Home Vacation Rentals By Owner In San Casciano Val Di Pesa, TOS

Showing 20 Of 21 Vacation Rentals
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$314.17

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Apartment

La Canonica In San Casciano Val di Pesa - Tuscany

San Casciano Val Di Pesa, Fi, Italy

In the ancient hamlet that surrounds the Bibbione Castle ,12 apartments have been extracted with an attentive restoration, all tastefully furnished with special attention paid to its particulars. The hamlet dates back to 1200 and is located in a panoramic position on the hills in front of San Casciano Val di Pesa. At guests disposal is a beautiful swimming pool (6.5x17) (01/05-30/09 open from 9.00am to 8.00pm), table-tennis, mountain bikes. In the nearby valley, about 2 km away, passes the superstrada Florence-Siena. Comfortable furniture with period pieces. On request and to be paid on the spot: cook, domestic help (extra hours), driver, baby sitter, breakfast service, guided tours, cooking lessons and health/wellness centre.brPLEASE NOTE: Check in: 3 - 7 p.m. Check out: 9 - 10 a.m. Pets are not allowed in the swimming pool or in the breafast room.ACCOMMODATION: (99 m2) Gr. fl.: living/dining room with fireplace and double divan bed, dining room, kitchen (dishwasher), 1 double bedroom, 1 bathroom with jacuzzi bath and shower, 1 double bedroom with bathroom with shower, private equipped outdoor area.LOCATION: 5 km San Casciano Val di Pesa, 18 km Florence, 45 km Siena, 6 km horse riding, 4 km tennis court, 25 golf course, 30 km Florence airport.brbrbr Refundable deposit (to be handed over on arrival) per booking by credit card 200.00 Eurobr Tourist tax per person/day 2.00 Euro
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Exceptional(8)

$1433.56

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Villa

Villa la Mandragola In San Casciano Val di Pesa - Tuscany

San Casciano Val Di Pesa, FI, Italy

***FROM APRIL 1ST FOR NEW BOOKINGS 2026, FREE CANCELLATION UP TO 30 DAYS BEFORE ARRIVAL***brProperty for exclusive usebrLarge independent villa in typical Tuscan style, 380 sq. m., for 12 persons with 6 double bedrooms and 4 bathrooms. The private, fenced swimming pool and the large garden with furnished veranda make the perfect place for friends or families with children looking to relax outdoors. The villa has air conditioning, Wi-Fi, satellite TV and parking in the property.brbrOutdoor AreabrVilla la Mandragola offers large open spaces which are completely fenced. In front of the house is a large paved area, with a veranda complete with table and chairs for outdoor meals and a stone barbecue. The fenced swimming pool, 8 metres by 4 and 1.5 metres deep, is in a nice raised position with a marvellous view, behind the house, and is accessible via a few steps. All around the pool is a paved area with shower, sunbeds, and beach umbrellas for great relaxing moments. You will also find a washing room with washing machine, and parking is in the property.InteriorbrThe house is on two floors plus attic and has been carefully restructured and furnished, with modern comforts and, at the same time, a classic feel in typical Tuscan style with high wood ceilings, cotto flooring and arched windows and patio doors. The main entrance is on the ground floor, where you will find a large living room with fireplace, satellite TV, a dining room and a fully-equipped kitchen, a double bedroom, a bedroom with two beds, a bathroom with shower and a large room with table perfect for children. A stone staircase leads to the first floor where there is another large living/dining room, a second equipped kitchen, 2 double bedrooms, a bedroom with 2 beds, 2 bathrooms with shower and a bathroom with shower and bathtub. A wooden staircase leads to the attic with a bedroom with two beds.brbrLocationbrThe villa is in a quiet, secluded position, surrounded by Tuscan hills and immersed in olive groves and Chianti Classico vineyards, a few kilometres from San Casciano Val di Pesa and offers many interesting outings for those looking to explore this uncontaminated countryside.brbrFacilitiesbrVilla La Mandragola is complete with Wi-Fi, central heating, air conditioning, mosquito screens at the windows, baby bed, high chair, complimentary toiletries in the bathrooms, parking in the property.brbrServicesbrThe price includes: bathroom, bedroom and kitchen linen (changed weekly), internet, air conditioning, water, electricity, gas, final cleaning, high chair (upon request). Upon request and to be paid for at the house are cookery courses, dinners, hired help, wine tours, mountain bike hire, reservations for museums, restaurants and hot-air balloon tours.brbrImportant InformationbrSwimming pool open from May 1st to October 31st. Check-in from 3-6pm (arrivals after 6.00pm are charged a supplement of 50 Euros). Prior arrangements must be made for all arrivals different from the normal times. Access to the property via 1 km of gravel road. Animals are admitted, upon request. For stays with a pet the amount of the deposit will be Eu 200.00. The reception does not provide transfer service to the villa (3 km away). Activities and DistancesbrThe country house is perfect for visiting the main towns and cities of the region, as well as the smaller villages and castles of Florence’s and Siena’s noble families. You can visit and taste the products of Chianti’s farms and wine cellars, go horse riding, go on excursions, hiking trips and take cookery courses.br4 km Sambuca, 8 km San Casciano Val di Pesa (all kinds of shops), 26 km Florence, 31 km San Gimignano, 54 km Siena, 84 km Pisa.brbrGroceries: Sambuca, 3.3 kmbrRestaurant: Osteria di Passignano, 4.7 kmbrGolf course: Circolo Golf dell’Ugolino, 20 kmbrAirport: Florence Peretola, 40 kmbrRailway: Poggibonsi, 20 kmbrShopping centre: Coop Valdelsa (Poggibonsi), 20 kmbrbr Heating (from November to April) due only if used, per week 350.00 Eurobr Tourist tax per person/day 2.00 Eurobr Baby bed per day 10.00 Euro
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$977.43

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Villa

Villa il Poggio In San Casciano Val di Pesa - Tuscany

San Casciano Val Di Pesa, Fi, Italy

Property for exclusive usebrAncient farmhouse surrounded by olive groves and terraced areas and situated inside the Castello di Bibbione estate in the Chianti area. The castle dates back to the early 11th century, whereas the stone-built houses of the hamlet date back to the early 13th century. The villa rental was purchased in 1511 by Niccolò Machiavelli and his descendants the marquis’ Rangoni Machiavelli personally tended to the recent restoration of the complex. From the house you can enjoy a stupendous view over the countryside. Bright and cosy, furnished with period pieces and ancient kilim rugs, the house is equipped with all the modern conveniences. The outdoor areas (4 ha.) and the swimming pool area (5x10)(01/05-30/09 open from 9.00am to 8.00pm) are well-kept to and equipped. The position of the house offers the possibility to organize easy excursions to Florence, Siena and Arezzo, thanks to the expressway which connects the cities and which can be reached in just a few minutes. In fact, the expressway passes through the valley below about 2 km away. On request and to be paid on the spot: cook, domestic help (extra hours), driver, baby sitter, breakfast service, guided tours, cooking lessons and health/wellness centre.brPLEASE NOTE: Check in: 3 - 7 p.m. Check out: 9 - 10 a.m. Pets are permitted upon a small extra charge per booking (they're not allowed in the swimming pool or in the breakfast room).brbrACCOMMODATION: (352 m2) Gr.fl.: (independent apartment): living/dining room with 2 single divan beds, kitchenette, 1 double bedroom, 1 bathroom with shower. 1st Fl.: spacious living room with fireplace, lounge with double divan bed, kitchen (dish washer), dining room with an 8-person table, equipped loggia with table and chairs, 1 bathroom with shower (washing machine), WC. 2nd Fl.: lounge, 1 double bedroom with bathroom with bath, 1 double bedroom, 1 twin bedded room, 1 bathroom with bath.LOCATION: 5 km San Casciano Val di Pesa, 18 km Florence, 45 km Siena, 6 km horse riding, 4 km tennis court, 25 golf course, 30 km Florence airport.brbr Tourist tax per person/day 2.00 Eurobr Refundable deposit (to be handed over on arrival) per booking by credit card 200.00 Euro
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Exceptional(5)

$125.67

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Private Vacation Home

Dependance di Villa Magna by Interhome

San Casciano Val Di Pesa, San Casciano Val di Pesa, Italy

On a vinyard country house Villa Magna, detached, surrounded by fields and vineyards. 3 houses in the residence. 9 km from the centre of San Casciano, 4 km from the centre of Cerbaia, 10 km from the centre of Scandicci, in a secluded, sunny position on top of a hill, 100 m from the edge of the forest, in the countryside. For shared use: property 10'000 m2 (fenced), terraced garden with lawn and flowers. Storeroom available. 300 m long motor access (via unmade road). Single garage at the house. Shop 4 km, grocery 4 km, supermarket 9 km, restaurant 2 km, bar 4 km, bakery 4 km, bus stop 400 m, railway station 10 km, sandy beach Marina di Pisa 75 km, indoor swimming pool 10 km. Golf course (9 hole) 12 km, tennis 10 km, walking paths from the house 100 m, fishing possibilities 2 km. Nearby attractions: Firenze 27 km, San Gimignano 41 km, Siena 67 km, Volterra 68 km. Please note: car recommended. Suitable for families, baby equipment (included). Residence with electric gates. The owner lives on the same property. The owner has a dog. Property ref. IT 5274.651.1 is situated on the same property. The complex has another 1 house for rent.brDependance di Villa Magna, 3-room house 70 m2 on 2 levels. Partly renovated in 2022, practical and cosy furnishings: living/sleeping room with 1 double sofabed and open-hearth fireplace (only for decoration), dining table and satellite TV (flat screen). Kitchen (oven, dishwasher, Gas stove, 4 gas rings, toaster, kettle, electric coffee machine). Upper floor: 1 double bedroom. 1 room with 1 bed (80 cm, length 190 cm). Exit to the terrace, to the patio. Shower/bidet/WC. Gas heating. Natural stone floors. Terrace, patio. Terrace furniture, barbecue, deck chairs, box-room. Beautiful view of the countryside. Facilities: washing machine, iron, children's high chair, baby cot for up to 2 year olds, hair dryer. Internet (WiFi, free). Garage (1 car) at the house. Please note: suitable for families. Non-smokers only. Maximum 1 pet/ dog allowed. Private entrance. Bed layout is flexible. There are more sleeping options available than the maximum number of people allowed which may, however, not be exceeded. No mandatory extra charges to be paid on-site except for local tax. IT048041C2WXSC9TQGbrbrIncluded in price:brERV cancellation insurancebrPower costsbrHeatingbrFinal cleaning (Basic cleaning is always carried out by the guest)brGarage 1xbrLaundry (initial supply of bed linen and towels)brNo Local Tax charged for childrenbrInterhome plants 100'000 m2 of flowering fields to save the beesbrWireless internet access (WIFI)brbrincl. in the price but needs to be booked beforehand:brCot (up to 2 years) / HighchairbrbrNot included in the price and needs to be booked beforehand:brPet 7.0 EUR Bookable extra per daybrbr #IT5274.650.1
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Exceptional(18)

$999.14

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Villa

Large Private Tuscany Villa Near Florence Pool Fireplace Superb Views Location

San Casciano Val Di Pesa, Toscana, Italy

Recommended by Condé Nast as one of the most beautiful home-stays in Italy with a pool. brbrTHE BEST VILLAS IN ITALY TO RENT: 13 BEAUTIFUL HOMESTAYSbrbr Villa is completely private-it is NOT an Agriturismo (Farm Stay Property) where you share the pool, gardens and common areas with other guests. brbr Poggio Canali is an exquisitely restored 500 year old stone Tuscan villa superbly located in the heart of the famous Chianti Tuscany countryside, conveniently close to Florence, Siena and Tuscany's most beautiful hill top towns. Our country house is perched on a hilltop at the end of a tranquil country road and has stunning classic Tuscany views over distant vineyards, castles and estates. brbr Enjoy a glass of Prosecco while watching beautiful sunsets from our terraces, gardens and pavilion. We also have a new pool with glorious views. A large beautifully carved stone fireplace makes our villa perfect in any season. brbrOur large 500 year old stone country house-villa (230 square meters or 2, 475 square foot) has been lovingly and completely restored to the highest standards and in keeping with the beautiful Tuscan aesthetic. It is superbly located 20 minutes south of Florence (direction Siena) in classic Tuscan Chianti countryside and is surrounded by rolling hills, tree lined valleys, olive groves, vineyards, castles and renaissance villas.brbr*Please note, this is a private villa, you do not share our private facilities, gardens and grounds with other guests as with many cheaper Italian rentals. Our house is quiet-at the end of a country road, and it is not isolated as there are two very nice non intrusive Italian families that live close by in the neighboring properties. brbrThe villa has large spacious bedrooms and living areas, antiques, stone floored bathrooms with high quality fittings, four poster beds in every room and traditional architectural elements including a hand carved large fireplace and ancient wooden beamed ceilings as well as a sensitive restoration of original doors and windows. brbrThe villa is on four levels and has traditional terracotta flooring throughout. The villa comes with fine furnishings and linens as well as antiques and high quality home wares including ceramics, cutlery and all new superb quality European kitchen appliances. It has three large double bedrooms, three bathrooms with the highest quality fittings; two large lounge rooms, (sleeps up to 8) and one large eat in kitchen as well as a separate laundry.brbrThe bedroom layout is- bedroom 1: One large master bedroom with large double queen sized four poster bed and ensuite bathroom with walk in wardrobe. Bedroom 2: One large double bedroom with queen sized four poster bed and an extra single bed. Bedroom 3: One large bedroom with double four poster bed. One Folding baby travel cot available if required. brbrLocal artisans have handcrafted to order fine furniture and fittings in traditional style including an iron four poster bed and an antique style traditional kitchen dresser. Out door areas include a large 'loggia' (traditional covered veranda with oak beams and terracotta floors) with beautiful views. The loggia has a large gourmet BBQ as well as a large iron antique table with wooden top (seating 10) with iron patio chairs and outdoor divan lounge. Off the loggia in front of the house is a large ancient stone court yard, a separate oak beamed pavilion with lounge seats and table with iron balustrade and beautiful views. The courtyard also comes with a medieval stone well and troughs and leads onto a lower court yard and terrace, a forest area with oaks, private gardens and a large above ground pool.brbrThe garden is planted in traditional Tuscan style with olive trees, lavenders, rosemary, traditional old style roses and pomegranates and many perfumed plants.brbrAll the rooms and gardens have beautiful views of the Tuscan countryside as the villa is situated on a hill and overlooks grand historical estates such as the 1,000 year old Castle of Bibbione, mentioned in Salman Rushdie's latest book 'The Enchantress of Florence'. brbrWe also have a new pool with large reclining teak lounge chairs set on a hillside with beautiful views. brbrWe can also help with planning your stay in Tuscany through that can also give 10 % off any bookings you make for tours and experiences. brbrbrKeywords: Poggio Canali, Tuscany villa, Villa, Country house, large old stone country house, casa, Tuscany villa with pool, tuscany villa near Florence, Tuscany villa chianti, tuscany house for rent, tuscany villa for rent
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$314.17

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Apartment

Le Ginestre In San Casciano Val di Pesa - Tuscany

San Casciano Val Di Pesa, Fi, Italy

In the ancient hamlet that surrounds the Bibbione Castle ,12 apartments have been extracted with an attentive restoration, all tastefully furnished with special attention paid to its particulars. The hamlet dates back to 1200 and is located in a panoramic position on the hills in front of San Casciano Val di Pesa. At guests disposal is a beautiful swimming pool (6.5x17) (01/05-30/09 open from 9.00am to 8.00pm), table-tennis, mountain bikes. In the nearby valley, about 2 km away, passes the superstrada Florence-Siena. Comfortable furniture with period pieces. On request and to be paid on the spot: cook, domestic help (extra hours), driver, baby sitter, breakfast service, guided tours, cooking lessons and health/wellness centre.brPLEASE NOTE: Check in: 3 - 7 p.m. Check out: 9 - 10 a.m. Pets are not allowed in the swimming pool or in the breafast room.ACCOMMODATION: (119 m2) Gr. fl.: living room with double divan bed, dining room, kitchen (dishwasher, washing machine), 1 bathroom with shower. 1st Fl.: entrance with fireplace and single sofa bed, 2 double bedrooms, 1 bathroom with shower. Private garden. LOCATION: 5 km San Casciano Val di Pesa, 18 km Florence, 45 km Siena, 6 km horse riding, 4 km tennis court, 25 golf course, 30 km Florence airport.brbrbr Refundable deposit (to be handed over on arrival) per booking by credit card 200.00 Eurobr Tourist tax per person/day 2.00 Euro
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Exceptional(10)

$215.27

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Guest House

Tuscan house on vineyard hilltop tucked inside lush gardens

San Casciano Val Di Pesa, Toscana, Italy

This private, quaint guest house is tucked inside the large Tuscan gardens of the 17th century farmhouse property. Enjoy walking through olive and lemon trees, roses, and herbs. Sits on top of a local Chianti vineyard with two bedrooms, two bathrooms, private kitchen, and outdoor patio to enjoy meals al fresco!brbrMy artwork and paintings are available for sale at the property. You can see some of the pictures on our listing.brbrThe guest house is perfect for 4 people, including a family with kids. The bedrooms both have air conditioning and heating, welcoming guests year-round. Guests will find an oven, stove, toaster, coffee maker, and all the essential items in the kitchen to prepare meals. Only a 3-minute drive from the local town of San Casciano to stock up on local Italian cuisine and wine to cook to your liking!brbrA separate entrance to this guest house maintains its privacy from the main house, where your hostess lives and is available for any questions during your stay.brbrSan Casciano has a local town, only 3 km from the property. It's filled with shops, restaurants, and wineries that are all walkable to explore. Though a car is advised for getting around Tuscany, it is possible to enjoy this local scenery by foot and stroll into town for some afternoon gelato.brbrThe location is very ideal for discovering all that Tuscany has to offer. The places we highly recommend spending a day in are Florence, Siena, San Gimignano, and Volterra. Each is filled with museums, restaurants, ancient ruins, and famous historical art and sites to see.
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$232.72

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Villa

Casale del Lago In San Casciano Val di Pesa - Tuscany

San Casciano Val Di Pesa, FI, Italy

***FROM APRIL 1ST FOR NEW BOOKINGS 2026, FREE CANCELLATION UP TO 30 DAYS BEFORE ARRIVAL***brProperty for exclusive usebrCasale del Lago is an long-standing property, 160 sq.m. sleeping up to 12 people made up of 4 double bedrooms, 3 bathrooms one of which has a Jacuzzi and two sitting rooms each with a double sofa bed. The house, dating back to the beginning of the 19th century has been perfectly restored and turned into a holiday home. The swimming pool is private and fenced for children’s safety, the garden has a playing area, an outdoor Jacuzzi as well as a gazebo, outdoor furnishing and barbeque for open-air lunches and dinners.brbrExternal Area and Swimming PoolbrThe country house has lots of open spaces and its main feature is a large terrace on the ground floor as well as several green areas between the garden and swimming pool, where there is a playing area for children with a swing and a ping-pong table and a Jacuzzi shaded by a characteristic gazebo for moments of leisure. The L-shaped pool with an outdoor shower measures 12x6m, 1.35m deep and is fully fenced so children are free to play. All the outdoor spaces are well-furnished with tables and chairs for outdoor eating, umbrellas, chairs and deckchairs. The wood-fired oven and barbeque are at the guests’ disposal.InteriorbrThe interiors are those typical to most country houses in the Chianti area, featuring ceilings with wooden beams, typical arches and terracotta floors. On the ground floor there is a very large, well-equipped kitchen with a dining area, a beautiful hall with a large fireplace and double sofa bed, a room with satellite TV and a small billiards table and also another double sofa bed, WC. You go upstairs on a flight of stone stairs where there are 4 double bedrooms with air conditioning, one of which has an ensuite bathroom with shower and another bathroom with shower. On the second floor, in a typical turret, there is a large bathroom with a Jacuzzi.brbrLocationbrThe country house is totally surrounded by countryside full of olive groves, woodland and charming glimpses of the lake, completely immersed in nature. brbrFacilitiesbrCasale del Lago has got wi-fi Internet connection, central heating, Jacuzzi, fenced swimming pool, car park on the property. All the bedrooms have air conditioning.brbrServicesbrIncluded in the price : bathroom, bedroom and kitchen linen (with weekly change), Internet connection, water, gas to cook (not heating) and electricity consumption (not air conditioning), high chair and baby bed.brUpon request and to be paid for on location are dinners, a maid, bike rentals and the possibility to organize cookery courses.brbrImportant InformationbrThe swimming pool is open from 01/04 to 31/10. Small pets are allowed against payment of 50 euros/pet/week. Access to the house with 1 km of dirt road not suitable for low and sports cars.Activities and AttractionsbrThe house is strategically situated also for visiting the famous and characteristic Tuscan hamlets. It is only a few kilometres away from San Casciano Val di Pesa, a characteristic town with its ancient buildings and glimpses of fascinating views which remind you of the ancient past with every step you take and Florence and Siena are not far either.brYou can visit farms and cellars of the Chianti area with tastings as well, go horse-riding, go on excursions, trekking and have cookery courses too. San Casciano Val di Pesa 5 km (grocers, all kinds of shops and supermarket), Florence 22 km, Siena 63km.brbr Tourist tax per person/day 2.00 Eurobr Refundable deposit (to be handed over on arrival) per booking. In cash 300.00 Eurobr Final cleaning . 100.00 Eurobr Heating (from November to April) due only if used, per kWh (kilowatt hour) 0.50 Eurobr Air-conditioning, only if used, per kWh (kilowatt hour) 0.50 Euro
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$202.75

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Private Vacation Home

Holiday Home 'Sweet Vallet' with Shared Pool, Private Terrace and Wi-Fi

San Casciano Val Di Pesa, San Casciano Val di Pesa, Italy

The holiday home Sweet Vallet in San Casciano Val di Pesa is located in the heart of Chianti and is the perfect accommodation for a stress-free holiday with your loved ones. The 2-storey property consists of a living room with a sofa bed for 2 people, a fully equipped kitchen, 1 bedroom, and 1 bathroom, accommodating up to 4 guests. It is ideal for couples or a couple traveling with a young child. Additional amenities include high-speed Wi-Fi (suitable for video calls) with a dedicated workspace for home office, a TV, a fan, and a washing machine. A baby cot and a high chair are also available. The property features a beautiful characteristic Tuscan terracotta floor.brbrbrbrThis holiday home boasts a private garden, a covered terrace, a barbecue, and an outdoor shower. Guests also have access to a shared outdoor area with a pool (open from May to October). Public transport links are located within walking distance. Nearby, you can find hot air balloon rides, bicycle rental, typical restaurants, and destinations such as Siena, Florence, San Gimignano, and Pisa. The property is also close to the Antinori winery.brbrbrbrTwo parking spaces are available on the property. Pets and smoking are not allowed. Air conditioning is not available. The property follows guidelines to help guests with the correct separation of waste, with more information provided on site. Light and water-saving features are present, and sustainable materials have been used in the insulation. Horseback riding and guided tours are available in the area.
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