
Check-In Time: 16:00 - 20:00
Check-Out Time: 08:00 - 10:00
Pool Open: 1 May - 30 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) 113 km (70 mi), Pisa (psa) 176 km (109 mi), Bologna (blq) 200 km (124 mi), Roma Ciampino (cia) 215 km (134 mi) and Roma Fiumicino (fco) 227 km (141 mi).


Dimora Di Castroncello

Casa Scopeti: Swimming Pool, Property, Real Estate, Leisure, Water, Resort, Vacation, Tree, Estate, Resort Town € 206 - € 494/night

Private Accommodation with A/C, WIFI, private pool, hot tub, TV, panoramic view, near Florence

  •   12
  •   4
  •   3
€ 206 - € 494per Night

Description

Nice independent villa situated in panoramic location in the heart of the Tuscan country-side. This property has been restored preserving its original architectural features and turned into a comfortable villa with private swimming-pool offering nice interiors furnished in a typical country style.
The access to the property is via an unpaved but well-maintained road.
Distances: the small village of Falciani with food shops 2 km away, San Casciano with all kinds of shops 5 km, Florence 10 km, Greve in Chianti with a charming central square and nice restaurants 20 km, Siena 60 km away.
At guests’ disposal: nice garden furnished with sun-beds and sun umbrellas, private swimming-pool (6 x 12 m – maximum depth 1,4 m – open from 01/04 to 31/10), heated outdoor Jacuzzi (7 seats), barbecue, veranda, playground for children. All of the bedrooms are provided with air-conditioning. Ironing facilities available. WI-FI internet connection available (free of charge for a usage of 15 hours per week - extra consuption to be paid on site at € 0,90 / per hour).
Parking within the grounds.
Extra services: maid service available by arrangement (€ 10,- / per hour to be paid on the spot). It is possible to arrange cooking classes and cooking service.
Small pets are allowed.

Please carefully check if there are any extra costs to be paid on site! Casa Scopeti

Villa Monteresi: Sky, Water, Cloud, Swimming Pool, Shade, Plant, Outdoor Furniture, Architecture, Tree, Sunlounger 0% Interest Installments € 821 - € 1234/night

Unique independent villa with WIFI, hot tub, A/C, private pool, TV and patio, near Siena

  •   12
  •   6
  •   7
€ 821 - € 1234per Night

Description

Villa Monteresi is a nice stone building (800 sq m) with hot tub, private pool and air conditioning. The property can accommodate up to 12 people comfortably in six bedrooms with seven bathrooms. Villa Monteresi is located in Monteresi, Italy and only 9 km (5 mi) from Siena in the tourist area "Siena And Surroundings".

Your Experience
After arriving 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 relaxing vacation 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. Outdoors you will also find a barbecue grill, patio and hot tub. There is a kitchen including coffee machine, microwave, toaster 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.

Places 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 9 km (5 mi), San Gimignano 34 km (21 mi), Greve In Chianti 42 km (26 mi), Montalcino 50 km (31 mi) and Florence 64 km (40 mi).

Some other major tourist destinations you should consider visiting are: Florence 64 km (40 mi), Viareggio 159 km (98 mi), Forte Dei Marmi 166 km (103 mi), Rome 248 km (154 mi), Venice 315 km (196 mi) and Milan 356 km (221 mi).

Additional Information
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) 77 km (48 mi), Pisa (psa) 114 km (71 mi), Bologna (blq) 164 km (102 mi), Roma Fiumicino (fco) 252 km (157 mi) and Roma Ciampino (cia) 260 km (161 mi).


Villa la Quercia

Casa Insieme: Sky, Building, Window, Plant, Azure, Architecture, House, Wood, Grass, Landscape € 1100 - € 1330/night

Pretty independent vacation rental with A/C, private pool, WIFI, terrace and panoramic view

  •   12
  •   6
  •   5
€ 1100 - € 1330per Night

Description

Casa Insieme is a nice stone building (490 sq m) with air conditioning, private pool and WiFi internet. The property can accommodate up to 12 people comfortably in six bedrooms with five bathrooms. Conveniently located 9 km (5 mi) from Asciano, Italy in the tourist area "Orcia Valley" and only 29 km (18 mi) from Siena.

The Experience
After arriving at Casa Insieme you’ll find a beautiful clean well-maintained property with views of the hills ideal for a splendid vacation in Tuscany. After a hectic day of shopping, 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 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 and refrigerator, as well as, plenty of tableware and cutlery for up to 12 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.

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: Siena 29 km (18 mi), Montalcino 38 km (23 mi), Montepulciano 44 km (27 mi), Arezzo 53 km (33 mi) and Cortona 54 km (34 mi).

Some other major tourist destinations you should consider visiting are: Florence 98 km (61 mi), Viareggio 192 km (119 mi), Forte Dei Marmi 199 km (124 mi), Rome 221 km (137 mi), Venice 349 km (216 mi) and Milan 390 km (242 mi).

Additional Information
Check-In Time: 15:00 - 19:00
Check-Out Time: 09:00 - 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) 111 km (69 mi), Pisa (psa) 146 km (91 mi), Bologna (blq) 197 km (123 mi), Roma Ciampino (cia) 230 km (143 mi) and Roma Fiumicino (fco) 242 km (151 mi).

Additional Services
Tours - The owner can arrange custom tours for your group. To learn about the tours available, speak to the owner after arriving or inquire prior to booking. The cost will vary depending in the specific tour and number of people.
Maid Service - Upgrade your holiday with maid service. This service can be scheduled by the owner. Ask for more details about the additional cost.
Pre-Stocked Fridge - If you'd like to have the fridge and pantry stocked before you arrive that is possible at Casa Insieme. Inquire for more details, including the additional cost and how to schedule this service.

Casa Insieme

Chianti Hills Apartment, Pool, Ac: Blue, Swimming Pool, Hacienda, Shade, Backyard, Water Feature, Eco Hotel, Landscaping, Villa, Resort 20% Off Discount  Special Offer € 108 - € 221/night

Fantastic flat with A/C, WIFI, TV, patio and panoramic view, near Florence

  •   5
  •   1
  •   1
: EAS208423
€ 108 - € 221per Night

Description

Chianti Hills Apartment, Pool, Ac is located 9 km (5 mi) from San Casciano In Val Di Pesa, Italy and only 16 km (10 mi) from Florence in the tourist area "Florence And Surroundings". Chianti Hills Apartment, Pool, Ac is a nice vacation rental (80 sq m) with air conditioning and WiFi internet. The property can accommodate up to five people comfortably.

The pool and garden are to be shared with the owner, who lives upstairs in the same property.

Your Experience
After arriving you will be greeted by the owner or manager where you’ll find a nice clean well-maintained property with views of the hills ideal for a peaceful holiday in Tuscany. For your enjoyment you will find a where you can unwind while enjoying a nice cold beverage after a busy day of visiting museums. A real benefit of renting a home, instead of multiple hotel rooms, is the ability to relax after a busy day of sightseeing with family and friends. Enjoy a meal together along with some local wine to finish the day. If you enjoy cooking for family and friends there is a well-equipped kitchen including coffee machine, microwave, toaster and refrigerator, as well as, plenty of tableware and cutlery for up to five people.

Visit the Area
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: Florence 16 km (10 mi), Greve In Chianti 27 km (17 mi), San Gimignano 50 km (31 mi), Siena 68 km (42 mi) and Pisa 70 km (44 mi).

Some other major tourist destinations you should consider visiting are: Florence 16 km (10 mi), Viareggio 99 km (62 mi), Forte Dei Marmi 111 km (69 mi), Rome 288 km (179 mi), Milan 313 km (194 mi) and Naples 478 km (297 mi).

Additional Information
Check-In Time: 16:00 - 19:00
Check-Out Time: 08:00 - 10:00
Pool Open: 1 May - 31 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) 19 km (12 mi), Pisa (psa) 72 km (45 mi), Bologna (blq) 118 km (73 mi), Genova (goa) 242 km (150 mi) and Venezia (vce) 272 km (169 mi).


Chianti Hills Apartment, Pool, Ac

Restaurants, Museums, Wineries and Attractions in Penna