Gaiole in Chianti Vacation Rentals by Owner

On your next trip, consider a Gaiole in Chianti vacation home rental for your accommodations. There are 3 vacation homes in Gaiole in Chianti resorts. Vacation home rentals are generally appealing for many reasons. Some of the foremost being cost savings, more space, and no tips or service charges that are associated with hotel rooms. Vacation rental homes have kitchens for cooking, living rooms for gathering together and offer the appeal of living in a real neighborhood and soaking up the rhythm of the locals.

With our friendly, responsive customer service and extensive informational website, renting a Gaiole in Chianti vacation home from Owner Direct Vacation Rentals is a breeze. Find your perfect location and home size to suit your needs, no matter what your criteria. We have vacation homes in Villa Vistarenni, and many more locations.

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  • Togna Self Catering

    Gaiole in Chianti: Villa Vistarenni: Cottage
    • 2 BDR
    • 1 BA
    • Sleeps 4
    • #40566
    avg €214 EUR/night Credit Card
    Just a few steps lead to the flat on the first floor of the 16th century cottage in natural stone. From the windows you can enjoy the view over the swimming pool and breathe the scent of the plants in the garden underneath. The room with incredible French canopy beds gives to the simple and rural style an elegant touch. The living room with fireplace provides a friendly environment for pleasant evenings in the stillness and peace of Chianti.
  • Casina Studio- Self

    Gaiole in Chianti: Villa Vistarenni: Cottage
    • Studio
    • 1 BA
    • Sleeps 2
    • #40565
    avg €105 EUR/night Credit Card
    This pretty studio apartment is located on the rear ground floor of the cottage and has its own small equipped garden where you may choose to have your meals outdoors and enjoy the peaceful site. Simple and cozy, it is an ideal nest for couples wishing to rest and surrender themselves to the magic of Tuscany and the Chianti hills.
  • Chiara self catering

    Gaiole in Chianti: Villa Vistarenni: Cottage
    • 3 BDR
    • 1 BA
    • Sleeps 6
    • #40564
    avg €230 EUR/night Credit Card
    Farmhouse of the 16th century built on local stone, adjacent to the villa and very close to the swimming pool. At one side of the house there is a garden with typical Mediterranean plants, including lavender, santolina and rosemary. This flat is located on the ground floor of the cottage and is connected through a French door to a small, cool private garden equipped for enjoyable outdoor breakfasts or candlelit dinners. Each bedroom is painted in pastel colours and the fireplace in the living room will make you feel at home.
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  • Beautiful Villa in Greve

    Greve: Villa
    • 4 BDR
    • 5 BA
    • Sleeps 11
    • #200221
    avg €392 EUR/night Paypal Pet Friendly
    The villa has two floors and is 450 sq.m. The first floor contains the entrance, a small bathroom, a living room with piano, a double bedroom with sauna, jacuzzi, bathroom with shower and a covered terrace. Another bedroom with double bed, single bed, bathroom with shower and bathtub. From the room you exit into a large open terrace with wonderful views across the valley. On the ground floor there is' a library, a large lounge with fireplace, dining room, kitchen, an ironing room / laundry room and a bedroom with bathroom. There is also an attic with double sofa bed. Externally the villa has a large paved area, furnished with tables, chairs, armchairs, sun beds to be used for lunches, relaxing, reading. The park is divided into many terrace and offers space for all kinds of entertainment, sports and games. Anessa the villa there is an outbuilding (former barn) with a gym on the ground floor and first floor bedroom with double bed and bathroom. Linens, towels, private washing machine (including detergent), dishwasher, sauna, Jacuzzi, bicycles, fuel for the the BBQ, electricity and final cleaning are all included in the price.
  • Charming Farmhouse in the

    Castelfranco di Sopra: House
    • 5 BDR
    • 3 BA
    • Sleeps 11
    • #218757
    avg €385 EUR/night  
    A charming 16th century farmhouse of about 250 sqm, is set in the foothills of the Pratomagno mountain range south-east of Florence and surrounded by acres of well maintained terraced olive groves. It commands sweeping views over the Val d'Arno and a countryside dotted with farmhouses, villages and bell towers - a perfect area for long rambles. The interior is comfortable in a rustic style, complete with beamed ceilings and terracotta floors with air-conditioned bedrooms. A shaded pergola on a terrace below the house has been fitted with a large stone table, chairs and a barbeque for al fresco dining. The outdoor pool, all-weather tennis court and a second pergola are set to one side of the house next to a barn, all with wonderful views. Lower ground floor: Large sitting room leading to a dining area with a fireplace and old stone walls and to a well-equipped kitchen. Dishwasher, Microwave, Kettle, Mixer, Toaster. TV in front of the dining area. 1. Air conditioned double/ twin bedroom with en-suite bathroom with shower. 2. Air conditioned double bedroom with en-suite bathroom with bathtub. Upper ground floor: Large sitting room with an open fireplace, TV with DVD and books. 3. Air conditioned double bedroom. 4. Air conditioned bedroom with three single beds. 5. Air conditioned double/ twin bedroom with independent entrance/exit. Common bathroom with shower. Nice balcony with view over the garden between the bedroom nr 5 and the sitting room. GROUNDS An informal garden set within 15 acres of private olive groves, fruit orchards and vines. The big swimming pool is set about 10 mt from the villa, next to a little pool house with a changing room and shower. The tennis court overlooks the pool - and the view and it is provided free. Facilities at your disposal Taxes, utilities and final cleaning included Bed linen and towels provided. Courtesy set provided. Detergents (for washing machine and dishwasher) provided Housekeeping staff (on demand) Baby cot and high chair provided free Hair dryers (3) Wood oven / Built-in barbeque Laundry room (washing machine / Iron and ironing board), behind the house. Two non-satellite TVs, one with DVD AIR CONDITIONING and Central heating (extra charge - consumption calculated) Two working fireplaces Free WI-FI Dinner on demand (Private chef) LOCATION Midway between Florence and Arezzo as the crow flies, both about 45 minutes’ drive, amid typically Tuscan scenery. A place where art blends with the gentle hills, the color of the olive groves and the shapes of the cliffs. Close to Siena, Florence and Arezzo, a world of art, history and traditions. -- The closest Train station is Figline Valdarno, only 30 minutes to reach Florence (frequent trips during the day). You can park your car free at the Figline station and proceed by train to reach the centre of Florence. This location is an ideal point of departure to visit most of the local territory or to quickly reach the famous regional cities or Chianti territory like : Montevarchi (19 km), Rignano sull'Arno (21 km), Vallombrosa (22 km), Greve in Chianti (28 km), Florence (40 km), San Casciano in Val di Pesa (46 km), Arezzo (40 km), Siena (68 km), San Gimignano (82 km), San Miniato (80 km), Volterra (104 km), Castiglioncello (152 km). A nice location where everything is at your fingertips : bar, restaurants, pubs, pizzerias, dancing, night clubs, banks, jewellers, beauty centers, hair stylists, supermarkets, pharmacies. Pian di Scò, 3km, offer a large selection of shops, bars and restaurants..
  • Tuscany, Charming Vacation

    Chianni: Villa in a gated community
    • 3 BDR
    • 2 BA
    • Sleeps 6
    • #211283
    avg €107 EUR/night Paypal Pet Friendly
    The holiday home is situated in a big, fenced property with look over the roofs of the village and the Tuscan landscape. The vacation villa offers approximately 200 ms of garden to the exclusive use of the guests, with shady places under the old fruit-trees,the veranda with dining table and chairs, a shared swimming pool (4x9 m) with sunterrace, beachchairs and outside shower as well as a fantastic panorama over the Tuscan hills. The property is entirely fenced and protected by an iron gate. The picturesque, a little bit sleepy village of Rivalto with bar and grocer's shop lies at 500-m height and is surrounded by forests, vineyards and olive groves.There are numerous beautiful footpaths arround for your daily walks. In Casciana Terme, the nearby health resort (approx. 4 kms) you find a very beautifully located swimming-pool, all important services ( post, bank) , cafés, restaurants and shopping possibilities and a beautiful spa area.
  • The Vacation Home You've

    San Donato in Poggio: House in a gated community
    • 2 BDR
    • 2 BA
    • Sleeps 4
    • #202549
    avg €126 EUR/night  
    Nestled in the magical rolling hills of the Chianti region, near the village of San Donato in Poggio, half-way between Florence and Siena, this brand new construction home offers all amenities for a perfectly serene and peaceful vacation under the Tuscan sun. The large living room, the two large sized bedrooms, and the two bathrooms can accommodate 4 people comfortably, the living room opens onto a tiled patio and a backyard with olive and fruit trees with mesmerizing views of the surroundings. You can access an Olympic-sized pool only a few steps away. Florence, Siena, San Gimignano, Certaldo are all within a 30-min car ride by the “superstrada”, but cyclists and explorers can instead enjoy the soft and winding roads and trails leading to Florence through vineyards and olive groves.…… Reliable transportation from Rome airport can be arranged upon request and availability.
  • On the Top of a Hill

    San Casciano Val di Pesa: House
    • 7 BDR
    • 3 BA
    • Sleeps 12
    • #200320
    avg €375 EUR/night Credit Card Pet Friendly
    The medieval fortified farmhouse, strides a hill covered in vineyards, olive trees and an oak wood. This hill extends along the Pesa Valley and the historic Roman road, the Via Cassia, which connects Florence and Siena. The property, along with its sister house on the Corzano part of the farm, witnessed countless conflicts between these city states in medieval Tuscany. The houses therefore have the aspect of fortified buildings, reflecting their defensive position. They belonged to the legendary Cavalcanti and Niccolini families, Florentine nobility. The Niccolini family left the profits from these properties to generations of daughters to provide for their dowries. The original watch tower dominates the facade of the property and over the centuries subsequent additions have kept the original character of the house while enlarging it considerably. The building forms a courtyard with a vine-covered pergola for outside dining. It commands a dramatic view over the vineyards and olive groves, towards the neighbouring hills, where where the sheep graze. The property has three double and three twin bedrooms. The bedroom in the tower has been used by the family as a painter’s atelier; it is a two story, galleried space with wonderful light. There are three bathrooms, two sitting rooms and a large fully equipped kitchen dominated by a walk-in fireplace. On the ground floor there is a laundry room with washing machine and ironing board and a double bedroom. Particularly attractive is the walled patio with a small octagonal plunge pool and a spectacular view towards the villas on the surrounding hills. PLEASE NOTE: There is a 1.50 EUR per person, per night (up to a maximum of 7 nights) tourism tax charged during certain times of the year. This is charged for guests 14 and older. It is paid locally and is not included in the totals provided by the website.
  • Beautiful Country House in

    San Casciano Val di Pesa: House
    • 7 BDR
    • 4 BA
    • Sleeps 14
    • #200305
    avg €375 EUR/night Credit Card Pet Friendly
    This property is an authentically restructured typical Tuscan farmhouse with beamed ceilings and terracotta floors. It is situated on a little hill in the heart of the farm Fattoria Corzano e Paterno, where we produce excellent wines, sheep cheeses and extra virgin olive oil. The house is furnished very tastefully and luxuriously, the rooms are big and bright. Sitting on the terrace you have a spectacular view over the Tuscan hills, olive groves and vineyards. On the ground floor you find one big living/sitting room with a fireplace, one double and one twin bedrooms, one single room with one bed and a sofa bed which open on a living-room, two bathrooms (one with washing machine). The kitchen is well equipped, with fridge, electric oven with gas stove, dishwasher and microwave oven and with an open fireplace. On the first floor there are 4 more bedrooms with 2 single beds or 1 double bed each, as well as a living/sitting room, two bathrooms. On the terrace there is a veranda for eating outside and a pizza oven. PLEASE NOTE: There is a 1.50 EUR per person, per night (up to a maximum of 7 nights) tourism tax charged during certain times of the year. This is charged for guests 14 and older. It is paid locally and is not included in the totals provided by the website.
  • Two Bedroom Cottage San

    San Gimignano: Cottage
    • 2 BDR
    • 1 BA
    • Sleeps 3
    • #201467
    avg €98 EUR/night Credit Card
    La Civetta, a lovely detached cottage, nestles in a very peaceful and private location in the countryside and yet is only 1.7 km from the town of San Gimignano. The private terrace of the apartment enjoys a lovely view of the medieval town and its famous towers, and there is a beautiful secluded swimming pool. A pathway and rustic steps lead from the cottage down to the swimming pool (12m x 6m) which is in a very private position below the house and enjoys fine views of the countryside and surrounding woodland.
  • Two Bedroom Detached Villa

    San Gimignano: Villa
    • 2 BDR
    • 3 BA
    • Sleeps 8
    • #201154
    avg €152 EUR/night Credit Card Pet Friendly
    <b>Local charges noted below are paid on arrival and are NOT included in the quote provided by Owner Direct - Heating Euro 10 per day if used Air conditioning Euro 15 per week Wi Fi internet access Euro 15 per week payable locally and must be requested in advance at time of booking. Accommodation tax from 1st March to 31st October, Euro 1,50 per person per night (max 5 night) children under 12 years free of charge</b> A beautiful detached restored barn with private swimming pool, surrounded by its own well kept garden with wonderful views over vineyards and cypress groves towards medieval San Gimignano visible in the distance. Immersed in the countryside yet only 2 km from the town, the villa provides very high standard secluded accommodation in a much sought after area of Tuscany. Built on a slope, the accommodation is on three floors, all connected by internal staircases, but each floor actually opens on to an area of the garden. Originally a hayloft, the house has been carefully restored preserving original characteristics, such as slanted brick windows in the spacious bedrooms, terracotta floors, beamed ceilings and brick archways, all so typical of Tuscan country architecture. There are 3 shower rooms, one on each floor, and 2 fully equipped kitchens ensure modern comfort, yet marrying perfectly with the classic furniture. Both living rooms have comfortable sitting areas with settees which can convert to double beds on request, and the lounge on the ground floor also has a characteristic fireplace, a specially commissioned hand painted mural depicting the beautiful landscape, and arched patio doors which open onto the large patio and garden. Within the well kept grounds close to the house is the large swimming pool (14m x 7m) which is private to the villa and has a lovely view over the countryside. The house and its garden is fully enclosed, and has its own parking area. It is only 2km from San Gimignano and its selection of shops and excellent local restaurants, and many of the regions other sights are within easy driving distance. Florence and Siena are both easily accessible via main road and rail links from nearby Poggibonsi.
  • Lovely Cottage for 2 to 4

    San Gimignano: Cottage
    • 1 BDR
    • 1 BA
    • Sleeps 4
    • #201138
    avg €55 EUR/night Credit Card Pet Friendly Star Rating
    A pretty detached cottage on a lovely estate close to San Gimignano, it has a large private terrace with pretty views of the medieval town of San Gimignano silhouetted on the hillside. Also on the estate is a pretty swimming pool surrounded by sun terrace and garden. Light and airy, this pretty cottage enjoys a delightful atmosphere. It has all its accommodation on the ground floor below there is only a basement floor and at the rear a storage barn. Comfortably furnished the living area has a traditional wood burning fireplace, settee/sofa bed, kitchen/dining area and glass doors opening on the terrace. There is also a double bedroom and shower room. A barbecue, utility room with washing machine, and metered telephone are available for communal use and parking is in the grounds near to the cottage.
  • Four Bedroom Detached

    San Gimignano: Villa
    • 4 BDR
    • 4 BA
    • Sleeps 11
    • #148259
    avg €276 EUR/night Credit Card Star Rating
    This is the perfect example of a Tuscan country villa, it is surrounded by mature gardens and has a large private swimming pool with a fantastic panorama of the surrounding countryside. Incredibly although the villa is immersed in all this peace and tranquillity, medieval San Gimignano, which is a joy to explore, is only 10 minutes walk away. Beautiful views of the surrounding coutryside all around. Rolling hills with olive groves and vineyards.
  • Fantastic Villa in Chianti

    Greve: Montefili: Converted barn
    • 6 BDR
    • 4 BA
    • Sleeps 10
    • #149946
    avg €400 EUR/night Credit Card Paypal Pet Friendly
    The villa is structured on three levels and can host up to 11 guests. It benefits from its own private garden an amazing view on the neighbourly hills and disposes of its own private « infinity » pool. On the ground floor you will find a large and and fully equipped kitchen with a fire place, next to a spacious living room on two levels, from which you have direct access to the garden and the pool. Still on the ground level, two double bedrooms have their own private bathrooms. Furthermore you will dispose of a convenient library/TV room with WiFi internet access. On the upper floor there is a large double air conditioned bedroom as well as a double bedroom with a bathroom (with Jacuzzi tub) in common. Finally outside, with an independent entrance from the loggia, there are two single bedrooms sharing a bathroom.
  • Region of Chianti Classico

    Greve: Montefili: Converted barn
    • 2 BDR
    • 2 BA
    • Sleeps 5
    • #39425
    avg €140 EUR/night Credit Card Pet Friendly
    Our farm is located in the heart of the region of Chianti Classico near Greve, looking out over Montefioralle, a splendid medieval village, in an untouched natural setting. It is on the top of a hill (1400 feet above sea level) with a magnificent 360 °view. This large apartment, which is part of the oldest building, is overlooking the paved little square hearth of the hamlet. There is a living room with a very large fire place and a double sofa bed, a dining room, a kitchen, two bedrooms, one with two beds and the second with three bed, two bathrooms.
  • Apartment in Restored Barn

    Greve: Montefili: Converted barn
    • 1 BDR
    • 1 BA
    • Sleeps 4
    • #39171
    avg €114 EUR/night Credit Card Pet Friendly
    This apartment, situated in a part of the carefully restored barn, offers a large living room with kitchenette, two sofa beds which turn into two full size single beds. The bedroom is up a few steps behind the kitchen. It is super large and has a nice double bed. There is an en-suite bathroom finished in soft cream Italian ceramic. The private terrace is covered by a grape vine. Even on a sunny afternoon there is an oak tree which will offer lots of shade.
  • Agricultural Cottage

    Greve: Montefili: Converted barn
    • 1 BDR
    • 1 BA
    • Sleeps 2
    • #39058
    avg €109 EUR/night Credit Card Pet Friendly
    The property, situated in a small agricultural cottage, offers a beautiful well-lit living room with a sofa bed; a small kitchen; a double room and a bathroom finished in travertino. Outside the room there is one private space for the guests.
  • Old Stone Farmhouse Full

    Anghiari: House
    • 3 BDR
    • 3 BA
    • Sleeps 8
    • #126337
    avg €122 EUR/night Pet Friendly
    Nestling in a Tuscan hamlet named Toppole, is a 130 square meter farmhouse built on the ruins of an eleventh century stronghold. It is independent, enjoys a panoramic view and is located 6 km from Anghiari, a medieval village classified as "one of the most beautiful villages in Italy”: the battle which took place there inspired Leonardo da Vinci. A few km along the road, you will find Caprese, the town where Michelangelo was born, and Sansepolcro, home town of the famous artist Piero della Francesca. The house has beamed ceilings and terracotta floors. It is quiet and restful with charming surroundings. There is a covered terrace with a large wooden table – very pleasant for al fresco dining in summer. The garden is strewn with olive trees, vines, lavenders, rose bushes, a fig tree, a giant rosemary bush, thyme and basil. There is a superb pizza oven, also useful for grills. An outside shower allows you to refresh yourself in the open air. In the cellar, two mountain bikes are available. A car is essential. Electricity: international plug
  • Villa among vineyards and

    Greve: The Old Pasta Factory: Villa in a gated community
    • 3 BDR
    • 3 BA
    • Sleeps 6
    • #201854
    avg €203 EUR/night Credit Card Paypal Pet Friendly
    The Villa is located between vineyards and olive groves, has a gorgeous view on the surrounding hills and it is also at walking distance from all facilities (restaurants, shopping, grocery, banks, church, bus stop etc.) .This house is 130 sqm. on two levels with panoramic vew, 400 sqm. of surrounding garden, swimming-pool 6,60mt. x 3,60 mt. 1.30 mt. deep, parking for 2 cars . Beautiful independent villa on four sides suitable for 6 people. First Level: dining-room with furnished kitchen, living-room with satellite-tv , 1 bathroom with wc and washing-machine. Second Level : 2 double and 1 twin bedroom, 2 bathrooms with shower ( one bathroom is en suite, the other one is in the corridor to be shared between two bedrooms ). The property has a blue theme. The blue ray is one of the world most powerful antiseptics. Its light is cooling, electrical, soporific, astringent. The blue light, lowers fever, sore throat carefully and if it is applied in an appropriate manner, a seemingly inexplicable things. It has a very calming effect on people who are too aggressive and impatient. Blue is a color that soothes and moderates, and that makes people forget the problems of everyday Color therapy use blue to treat stress, nervousness, anxiety, insomnia and irritability Available on request at no additional costs : baby crib, high-chair, additional bed
  • Between Vineyards and

    Greve: The Old Pasta Factory: Villa
    • 5 BDR
    • 5 BA
    • Sleeps 10
    • #201837
    avg €261 EUR/night Credit Card Paypal Pet Friendly
    Our Villa is located between vineyards and olive groves, has a gorgeous view on the surrounding hills and it is also at walking distance from all facilities (restaurants, shopping, grocery, banks, church, bus stop etc.) This house is 200 sqm. On three levels ( the third level is a tower with panoramic view ), 400 sqm. Of surrounding garden, swimming-pool (9mt x 2,50 mt 1,40 mt. Deep), parking for 3 cars. Beautiful independent villa on four sides suitable for 10 people . First Level( ground floor ): dining-room with furnished kitchen, living-room with satellite-tv, small laundry-room with washing-machine, iron and iron board and one bathroom with wc and shower. Second Level( First floor ): 3 double bedrooms and 1 twin bedroom each with en suite bathroom with shower. Tower Level ( Second floor ): double bedroom with panoramic view (this bedroom can use the bathroom on the ground floor). The house is mostly green inside. Green has a balancing action and general welfare. The green is 'the color of nature and it promotes harmony because it has a calming influence on the nervous system. The desire for green lawns and trees that comes after a period of time between the gray stones and red brick of the city is the instinctive yearning for toning the color of nature. Green is peace and refreshment Available on request at no additional costs : baby crib, high-chair, additional bed
  • Tiny Cottage on Farm

    Greve: Montefili: Converted barn
    • Studio
    • 1 BA
    • Sleeps 2
    • #39456
    avg €69 EUR/night Credit Card Pet Friendly
    This farm is located in the heart of the region of Chianti Classico near Greve, looking out over Montefioralle, a splendid medieval village, in an untouched natural setting. It is on the top of a hill (1400 feet above sea level) with a magnificent 360 °view This tiny little cottage apart form the rest of the cluster, located on the top of the hill overlaying the swimming-pool with a magnificent 360° view. The apartment consists in one single room with a small living area with fireplace, a kitchenette and a double bed and a bathroom. A solar panel, respecting the environment, provides the apartment with the necessary energy and hot water.
  • Apartment in Restored Barn

    Greve: Montefili: Converted barn
    • 2 BDR
    • 2 BA
    • Sleeps 4
    • #39339
    avg €126 EUR/night Credit Card Pet Friendly
    The apartment is situated on the first floor of the barn, above the baking oven and guests can reach it with a small staircase. It is composed by lovely living room area decorated in soft ivory colours. with a full size sofa bed, a small kitchen and two bedrooms with two bathrooms one of which has an interesting sink counter made from the bottle of a wine barrel.

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